what to do about an over-sharing crossdressing manager

A reader writes:

I work in a very open, casual workplace (think jeans and tshirts) where “inappropriately personal” conversations happen a lot and many people are close friends in and out of work. We never interact face-to-face with clients. As such, the lines of professionalism often blur internally, though we are very professional with clients over the phone and email.

One of our managers has recently “outed” himself (his words) on Facebook as a crossdresser and has been talking about it a bit at work too. He has a lot of coworkers on his facebook, not just close friends. On a personal level, I don’t care and neither do any of the people he’s been chatting with. It also has no bearing on our work and would not impact our work or clients if he were to wear women’s clothes and makeup at work. But it’s still making some people uncomfortable because they aren’t necessarily close friends with him outside of work. I think he’s just so relieved to not have to hide this side of himself, that he’s oversharing without realizing it. Also, I think the fact that he’s a manager somehow makes it more uncertain and uncomfortable.

Basically, what phrasing would you suggest for someone to use to let him know they aren’t comfortable discussing it at work without making him think they disapprove of crossdressing itself? (He’s a super nice guy and would not retaliate or become angry. At most, he might get his feelings hurt and be a little melodramatic about it all. Possibly some vaguebooking along the lines of “learning who your real friends are.”)

A friend of mine was talking to me about it and I wanted to see what you had to say since I think you have great advice and a wonderful way of phrasing things.

Hmmm. I want to say up-front that this issue is outside of my area of expertise, and probably my comfort zone, so I’m just going to be feeling my way through this and might get it wrong.

First, it’s worth saying for general education purposes for people reading this who may not know: Crossdressing doesn’t indicate the crossdresser is gay, transgender, or straight. Some people who crossdress are gay, some are transgender, and some are straight. Without knowing more about this particular person, the only conclusion you can draw is that the person enjoys crossdressing.

Okay, that out of the way…

It’s great that you’re in a supportive environment where people feel free to be themselves. And if in fact your manager were crossdressing because he’s transgender (meaning that his gender identify is female), at some point he might make that transition in the workplace because that would be about who he is, on a fundamental level. However, assuming that’s not the case — that he’s not in fact transgender — then I think it’s reasonable to ask him to keep it out of the workplace.

If I were in your shoes, I’d say to him something like, “I’m glad for you that you’re feeling you can be more open with this part of your life, but I’m starting to feel uncomfortable with how it’s being discussed at work. I know it’s a part of your life and I have no issue with that, but it’s becoming part of the workplace in a way that doesn’t feel comfortable to me, just like bringing other parts of our private lives to work wouldn’t feel comfortable.”

I want to be clear that I’m recommending this because it’s not about sexual orientation. No one has any moral standing to tell someone not to mention their sexual orientation at work just because it makes them uncomfortable. It’s entirely reasonable for people to be able to share who their partner is, as straight people do all the time, and if that makes someone uncomfortable, too bad.

But this is different because it’s not about who he is; it’s about something he does. Something like sexual orientation is about who you are at a fundamental level — who you fall in love with, who you partner with, who you create a family with — and so it’s unreasonable to expect someone to keep it private.  But crossdressing is something he does, and that’s different. There’s no reason he needs to share it at work any more than you need to share what you do for thrills, particularly when it’s something so closely associated with sexual proclivities. (Note that I’m avoiding saying it’s sexual for him, since I have no idea if it is. But it’s widely understood as a sexual kink for at least some people who practice it, and that means it’s private and doesn’t belong at work.)

Now, if in fact he’s crossdressing because he’s transgender, then it is part of who he is. But until/unless he explains that, it’s reasonable to proceed as I’ve outlined above.

What do others think?

{ 177 comments… read them below }

  1. Camellia*

    Perhaps the OP could just start saying, “TMI dude, TMI!” and maybe go ahead and leave the conversation if that’s possible, or put their fingers in their ears, or go ‘lalalala’, or something else in a joking-but-not-really way that might get the point across without being too heavy-handed about it.

    If others are also not feeling comfortable that might give them an opening to add something, even it is just ‘Yeah, dud, TMI!’ Then see what the reaction is. If he is hurt or upset, then perhaps the quiet conversation as Alison outlined.

    Also, I wonder if he is discussing this more at work to prepare the way for him to begin wearing his alternate wardrobe to work? The OP might want to start mentally preparing for that possibility.

    BTW, C. E. Murphy writes an urban fantasy series, The Walker Papers, that includes a cross-dressing detective and is handled quite skillfully. Might be interesting reading for the OP.

    1. majigail*

      I really think a quiet conversation first is important. Saying TMI in that manner in a group setting could be very embarrassing and hurtful and stifle what sounds to be a very positive and open culture.

    2. Kathryn*

      That could come off as judgmental or hurtful, not that that I think you meant it that way. I think a quiet conversation where the OP could address it one on one would probably be best.

    3. Soni*

      I agree with Camellia – TMI was my first reaction. I can see how some people feel that “TMI” could come across as hurtful or judgmental, but in my experience it’s always been a way of telling friends and family, “This is just way more personal info than I want to be thinking about when I talk to you.” More often than not, it’s used to deflect discussion about bodily functions, but sometimes it’s about personal sexual information that I just really don’t need taking up space in my head and popping into my forebrain when we interact. There’s no judgment involved, aside from judging that it’s too distracting, too weird for me to know this or (in the case of bowel movements, etc), too nauseating for casual conversation.

    4. Anonymous*

      I don’t think this is a good idea– pretending to be joking when you’re actually serious and hoping he’ll decipher your true meaning from it is neither helpful nor professional. At best he won’t understand, and at worst it will look like you’re mocking him.

      1. jmkenrick*

        I’m with Anon – I hate it when people joking tell me something they’re serious about. It feels really rude to me. Maybe I’m oversensitive?

  2. Ryan*

    I wouldn’t care, personally…but if his yammering on about it started to irritate me I’d just say, “Dude…I don’t care…stop talking about it.” just like I would in response to ANY verbal diarrhea my co-workers might be suffering from.

  3. Realistic*

    I just want to say how much I <3 AAM for such a sensitive, empathetic, educational post about this. Alison, if this is how you handle a situation you say is out of your comfort zone, then just know that I want to be you when I grow up. Or have a BFF like you.

    1. AG*

      Agree – thank you for taking the time to educate your readers first and make sure that everyone is clear what the topic is and what the specific issue is.

      I have never worked in one of these super-casual offices but I just moved to San Francisco and a lot of the companies (particularly startups) are like this. It makes me kinda uncomfortable, because I’m used to having “work me” and “personal me.” I think a lot of people are not good at setting boundaries in these types of ambiguous cultures.

      1. jmkenrick*

        Welcome to the neighborhood. :)

        There is less formality here in general, which I think is one of our charms. However, there is definitely still some divide between “work” and “non-work” personas. Just play it safe at first.

  4. Joey*

    Is it merely because its different that you want to put a stop to it? It’s not affecting work and it sounds like some people are uncomfortable with it just because its different. My guess is that other people in the office share or do things that aren’t necessarily professional behavior, right? If that’s the case the people who have a problem with should try to avoid it by not engaging or participating in the conversations, same as they do for all other non work related chatter.

    1. Anne*

      I think the OP went out of their way to make it clear that they didn’t have a problem with their manager crossdressing, or even doing it at work. Sounded sincere to me, at least. But there are details of people’s lives which can get uncomfortable if over-shared, regardless of whether they’re unusual or not. Like – I don’t want to hear about an argument my co-worker had with her spouse. That’s perfectly normal, and it’s not an unusual thing to have a bit of a gripe about to a close co-worker, but it’s also just a touch too personal for some people.

    2. Victoria*

      Agreed. From your description of your workplace, it sounds like non-work conversations are a normal part of the day… which suggests that people are uncomfortable with the cross-dressing conversations not because they are off-topic and personal, but because they aren’t comfortable with the cross-dressing itself. That’s fine, obviously, but it makes it tough (and disingenuous) to convey the message you’re hoping for (cross-dressing is ok, just don’t talk about it).

      1. Anon*

        Just because people are able to speak about some personal matters at work doesn’t mean everything is on the table. I can talk about a date with the GF to many people with whom I wouldn’t share the possible fact that we tried butt stuff afterwards or that the meal gave me the runs. If the manager is oversharing in that he’s discussing the fit of womens’ undergarments or the ventilation of a skirt, that needs to be shut down.

    3. AdAgencyChick*

      I completely agree. I think the litmus test is: Would you want to stop this coworker if he spent that much time talking about, say, playing touch football on the weekends? If the answer is yes (say he’s spending so much time talking about it that work doesn’t get done), then I think you can say something; if not, any employee’s discomfort with exactly WHAT he is doing should be that employee’s to deal with. (It would also be different if he were going on about something that should obviously stay private, like exactly what he did in bed while wearing women’s underwear.)

      Employees who don’t want to hear about it on Facebook, shouldn’t be friends with the boss on Facebook. (In fact, I think it’s generally a bad idea to be friends with the boss on Facebook!)

      1. Not So NewReader*

        AdAgencyChick, I think you nailed this one. It is more about saturation level than anything.
        I loooove dogs. Lots of people love dogs. But if I spent my entire workday talking about dogs, how long would it be before my coworkers attempt to strangle me? Let’s say my entire work group looves dogs, they might give me three minutes more wiggle room before exclaiming “ENOUGH! Talk about something else! Focus on your job!”
        OP, I don’t think that there is anything wrong with saying that people are having difficulty in focusing on the job at hand. Happily, this coincides with the boss’ desire to just live an open/honest life. He is who he is just like the rest of us. We are who we are. His cross-dressing is a part of his life but not the sum total (or main focus). You could suggest that conversations be re-focused on the work place and go forward with living life.
        Clearly, he has a core group friends who support him and people who believe in him. Many people do not get that much- he is very fortunate.

        I think that once conversation returns to a normal variety of topics, the concerned folks will settle down.

        1. Ryan*

          exactly…I wouldn’t strangle you..I’d just say, “dude…I don’t care…stop talking about dogs already.”


      2. Ellie H.*

        I think the situation is a little different because as AAM stated, cross-dressing is often associated with sexual behavior. Apparently I’m wrong, per the comments below, but I’m having a hard time accepting that cross-dressing should default be interpreted as nonsexual. I’m 25, have always lived in very liberal climates, am an avid Dan Savage fan and very “up” on alternative culture of various kinds. I’ve known guys who wore skirts, but I wouldn’t describe their dress as “cross-dressing.” I would interpret someone who identified as a “cross-dresser” as someone who enjoys dressing as a female for the psychological enjoyment of it, not some punk guy wearing a rad skirt. I also think that the context of his having been “in the closet” about it and the fact that it occupies a lot of his mental energy, as evidenced by the fact that he is talking about it a lot, is the best signifier that it is psychologically gratifying/sexual in some way. And that this evidence of it being “a big thing” for him is a big part of what is making people uncomfortable. I think there’s a tendency to automatically get uncomfortable when someone says “I haven’t told anyone this, but . . .” even if what she subsequently reveals is very banal.

        And per the above, I think that the issue is specifically that it’s uncomfortably personal, not annoying. I think that the comparison of “argument with spouse” is a much better analogy than “talking about skiing hobby or dogs.”

        1. Natalie*

          “psychologically gratifying/sexual”

          I think these are different enough that we shouldn’t conflate them. “Psychologically gratifying” could cover tons of things that are theoretically appropriate to talk about at work – picking up a new hobby, losing 50 pounds, getting a pet, having a kid, ending a bad relationship, etc.

          1. Ellie H.*

            I agree, but I couldn’t (and still can’t) think of a better way to explain exactly what I mean. I was trying to draw a distinction between something that is basically a sex act (e.g. a foot fetishist asking to give a coworker a foot massage) and something that is more personal than the average subject of conversation, but still not quite “neutral” enough not to make people feel uncomfortable. For example, talking about being on a diet can be neutral and banal (though, I think we’d all agree that it’s not a great topic to bring up at work) or it can be very psychologically charged and bring to mind body dysmorphia or eating disorder issues, which I’d also consider too personal to bring up at work, even though there is nothing “wrong” or “creepy” about being a person with that kind of issue. Also, sorry for the comparison of cross-dressing to a psychological pathology but I can’t think of a better analogy at the moment. This is just my perspective and I recognize that it might not be the best way of looking at the situation.

        2. Emily*

          Eddie Izzard is a good example of a non-sexualized cross-dresser. In his show Dress to Kill he does some great jokes about being an “executive transvestite” – i.e. not the weird J. Edgar Hoover kind.

      3. Louis*

        “From your description of your workplace, it sounds like non-work conversations are a normal part of the day… which suggests that people are uncomfortable with the cross-dressing conversations not because they are off-topic and personal, but because they aren’t comfortable with the cross-dressing itself.”

        Well there are categories of personnal stuff are less appropriate to office sharing.

        You like golf… ok great
        You like the work of porn actress XYZ… not so great.

        Crossdressing is somewhere in between those two but for a lot of people, it can at least be mildly associated with sexual content so it not the most work friendly topic of conversation.

        1. Nichole*

          I agree. There’s a big difference between him saying he got a steal on a pair of patent yellow pumps and discussing how those pumps played into his intimate activities with his wife last night. I’m very pro the casual “TMI, dude” when that line is crossed provided it would be taken in the spirit in which it’s given. Since the OP says he’s a decent guy, I think it would be ok. I believe the OP that the crossdressing itself isn’t the issue from the tone of the letter (which is super cool, props to the OP’s workplace culture), so I’m assuming that it’s just the over the line comments that would be mentioned, not everyday references to women’s clothing. He’s probably just feeling out his boundaries, and speaking up in a casual way would be helping him out.

        2. Hari*

          It all just depends on what kind of conversations are normal for that particular office. If everyone always discussed openly their sexual history or hookups then talking about porn isn’t going to ruffle any feathers, or it shouldn’t. What AdAgencyChick is getting at is if everyone was comfortable talking about sex, particularly in this situation straight sex, then someone who is gay should be able to talk about gay sex.

          1. Ask a Manager* Post author

            In theory, yes. In practice, no one at work should be talking about sex of any sort, because they can’t know for sure that it’s not making someone uncomfortable, and it’s a good way to set your workplace up for a sexual harassment / hostile workplace lawsuit.

            1. Hari*

              Oh totally in theory lol. I while I wouldn’t mind if a co-worker I’m close to told me they hooked up with a cute guy/girl over the weekend. Sharing details of sex would be wayyyyy to personal and dangerous legal wise for most people and offices besides the adult entertainment industry.

    4. Ivy*

      Agreed. While AAM’s suggestion would work in a setting where people maintained personal boundaries, OP has said that that is not the case. People discuss their personal lives regularly. So, how can OP tell her manager that he’s giving TMI when everyone regularly does (I’m assuming they share things like spousal arguments from what I can tell Anne). While OP and her coworkers are saying they don’t have a problem with his crossdressing, they do. If you’re fine with Jane telling you she wore a lovely dress to x event, then why is it TMI for Bob to tell you the same.
      OP, if you worked in an environment where there are strict professional and personal boundaries, then take AAM’s advice. However, since you don’t. I think the onus is on you and your uncomfortable coworkers to get over it.

      1. Ivy*

        Also wanted to add. OP, I really don’t think there’s any way you can tell him not to talk about his cross-dressing without coming across as disapproving. Your pretty much saying, “Bob, we’re an open environment where people can talk about anything. But, since the something you want to talk about is cross-dressing, well, that’s not ok.” Whether you mean it to sound like that or not, it will sound like it to Bob. It can be tough to come out, especially at work. Be supportive.

        1. Zed*

          I agree, Ivy. Coming out as a cross-dresser, even (or ESPECIALLY ) if you’re straight is no doubt an incredibly difficult thing. And he has recently come out on Facebook and at work, in his personal and professional lives. Cut him some slack, OP. After all, if a gay man or woman came out at work, it wouldn’t be so weird for them to chatter about their partner for a while. I’d imagine that talking about previously verboten topics at work is new, strange, and freeing.

          1. twentymilehike*

            I’d imagine that talking about previously verboten topics at work is new, strange, and freeing.

            Agreed. I was curious how long it has been? It it was fairly recently, I would probably give it some time and the hype will die down, as with anything. I’m sure my coworkers were all rolling their eyes at me everytime I said, “husband” after I got married. I was practically rolling them at myself because it was just so exciting and new that I couldn’t stop saying the word “husband.”

        2. Anon*

          On the other hand, there are setting at which I can talk about dinner but not the furious dysentery it gave me. Similarly, it sounds like the manager is, rather than talking about a dress, talking about the fine breeze said dress supplies to his nether regions.

  5. Mike C.*

    Yeah, I’m not seeing much of a difference between this or having to hear about the intricacies of Formula 1 or fountain pens.

    1. Eric*

      You mean when everyone left the lunch room when I started on about fountain pens, it wasn’t because they were all running out to the store to buy some?

    2. Ask a Manager* Post author

      I think the difference is that, at least for many crossdressers (and I believe the majority, although I don’t know that for sure), it’s a sexual kink. If that’s the case here, it would be like discussing any other part of your sex life at work. I don’t care what you do for sexual thrills, but it’s not appropriate to talk about it at work.

      1. EJ*


        Discussion of crossdressing would make people uncomfortable because if this is not someone who is transgender, it may well be related to sexual habits. And that does not belong in the workplace.

        In fact if argue that if I liked…oh I don’t know…being handcuffed or tied up in a ‘non-sexual’ way, it still borders too closely on what most people see as sexual kink that it also should stay out of the workplace. I think this might be one of those times.

        1. EJ*

          Sorry…it may well be “perceived to be” related to sexual habits. Nobody but the manager knows for sure.

      2. Anonymous*

        I kinda think we don’t have enough information here to tell – whether this is part of a gender identity or sexual kink, and the discussion really hinges on that difference. I will say I didn’t get any impression from the OP that this was a sexual kink thing at all – for me, it more brings up drag queens/performance. If it *is* a sexual thing, then I think it’s totally fair to say, “Can we not talk about sex at work? please?”, which doesn’t even require referencing crossdressing specifically. However, because I don’t get the impression it is a sexual thing, I agree with those who think employees who are uncomfortable with the topic need to figure out how to deal with that. (Assuming, as others mentioned, that it’s not such extensive discussion that it’s interfering with work.)

        1. Hari*

          +1. I didn’t get the feeling that this was a sexual kink at all but more of a lifestyle choice that this man would like to wear ladies clothes to work.

      3. Joey*

        So are you saying it would only be okay for him to talk about it or cross dress at work if an only if he first volunteers its not sexual? You’re trying not to make it sexual, but you’re doing exactly that.

        1. Ask a Manager* Post author

          Honestly, I have no idea how to resolve that part of it. I can’t think of any other kink that raises this problem — where it might be sexual or it might be gender-identity-related. My understanding (which might be incorrect) is that it’s far more common for it to be sexual kink than for it to be gender identity, so I don’t think it’s unreasonable for coworkers to assume that, and I don’t think it’s unreasonable to expect him to set the record straight if it’s not that. And I think it’s reasonable for coworkers to be a little uncomfortable with the discussion while that element is unclear. I really wouldn’t want to have to wonder if my coworker’s talk about topic X is about his sex life or not. (And yes, one response to that is to assume it’s not, but again, I think the statistics here say that it’s more likely that it is. But this is where we get into me not feeling confident about my answer.)

          1. Joey*

            Isn’t it unfair to assume its sexual? For all we know its the guy who’s wearing women’s clothing to support his 6year old son who likes to wear dresses.

            1. Ask a Manager* Post author

              But since he’s talking about it at work so much, why wouldn’t he mention that part of it too, if that were the case? It seems unlikely that he’d be spending this much time talking about it at work without mentioning that he was doing it to support his son, if in fact that were the situation.

              1. Joey*

                I’m sure you can agree that its really no ones business to know if he doesn’t want them to know. If he volunteers it great, but if not I think you have to give him the benefit of the doubt until he says otherwise.

                1. Anonymous*

                  Agreed this is not his co-workers’ business – the problem is this guy thinks it IS because he is talking to them about it.

          2. Anonymous*

            I really have to disagree with you on this one — I don’t think it’s fair to assume that it’s a sexual kink, and why would he have to set the record straight if none of the conversations he has been having with his coworkers are sex related? (That would clearly be inappropriate, regardless of the crossdressing issue).

            Imagine if a guy who “acts gay” was asked to set the record straight on that — that would be discriminatory. I’m failing to see how your viewpoint on this is different.

            1. Ask a Manager* Post author

              Because my understanding is that it most often is a sexual kink — unlike being gay. If I’m wrong about that, then I’d absolutely revise my answer.

              Either way, it’s really encouraging to see that the majority of comments on this are so open-minded/accepting. (And I’m open to the possibility that I’m the one who’s behind the curve on this.)

              1. Anonymous*

                I really appreciate your responding to this question publicly and allowing the peanut gallery to chime in. But I have to push back on your assumption of crossdressing as a sexual kink – I have never heard that substantiated. And even if somehow that were true for most crossdressers (that it is a sexual kink), if he doesn’t talk about sex, does it really matter? I mean is the concern that he is somehow getting off on dressing like a woman at work and looking like it? I think the OP would have spelled that out clearly if that were the case.

                It could very well be that he likes to dress as a woman while having sex. But some people like dressing as a office secretary while having sex – as long as it’s not discussed at work, I don’t see where we can draw the line.

                1. Ask a Manager* Post author

                  It strikes me as similar as talking about any other fetish at work even if you don’t explicitly talk about sex — for instance, if he were talking about enjoying handcuffs or latex or something.

                  But again, my answer here is based on the understanding (perhaps wrong) that most of the time, this is a fetish, not an identity thing. That understanding is courtesy of Dan Savage, who I typically trust on such matters, but it may be wrong.

                2. Marie*

                  Replying to Alison re: Dan Savage

                  I don’t know much about crossdressing and how that operates for people who do it, so I don’t have much to say of substance on that. But, as for Dan Savage, two things:

                  It’s worth noting that the people who are writing into Dan Savage are specifically writing to him to talk about sex, so that’s a pretty self-selected sample of crossdressers. That is, the crossdressers who don’t consider it sexual aren’t sending letters to his column.

                  Secondly, Dan Savage has a TERRIBLE reputation among the trans* community. He’s pretty well reviled by trans* activists and allies for his frequent use of slurs and engaging in transphobic, ignorant commentary. He’s definitely not a go-to source for understanding anything about trans* folk, culture, lives, sexualities, etc.

                3. Ask a Manager* Post author

                  Marie, thanks for noting that. I didn’t realize that, and I guess it’s a good illustration that just because someone is insightful and open-minded about A, B, and C, it doesn’t mean that they are about D as well.

                4. Ellie H.*

                  I agree that Marie’s point is a good one . . . reporting bias!

                  I do agree with AAM though. Above I said that I’ve known a couple guys who wore skirts on occasion but that I would never ever think to describe as cross-dressers. And I just remembered this – I actually did work with a guy who was a cross-dresser once, and he would cross-dress at work (lipstick, heels etc.) and would also talk at about going to cross-dressing events, about him and his wife dressing up together on weekends, etc. Him I would describe as a cross-dresser because it was clear from his manner and comments that he got psychological enjoyment out of his manner of dress, it wasn’t just something he happened to be wearing (the previous guys I’d known who wore skirts on occasion were more along the lines of “Hey man, Balinese men wear skirts, we don’t need to adhere to Western customs, far out!”). And honestly, it made me uncomfortable because witnessing this manner of dress made me feel like I was being made a participant in his sex life, albeit to a very minor degree. I also could tell that it made some customers uncomfortable on occasion (he would mention it to them sometimes; he was a big over-sharer and over-converser about other things too). I’m not saying it was right or fair that I felt this way, but it is how I felt. However, his manner of dress was acceptable to the workplace, nobody ever made negative comments about it, and I’m totally down with all of this as being part of nondiscrimination.

              2. Anonymous*

                My understanding is that cross dressing is more about personality than sexuality. Without any additional contextual information, it seems premature, presumptuous & probably inappropriate for any of us to assume any sort of component relating to this person’s sex life.

              3. Brightwanderer*

                Honestly, I do think you’re wrong here. I can’t point you to a web page or resource that definitively lays out the one true definition or anything, but my own experience is that there’s a difference between “dressing up for kink” and “cross-dressing”, and that the latter is devoid of sexual kink – though its adherents may also enjoy the former!

                If this guy is saying “Man, I had so much fun the other night when I dressed up as a sexy nurse for my girlfriend” – sure, kink, inappropriate. If it’s just “Man, I had so much fun the other night when I wore this awesome gown to a party”… I don’t see how that’s different to a similar comment from a woman.

              4. Hari*

                I live in a really open and very liberal city so I know that crossdressing can be a part of an identity not just a sexual kink. However, I can totally see why anyone who didn’t live in such a place that didn’t have a great variety of all types of orientations (yes people have defined quite a few these days not just gay/straight/bi) that they would think of it as a kink. I think patriarchal society has played a big part in its misconception too. Men would be looked down upon as “weak” if they identified with crossing dressing as a norm for themselves. However, having it be a sexual kink, would be more acceptable because many people have a “behind close doors, anything goes” view on sex. So many men who would consider it enjoyable separate from sex would be likely to justify it sexually so they would not be looked down on.

                1. OP*

                  You are correct in this case. From what I gather, he denied this part of himself due to societal censure growing up. When he became an adult, he found outlets for it that were of a sexual nature (dressing up for role play, etc) and relegated it to just a kink of his. The last few years he’s been doing a lot of soul-searching and personal growth and realized that it is more than a kink, that it is truly a part of his personality. To my knowledge, he does not feel like he is transgendered.

                  We also live in the midwest US, if that helps for geographical context.

                2. Ask a Manager* Post author

                  The fact that you know about his “outlets of a sexual nature” indicates that he’s crossing boundaries of what’s appropriate to share at work.

                3. OP*

                  @ Alison – Sorry, to clarify, I’ve known about his crossdressing/role play stuff for years as I am personal friends with him. To my knowledge, he is not talking about that and I know he did not talk about that with our other coworker.

          3. Anne*

            Following on from chat on previous post, I’d be interested to hear where you put polyamory on that spectrum. ;)

            I default to “no information about this at work ever”. But it’s not swinging. It’s not more sexual than dating normally is. My relationships are just as long and involved as other people’s – I’ve been with the same people for years. There just happen to be three of them. It makes me bitter to think that my co-workers are happy to hear about my plans with my fiance, but not about the other people I love and have actually been with longer.

            1. Elizabeth*

              My own personal opinion is that I’d be comfortable with you talking about any of your relationships in a professional way. I know not everyone feels that way, but I think it’s totally appropriate to talk about more than one partner in the same work-appropriate way that you talk about just one. Over-sharing would be over-sharing whether the speaker is detailing adventures in swinging, or her sex life with her husband of ten years – and, conversely, appropriate relationship talk is appropriate no matter who the speaker’s partner(s) are.

              That said, I think that unfortunately you might be wise to be secretive about this at work. You have a better read on your own coworkers than anyone here will, and some people would be upset enough by your being open that it would make your life harder at work. :-(

              1. Anne*

                Thank you for this. It’s reassuring to know that some people would be okay with it, at least.

                I actually think that most of my co-workers would be okay with it, too – we’re a very young tech company for the most part. I just worry about my managers thinking I’m a horribly immoral person, or more likely that I’m a young immature party-girl. What can you do.

                Maybe I’ll “come out” when I’m in middle aged, with kids and my own management job. ;)

            2. Joey*

              I was hard pressed to find one, but this is a good parallel to cross dressing- out of the norm and typically associated with sexual activity. Given the same type of culture I wouldn’t see anything wrong with discussing this either. Although just like cross dressing its hard to control other people’s perceptions.

          4. Ivy*

            I actually do think it’s unreasonable for coworkers to assume that. I think it comes from a place of ignorance, which in my opinion, is unfair and not right. Many, if not most, cross dressers do not cross-dress for sexual reasons. It would be weird for him to assume others thought of it that way. When someone has told me he cross-dresses, or I have met a cross-dresser, I have NEVER assumed they did it for sexual reasons. I think it would be more unprofessional for OP’s coworker to mention it’s not sexual. He would first have to assume his coworkers are thinking about it in a sexual manner, which probably hasn’t even crossed his mind. It would as unprofessional as me saying “he stood erect… oh I totally don’t mean that in a sexual way”.

            1. Ask a Manager* Post author

              Do you actually know for sure that that’s the case about the majority? What I’ve read on it (which is mainly limited to Dan Savage) and when I’ve talked to people in real life, the opposite has seemed to be true. Is there actually research on this that would say conclusively which is the case?

              1. fposte*

                Even if it is, is that a useful direction to go? We don’t ban shoe fetishists from talking about shoe shopping. Again, it’s hard to say without knowing what the guy is saying and how he says it, but my inclination is that if the conversation isn’t sounding sexually charged or focused that you take it at face value as nonsexual.

              2. Ivy*

                I have no idea. I’m talking from personal experience, which is obviously different from the experience you have had. To be honest, I think it doesn’t matter. I think it would still weird for someone to assume the other is doing it for sexual reasons. It should be assumed that it’s not sexual unless otherwise explicitly said. Not the other way around. (Where your suggesting people will assume its sexual until the coworker clears the air). While I can appreciate that what SHOULD be thought and what IS thought are two different things, I still think it would be wrong for the coworker to say say, “oh its not sexual”. Because to me that is bringing attention to the fact that it COULD be sexual, which isn’t wrong, but which is unprofessional. Long story short, I don’t think the coworker is unprofessional or handling things poorly by not explicitly saying his activities are not sexual.

                1. K*

                  I could also be non-sexual but something that also figures into his sex-life (much like mentioning your SO, really). In which case it’s not accurate to say it’s non-sexual, per se, but that doesn’t mean it’s not an important part of his identity that’s reasonable to talk about at work.

                2. fposte*

                  Agreeing with you, Ivy; also, as a manager, I don’t want the precedent set of my being the kink police. There are a lot of noises people make about desserts that I’d feel obliged to investigate.

                3. Ariancita*

                  Ivy, I don’t have a ton of knowledge on this, but the few men I knew who cross dressed (both straight and gay) didn’t do it for a kink. It was not sexual. One guy had a full beard and wore a deep cut gown with a hairy chest. From what I gathered, it wasn’t even about it being particularly feminizing (though in theory it could still be feminizing and still not sexual).

              3. Clare CD*

                The description that OP gave that his crossdressing started out as sexual and became non-sexual is pretty typical. But what isn’t sexual to an adolesent boy when these feelings first express themselves, and then because of cultural norms the crossdressing is kept private and cannot be fully explored in a non-sexual way. This guy is well past his crossdressing being sexual, much like attraction to the opposite sex for an adolesent changes from being sexually dominated as an adolesent to being more refined as an adult. You cannot say that it is sexual or that it isn’t, being gay is sexual and it isn’t, being married is sexual and it isn’t, being polyogamous is sexual and it isn’t, people are uncomfortable because they are not used to the idea. The poor guy would just like someone to engage him on the subject, him might even be feeling people out to see where they stand with him, his whole life has just changed, cut him a bit of slack. He might just even want to find a girl to talk fashion with. Do I need to say again that the issue here isn’t sexual.

          5. Not So NewReader*

            Just from a hypothetical standpoint: He cannot say it is a kink of his. He can only say if it is a gender identity thing.

            If he states that it is a kink of his – that goes into inappropriate stuff in the work place.

            The next step in logic- is he violating work place policies in words or actions?
            That depends on the work place- where the management draws the line.

            I have worked for some places where the talk was rank. I mean NO topic was forbidden. Every thing was just discussed in color. Just thinking about this makes me want to run and hide.
            My point is context. From what I have seen of these types of environments it becomes a case of who can be the most “candid”.

          6. Jack*

            On the other hand, there are plenty of shoe/foot fetishists out there, but nobody looks at you sideways if you talk about your amazing new shoes at work. If somebody assumed you were talking about your shoes because you’re sexually excited by shoes, you’d think that said more about them than it did about you, wouldn’t you?

        2. Anonymous*

          It doesn’t have to be sexual to be too personal for work. Talking about what kind of underwear you wear is unprofessional and inappropriate- even though it’s probably not sexual. Similarly, I don’t go around telling my colleagues I sit around naked in my apartment sometimes. Again, not sexual, but weird to share.

          1. Anonymous*

            Good point. Anything that draws up an image that’s not workplace appropriate should probably be kept mum, whether that’s sexual imagery, toilet talk, or the vision of you accidentally spattering your junk with pancake batter during a non-sexual naked breakfast.

      4. Brook*

        I don’t know, I’d be given to assume that because he’s bringing it up at work, this is about him exploring his gender identity and considering changing how he presents himself. And therefore not something I want to address at all- save to maybe redirect his enthusiasm towards a more understanding avenue (there are groups to support those who are discovering their cis identity, finding the name of a couple and asking him if he has good support for this time wouldn’t be out of line.)

        Basically, I’d assume that this is about identity, not kink, because everyone knows not to bring up their proclivities at work, right? And if it is about identity, the talk will die down as he becomes more sure of what he wants and finds more appropriate avenues of expression. This might be a temporary burst of enthusiasm that will resolve itself with no intervention at all.

        1. Not So NewReader*

          Well said Brook. I tend to agree that in this case it is probably not a kink. This is probably someone looking for their identity. Other people have mentioned there are support groups that help that process along. Generally speaking, the average coworker is not qualified to make a meaningful contribution to that process. At some point, the boss will have to figure that out.

          Using another example: Suppose a coworker loses a spouse or a child. Not everyone in the work group is going to be able to deal with that topic. Coworkers were never intended to be support groups for everything in life. It is asking too much of them.

      5. Mike C.*

        My understanding is that they simply enjoy wearing those clothes because they feel more comfortable doing so. If kink is being discussed at work then that’s an issue, but a guy simply wanting to put on a skirt doesn’t mean it’s for sexual reasons.

      6. Lisa*

        Cross-dressing is also the first step toward gender reassignment. But I think it would be better to address this person as transgender rather than a cross dresser. Sorry AAM, but you are assuming its a sexual thing when it may be a man that identifies as a woman and therefore is transgender. wearing clothes of the gender they identify with is the first step, and it is not sexual in nature.

        1. KayDay*

          But there are people who are not transgender but do wear the opposite gender’s clothing–for example, a family member once worked with a man who liked to wear dresses, but he completely identified as male, beyond the dress. (and even had a beard! that turned heads.) I’m not sure if the manager himself used the word “cross-dressing” but term (in my experience) had tended to mean the above; most transgendered people say “trans” not “cross-dresser”.

          And while this would fall in the category of transgender (I think–I just read femisting sometimes, I’m not an expert), there are also people who don’t identify with either gender, so they might wear styles typically associated with both men and women. But they wouldn’t necessarily be seeking gender reassignment.

          1. Lisa*

            I get that, I am just worried that the OP is seeing the manager as a cross dresser, when he may really be transgender which can be demeaning to a transgender person since it really is about identity and not the clothes.

            1. fposte*

              Though if the manager hasn’t categorized his own dress, he doesn’t really get to feel demeaned if people put a reasonable interpretation on it.

              1. Marie*

                Addressing individuals however they prefer is key here, I think. If the manager says he’s a cross-dresser, it’s appropriate to refer to him as such.

      7. Anonymous*

        Assuming this is not an issue of gender identity, but a kink, it has no more place being discussed at work than any other kink does (which is to say: NONE).

        At this point, we don’t have enough info to know but if it is a gender identity issue and the person is planning to start coming in to work dressed as a women, than he’s likely trying to get people comfortable with the idea.

        I’d say someone needs to ask him (radical notion!) When he brings it up again, since he’s obviously open to talking about it, just ask him if this cross-dressing is something that he plans to integrate into his daily life.

      8. Anonymous*

        It’s not for a HUGE portion of them, though. It’s just for fun because costumes and makeup are fun and it’s a challenge. It’s not a kink for anyone I know who does it, in fact. People absolutely ASSOCIATE it with that, but I think that’s an unfair assumption to apply to everyone and just blanket it as inappropriate in all situations.

    3. Esra*

      Pretty much. I’m not totally reading what the overshare is. That he’s talking about it period? Or some specific details?

      1. fposte*

        Yeah, I’m fuzzy on 1) what he’s saying and 2) where he’s saying it–is it only on Facebook? If it’s “God, I love Banana Republic wrap dresses,” then I don’t see that as a problem either place, given the stated informality of the workplace. If it’s descriptions of sexual arousal, then somebody could explain status settings to him (and maybe use it as a metaphor for work conversations as well). If it’s described in nonsexual terms, he’s just boring about something, and if it’s not described sexually, I would default to the nonsexual assumption.

  6. Rachael*

    But aren’t the clothes we wear a direct expression of who we are? Why should someone be shamed for wearing clothes that they feel comfortable in – even if it has nothing to do with their sexuality? I don’t understand. Cross-dressing is often misinterpreted as being related to sexual thrills. More often than not – it’s not at all. If women can dress as boyish as they want, why cannot a men dress in clothes he feels comfortable and confident in?

    1. EJ*

      I took from the OP that he was talking about habits at home, not actually cross dressing at work. Agreed that if its a gender identity thing, it needs to be accepted. But it sounds like that’s not quite clear.

    2. Anonymous*

      I completely agree– especially since with men, the line for what they can and cannot do stylistically is so firm. I can wear pants and a men’s shirt and no makeup and be normal, but a guy with a blowout and makeup is suddenly some kind of kinky weirdo doing it for sexual thrills.

  7. Samantha Jane Bolin*

    It seems to be that if his conversations are going to be limited to discussing things that people are completely comfortable with, then that needs to be the case for everyone. Otherwise, he’s likely going to feel like he’s the only person to whom certain rules apply and it sounds like that’s the case. I’m not sure what the answer is other than to either set up some ground rules that apply to everyone or leave as is.

  8. Allison*

    The fact is, as Western society becomes more and more accepting of different sexualities and gender identities, workplaces are going to need to adapt and becoming more accepting of crossdressing at work. People who don’t like it are, eventually, going to have to deal with the reality that some men prefer to wear women’s clothing, just like some women prefer pantsuits to dresses and pencil skirts. As long as it’s professional, neat, and clean, there shouldn’t be a problem.

    That said, people should, in general, keep ultra-personal details private and use discretion in what they reveal to co-workers to avoid discomfort. Religion and politics are usually off limits for this reason, as are things like sex lives and certain medical conditions.

  9. Juni*

    “Jim, it seems like you make this out to be a bigger deal than everyone else thinks it is. Is there something else we need to know about your life that affects you here at work? Because if all there is to know is that you like to cross-dress, that’s old news.”

  10. Long Time Admin*

    I think we’re forgetting that this guy is the OP’s manager, which adds another layer of discomfort in addressing the issue.

    After reading all the comments so far, I have to agree with the first poster who suggested the OP simply say “TMI, dude!”, and stop there. Best if there aren’t other people around at the time, but if it needs to be done, do it.

  11. BCW*

    Sorry if this double posts. But I think we don’t have enough to really judge this situation. For all we know, he is just talking about how he dresses while not at work. Its similar to if a girl discusses a great bikini she bought to wear on vacation and how cute she looked. Its not necessarily sexual, but it kind of a sexualized thing. If people are that uncomfortable to him discussing what he wears outside of work, they need to get over it.

    1. V*


      I think we need more context about what he saying before we can give good advice. One thing to consider is if the comments would make people uncomfortable if they were coming from someone else. For example, I’d be uncomfortable hearing about a new bra purchase, regardless of whether it was the cross-dressing manager, an attractive young female intern, a matronly CEO or a middle-aged male CFO buying it for his wife. I shouldn’t see bras at work (even if they are there), so I don’t want to hear about them at work. But discusion of a new skirt suit purchase – that doesn’t raise any eyebrows if it’s coming from the intern, CEO or the CFO, so I think it is also acceptable coming from the cross-dressing manager. In other words, I would try to seperate the comments that are making people uncomfortable from the context of cross-dressing to determine if they really are inappropriate for work before talking to the manager about them.

      1. Laura*

        This. There’s a HUGE difference in appropriateness between, “I just bought the cutest red dress!” and “I just bought the cutest red panties!”…for *everyone*. I read the letter as that the manager is so excited to be “out” with his cross-dressing that he’s sharing details about said cross-dressing that are inappropriate, not as much that people were upset about the general conversations about cross-dressing.

        Also (after another re-read) that he’s having some of these conversations with people that he doesn’t normally interact with on quite so personal a level, and those people are uncomfortable. I think it’s a question of appropriateness to the relationship…if it’s not someone you regularly chat with, it’s just as weird to be chatting about your cross-dressing hobby as it would be to suddenly start telling them all about the date you went on last night. It’s not weird in and of itself, but it’s weird and probably uncomfortable in the context of the established relationship.

        1. Mints*

          I agree with this whole thread.
          If it’s normal for women to gush about cool things they were wearing, then it’s okay for the cross-dresser to do the same. If the specific audience usually isn’t that close (“Why are you telling me about your skirt? I don’t remember if you’re Kristen or Christy”) then it’s a bit weird.
          Also, like people said up-thread, it may be just excitement about outing himself. When everyone knows, he may stop telling everyone.

  12. Anon*

    If you are going to say this guy is giving TMI, then you have to shut down other overly-personal conversations that are happening as well. You can’t let one coworker talk about his sex life, then tell another that cross-dressing makes you uncomfortable.

  13. Zed*

    From what little information we have, it seems clear to me that there is a progression here – “outing” oneself on Facebook and then at work – that parallels the way that people, say, make their sexual orientation public knowledge. To me that suggests that the manager feels that his cross-dressing is closely tied to his identity… and I wouldn’t be surprised if this were the way that he was “feeling out” people in his personal life in preparation for being more open about some facet of his gender identity (not necessarily that he is transgender, either – he could be genderqueer, he could be questioning, he could be a drag queen, or he could just be a man who likes to wear women clothes).

    Unless he is implying connections between his cross-dressing and his sex life, I don’t think there is any reason to assume a sexual dimension. The implication that talking about non-traditional gender performance is talking about sex is just as problematic as implying that talking about sexual orientations other than homosexuality is talking about sex. Too many people say things like, “I don’t care what gay people do in the privacy of their own homes, but why do they have to talk about it/have parades about it/hold hands in public/have photos of their same-sex partners at their desks?”

  14. Anonymous*

    I wouldn’t want to listen to any of my coworkers talk about how they dress. I’m the type who leaves my personal life completely out of my work life, so I definitely wouldn’t sit at the water cooler and listen to this guy talk about his dresses, just as I wouldn’t want to sit at the water cooler listening to a recent grad talking about her dresses. I basically tune out everyone who likes to over share, so I’d do the same to this person.

    1. Anon2*

      Yes, this is what happens when lines are blurred. If the office just remained professional in the first place, this wouldn’t be a problem, but there is no going back now, I assume.

    2. Katie*

      How you dress is hardly personal. It’s actually a really public thing (cuz, you know, folks can see it). Just because you don’t like talking about clothing doesn’t make it a standard workplace norm.

  15. KayDay*

    Given that this guy is the OP’s manager, I don’t really think it’s the OP’s place to correct his work place behavior, especially when the culture of this workplace is such that people normally talk about personal matters.

    If the guy keeps going on (and on and on) to the point that the OP & co. wants to strangle him with a pair of fishnet stockings, I think a simple “TMI!” or “yes, I know, you said that already,” is enough. If his personality is such that you think he needs a more long form response, Jumi’s suggestion is very good.

  16. Anonymous*

    The cross-dresser has committed the breach of etiquette here, not his co-workers. He should not feel offended to learn that this kind of sensitive topic might not be something his co-workers want to hear about. If it were any other topic, like the boss’s prostate problems or the secretary’s restraining order against her stalker ex, this would not even be a question.

    The best the OP can do is use body language or the “TMI” approach to show the coworker that he is oversharing, or say directly that it’s not an appropriate topic for work. Because it’s not. No need to pussy-foot around it!

    1. Anonymous*

      I think some of us here may be confusing a topic many of us know very little about with a sensitive topic. So far any sensitivity, sexual aspect, etc. is all in the eye of the beholder.

      1. Anonymous*

        I think any topic like this is “sensitive” in terms of being something that most people feel uncomfortable with in the workplace.

        1. Anonymous*

          And I think some people are assuming, and sometimes outright stating, that because it makes them uncomfortable as individuals that automatically means the topic itself is inherently sensitive and therefore automatically inappropriate.

          It is really important to be careful about our assumptions and possible misunderstandings about topics like this. So in that sense, yes, I agree it is a sensitive topic. But I also get the sense that framing it as a sensitive topic can also be code for some people for “well, I don’t really know much about this and I think maybe it might be sexual so that means this guy is being really inappropriate”.

          1. Ask a Manager* Post author

            Totally agree with this point — just because something makes you uncomfortable doesn’t automatically mean it’s inappropriate for the workplace. After all, some people are uncomfortable hearing that someone is gay, or an atheist, or vegan, or Muslim, or all kinds of other things. Their discomfort doesn’t automatically mean the other person has an obligation to silence themselves.

            My struggle with this question has been whether crossdressing falls in a category like that or not. Certainly for some people it does (if it’s part of gender identity), for others it doesn’t (if it’s nothing more than sexual kink), and then there’s probably a whole grey area for others. That’s why I find it difficult to sort through, and I’m still not certain where I fall … but I’m surprised/impressed by how open-minded so many commenters here are. I wouldn’t have predicted that (not because of this group specifically, but because of people in general, myself included to some degree).

            1. OP*

              That’s why I wrote in actually. I wish I had phrased my original question better. If the manager was coming to work in women’s clothes, I would consider it a non-issue. For me, actually crossdressing at work would be analogous to protected statuses like age, sex and nationality even though it isn’t actually a protected status. However, since he is so far just talking about crossdressing, it has more of the feel of sharing something personal at work that is maybe better left to coversations happening in your personal life. But, since we so often share our personal lives, this is where I’m struggling. As other pointed out above, I hadn’t realized that if so many other topics are fair game, is it really that he’s oversharing or that people are simply more uncomfortable with the specific topic of crossdressing.

              Also, I just want to point out that while it seems like the old cliche “I have a friend who …”, I really do have a friend who’s uncomfortable – I am not personally uncomfortable talking with the manager about his crossdressing at work. In fact, I am someone who has few natural filters and struggles to make sure I also don’t TMI my coworkers too much. I have worked here long enough, that reading this blog has been a nice wakeup call for me about keeping things more professional at work.

  17. Erica*

    What I’m a little confused about (and maybe makes me even a little sensitive) is — what exactly IS he oversharing? I mean, how much can you say about wearing skirts? Is he just talking about clothing too much? Or about his newfound freedom in loving skirts? Is it sexual?

    My fear is that the OP actually IS freaked out by the cross-dressing, and is labeling it as oversharing; the same way people who say they are fine with people being gay, as long as it’s not “in their face.”

    Granted – this is me being totally uncharitable to the OP, and for that I’m sorry. I’d just love a bigger picture.

    1. Esra*

      That’s what I’m not getting. If it’s just too much clothes talk, then I would lump him with my coworkers who talk about their love of Taylor Swift or foreign cars etc. I feel like if you really aren’t uncomfortable with the cross-dressing, then it would be like those other topics you may find boring but other people love to go on and on about. You just try to change the subject or throw on your headphones or occasionally grin and bear it.

    2. Liz T*

      I had the same thoughts. I don’t think we need to worry about criticizing the OP, though–this is a very new situation for hir, and it’s understandable that ze might not react with perfect comprehension of the topic.

      We do need to hear from the OP about what the “overshading” entails. If it’s not sexual per se, two things will probably happen:

      1) The manager will start to talk about it less. His outness is brand new, and he’s very excited, but once it’s just a fact of life you’ll hear less about it.
      2) The uncomfortable people will get used to it, and all will be well.

      If he’s not saying anything more ovely sexual than what people already discuss in the office, this is something the OP can just leave alone.

      1. Mints*

        I agree with you and am so excited I saw hir & ze on this blog.
        Seriously, I’ve only ever seen it on liberal / feminist / whatever blogs.
        AAM and commenters are so great!

        1. Liz T*

          I REALLY wish gender-neutral pronouns would catch on–not just cuz I’m a queer ally, but also because I’m a grammar snob.

  18. Yuu*

    I actually would be more likely to communicate with my silence on this one. Just refrain from contributing to the conversation, zone out, or change the subject when it comes up and let things die down naturally. You don’t want to hurt the manager’s feelings – well, this is a personal issue for him, and he’s worried people will judge him negatively for it. So if you don’t judge him negatively for it, then just let the topic die down naturally. Everyone has different ideas of going over the line, and if that line is blurry in your workplace, I am sure there were times you over stepped it to other people to.

    I also agree with Ryan. Maybe I’d phrase it more like, “I don’t understand why we keep talking about this – it’s really not that big of a deal,” if people push you to talk about it directly.

  19. fposte*

    I think one of the things we’re talking about here is how something key to your identity can be both sexual and nonsexual, and how the social tendency is moving from “if there’s a sexual component, shut up about all of it” to “as long as you’re not talking about the sexual aspect, it’s not fair to silence it.”

    1. Ask a Manager* Post author

      Is that really true though? I mean, if someone were into bondage in his sex life, would it really be okay for him to talk about bondage gear at work as long as he didn’t make it explicitly sexual? I think we’d all say no.

      I do agree that what you’re saying applies when it comes to sexual orientation, of course.

      1. fposte*

        I was thinking about that. I think BDSM stuff is going to be the last preserve because so many people have problems with its echoes and because it’s such a culturally loaded symbol–handcuffs are functionally pretty vanilla nowadays, for instance, but they still carry a meaning that’s different from Victoria’s Secret lingerie. (I also think that non-sexual dom/sub relationship aspects get into the emotional TMI area anyway, so even if somebody wants to tell me how their submitting to their partner’s will isn’t sexual, I still think it’s tedious.)

        But I think there aren’t bright lines here, and the sexual orientation shift has done valuable work across the board in making people consider that people’s differing identities, even if they involve aspects of their sex life, are okay to be open about. And since we no longer have so many things we automatically know we’re *supposed* to be not okay with, we’re falling back on figuring out whether things actually impact us. Which is no bad thing.

        1. Anon*

          This is a little like talking about 50 Shades of Grey at the office. I don’t particularly care if you read it, I don’t mind a bit of discussion of its literary merits or otherwise, or possibly about the characterisation – but I really don’t want to hear about the ideas it gave you or how it compares to your own sex life. I also don’t think the office is really the right forum for your opinions on and/or experience of D/s relationships. After a few drinks on a work night out, perhaps, but that’s a different context.

          It’s hard to define where the line falls, and it probably lies in a slightly different place for each person and group of people.

          1. K*

            Oh, 50 Shades of Grey has been responsible for more than one awkward conversation at the workplace. “So what’s that 50 Shades of Grey thing I’m seeing everywhere? I just don’t understand why it’s so popular!” Sigh.

      2. Liz T*

        Well, then the question becomes: is everyday crossdressing like BDSM, or is it on the spectrum of gender identity? In this case it sounds to me like the latter, but we don’t get enough from the OP to know for sure.

        1. fposte*

          Call it cowardice, but my feeling is that we really don’t want a workplace where managers have to determine the degree of sexual significance any particular experience has for an employee. There’s not much in the way of plausible deniability on handcuffs, but for stuff that isn’t necessarily sexual, I’d go with manner of speech and context for judging appropriateness. If somebody’s clearly using a conversation for sexual gratification, the topic at hand doesn’t really matter–it needs to stop.

      3. Liz T*

        Also, part of why it’s different with BDSM is that violence is objectively BAD unless it’s in a consensual sexual context. To talk about BDSM is to talk about violence and/or sex, both of which are inappropriate for the workplace. I think everyone here agrees that unconventional gender expression is not inherently a negative.

        1. fposte*

          Right, that’s what I meant about the “echoes”–that BDSM involves actions that have been used to harm and oppress. As you say, if the action is either violent or sexual, it’s probably not one you should be sharing breezily with your co-workers.

      1. fposte*

        Sorry, it’s actually it’s time order, not threading–Ryan’s comment has stayed at the bottom despite more recent comments appearing above it.

  20. BCW*

    I think the biggest issue here is that if “inappropriately personal” conversations happen all the time, as stated, its not really fair to just decide that this persons personal thing is off limits, but everyone else’s is ok just because its not something you don’t like.

  21. Cup of Coffee*

    As someone with two crossdressing friends, and who knows another, I have to disagree here. I don’t know anyone who crossdresses for sexual reasons who does so at work, and for most of the people I know, it is very much about identity.

    I also think the line here between “sexual” and “not sexual” is also not as clear as AAM is making it out to be. A close friend of mine admitted to cross dressing as a fetish before eventually cross dressing in normal situations and then undergoing gender reassignment surgery. I think in many cases, a kink you do in private is an easier way to explore crossdressing than going to work in womens clothes.

    Ultimately, unless there is some indication that he’s getting off on coming to work wearing skirts, assuming it’s sexual seems unfair.

  22. Anonymous*

    “So about that deadline…”

    I guess I’ve never been comfortable in open/casual/relaxed/gossipy offices which is where I’ve been for a large part of my career. So what I do is in every break in conversation swing it around back to the job. (super ultra bonus points if you can actually create a transition from the unrelated personal conversation to the work, you know an a-line skirt looks a lot like this conversation’s productivity graphed out so I’m going to step back to my desk unless anyone has a question about the project) This won’t work if this is the only item the OP is uncomfortable talking about. But really, why not simply focus on the work?

    1. KayDay*

      I know someone who randomly shouts out “segue!” and then changes the topic. As in:

      Manager: “I found this really gorge flowered dress on sale at Marshalls, but I can never figure out what size I wear in women’s clothes. Compared to men’s clothes, the numbers just don’t make any sense. And the hips, man, the hips!”
      OP: “Yeah, that’s tough. Segue! I finished the budget report, but I wasn’t sure about item X.”

      1. Jamie*

        That reminds me of that part of the Catcher in the Rye where they shouts DIGRESSION in the class room when someone strays off topic.

        Sometimes in meetings I so badly want to do that – just to see if it would work (and see if anyone catches my Salinger reference.)

      2. Ellie H.*

        I love that too. I’ve definitely said “segue” out loud before but I love the idea of someone who is in a habit of it and known for it.

  23. Heather*

    Honestly, I wouldn’t say anything unless it is clear that this is a sexual kink… and right now we don’t have enough information. We also don’t know if the manager will ultimately identify as a crossdresser or if this is the first step towards identifying as a genderqueer, transgendered, or transsexual person. It is common for people to try on other identities that may seem less threatening before arriving upon the identity that resonates closest with them.

    Additionally, people are annoying when they first come out (I say this as a dyke who has been through it with myself and friends decades ago). Sometimes all a newly out person wants to talk about is the stuff they’ve been hiding or denying for years. They’ll get past that eventually and recognize that they don’t have to talk about their identity all the time to be that person. Right now, however, it’s important for them to let their true identity flag fly. Unless it turns into sexualized comments, just let it be.

    One thing you might want to do is let them know that they are a great person and that if they ever realize that they are genderqueer, transgendered, or transsexual that they will find a supportive atmosphere. You may want to warn them that some people are assuming that the crossdressing is a sexual fetish and are a little bit uncomfortable. I would more likely tell the uncomfortable coworkers to suck it up unless the comments are sexualized. I know I’d be upset if people were yelling “TMI!” at me for telling them that I had a romantic dinner with another woman, while I would never say what we did after we got back from the romantic dinner, which would be serious tmi.

    1. Marie*

      Ha, yes, THIS! The newly coming out are, in retrospect, adorable, but at the time, they are obnoxious talk-machines.

      Actually, this may not be such a bad way to approach it, if you feel like you have to at some point. As in, “Oh my god, Bob, you are having such a typical coming out party, it’s just shoes shoes shoes all the time with you.”

  24. Victoria*

    Just a note – I don’t think it’s clear that the cross-dresser is the OP’s manager. He is “one of our managers,” but we don’t know where the OP in the hierarchy.

  25. twentymilehike*

    What about just blatantly talking about it? We all too often forget the innocent curiousity we had as children.

    My first expereince talking to someone who cross-dressed was someone that I had become friends with through a place of business. He is not gay, he is married to a woman, and they are both performance artists. When we met he was not working as an artist, so I knew him as someone who wore a uniform to work like the rest of us. Later it came up in conversation that he liked to go to art shows and clubs dressed in outlandish dresses. I was young and didn’t display much candor with my responses such as, “wait, are you really gay? What about your girlfriend? That’s not weird? You mean there’s a time and place for that? This is so new to me! Whoa.” And he proceeded to excitedly show me his favorite outfits.

    It is entirely possible that sweeping this topic under the rug is not the proper thing to do. I’m not sure that I personally understand why people dance around certain topics so much. Just ask. “So, Bob, when do you cross-dress? Is is like just for shits and giggles, or are you going out and meeting people? Do you perform in drag shows? I don’t know anything about it.” Obviously he is open to talking about it, and having that one discussion may just put the whole issue to rest. If he answers, “well it’s how I get my jollies!” Then by all means, I’m sure he would undertand your appropriate reponse of, “Oh, well we probably should be doing to much talking about our sex lives at work, right?”

    You have a casual work environment, so my personal suggestion would be to just be frank.

    1. Liz T*

      Wow, I cant’t believe the rest of us didn’t think of, “Ask him about it, duh.” You’re so right–when it’s an area we’re ignorant about, even a little, we should approach it with question marks rather than exclamation points.

    2. Kou*

      I completely 100% agree. Now, when you’re talking about anything in this family of topics, there is always the chance you will hit someone who will rebuff curiosity as inherently hostile and offensive, and if the manager is like that it would be unfortunate. I dislike of the rhetoric that a person being unfamiliar with something gets them lumped together with people who are also actively opposed to it. How are people supposed to learn if we treat all questions like accusations?

      That said, for me, I wish people who were confused or uncomfortable would ask me more. It’s easy to be uncomfortable with something you don’t understand, and a little information can assuage that feeling. When people find out I do drag and are clearly surprised or confused, I never know how to assure them that I’m NOT flaunting my fetishes all over the place. I don’t want to keep talking if they look like they don’t want to hear about it. But I want to tell them that I just love makeup, and trying to completely change your face in a way that looks natural is a fun challenge for me. And I love costumes– I also do ren fest and cosplay, it all falls into the same category for me.

  26. T*

    Here’s something to ponder. I’m a butch lesbian. Technically, I cross dress every day. Wearing men’s clothes doesn’t “do” it for me. In fact, when I was young, I “passed” and looked femme. Now, it’s just how I see and present myself. Remove my gay predilections (“who I am”), and … does it bother people as much when women dress as men? Again, just something to think about.

    1. Katie*

      I think you already know the answer to you question, but a certain degree of gender flexibility is tolerated much more in women than in men. There have been times in my life where I engaged in what I guess I could describe as “light” cross dressing, and it didn’t do anything more than raise an eyebrow. No manager ever had to wring his/her hands over me wearing a tie. Maybe we’re not quite at that place with men yet, which is why this is even a discussion.

      1. Liz T*

        Yeah, but, exactly! We should check ourselves for societal programming before we treat female mon-conformity differently from male non-conformity. (I say male because that seems to be how the manager identifies.)

        1. Laura L*

          Right! We should also remember that there was A LOT of pushback against women who started wearing pants (aka Bloomers) in public in the early 1900s, although it’s acceptable now. (Except for the most formal situations, then its generally expected that women wear ball gowns or other fancy dresses.)

          I think that there’s still some sexism behind the acceptability of women dressing/acting like men. Society as a whole still tends to view masculine things as “better” than feminine things, so, of course a woman would want to be more masculine (but only to a certain extent) because that makes her a “better” person. But a man wouldn’t want to be more feminine because that makes him a “worse” person.

          Although, there’s still tons of pushback towards women who are TOO masculine.

    2. KayDay*

      Yes! This is a good point (and I could go on all sorts of tangents, so I will have to restrain myself) but I would definitely agree that it is easier/more accepted for women to dress masculine than the reverse. It’s not just dress,too, in general it’s easier for women to get away with masculine behaviors than it is for men to get away with feminine behaviors. You definitely see it in children, where it’s very accepted to see a girl playing with a super soaker or skateboard, but less so for a boy playing with a barbie or ken doll.

  27. Not So NewReader*

    When a workplace over shares information anyway- that creates an environment without boundaries. Boss may feel that since everyone else is talking about stuff in their lives then he wants to talk about stuff going on in his life. It could just that kind of work place culture.

    I read the question as the OP is trying to build bridges between the boss and the concerned people so that everyone can just move on.

    OP, you see the wide range of angles and opinions here on this forum. It probably gives a good idea of what people are thinking at your work place. After reading all this, if it were me, I think I would opt to just go about my own day and let nature run its course. Someone says something to you then you can reply with something like “Yeah, but really that has no impact on my job here. He’s a nice person, I wish the best for him, but I really have to focus on X because it is due in three days.”

    If the boss has poor behavior, of any sort, that falls short of company expectations, then it is up to his boss to say so.

  28. Ethan*

    As the T in the LGBTQ community, this one is just too good not to talk about. Here’s my take:

    If it’s an overshare in the sense that you’re just hearing about, say, clothes shopping all the time, the response might be as easy as, “Whoa dude, you seem to go shopping a lot. I can only offer so many insights into shopping and I might be reaching my limit.”

    If it has to do with some fundamental discomfort people are feeling, then it’s gotta be about the issue of cross dressing itself somehow (and maybe he’s not oversharing, but people are uncomfortable). Be honest, candid, kind, and ask some questions (maybe in a more private setting). If he has come out pretty publicly, hopefully he can speak about it well enough to be an educator. Be supportive. If he is using this to test his gender identity, one or two supportive and understanding people at work can make a big difference. If it’s simply something he likes to do, that should really be okay. Oftentimes, cross dressing isn’t a kink. Heck, in the metropolitan area I live in, there’s a support group for straight men (whoa are male identified) who like to wear women’s clothes.

    There’s a third option, too, and that’s that he feels comfortable enough in his work place to his coworkers as therapy a little bit as he works through coming out. That would be stepping over the line, and I could see that (justifiably) making people uncomfortable. If that’s the case, you might be able to play the concerned coworker (or ask the HR manager to play concerned HR manager) and steer him in a better direction. “Hey Jim, that sounds pretty heavy, have you ever talked to a therapist about this? Maybe there’s a group you can go to. Yeah, this is totally out of my area of expertise, but I’m sure you could find someone with some experience to help you out.”

  29. AG*

    I’d love an update from the OP about specifics of the person’s behavior and also her work-relationship to him

  30. Diane*

    I assume that the manager, described as a nice guy, is just so relieved to share part of his identity that he’s not aware of boundaries. It’s like my pregnant coworker so wrapped up in her life-changing experience that she no longer sees the difference between talking about nursery colors or cervixes. There’s a whole lot in between that’s interesting to some and way way too much for others.

    I would bring it up in a non-work setting–at happy hour or whatever. I’d say something like, “Bob, it must be a relief to be able to talk about something so important to you with your colleagues and friends.” Then listen. Then steer the conversation to examples of work-friendly details and after-work or private details, using examples from other people’s conversations at work. It’s possible to be specific, cast it as a workplace issue and not just Bob’s issue, and minimize the awkwardness.

    1. fposte*

      “It’s like my pregnant coworker so wrapped up in her life-changing experience that she no longer sees the difference between talking about nursery colors or cervixes.” That’s an excellent comparison that I think a lot of us can relate to!

  31. Stells*

    My advice would be for the OP, or another coworker close to him, to just tell him a shortened version of this letter – in a one on one, private setting.

    A simple – Hey, I just wanted to let you know that there are a few employees that are feeling uncomfortable because you talk about XYZ often. You know I don’t care one way or another, but I’d hate for people who don’t know you well to make assumptions that aren’t true about you or your lifestyle based on antiquated ideas. Unless you plan on doing it at work (or coming out as trans, etc etc), I’d limit these conversations around people who don’t know you very well, at least for the time being.

    That last sentence can be reworded, but the idea is to give them a chance to talk to the person about coming out if it’s a gender identity issue.

    I’d only have someone really close to him do it though. It’s a sensitive topic and one that will definitely hurt him if handled badly.

    1. Liz T*

      Careful, though: most people don’t want to be on the receiving end of, “I wouldn’t want people to make baseless assumptions about you because of certain behaviors that are really important to you, so you should change.” If other people are prejudiced against you, you don’t want to hear, “Hide your true self from the bigots.” It really has to be a conversation about what’s appropriate at work and what’s not–if it’s the manager’s fault, don’t blame it on the workers, and vice-versa.

      1. Stells*

        I totally agree, which is why I say it needs to be someone he feels comfortable with. I would say the same if it were, say, telling a friend to dress more appropriately for the office. Not in a trans or cross dressing way, but say, if she was dressing “too provocatively” for the office. On one hand, who gives a crap- as long as they are good employees. And, say, it was an office where a lot of women did so. As a friend, I tell her to tone it down at work,because she would be taken more seriously. As a manager/coworker, that discussion would do more harm than good and would be inappropriate and/or considered harassment.

        1. Liz T*

          That’s a great comparison! I would want to hear, “Liz, that’s too low cut for this office, in the future please dress more conservatively.” I would NOT want to hear, “Liz, I’m worried people are going to think you’re a slut. You should dress more conservatively so others don’t judge you.”

          1. Stells*

            Exactly! If you were to apply it to the OP’s letter – say it was a female manager who was dressing provocatively in an office were it was very common for other women to do so, but you overheard employees they supervised were making comments about her “sexy” appearance. It’s easier for someone you feel comfortable with to say “Because your’re a manager, you might want to avoid dressing with low cut tops because it will help with gaining respect (or credibility, or whatever) with some employees (who are jerks) that individual contributors don’t need to consider” versus being singled out that YOUR provocative dress is out of line when no one else is being chastised for it.

          2. Stells*

            Also, I’m horrible with words, so I’m never the friend in these conversations. LOL. I tend to just spit it out instead of crafting it more carefully. I’m working on it though!

  32. Beth*

    I think that the topic of cross-dressing has caused us to look past the real issue: whose place is it to correct behavior in the workplace? If the OP is concerned on a personal level, then pull him aside and say “Look, Joe, I realize this has been a big step for you and I support you, but I am concerned about how you are viewed in this office. You might want to be a bit more careful about how you share information about your personal life as everyone doesn’t understand or everyone might not be comfortable with the conversation.”

    On the other hand, it would really be up to HR to have that type of conversation with him if the OP is not that close or is uncomfortable. It doesn’t matter if the topic is body odor, cross dressing or frequency of showering habits: if it makes you uncomfortable speak up to someone who can deal with the situation. If you are hearing from others that it makes them uncomfortable, don’t take that burden on as yours unless you are HR or the supervisor. Direct them to the appropriate person and ask them not to discuss their discomfort with you. That, IMHO, is gossip.

    1. Ask a Manager* Post author

      Hmmm, I’d actually modify that a bit. Ideally managers should be addressing issues, not pawning them off on HR. I know that some companies use HR that way, but that’s not really ideal or what they should be there for; managers should handle issues in their own departments unless there’s some reason why they can’t.

      I’d also add that it’s optimal if coworkers are willing to address issues amongst themselves. Some people are, and that’s better than having to involve someone higher up.

  33. Jamie*

    I have been thinking about this and trying to imagine how I’d react in this situation…because I do admit I am completely out of my element with this scenario as nothing like this has happened to me.

    I think for me it would depend 100% on what the over-shared information is. I think I’d do a little mental swapping to reality check myself. If he were talking about shoes if I wouldn’t say anything if he were yammering on and on about high tops then I wouldn’t say anything if he were doing the same about high heels.

    Talking about some fabulous dress he bought…if he were talking about a suit would it bother me? It would bore me, to be sure, but bother me? No more than most small talk bothers me.

    I actually don’t think I’d address it directly unless it crossed a line and felt personally creepy. Without being too specific, I’ve known people who had unconventional aspects to their sex lives and seemed to enjoy telling me about it, and the enjoyment was creepy because I got the feeling that my being uncomfortable with the conversation was the point. Don’t drag me and my reactions into your games that I don’t fully understand. Leave me out of it.

    Other than that – if it didn’t feel sexual – I’d either ignore it or change the subject.

    I do agree with the others who said this is probably the topic of conversation because he’s newly comfortable talking about it. The novelty will wear off eventually.

  34. ARM2008*

    If this isn’t sexual, isn’t it just a topic that some people are uninterested in? I work in a former storage closet with 4 other women. Talking about shopping literally makes me feel like upchucking. I haven’t carried a purse since 5th grade and really don’t care about the cute one any of them bought over the weekend. My highest heels are on my hiking boots.

    When these conversations come up I put on my headphones, tune out, or take a walk. On the occasions when they have tried to engage me in these conversations I just shrug and say I’ve never paid attention to that and it doesn’t interest me. When they ask if their conversation bothers me I say nope, and turn to my computer and IM one of my non-girly friends so we can laugh about how silly they are and then go on to chat for a few minutes about one of our silly favorite topics, like medieval weapons.

  35. Diane*

    I think that’s the most sensible thing I’ve read all day (especially the part about the medieval weapons) :-).

  36. OP*

    I would have commented in sooner, but I was out of town until today.

    He is not my personal manager, but our management structure is such that there is a team of managers over our department so he is still in a management position over me.

    I asked this question a couple of weeks ago and since then, as many suggested, it’s died down. I went back to my coworker for some clarification – the conversation was along the lines of the manager saying “I guess you’ve heard”, which the coworker had not and the manager then enlightened about his declaration on facebook and they talked about fashion, discounts, shoes, etc. It’s not that it was salacious, but it jolted my coworker because they are not particular friends.

    I think there’s been a valid point made that it might be more the person who is uncomfortable with the topic than the topic itself. In her defense though, I would say that it came out of the blue, he’s a manager, it’s at work and she wasn’t sure how to respond. Our work setup also means that we will be stuck together on various short-term calls all day, so you can’t really move away from someone until the call is done. In that fashion, we all learn so much (sometimes too much) about each other’s lives. He approached it as something he assumed she already knew (and wanted to know).

    But, I love the comments and it’s wonderful to see how accepting most people are. Personally, I already knew years ago that he liked role play/crossdressing, so I was not surprised when he let everyone know he was a crossdresser. I haven’t asked, but my personal opinion is that he is not in gender transition but I could be wrong. The problem with our workplace is that it IS very open, but not all employees are okay with how open it is. Since it is so open, it is easy to get carried away and forget that not everyone is as comfortable with sharing personal information.

  37. A S*

    . . . vaguebooking . . . lol!!

    There is a lady I know socially who is trans. she is sweet and wonderful and fun!

    I was quite surprised to see her in my office complex a month or two ago, and when she told me her real name & I looked her up on the company intranet, found she is a distinguished member of staff!

    Since I only knew her from night clubs, I was hesitant to reach out to her – what if people at work didn’t know, right??? (she is very feminine so you’d really have to be looking to know!)

    It was so awkward that I just never spoke to her at work, and recently told her I didn’t want to potentially embarass her by mentioning a social interaction she didn’t want shared.

    I felt like I missed out on making a closer friend, but wasn’t sure how to deal with it. I definitely feel for OP – I’m sure it’s uncomfortable for lots of folks in the office.

  38. Dawna*

    Its hard to define what is and isn’t allowed to be discussed in that kind of workplace- everything is open for discussion.
    So long as no one is being directly hurt, I see no problem for him to continue to explain that he occasionally (or often, I don’t know) wears women’s clothes.
    If you wish to claim comfort-level, just be careful, because it can come back and bite you in the bum.

  39. LoriQ*

    You said you don’t have much expertise on this subject. First I wanted to point out something you said. “Crossdressing doesn’t indicate the crossdresser is gay, transgender, or straight.” A lot of people use the word transgender in the wrong context. Transgender is an umbrella term that consists of, crossdressers, transsexuals and any other gender varient people. I think you meant to say transsexual.

    So back to the topic. My advice would be to talk to him with maybe another coworker outside of work. Don’t make it a large group. It may make him feel like all of you are ganging up on him. Just be honest with him and tell him exactly the way you feel. Bring up that you have nothing against crossdressing and tell him you even wouldn’t mind going shopping with him or helping him with makeup or something. Just tell him you feel that talking so much about it and with so many people at work is a bit overwhelming for some of the people. Be gentle yet firm. How would you handle it if it was a woman at work that kept talking about her boyfriend and how he satisfies her and how good he is to her and all the expensive gifts he buys her, etc. How would you tell her she’s being overwhelming?

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