my coworker constantly asks us to loan him money

A reader writes:

There is someone in my company who every week hits up people for money. It’s usually between $20-$100 and he promises to have the money after payday, but then there is always some emergency. I loaned this guy about $200 over two months that I have not gotten back. In the spirit of Christmas, I said let him keep it, he needs it more than I do.

The other day, he tells me that if he doesn’t come up with a certain amount by the end of the day, he would be arrested, but he could pay me back the next day. I told him that mathematically I do not have the ability to help him and that I am sorry. I also told him that I will not react to this pressure, and that the situation did not get to this point overnight, so it was probably his own fault.

From what I am hearing around the office, he has “borrowed” more than $1,000 from everybody, but I do not think the boss is aware of this. He has no money to pay anyone back, yet he is always finding enough money for cigarettes and lottery tickets.

It is more of a nuisance, and I am not about to go tell on this guy, but it really is making it difficult to work professionally, because every time he comes around, I figure he wants to talk about money problems.

The next time he approaches you about money, say this: “Bob, I cannot loan you money. Please do not continue to ask me.”

Don’t tell him that you’re sorry you can’t help, or that you don’t have the money to help him; just say no and tell him to stop approaching you about it. Also, don’t get into telling him that the situation didn’t get to this point overnight or anything else along those lines — that’s just engaging with him on the issue, and what you want is to not have to engage with him about it at all. So it’s a flat no, a “stop asking me,” and that’s it.

If he continues after that, then you say: “Bob, I’ve told you in the past to stop asking me for money, but you’ve continued. This is becoming a distraction from our work.”

At that point, if it still continues, you’d need to either decide to (a) deal with this whenever Bob is around, or (b) give your boss a heads-up about the situation — not that Bob asked for a loan, but that Bob is constantly asking for loans, and it’s making it difficult to work with him because you’re always braced for being hit up for money. Frankly, I think there’s an argument for doing the latter, if only to prevent him from suckering others into giving him money that he won’t repay.

Read an update to this letter here.

{ 148 comments… read them below }

  1. Laurel*

    I don’t quite understand the culture of “I don’t want to tell on [my coworker].” Yes, I get that there are circumstances when going to your boss to complain about a colleague is petty, but this type of situation strikes me as different. It seems clear to me that Bob has a problem with drugs, gambling, or something else. This problem is out of control and clearly leaking into his work life and, as a result, affecting his relationships with his coworkers. Given this, maybe this is something the his boss *should* know? I agree with the advice to say “no” while refraining from apologizing or offering an rationale, but I’d also urge the OP to inform the boss of the situation. It really seems relevant to Bob’s professional interactions and overall work performance.

    1. Joey*

      I don’t get it. What possibly can or should the boss do about non work related agreements between co workers?

      1. Kelly L.*

        If he’s always doing this asking at work, then it’s disrupting the work environment, same as if he were proselytizing them or trying to sell them Amway. That’s the angle to use in the workplace, IMO, rather than the agreements themselves or what he’s using the money for.

        1. Joey*

          If someone came to me with this my first question would be “did you tell him no?” If you can’t answer in the affirmative you’re part of the problem.

          1. thescientist*

            You might not be aware of how persistent people like this can be. I have such a person in my life, and there is always ( and by always I mean several times per week to daily) a crisis that needs to be dealt with right now. Food or clothes for his kids, rent money, bail money, heating bill, and on, and on, and on. “No” does not register. It might defer him for one day, but he comes right back the next. There is no shame, there is no concern for anyone but himself. The person described by the OP sounds so much like the person in my life, and I can tell you that his behavior will not change. You should absolutely tell the boss because it needs to be dealt with ASAP.

            1. Joey*

              If you say no politely the proper response is to throw politeness out the window and be blunt before you approach the boss. Something like “is there something you don’t understand about no. That means not now or ever. Don’t ask me again.”

              1. Anonymous*

                In a professional environment the proper response is typically not to throw politeness out the window, particularly if you’re not in a position to insist on a change in behavior (as the manager would be).

                1. KellyK*

                  Yep, I agree. If you can’t get anywhere by being firm without being rude, it’s more than reasonable to mention to the boss that it’s an issue. Some bosses might want you to take Joey’s approach, but others are going to be more upset with you that you were impolite to a coworker.

                2. Zillah*

                  I agree. While there’s certainly something to be said for being willing to answer unreasonable persistence with blunt rejection in your personal life, I feel like the professional world is a little different.

                  That’s especially true in this case, because the LW is not the only one who is being taken advantage of, and I can’t imagine everyone else is okay with Bob’s behavior. It’s disruptive to their environment as a whole. IMO, the manager should be told about this.

            2. The Cosmic Avenger*

              That’s an excellent description thescientist. These people are very much like telemarketers, master manipulators with reasons that are always unverifiable and counterarguments for every conceivable excuse you might give. I’m just glad I’ve been able to avoid people like that for a while now.

              1. Grace*

                Tell the co-worker with financial problems to go to Debtors Anonymous, a program that deals with people having money problems (debt, underearning, etc.) and teaches them invaluable tools to stay out of debt, pay off debts. There are in-person meetings, telephone meetings, and Skype meetings.

            1. Joey*

              If he’s bugging people at work after they’ve told him no Id wag the finger at him and say “stop it.” If multiple people came to me I’d probably have concerns about his workload.

              But if an employee has a difficult time saying “no” to a co worker well I’m going to wonder about whether he has a hard time in general being straightforward.

              1. De Minimis*

                To me that’s the line that he’s probably crossed, that he is badgering so many co-workers for money that he may not be getting his work done. It’s not that he’s borrowing money and not paying it back, I agree that isn’t the manager’s job to police that.

                Of course, at my workplace he would be violating our policy against soliciting…

              2. Anonymous*

                Why is it more of a concern that someone would be not straightforward than that someone might steal from the company? It seems like there is a disconnect.

                We had a very similar situation at my workplace recently and the begging only stopped when the coworker was fired and jailed for stealing computers. How are my thousand nos that aren’t listened to worse than that?

                1. Zillah*

                  No, but if he’s borrowing from coworkers and not paying them back and they’re starting to tell him no… is it really such a leap to wonder whether he’d steal from the company if the opportunity arose?

          2. Colette*

            I probably would bring it up as “Hey, FYI Bob has been asking me for money. I’ve told him no, but I’ve heard him asking others and I’m concerned that this will cause problems as he has borrowed money in the past that he hasn’t paid back.”

            In other words, while individuals can (and should) say no, but really this isn’t something they should reasonably be expected to have to deal with at work, and Bob needs to receive the message once and for all that this is not acceptable in the workplace.

          3. EngineerGirl*

            That answer works well for rational people. But my experience is that people that do this sort of thing don’t have boundaries and don’t respond to “no”

            1. Grace*

              I’d just tell the co-worker to seek help for their financial problems in Debtors Anonymous, a program that deals with people in debt, under earning, and the like. There are in-person meetings in most large cities, phone-in meetings, and Skype meetings. I told a co-worker who hit me up for money about D.A. and she never asked me again for a loan.

      2. FiveNine*

        But bosses get involved all the time with policies like no soliciting for coworker contributions to your child’s band fundraiser/your Avon side business/etc. (or policies outlining how/when/where you can lay out order forms etc.)

    2. RLS*

      I don’t think that Bob or his co-worker mentioned anything about drugs, gambling, or “something else.” Who has any idea why he needs the money or if he’s actually going to be arrested (doubtful) is not really for anyone to infer.

      1. Laurel*

        True, my speculation regarding the source of the money problem is irrelevant. I maintain, however, that Bob’s requests are creating a very uncomfortable and inappropriate work culture. Given this, Bob’s boss needs to be aware because, simply put, Bob is not conducting himself in a professional or collegial manner.

        1. RLS*

          Agreed. His behavior is definitely uncalled for, and I think that it would be better for a leader to intervene. In all honesty, instead of drug issues, I think the guy just might have social skills problems – lying, boundaries, lack of life skills, etc.

      2. Elise*

        Well, the letter writer did mention nicotine and lotto. But he could also be using the money for other things.

        1. RLS*

          Whoops, I missed that part D: either way though, I just don’t think that the cost of cigarettes (outrageous as they are) would really put someone in that kind of hole. Lottery, maybe. My guess is that it’s just poor money management and a lack of boundaries.

      3. Jamie*

        Not that it matters, it doesn’t, but I was wondering too – about the jail thing. Is there a thing where if you don’t pay a fine by a certain time they lock you up? Or I know a judge can lock you up for non-payment of child support…but by the time you’re in that kind of arrears 20-100 isn’t going to help.

        I’m just curious.

        1. anon in tejas*

          you can be jailed for parking ticket, failure to appear (traffic/criminal court), traffic warrants, unpaid citations, child support, IRS, contempt actions. All of which can be based on not paying the government some form of money. The amount is pretty variable, and if you pay something* the consequences in some cases can decrease substantially

          *something depends on the type of action, total amount and payment amount generally speaking

        2. Cathi*

          My brother in law went back to jail today for being unable to pay a fine.

          From what I understand (we’re in IL), he plead guilty to the thing he was arrested for, and part of his plea deal was probation and paying a fine. Not paying the fine by X date would be a violation of his probation, and he’d go back to jail, which is exactly what happened.

        3. Jessa*

          Yes you can be, however, depending on the offence, if you’re due on Wednesday night and you get paid on Thursday and you can prove this, you can often call the clerk and ask for a one day extension. Unless you’ve repeatedly lied to the Judge, or failed to pay in the past, a lot of them will be reasonable. Particularly if you’re in a situation where you’re not in jail and being allowed to work your regular job (obviously to be able to pay whatever.)

          On the other hand I have never heard of any settlement, fine or fee from a court that didn’t have a date on it, given to a person when they got it.

          So unless the person was stupid enough not to say to the Judge at the time the payment was ordered “Hey I get paid the day AFTER that, please can you make it the next day,” well something is wrong, because the person had notice and should have worked it out earlier than that.

    3. Lindsay J*

      Usually I err more on the side of telling the boss rather than not, but in this situation I don’t really see the need.

      Unless Bob is getting aggressive about asking for money or doesn’t respond to requests to stop asking for loans, I feel like this is something that doesn’t need and wouldn’t benefit from manager intervention.

  2. Ruffingit*

    I would be mortified to have to ask co-workers for money. Amazing how many people have no qualms about it at all.

    1. Guest*

      I might borrow money from a co-worker if we decide to go to a cash-only food cart for lunch, and I will then need to find an ATM so that I can get cash to pay them back. But usually I’ll find an ATM after lunch, even if it means paying the fee for going to a different bank, just to pay them back immediately. At the very worst, I pay them back the next day. Even then, it’s lunch money because they wanted me to join them for lunch, not rent or bail money.

      1. Windchime*

        Totally different. I borrowed a couple of bucks from a co-worker when my Starbucks card was short, but I will pay for his coffee the next time (or two) and it will come out even. That’s different, in my opinion.

        1. Ruffingit*

          Agreed, that isn’t what I’m talking about at all because my co-workers and I have done that countless times. Someone pays for coffee for all, someone else pays next time, someone borrows $5 for lunch because they’re short that day, they pay it back the next day or at pay day or whatever. That is not an issue and is pretty normal. But asking for rent money or money because I have legal issues or whatever? NO. That is not acceptable and would mortify me.

      2. Jamie*

        Totally different – the lunch give and take happens and as long as no one takes advantage it’s fine.

        I will say I’d hate that someone went out of their way to hit an ATM just to make sure I was paid back immediately. If I didn’t have the room to float your burger until tomorrow or whenever I wouldn’t have offered. :).

        1. Natalie*

          Eh, I could see myself doing that just so I wouldn’t forget to pay someone back. This is one reason I try not to borrow money from people!

      3. Mike B. (@epenthesis)*

        Yeah, there’s a crucial difference between “I don’t have cash handy” and “I have almost no financial resources” as a reason for borrowing money.

    2. Emily K*

      Those who are unphased by violating social norms often reap the benefits of people around them being unprepared to hold their ground in the face of such unexpected transgressions.

      1. Ruffingit*

        Absolutely perfect way of putting this Emily K! +1 million to your summation of the issue.

      2. A Hiring Manager*

        Emily-nicely put. There are people who use this as a strategy. Unsuspecting, generous people are targeted by these individuals. Unsaid, it’s expected that if I float your lunch, at some point, you will reciprocate. I have worked with a couple of people over the years like this. If I wanted to ‘remind’ them it had to blunt, and they still don’t pay. I just don’t play that game anymore. Most people are great, but there is always that ‘one’ who benefits without payback.

      3. Grace*

        @Emily: The best response to the borrowing co-worker is to say, “It seems like you’re having financial problems. I can’t help you but the program Debtors Anonymous can help you. Why don’t you go to an in-person meeting, a telephone meeting, or a Skype meeting. They deal with debt problems.”

    3. Windchime*

      We used to have a guy like this at work, years ago. He fancied himself somewhat of a charmer, so he was able to con several women at work into “loaning” him money until it was obvious that he wasn’t going to pay it back. He made a lot more money than we did, too. He was a real piece of work. I was too poor to loan him money so I didn’t get caught up in it, but several others loaned money that they never got back. He didn’t seem to have any shame at all about asking.

    4. Allison*

      Agreed, was under the impression it was generally inappropriate to talk to coworkers about money, let alone actively try to get them involved in your financial situation by way of asking for help. Now, if I’m close with a coworker I might mention snagging something on sale or wishing I could afford X, or whatever, but even then, asking for a loan? Not sure I could put people in that position.

  3. anonymous*

    I have to agree with Laurel on this one. It crosses into a boss’s territory if someone’s behaving inappropriately or unprofessionally and it seems like Bob’s behavior qualifies under both of those descriptors.

    I manage a team of three (ranging from straight out of school to mid-level) and I would want to know if someone was poking around for money and then borrowing money from coworkers but not paying it back. It can destroy the camaraderie in an office and can kill the culture. I consider it part of a manager’s job to try and protect those things.

    Also agree that there’s a clear substance abuse/addiction thing component to this type of behavior so it might be tougher to clear up with a simple talking-to.

  4. Joey*

    Um why is it hard to say “Dude. I’m not loaning you anything anymore because you’ve shown me you don’t pay it back.”

    1. J*

      I think at this point the OP waived that option when he/she said to forget about repayment “In the spirit of Christmas…” But yeah, I would have gladly used your line the first time the coworker tried to hit me up for money again.

      1. ExceptionToTheRule*

        I think the OP can still say that they won’t loan money going forward because they had to write off past unpaid debt. Those aren’t mutually exclusive behaviors to me.

        1. A Bug!*

          Why offer any reason at all? The OP is more than entitled to say “Bob, I will not be loaning you any more money. Please don’t ask me again.”

            1. Jessa*

              I agree no excuse is needed, but I think sometimes you have to hit someone like that over the head, “No I will not loan you anything, and the reason is you never paid me back so I finally got fed up and wrote it off as a holiday present to you, stop asking me. I will never loan you another cent.”

    2. Mints*

      Alot of people are socialized to be nice/polite to the point of being uncomfortable. Not to disagree with being direct, OP should absolutely start saying No flat-out, but I do understand why it’s difficult.

      1. Jamie*

        I know this is hard for some people, but I’m not that sweet. I would be so thunderstruck by the request I would not be able to keep the wtf off my face.

        Trying to imagine a co-worker asking me for money I think my immediate reaction would be unintentionally rude because I’d be so incredulous that someone was asking.

        While technically loans between co-workers are personal business, it’s happening at work and there is no way he’s going to be effective at a job if he’s busy either hounding people for cash or ducking people he owes. A lot of companies have rules against solicitations for charities…this is even worse.

        What a nightmare.

        1. ThursdaysGeek*

          Um, Jamie, I’ve been reading and commenting for awhile, so I feel like I kind of know you a little bit. (Although you might not say the same about me.) Could I borrow about $50 for a couple of weeks?

    3. Tiff*

      Something I’ve learned just from reading this blog….there are a lot of people in this world who don’t know how to politely tell someone else to shove off. I thought most adults knew how to do this, but I will admit that I was wrong, wrong, wrong.

      1. Joey*

        If I had a nickel for every conversation like this….:

        Ee: Joey, bob is doing x and I don’t like it?

        Joey: did you tell bob to stop?

        Ee: well no, but…..

        1. Zillah*

          But there’s a difference between tapping your pencil loudly/chewing gum/whatever and hounding your coworkers at work for “loans” you never pay back.

          1. Joey*

            These are similar problem solving skills I teach to my toddlers. Joey Jr, now did you tell Little Bobby you didn’t want to play with him? Sofie, if little Mikey keeps waving his finger in your face you need to tell him to stop. And if he doesn’t stop then go tell the teacher.

            1. Zillah*

              Yeah, I don’t understand how that analogy makes any sense. We can all agree that there are many issues that should be raised with the person in question before going to an authority figure. However, just because Joey Jr. and Sofie have encountered those sorts of situations in their toddlerdom doesn’t mean that there are no situations that someone in a position of authority is better equipped to deal with.

              1. Jessa*

                The flip side of that is if Joey and Sofie are socialised to NOT make waves or be nasty to people and to go to teacher all the time. “Sofie if Sam takes your crayons you tell the teacher, you do not engage with Sam at ALL.” Is also a lesson kids learn in preschool. That they are never ever to tell the other person anything but to tell someone in authority to stop it.

                1. Jen in RO*

                  I was taught to not make waves and not go to the teacher either… it’s pretty hard to break this “conditioning” and very often I decide that bearing the unpleasant thing is better than confronting it. I’d like to say I’m getting better at this… but I’m probably not.

                2. ew0054*

                  I like to think we have evolved in our society to the point where we don’t just “tell someone else to shove off” as Tiff puts it. We are not in the age of cavemen anymore, where the person with the strongest arm and biggest club wins every argument. We are a society of people with feelings and emotions.

      2. Adam*

        I think society has gotten more sensitive in general these past few decades. This could be seen as a good thing in many ways, but it can have some unintended consequences of not knowing how to properly stand up for yourself when your space is being violated. “Everyone has a story” and all that.

        And yes, everyone does have a story and maybe this guy has some serious issues and isn’t just a poor money manager. Either way though, if you’re not comfortable it serves no purpose to let this guy continue to bug for sake of keeping the peace. Carrying the weight of the world on your shoulders only serves to give you a sore back.

        1. Ruffingit*

          Amen and you know, everyone does have a story, but it’s not the job of everyone in that person’s life to help that story have a happy ending. That is something many people forget. Your place as a co-worker is not to help someone pay for a lawyer because they were arrested for a DUI for example. That is the role of that person’s family or friends – if they even want to do it, it’s not a role the family or friends have to take on either, I’m just saying that it’s more appropriate to ask family or close friends for that kind of help as opposed to co-workers.

      3. Ruffingit*

        It’s actually pretty rare for someone to not only understand what good boundaries are, but be able to enforce them assertively (not aggressively).

      4. JCC*

        Many businesses select for this type of person. If you have trouble saying “no”, you won’t say no when the company needs you to work on the weekend, when the boss needs you to cover for them, or when the company needs you to transfer to another branch.

  5. Mere*

    Our company cafeteria is cash only. If a coworker wants to borrow $10 to go buy lunch, that’s fine. Other than that, no way would I let someone borrow money!

  6. Lucy*

    I will never loan money and expect to get it back. If someone asks me for money, I see it more as a gift. If they want to pay me back, sure. If not, I’ve already moved on with my life. If the amount is too high for me to give as a gift, then I just can’t help that person.

    And I would never gift $100 to a coworker. :)

    In addition – this definitely seems as though something bigger is going on, whether it’s addiction or just flat out inability to handle money. If you’re giving someone money that will allow them to continue destructive behavior, you’re not really helping them at all.

    1. Adam*

      I learned this lesson from a mentor and I think it’s saved me a lot of peace of mind.

      If you loan someone money expect to never see it again. Consider it like gambling. Only walk in the casino with an amount your ok with losing.

    2. Ruffingit*

      I’m the same way. I don’t expect to get the money back. If I do, that’s awesome. If I don’t, it’s no problem because I never put that expectation on it to begin with.

    3. Jessa*

      I never lend money over a few dollars (as others have mentioned for lunch or something,) without a writing. You want more than $20 and it’s going to be “On x date Jessa loaned Louise $50. Louise will pay it back $25 on paydate, and $25 on paydate next.” Signed Jessa and Louise.

      I don’t care if it’s on the back of an envelope, a napkin, a post it note, or an email to Louise from my phone that she sends a response to, but no acknowledgement, no money. And I don’t care if Louise is a friend, a coworker or my cousin either.

  7. Kevin*

    Ugh, this sounds awful. I found back in my day of working retail when people would plead after you say no, you tell them no and I’m not changing my mind. For some reason when you state they can’t sway your opinion it worked.

    I had a coworker once who repeatedly say how she had no money. At least she did not ask for a loan but it would be pay day and she would say how she already only had 38 cents in her bank account when she drove a car that was no doubt way beyond her budget. While I stand by it’s your money and you can do with it what you want, when you talk about people are going to form opinions of you. This woman got promoted but if I had to make the decision on her promotion it would have counted against her.

  8. Kate*

    Only once have a asked to borrow money. I realized right after I ordered food I didn’t have my wallet and it happened to be a bank holiday. My coworker lent me $20, but by the time he got in the next morning I made sure there was a $2o bill and a coffee on his desk. Everyone has stuff happen like that, but if you ever want to borrow money again in an emergency you pay people back in a timely fashion.

    I think at this point your manager needs to be told. This will start to cause bad feelings in the office (if it hasn’t already) and that will effect everyone.

  9. Michele*

    Since the guy has been asking more than one person, and definitely more than once, it’s should be brought up to management.

  10. Lamington*

    We had a coworker like this when I worked in the courthouse. after being asked week after week for lunch money, utility money, money to buy a mattress, etc. I flat out told her: “You are making 40k and you are asking me that I’m part time making minimum wage as a clerk? my check barely covers my gas and parking here.” After that no more requests. Our coordinator told het she will not be the one enabling her bad spending habits. Btw, she was single, no kids, pets, not paying rent either living with someone. We suspected she racked up her credit cards.

    1. Ruffingit*

      Geeze yeah, you don’t ask the homeless guy if you can have his shoes. This is really crappy, the general bills a person might have she did not and yet still had money problems? No excuse for that and clearly she had no shame since she was asking you for money when you made so much less than her. I’m thinking expensive tastes or an addiction on this one.

  11. PoohBear McGriddles*

    If Bob has access to cash or anything of value that might go “missing” from the workplace, his desperation for money needs to be brought to the manager’s attention. I certainly wouldn’t want him making the nightly deposit if he needs money that bad – why tempt him in that way?

    Also, since the OP has told him to stop asking and he continues, that is a work-related problem because it is affecting their work environment.

    If it was just a loan between coworkers that Bob kept “forgetting” to repay, there wouldn’t really be anything the manager could (legally) do about it.

    1. Accountant*

      Completely agree. One of the most common reasons people commit fraud is financial desperation. This guy is already willing to go outside the normal social boundaries of dealing with money in the workplace, so I’d also suggest either mentioning him to your boss, or at the very least keeping a close eye on him.

  12. Ethyl*

    OP, I just want to remind you — “No” is a complete sentence. Reasons are often seen by manipulative people as openings to negotiation. You need to be a broken record on this, and if it is impacting your work then it is definitely a problem to discuss with your manager. You can approach it the way AAM often advises folks to approach difficult issues with their manager — ask your manager for advice on how they would like you to handle this, no tattling necessary :)

    1. A Bug!*

      “No” is a complete sentence. Reasons are often seen by manipulative people as openings to negotiation.

      Yes, this. By attaching a condition to your “no”, you are giving him room to infer that you would give him money if the condition were no longer present. Maybe that means rebutting your reason, maybe it means waiting a while and asking again. Since you’ve given him money in the past – and forgiven the debt – he’s got more to gain from taking the most favorable impression of anything you say to him.

      Yes, Bob should catch the hint and stop asking. But some people are not very good at recognizing hints, and some people are very, very good at actively ignoring hints when it suits them. (The second type of person pretends to be the first type of person, because it allows them to avoid social consequences.)

      Regardless of which type of person Bob is, a clear, unequivocal, unconditional “No, Bob, I will not lend you money, so stop asking me” is the best tool in your kit. If Bob’s just oblivious, then you’ve cleared it up for him. If he’s manipulative, then you’ve taken away his pretext for asking again.

      That way, if he does ask you again, you can go to your manager with a firm foundation. “I need your advice on something. Bob often hits us up for money. I explicitly told him last week to stop asking me, and he’s asked me twice since then. It makes me uncomfortable to have to keep saying ‘no’ to him. How should I be handling this?”

        1. Ethyl*

          Yup. Captain Awkward is a pretty great resource for boundary enforcement, up to and including scripts you can use. I’ve also seen “The Gift of Fear” recommended a lot to learn how to listen to your gut in interpersonal situations (have not read it, have heard the chapter on DV is bad). It can be scary, but standing up for yourself is a habit you can learn!

      1. khilde*

        I think my comment will fit under this discussion. I agree that “no” is a complete sentence and with everything you guys are saying here. One of the hardest things I have had to learn (and am still learning) is saying no and being assertive because I don’t want to hurt someone’s feelings/jeopardize a realtionship, etc. But it occurred to me along the way that I shouldn’t have to worry about hurting people like Coworker Mooch’s feelings because if he cared about being decent to me then he wouldn’t be repeatedly asking for money/making me uncomfortable, etc. In other words – at this point I don’t really need to care about his feelings because he’s so blatantly disregarded mine. That concept has really freed me up from pussyfooting around people that I need to be frank with because they have crossed into jerk territory. If that makes any sens. (I haven’t been commenting much lately because I have too many thoughts, not enough time to type it all out, and I’m not very good at succinctly getting my point across! haha).

        1. Ethyl*

          Yep, that makes total sense — when someone violates the social contract, THEY are the ones making it weird. You are under no obligation to protect the feelings of liars, manipulators, dramallamas, and others who seek to violate your boundaries.

          It’s a hard lesson to learn. My anxiety brain and my depression brain tend to try to convince me I am unworthy of self-preservation, self-care, or basically being treated nicely. I also have an acute case of “OMG maybe they’re right and I’m actually the weirdo!” It’s been a process, learning to care for myself and believe in myself. Good luck!

  13. Ann Furthermore*

    For the life of me I can’t imagine any situation where I’d ask a co-worker to loan me money, other than not having my wallet or any cash on me for lunch. And it certainly wouldn’t be a $200 lunch.

    I don’t even know what to call this. Is it audacity, gall, cluelessness, maybe a combination of all 3?

  14. Just a Reader*

    I wouldn’t hesitate to report this since the behavior isn’t stopping. Looks like the “feeding stray animals” effect.

    In any case, it’s completely inappropriate to badger coworkers for money, and it sounds like the OP is uncomfortable. That’s reason enough to escalate.

  15. Malissa*

    I work with a “bob.”
    First is was she had the wrong card for lunch, then it was she needed $20 so her power wouldn’t be turned off.
    Then I saw her drinking rockstar’s and starbucks and other expensive drinks all day long.
    She hasn’t got a lunch invite and I’ve always been out of cash since then. It only took her two weeks to stop asking.
    The point is when the answer becomes a constant “no” the questions stop coming.

  16. EJ*

    OP, just remember that it is your coworker putting YOU in an awkward situation by asking for money and not paying it back, not the other way around. He broke social convention, not you – so don’t worry about getting slightly impolite or calling him on the fact that he can’t have any more of your money because he doesn’t repay it when he says he will.

  17. Nonprofit Office Manager*

    Poor Bob. This post made me sad. I agree with the group that lending Bob money is a terrible idea for all involved (including Bob), but I really hope he eventually gets help to deal with whatever his root problem is, be it gambling, chronic legal problems, or just terrible money management skills.

    1. Mena*

      You are generous to feel bad for Bob. It well may be that he is lazy and manipulative. Not Poor-Bob in my book.

      Just say no and say no again; he’ll move onto someone that will give him his way.

      1. Nonprofit Office Manager*

        Bob wasn’t born a cigarette-smoking, lottery ticket-buying, coworker-pestering deadbeat with legal problems. Something happened between point A (when he was born) and point B (now). It’s possible that “what happened” is nothing more than a series of bad choices on his part, but I wouldn’t be surprised if he was dealt a bad hand in childhood, perhaps a hand that was tough to overcome as an adult. I’m not defending his inappropriate workplace behavior, and I’m not even saying his personal problems should be a factor in how his behavior is dealt with. I’m just saying that there’s likely a back story behind Bob.

    2. tango*

      Bob might not be broke at all or certainly not be one step away from homelessness. Kinda of like the shoplifter who has $150 in cash in her purse who steals a $5 scarf. Some people do things for the thrill, to get away with it, to see how far they can push the boundaries, to feel alive.
      And then again, Bob could be one of those sociopaths who just doesn’t care. He wants what he wants and if he can get someone else to pay for it, he has no qualms doing so. I’m sure this guy is manipulative in other ways too.

      1. Revanche*

        I have this sibling and yes, he was born that manipulative. He was conning me from Minute 1, because he could. He’d invent sob stories to get my milk bottles (til Mom caught him), he’d talk me out of my candy (it wasn’t for him it was for someone I’d feel bad for!), etc. It literally never stopped no matter how many times he got in trouble and even after I learned he was a user-jerk and said no for ten years consecutively. He’d still put on the Con Man Voice with me and try anyway.

        People who didn’t know him long thought he was *charming.*

        Some people have stories and reasons but some people are just selfish manipulative jerks and it’s not always clear which is which. (Except the former will be very comfortable making you uncomfortable with their inappropriate requests.)

        1. Ernest W*

          I had read a good book a while ago that discusses what you describe. “The Sociopath Next Door” by Martha Stout. It is about 8 years old but was well-written and very memorable. It also goes into how to deal with these people. Like you said, they appear charming and come up with sob stories, and the only real way to protect yourself is to avoid them.

  18. Ann Furthermore*

    I wonder if the OP is a woman, and if he only approaches other women in the office for loans. Women are often seen as a softer touch, especially if you have a tale of woe to tell.

    Last summer after we sold our house we had to stay in a hotel for a few days. One morning I was in the parking lot, getting my 3 year-old into her car seat. A guy approached me and told me a sob story about how he and his wife had run out of money, and needed $80 for gas. The hotel was right off the highway, and he was carrying a gas can, so it was a plausible story, but still. No. Plus I was on high alert since I was a woman alone with a child. He was standing maybe 15-20 feet away from me, and my open car door was between us, but it still made me uneasy. He said, “You can see that I’m not some kind of psycho,” and I said, “Actually, no, I can’t see that at all. And I’m sorry, but I don’t have any cash on me.” Then he got huffy and said, “You could have just said no, you didn’t have to lie!” and walked off. Had he come any closer I would have started screaming at the top of my lungs, but he didn’t.

    I told my husband (who is a very big, scary, intimidating looking guy to people who don’t know him) about it later, and he said, “I wish that guy would have walked up to you when I was there.” And I said, “Honey, that guy would not have gotten anywhere near me if you’d been there.”

    1. Chris80*

      Um, $80 for gas? That amount made his story instantly unbelievable for me. I’d been asked for money for gas before, but that was like $5 so the guy could get home (where he supposedly left his wallet). I don’t think I ever would have done more than $5, and never would have given money if I had felt intimidated at all. I was not alone when he approached me, which helped with that.

      1. Ann Furthermore*

        Well, it could have been that he was asking for $8, I didn’t clarify. But that’s still a weird amount. I told a friend about it later, and he said he had heard that at least in our city, it was the newest scam: asking people for gas money. Because it’s gotten so expensive, I guess the theory is that people will be more sympathetic. But the guy made me very uneasy — just because it’s pretty much common sense for a guy not to approach a woman who’s alone, and his opening remark after, “Excuse me,” was, “I can see that you’re trying to get your little one into the car, but….” and then launched into his sob story. It made me feel like he’d been watching me, and it freaked me out. I’m admittedly paranoid, especially now that I have a child, so it’s possible I overreacted.

        2 weeks later, I was approached by a woman in the parking lot at a grocery store, with a tale of woe about how she’d left her cell phone in the diaper bag at the babysitter’s house, and she was out of gas and couldn’t call anyone and needed money. Or something like that. Included in her story was how she’d been in the parking lot all afternoon and was getting a horrible sunburn. But since there was an air-conditioned grocery store right there, where she could have gone to get out of the sun, I found her story to be suspicious. So I said no, and went on my way. Now, if she had asked to use my phone to call someone, I would have been happy to let her do that. But no, she was asking for money.

        1. Just a Reader*

          This happened to me in a grocery store parking lot at night. The guy was driving to see his dying aunt in florida and needed gas money.

          The fact that he approached a woman on her own in a dark parking lot was enough for me to say no and get in my car and lock the doors till he left.

          There’s a phrase from the Gift of Fear that sticks with me. I’m paraphrasing, but it basically says that if you ask a man when the last time he felt wary of others was, he likely wouldn’t be able to recall. Ask a woman and the answer is recently, today or even every day.

          1. Ann Furthermore*

            Yes, that’s very true. I don’t feel that way very often, but when I do, it sticks with me. Last time was over the summer when I was in Poland on business. The hotel where I was staying was right next to the old city in Gdansk (which is beautiful by the way), but to get there, you have to walk through a pedestrian tunnel that goes under a busy highway. Super convenient, but dark and creepy. I walked through there one day and saw 2 people coming the other direction. I didn’t turn and run, but I definitely gave them a wide berth.

            My husband gets alot of things but he’ll never understand what it’s like to feel intimidated or uneasy by someone else, simply because he himself is a big, imposing guy. People just don’t mess with him. Now of course I know that he’s a great big softie on the inside, but someone seeing him walking down the street doesn’t.

          2. Ann Furthermore*

            And also, good for you for having the sense to get into your car and lock the doors until that creeper left.

          3. Anonymous*

            A lot of men I’ve talked to about this don’t get the size/mass differential that often comes with being female. It’s kinematics – basic physics. It is much easier for average-man to hurt average-woman, even without trying, than the reverse because of the difference in average body masses.

            I happen to be on the very small side. Sometimes when I need to explain to a male why I regard them all as a threat until proven otherwise, I point out a 7-foot guy, or a famous football player. I ask the guy if he finds the larger person a little intimidating. Then I ask how he’d feel if everyone he interacted with was that big. Usually, the prospect of working with an office of football players is enough to communicate the concept.

          4. Kathryn T.*

            I was approached by a guy in a parking lot at 9:15 PM saying he was about to be late to get his daughter from daycare and he was out of gas and he just needed $22 for gas money.

            I said “Oh my GOD!! Where on EARTH did you find a daycare that’s open until 9:30 PM?! I need their name and number — hold on while I get a pen –” and he took off running across the parking lot like the hounds of hell were chasing him.

        2. Rhoda*

          The funny thing is if people just say ‘spare any change’ I might actually give them some.
          But the convoluted sob story is just off-putting and makes it sound like a scam.

        3. Zillah*

          No way. He made you feel uneasy; that’s excellent reason to react strongly, which IMO is a much better term than “overreact.”

          There’s a judgmental aspect to “overreact” that I don’t like; it implies that you were unreasonable. I don’t think you were. You had a strong reaction to a person who approached you asking for money while you were in a vulnerable position in a way that creeped you out. There’s no “overreaction” there.

          IMO, it’s better to have strong reactions in the face of potential danger than to worry about overreacting during or after the fact.

          1. Ann Furthermore*

            Thanks for the validation. It was broad daylight, and there were some other people in the parking lot milling around, so I wasn’t completely isolated. But still…it really rattled me. So much so that I texted my older daughter, who was hanging out in the hotel room by herself, to make sure the door was bolted. The hotel required card key access, and all the rooms were inside (no doors opening directly to the outside) but still, I wanted to make sure she was OK there on her own.

            1. Anonymous*

              Something else you might not have considered: some people approach vulnerable targets when they are in trouble because they personally feel very vulnerable at the moment. They just want to talk to someone who likely won’t make things worse, someone who isn’t scary. This is, in practice, a terrible instinct precisely because it makes the approached person feel exactly the way you did, and thus unlikely to help.

              I am a small woman, and I’ve run into this behavior quite a lot. Sometimes it is scary situations like what you mention – and some of those situations are also exactly what you fear. Other times, though, it’s a genuine request for help. I’ve had complete strangers ask me to help them with the strangest things, just because I am the least scary person to ask. Co-workers also do this to me.

              1. Zillah*

                Hmm. While this can certainly be true, I think that it’s important to draw a distinction between approaching someone vulnerable when you feel vulnerable and approaching someone who’s simply unintimidating. What you seem to be describing seems more like the latter.

                There can be a fair amount of overlap between those two, of course, but approaching someone who looks vulnerable is not only unlikely to get you what you want if you do need help, because you’ll freak them out, it’s also a really entitled, unpleasant thing to do.

        4. Mimi*

          Good for you for listening to your instincts. Like Gavin DeBecker says, there are a hundred little clues that your subconscious picks up on – and that you often dismiss as being “unimportant” or “silly”. But it’s simple survival.

    2. A Bug!*

      I wonder if the OP is a woman, and if he only approaches other women in the office for loans. Women are often seen as a softer touch, especially if you have a tale of woe to tell.

      You are right that schemers will choose their targets carefully. But in the context of the letter, I don’t think it makes a difference who he’s asking or that he doesn’t ask men in the office, if that’s the case.

      If Bob is trying to use physical intimidation to “encourage” women in the office to give him money then that changes the letter’s context entirely. But I don’t think that’s implied, and I don’t think it should be assumed at all until the OP provides information to that effect.

      If Bob is just selecting women because he thinks they’ll be a softer touch, then AAM’s advice is still applicable as-is.

      1. Ann Furthermore*

        I wouldn’t necessarily think it was physical intimidation, just that the perception is that women are an easier mark because they’re going to be more sympathetic to a sad situation.

    3. Nonprofit Office Manager*

      $80.00 for gas?! Talk about a high ball request! I was raised by single mom and while she would sometimes give homeless people money in crowded areas, her hackles always raised when we were approached by strangers when was no ones else was around. I always thought she was overly paranoid and when I became an adult I took the opposite approach, always picking up hitchhikers, etc. That is, until one day, I unknowingly gave a wanted sex offender a ride through literally the most remote area of Washington State. I shudder to think what could have happened. And for better or for worse, I am now paranoid like my mom.

      1. Ann Furthermore*

        OMG! Don’t you hate it when you realize that your mother was actually right! I’m glad nothing happened to you. I would have been sleeping with the lights on for weeks after that.

    4. Allison*

      That’s a pretty common story for scam artists. My city if full of people like that; if you take public transit regularly or spend a good amount of time downtown, you’ll run into someone claiming to be stranded and needing money to get home, or get to a shelter/rehab, needs money for interview clothes, needs to see his/her dying grandma, etc.; a seasoned Bostonian knows to ignore all of these sob stories. Most of us are decent people who want to help those truly in need, but schemers like this ruin it for everyone.

      1. Ann Furthermore*

        I know what you mean. I always say no to people who ask for money, and I never give money to the people standing on the corners with signs either.

        One guy I used to work with said he saw one of those guys one day, standing on the corner by the highway with a sign, and something made him roll down his window and give the guy $40. The guy started crying, thanked my co-worker, and said he’d just been trying to get another $10 so he could get a room at the motel that was right there, so he could get a decent night’s sleep and clean up for a job interview the next day, and now he’d be able to have a decent meal too. And packed up all his stuff and hustled over to the motel before my co-worker made it through the light.

        So there are people out there who are down on their luck and could use a hand, but like you said, the scammers make almost everyone jaded and cynical.

        1. khilde*

          My husband and I talk about this often. I am so torn because I do believe there are some genuine people that chose to ask for help this way. But then we all know of the scammers. I wish there was a better way to weed out the ones that I’d gladly help from the slugs. So I don’t tend to help anyone in those situations because I can’t be sure.

          I have always wondered: Are there other alternatives to begging (or I should soften that and say — alternatives to relying on the kindness of others). But really, are there? Has anyone ever been woefully stranded and was there anything you did on your own to get yourself out of that position without being given straight up money by anyone?

  19. Katie the Fed*

    As a boss, I’d want to know, and here’s why:

    1) Bob is already distracting his coworkers and making them uncomfortable
    2) Bob’s actions could cause problems down the road
    3) Bob may be having some personal problems and I could recommend some things to help him like Employee Assistance Program
    4) Bob may be having some personal problems that make him a liability to the employer, and I need to know that, in case I need to move him away from a petty cash drawer, etc. His inability to manage his finances AND keep it out of the workplace might also make me question if he’s ready for further responsibility in case I have to make a decision like that

      1. Zillah*

        Being a slacker doesn’t negate points 1 and 2, and either way, an employee being a slacker is also something a manager would presumably want to know.

    1. Wong*

      At my first job, I had a team secretary who borrowed money from me a couple of times, and took a long time (weeks or months) to repay. I’d heard that she constantly borrowed money from other colleagues for lunch, transport, etc., and would similarly take a long time to repay them.

      As part of this person’s job, she would help the team with petty cash reimbursements. She would process my taxi reimbursement claims by accumulating the amount over time and giving me the reimbursement, instead of reimbursing me immediately after I made each claim.

      Unknown to her, I kept a record of every single claim I made. One day I realised the amount she gave me was way too low, and I asked her about it. She could see on my computer screen that I’d been keeping a record, and she suddenly became noticeably nervous, and gave me the correct amount almost immediately after that (within an hour).

      I had a teammate who was too busy, or just didn’t care, and took the money presumably without checking.

      I was fresh to the working world then, and if such a situation were to happen now, I would have reported this person’s behaviour.

  20. ConstructionHR*

    Paraphrasing from a thread long ago, by a poster more eloquent than me:

    “Instance 1: No.

    Instance 2: No. Don’t ask me again.

    Instance 3: No. I’ve repeatedly said ‘No’, are you able to stop asking me?

    Instance 4: No. I’ve repeatedly said ‘No’, you said were able to stop, but now it has happened again. Let’s you and I go talk to the boss.”

    1. Lynn Whitehat*

      Mine is “I’ve said no nicely 3 times now. If I have to do it a fourth time, I’m going to stop being nice.” It usually shuts them down. And remember, THEY are the ones making it awkward by violating social norms, not you.

  21. D*

    I think you absolutely need to go to your boss and report him. He isn’t “borrowing” bus money here and there (which can get old pretty fast). He managed to get his hands on $1000 yours and your co-workers hard earned money (which is a lot of dough), and will continue to do so, to probably to fund a drug or gambling problem, like OP said. As suggested, you should tell him you’ll no longer lend him money, but you need to tell your boss. This is a bigger issue that the boss needs to deal with. Why should you and your co-workers have to put up with this? It’s completely out of line.

    People like this play on your good manners, social mores, and your being a helpful, good person. Whether it’s a behavior personality disorder or other problem, it shouldn’t be your problem (any longer). I know I sound callous, but he’s the one who ultimately needs to deal with his own problems, money or otherwise.

  22. Tiff*

    And this is why I will never put “stop cussing” on my New Years resolution list. My mouth would say, “HAY-UL no!” before my brain had a chance to check it.

  23. Wapunga*

    I know I posted this before, but I still think this is a brilliant solution. Here is how my husband handled a similar situation. He was relatively new to his job, but had been given a heads up about a moocher employee.

    Moocher eventually comes around to asking him for money. My husband said he didn’t have the money presently, but he had an empty bottom right drawer to his desk, the only one he kept unlock, and he would put twenty dollars into the drawer just as soon as he could. The moocher could come at anytime without my husband being there and get the money, and when he was ready to pay it back he could just put it in the drawer (ie my husband would never bug him to pay it back).

    Moocher of course agrees. Moocher doesn’t put money back. Months later another person asks my husband to borrow money. My husband explains that there is twenty dollars in his desk that should be there, explaining the system he had with Moocher. If it wasn’t there he could just ask Moocher for it. Person goes to Moocher for it. Moocher doesn’t have it. Moocher keeps getting pestered for the money. Third person asks husband for money….same thing follows. Now Moocher has two people hounding him for the money, husband is out of the loop.

    I know that scenario couldn’t happen in a lot of offices (money would probably be stolen by someone else ) but my husband office was uniquely situated where theft was very unlikely to occur.

    Once word got out about Moocher shenanigans no one lend him any more money. Husband said it was the best twenty buck he ever spent.

  24. PoohBear McGriddles*

    If Bob were constantly asking for a date instead of to “hold a dollar”, he would hopefully be looking at a sexual harassment complaint. In both cases, he is creating an uncomfortable work environment.

    I’ve been approached by guys with gas can in hand needing money. There was this one parking lot where it happened a couple of times. Fortunately, the police precinct was just around the corner in the shopping center, so I referred them there.

    And what kind of gas is he using that needs $80 for 5-10 gallons? That’s between $8 and $16 a gallon. Even jet fuel doesn’t cost that much!

  25. Interviewer*

    I had a guy on my staff who pestered others for money, constantly, including me. He was a courier and got a weekly mileage check at the IRS rate for all of his courier trips, but it was never enough for him. He was always asking me for an advance on that check, or even money for gas to just get to work. It was absolutely ridiculous, and never-ending for the 2 years he was employed here. Finally, he disappeared one day for what he said was a car accident, and he was taking care of the repairs, but it went on & on for a week where he never answered his cell. Finally when he came back to work, we let him go for no-call, no-show. Turns out he had been in jail, something about his car wreck and driving under the influence (pills). It was fairly insane to think of him out there driving around town for work, possibly high, and begging everyone here for $20 for what was probably going straight toward his dealer. Not going to let that go on here anymore.

    I’d tell this guy no, and I’d report him to the boss for pestering you at work. You may have grandly forgiven him in the spirit of the holidays, and I applaud you for being charitable, but you may not be doing him or anyone else any favors by letting it continue. It’s disruptive to the team, the workplace, and possibly the bottom line when you have someone acting like this at work. And as others have speculated, it may be motivated by some very bad vices. Good luck!

  26. Coco*

    My husband had coworkers that asked to borrow money. He solved it by keeping a stash of $100 and told the coworker if & when it wasn’t paid back that was it. There would be no more. Sure enough about a year later is wasn’t paid back. The coworker understood the terms and has never asked for more.

    At my office, borrowing money is addressed in the company policies and I would go to HR if something was as out of hand and disruptive to work as this case.

  27. Book Lover*

    As a manager myself, I would want to know if anyone in my staff was engaging in this sort of begging behavior. These personalities always have other problems associated with productivity and/or moral.

  28. mel*

    Oh man, this guy sounds a lot like my last neighbour who used to constantly bother us for money which I assumed was for drugs, but he’d tell me it was for utility bills. He always had some kind of excuse when we offered to pay the bill directly, and always had a sob story ready for when we said no.

    I agree that the worst thing you can do is look away and say “sorry…” and then come up with an excuse why not, because an excuse is an invitation to more bargaining! After I started challenging my neighbour’s faulty logic and presenting him with his running tab, he wouldn’t ask me anymore (would ask to speak to my spouse because he did the whole “sorry I can’t because…” thing.

    If he owes you $200, then say “I’ve got nothing, but hey, since you’re here, do you have that $200 you said you’d pay me back?” You won’t see him again, heh.

  29. SA*

    When a coworker with bad habits of gambling and spreading nasty rumors about people came to pester me about “borrowing” money I told her to seek help since she made nearly twice what I did and that under no circumstances have I ever loaned anyone I know money. I wasn’t mean but made it abundantly clear she would get no money from me. She was mad and I had to confront her later about a rumor since my idiot employers refused to. I made an enemy then and I still don’t care. Some people are not capable of making friends and use people or try to manipulate them only for their benefit. She was that kind of person. The stench of cheap purfume desperately trying to cover alcohol, fried food, and smoke always made me nauseated around her.

    I would state that what this Bob is doing is harrassing other employees while aggressively trying to manipulate people in to giving him money. He’s created a hostile work environment that will self destruct, has violated company policies (most likely), and has been told no only to make excuses. A supervisor has to step in and if he ignores an authority figure he needs to go. The horrible woman I worked with harrassed coworkers about loans that kept getting bigger but when other employees said no she started stealing from everybody. Another employee brought this to the employer’s attention he refused to believe it and fired them instead. These people are toxic and need to be taken out of the environment that allows them to victimize others by emotional manipulation. If someone doesn’t step in the company and the employees may have money stolen from them. If this Bob has no qualms and seems to justify anything and everything he does to get money from coworkers then there’s no doubt in my mind he will steal from the company or coworkers when he can’t get his way. I’ve seen it happen and it’s not pretty.

    Have a manager/supervisor talk to Bob about getting help. He’ll either get help or start stealing. No one wants to work at a company where a coworker will harass them for money and won’t take no for an answer. It sounds like this person dreads going into work and I can’t blame them. If anything other employees may end up leaving for other companies as that too ended up happening where I used to work.

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