my client won’t stop asking about my dating life

A reader writes:

I work in sales. I recently landed an account that my boss was really after me to get. I went to have a business lunch with a person from their organization prior to assuring their business, and he asked me about my dating life (this man is old enough to be my father). I simply mentioned that I was not single, how we met, and that we lived together, then politely changed the subject. I hoped that was the end of it, but the rest of the meeting he continued to make comments about my relationship/ dating life, and continues to do so via our phone and email communications — anything from, “Is he treating you well?” to “You’re living together and not married?” and “Does your mother know you live together?” and other similar little comments.

This is a huge account, so I don’t want to lose their business, and I feel pretty uncomfortable talking with my boss about it. Luckily, they are only a summer seasonal account, but I still don’t want to revisit this every year. Any advice on the best way to handle it without offending anyone?

You’ve got to shut it down. It sounds like you’re continuing to answer his questions — which I understand, because there’s a power imbalance here and you feel like you can’t be rude to him — but one of the reasons it’s continuing is because you haven’t stopped it yet. (The other, larger reason it’s continuing is because this guy is an enormous ass. But you’re not obligated to play along.)

By answering his questions, you’re telling him that this is a subject you’re willing to discuss with him, so you’ve got to stop. You don’t need to make a big deal out of it — you can just stop participating. For instance:

Him: “How’s your boyfriend treating you?”
You: “Let’s talk about your account, not my private life, Bob.”
Him: “Are you still with him?”
You: “Let’s get away from my personal life and back to your account.”

Repeat as necessary. Alternate versions include “I really don’t want to discuss it,” “That’s off-limits,” and “I’m not here to talk about that.”

Now, don’t say this stuff in a snotty tone. Say it pleasantly — but say it. (Frankly, because he’s being so casual with you, you can probably say it in a joking or long-suffering tone, as long as you’re firm about the message itself and don’t give in — but judge that according to the tenor of your conversations.)

Also, keep in mind that because you’ve answered his questions in the past, this is going to be a change, and he might not quite get it at first. So be prepared to go through it a few times.

The other thing you need to do is to bring your boss into the loop on this. I realize that you don’t want to, but you’re going to need to, if only to protect yourself if the client complains that you’re being cold to him or anything like that. I get that you feel uncomfortable about it, but sometimes there are things you need to discuss with your boss that aren’t 100% comfortable. That doesn’t mean that you just opt out of discussing them. So raise it, please: Explain what’s been happening, explain how you’re going to handle it, and say that you want her in the loop because while you plan to handle it perfectly pleasantly, you can’t discount the possibility that he won’t like it.

People who use power dynamics to get away with behavior that would be shut down in other contexts are jerks. I don’t care if this guy thinks he’s being charming or flirtatious or whatever; he’s taking advantage of the fact that you don’t want to alienate him, and that’s BS. But you can stop it in a way that a reasonable person wouldn’t be offended by. And if he’s not a reasonable person, well, that’s when your boss would need to be in the loop, so take care of that part of it now.

Read an update to this letter here.

{ 59 comments… read them below }

  1. Rob Aught*

    There really is nothing to be gained here by playing along.

    If he’s going to be a threat to the account because you won’t talk about your personal life, then he’ll also be a threat later when he doesn’t get whatever it is he thinks he’s going to get from this line of questioning.

    Not saying he will do something, I’m just saying that if he can’t separate personal from business and is going to pull his business because of it, that will happen sooner or later.

    Why not make things easier for yourself and go through the short-term pain of redirecting his questions, exactly like Alison said, rather than continuing to play his game? Believe me, this is a game for him. He is probing for something. It may not be anything tawdry, it may just be asserting his perceived superiority. Thus the question about your mother being ok with you living with a guy. A “Nunya” question if there ever was one.

    1. Elizabeth West*

      Came here to say something similar. He seems like the type that might decide anything doesn’t please him; he’s used to messing with people and getting his own way. Jerk x 1000. Definitely do what Alison says to do.

    2. EnnVeeEl*

      I agree. You can’t win here. Once your managers know about this, because you should say something, they can plan to deal with the inevitable (possible) with this guy. Be prepared for him not to take your new method of dealing with him well.

      1. Jessa*

        This. Your best bet is to try and refocus him on business. But also find some strategy for the future and don’t be drawn into these questions beyond maybe “no I’m not single per se,” so you don’t get stuck in the future.

  2. Nameless*

    Sometimes i feel very sorry for my wife and women in general. You get hit on for any any reason. I guess it’s one of those “it happens”

    1. Chinook*

      Nameless, belive it or not, some of us women don’t get hit on at all *sigh.* I suspect I give off an aura of “not worth the effort” to guys and have never had this issue. DH, on the other hand, regularly gets hit on by women and men even when I am standing next to him. We once saw a male Chapters cashier run over to his till when he saw DH and were next in line and proceed to chat DH while ignoring my questions while he rang through my sale. (Standing next to DH turns my invisibility powers to full strength)

      1. SW*

        It really stinks that people can be so rude. I hope your husband is very clear about shutting them down.

        1. Kinrowan*

          I don’t think “it happens”, I think both come from our patriarchal society – both that men feel they can hit on women at will, but also that when men are with women, women are ignored, “invisible”, and only the male gets the attention.

    2. Michelle*

      It’s hard to tell if the LW is being hit on or is suffering through the “let me offer you unwanted advice because as a young woman you need guidance and protection from a wise older man.” Which is also frustrating and happens all the time to women. Although given how often he is returning to the subject, he either has serious issues with unmarried women living with their boyfriends, or he is being a deliberate creep.

      1. Rob Aught*

        It’s really bad either way.

        Now maybe I’m just stodgy and I’ve had personal relationships with employees but only after the professional relationship is well established.

        I make a point of learning about spouses, children, hobbies, etc. Having this information is useful especially when time off is needed. It also avoids awkward conversations around flex time. I don’t need a big long explanation and usually just letting me know “My kid has a thing” or whatnot is fine.

        Still, it’s all about setting that professional relationship first and foremost and I respect boundaries. I don’t discuss personal details with salespeople. Maybe after there is some give and take, but an outright “Are you married?” would seem strange to me. I sure as hell don’t ask that question!

        At the very least, the whole line of questioning strikes me as rude and condescending. Like I said before, it may not be tawdry, but that doesn’t mean it is appropriate.

        1. Ruffingit*

          I could see learning some personal details about someone who works for you directly. As you said, that can be helpful with flex time issues or what have you. Not that it’s necessary, if someone doesn’t want to share those details, that’s fine, but I’m just saying I can see why you might know them as the boss.

          But in this case, this guy is a customer and a seasonal one at that. Definitely no need to be privy to personal details of the life of his account rep.

          1. Rob Aught*

            Like I said, I prefer to get a good professional relationship established first. The personal comes in time.

            Still, boundaries. Some things are just none of anyone’s business. In this case, way over the line. Yeesh.

  3. Kat M*

    Oh man, being a massage therapist I get boundary-pushers on a regular basis. They’re like toddlers, testing you to see where you put your foot down. The sooner you take care of this the better.

      1. Kat M*

        It’s not bad if you know how to deal with it. Once you put your foot down and they know they don’t have power over you, they quit. Some of them have turned into really great regular clients from whom I’ve never had even a bit of trouble since. I know some folks have had genuinely scary clients, but since I work in a clinic rather than a spa, it’s never happened to me.

  4. the gold digger*

    I had a broker kiss me once when I ran into him after work when he was coaching a soccer game.

    I stole his biggest account.

    A customer once asked me why I wasn’t married. This was after he had insisted on driving us to lunch, even though I wanted to drive, and he popped in a Kenny G tape to set the mood.

    He asked the question. I stared blankly at him and said, “I beg your pardon?”

    He blushed (bless his heart) and never said a word about it again. I think maybe he wanted to ask me out as opposed to playing power games, but it was still inappropriate.

  5. Sarah*

    “Bless his heart” = He is an idiot

    The only thing I’ve learned since moving to the South.

    1. Rindle*

      “Bless his/her heart” is one of my favorite Southernisms. I’ve used it and heard it used to mean anything from “he’s such a sweetheart but such a loser” to “he’s a great guy in a terrible situation” to “that witch can go straight to Hades!” It all depends on context and inflection. It’s absolutely … smurfy.

      1. BookWorm*


        If you think fried pickles sound gross – believe me – as a “D*** Yankee” they are WONDERFUL.

        Cheese grits are really good too. Just make sure to get good grits, and never EVER use instant grits.

  6. Michelle*

    This may not be flirtation or a deliberate power play. My experience in sales is this is fairly common. Some accounts like to feel they have a personal relationship with their sales rep. I’m not saying the OP should participate if this makes her uncomfortable, but this is not really uncommon. Set boundaries, nicely, but set boundaries. My approach would be a little more direct than AAMs. My initial response to the account would be to acknowledge the change in – “I know we have discussed my personal life in the past, but I’m not comfortable talking about my relationship.” If he tries again, I would remind him and then redirect the conversation – “Hey Bob (whatever his name is), I’ve mentioned this before. I’m just not comfortable talking about my personal life. So how is business going?”

    And now that you know this is something you don’t want to encourage, make sure you are clear about this with new accounts as well. Good luck!

    1. Jamie*

      Agreed – can’t tell if he’s flirting or this is just a totally inappropriate way of trying to be friends…asking personal questions. Creepy either way.

      Worst one I ever got? Upon hearing that my husband is a cop…”Oh, so he has his own handcuffs – that must be fun!” From some guy I had known minutes…

      It absolutely wasn’t flirty, just stupid. I ignored it and started hammering the work talk.

  7. Yup*

    Another thing to remember is that you don’t actually have to answer his questions at all. You can maintain a neutral expression, wait a beat, and then just carry on with business.

    Client: Are you still living with your boyfriend?
    You: (pause) I’ve brought the XYZ brochures we discussed last time. Are you still interested in the teapot glazing aspect?

    I usually go the direct route and address the problem outright when somebody’s being inappropriate, but this can be a useful fall-back option. It’s sort of a polite freeze-out. Mentally, it’s almost like when somebody behaves really badly at a party, and there’s that slight skip on the record where everyone is like “What just happened?” and then decides to just return to business as usual. Which works well if the person behaving badly is just trying to get your attention. You control the situation by just not giving it.

    1. Anonymous*

      I’m with this one. Just pretend he didn’t say it. If he persists, then give him a silent, meaningful look and then say something unrelated.

      Alternately, I’m kind of a smart ass, and it would be just like me to say something in response to him like, “Will answering these questions mean you’ll buy more stuff?” Said in the right tone, this can put it out on the table in a humorous way but it really gets the point across.

      Everyone’s mileage will vary, of course.

    2. Ruffingit*

      This is a good technique and can often get the point across without saying a word at all. Simply ignoring a topic is often a good approach. Depends on the situation of course.

  8. Liz*

    See…this doesn’t sound that weird to me because my older male bosses (not creepy in the slightest) ask me things like that in a joking manner or when the only other single girl got engaged looked at me and said “alright, when’s your announcement coming?”. It is almost in a fatherly way and certainly doesn’t offend me. I also kid them about their teenage daughters as well.

    So I’m wondering from the OP if he seemed like he was hitting on her, judging her for her lifestyle choices, or what? Typically I agree with all of the answers here but am a little confused by this one. Also, In relationship based sales this is pretty common to talk about personal lives, do happy hours, etc. My brother once took a client out to drinks and said the guy complained for 3 hours about how awful women are, they always screw him, etc. He said it was uncomfortable but realistically in business you have to decide where your moral limits were and how much this issue is worth it to you. It was one lunch where the topic came up, he didn’t invite you to his hotel room, personally I don’t mind sharing some details about my life to create more of a personal relationship with my clients.

    Keep in mind, this is coming from a die hard feminist here with a complete feminist mom and I am more than willing to stand up for myself (got a high paying regular banned from bar in first bartending gig at 19 for being inappropriate as just one example)

    1. VintageLydia*

      I’m thinking the issue here is he seems pretty fixated on the topic (since she mentioned he keeps bringing it up in other communications with her.) There also doesn’t seem to be much of a personal relationship otherwise which makes his constant harping on the issue cross over to skeevey (rather than just mildly inappropriate.)

      1. Ask a Manager* Post author

        Yeah, that’s my take too. I definitely get that in sales relationships, people often like to feel like they have a personal connection, but this seems to be a fairly pointed harping on her relationship with her boyfriend, which is not appropriate.

        1. Liz*

          Right, see, I wasn’t clear on if he did keep bringing it up past the lunch/meeting. When I read it, it said “the rest of the meeting”, not further communications. Obviously if it bothered her this much it probably is continuing, but the letter didn’t mention that.

          Obviously those are the types of questions from certain people that you can tell are joking/friendly but from the wrong person are just completely creepy. I had a boss who was like that – total creep, would always ask about boyfriends when I was an 18 year old intern. Once came up behind me at open desk in reception area and put his hands on my shoulders and massaged them (that was clearly inappropriate). I quit shortly thereafter and ever since have purposely tried to give off a “don’t mess with me” vibe, so never get harassed in the workplace but plenty of female coworkers get subtly harassed and don’t know how to respond so it continues.

          If it’s someone you can’t completely stand up to I’ve found an innocent “I’m sorry, say that again?”, while acting dumb as if you didn’t hear them, can often can be enough to make men (and women!) stop acting like idiots!

          1. Liz*

            Oops, and now yes…I do see the “phone and communications part”. Long Friday, I reread it twice to make sure and still missed it!

    2. Pussyfooter, aka. OneoftheMichelles*

      I think you missed something the OP said: “and continues to do so via our phone and email communication.” The OP’s letter gives me the impression that these statements are fairly pointed and continuing well past that first lunch.

      Since OP gave some conversation on the topic, she doesn’t seem to have a problem with clients knowing some basic social facts about her life. But if it’s gone outside her comfort zone and she doesn’t know how to fence in what’s comfy for her versus what’s not, then boundary enforcement is definitely an issue for her to strengthen.

  9. SW*

    That’s so creepy. I’ve had times when I should have reported someone to HR but didn’t because the man was straddling the line between what was and wasn’t reportable.

    A coworker started out by talking to my boyfriend when he was over to pick me up from work one day. He told my boyfriend, “You take care of her — she’s my favorite.”

    Then every time he saw me he would grill me on our relationship and why I would date a Philosophy major when there’s no money in that career path. I said I believed in him. Coworker said, “You stand by your man — I like that.”

    Another time: “Do you call your boyfriend ‘daddy’? He’ll like it if you call him ‘daddy.'”

    In hindsight I really wish I had reported him sooner, but at least he got fired not too long after (for something unrelated).

    1. Liz*

      The daddy comment – EW! I would’ve reported him immediately. It is a fine line these days because I have male bosses who could say “you take care of her” and I wouldn’t think it was creepy. But I’ve had other male bosses where I would be completely put off because I knew they were slimy. The language alone is so hard to tell with these things.

      1. SW*

        That was my problem — my instincts told me he was a creeper, but I worried that “he keeps asking about my relationship” wasn’t enough to take to HR.

        As for the daddy comment, yes, VERY unsettling, but at the time I just meebled something like, “that’s weird,” walked away and tried to forget about it. If anyone tries it again I’m definitely reporting it.

        1. Jamie*

          The daddy comment is disgusting. If that were me the world would stop and I’d let him know in no uncertain terms that he is not to say that to me or anyone else in the workplace again.

          Isn’t it funny how once you know how and have the authority to handle this kind of crap it stops happening to you?

          1. SW*

            Isn’t it funny how once you know how and have the authority to handle this kind of crap it stops happening to you?

            Happens to me all the time. :(

            My brain tends to shut down and choose flight instead of fight in plenty of instances of sexual harassment.

            1. Anonymous*

              In response to the ‘daddy’ comment:

              “And you know this because you call your girlfriend ‘mommy’?”

              Which is unhelpful, of course, because it won’t shut down the creeper. But it’s just the kind of thing I wind up saying. (I don’t get many creepers, though. Maybe this is why?)

            2. Natalie*

              Sometimes it can be helpful to practice a couple of universal responses to inappropriate comments, e.g. “That’s pretty inappropriate, Joe” or even the Carolyn Hax style “Wow…”

  10. SW*

    Also, I’m always irked when instead of asking, “How’s your boyfriend?” they ask, “Are you still with your boyfriend?”

    Or, even more pointedly, “Are you still with that guy or have you kicked him to the curb yet?” Especially when I haven’t indicated being the least bit unhappy with him.

  11. Laura*

    Ewwww. Just, ewwww.

    Maybe this guy is just going for being waaayy too familiar when he and the OP don’t know each other that well yet, and he doesn’t get that the more personal side of a business relationship should develop a bit more organically.

    This reminds me a former boss, who was the biggest jerk I’ve ever encountered. He would joke around, yank people’s chains, etc. It was like he wanted the office to be like a glorified locker room. The problem was he’d only been with the company a short time, and before you can assume that kind of familiarity with someone, you need to establish your professional relationship and boundaries first.

    So if someone said they didn’t have something done, he would say, “What are you, some kind of slacker?” and because that person didn’t know him all that well, he or she would wonder if he was actually being serious, and then start worrying that their job was in jeopardy. A female member of the team asked for a day off once, and he said, in a pretty lascivious tone, “Why, have you got Spring Fever?” and she was completely skeeved out. Just way off the mark and totally inappropriate. And not because the team was a bunch of uptight killjoy prudes, but because you can’t be overly familiar with someone if you haven’t taken the time to get to know them.

  12. AdAgencyChick*

    Ugh, OP, I feel for you. I used to have a client who asked inappropriate questions of all the women who worked on his account, and nobody was willing to say anything because of the size of the account. Grrrrr.

    I recommend having a few stock answers for this kind of thing, because the shock of an inappropriate comment (even if you know it’s coming, because this guy makes them so often) can leave you feeling flustered and scrambling for a reply. I like Alison’s suggestions.

    When my gross client made gross comments (including “if I get [agency CEO’s name] to give you a raise, will you go out to dinner with me?”) my stock response was a shocked, “[Client name]! Did you just say that OUT LOUD?!” It shut him up…temporarily, at least. Some people need several hits with the clue stick before they feel anything. :P

  13. KYM*

    ugh I can relate. I have a client who says completely inappropriate things to me- calls me sexy, talks about “girls” he meets and likes (I say girl cause he does- I get the sense he likes 20 yr olds when he has got to in his 60’s), makes comments about our “relationship”, even went so far as to comment about me and a sexual position! I have tried to shut him down jokingly, which does not work and it has turned to my being very short with him and keeping conversations about business only and won’t even discuss the weather. I have told my company so they did not get sudden complaints about my behavior- I did not want to at first and wanted to handle it on my own but realized it was past that point . they were supportive (how can they not be??) but I still have to work with him. It is awful to have to deal with. And I frankly am just about done with it. I feel sorry for anyone who has to put up with that crap- there is not excuse for it. trust me, I am an assertive person but when it comes to this stuff I am just more in shock and I cannot think of anything to say other than ending the conversation.

    1. Vicki*

      Why do you still have to work with him?
      If this were a co-worker, there would be a sexual-harassment charge in the making.

      Is this client worth so much more to the company than you are?

  14. Ruffingit*

    One thing this letter illustrates is the need to decide, in advance, what you’re comfortable sharing with clients, bosses, etc. If you don’t want to share anything about your relationship, then having some stock answers at the ready for questions that come up is a good idea.

    So many people are simply shocked when they are asked so they reflexively answer. Thinking about it ahead of time and deciding what you’re good with in terms of revealing details can help. It’s definitely something I’m thinking about now that I’ve read this letter.

    1. BookWorm*

      “So many people are simply shocked when they are asked so they reflexively answer. Thinking about it ahead of time and deciding what you’re good with in terms of revealing details can help.”

      Great advice.

  15. Karyn*

    My former boss asked me to take a client to dinner once. He told me to bring my then fiance and another couple to make me more comfortable. I thought, “Great! A way to network with people and impress my boss!”

    The client was the rudest man I’ve ever met. Snotty comments all night about what we all chose to eat (“Red meat is TERRIBLE for your health!” “I can’t believe you eat pasta twice a week!”)… but the kicker was when he (a Jew, as am I), said to me, “You know, you and your fiance won’t stay married. He’s not Jewish, after all.”

    My response, “Well, bless your heart.”

    It’s AMAZING how that will shut people down.

  16. Tbird*

    I have found some great advice on here. I am going through a similar situation, except I am my own boss and I have a new client/partner that has been asking inappropriate questions, flirting, etc.. I opened the door by answering at first too, but I think I was caught off guard by the questions and I am now also in the same position: I need to shut it down!

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