I'm a developer/dba in my mid-twenties working in a fairly large company. Recently, I was brought onto a project to help refactor/update a legacy codebase. My task lead (who I'll call Bob) is a bit older (early/mid-50s) and is generally a nice guy. However, he'll often talk about things that really irritate me or make well-meaning, but hurtful comments.

For example, he'll be talking about hook up culture and ask for my opinion on particular situations. Or he'll be reminiscing about some woman he did or didn't get and expecting me to give my view. I don't really mind hearing about it, but I don't really want to discuss it. Just not my style. However, he'll often preface the whole thing with "As a woman, what's your opinion on [insert topic here]?" And I'll feel obligated to give some kind of answer. I can deal with it, but it annoys me and I'd rather find a way to redirect the conversation.

On a similar note, Bob will sometimes make comments or do things that end up making me feel a bit hurt. For example, he'll tell me that I shouldn't have such high standards when it comes to dating (and seeming to insinuate that if I don't, I'll end up alone). I've never really had a problem with dating, but comments like that still hurt. He's also tried multiple times (unbeknownst to me) to set me up with some of my male coworkers, which I consider borderline inappropriate and something I'd prefer to avoid.

This is all stuff that is annoying/mildly hurtful, but is mostly manageable because Bob only talks about this stuff if no one else is around. However, the thing which I absolutely cannot stand is that he'll almost always make some comment that draws attention to my gender when we're meeting with clients. I'm often the only woman in a group of 20+ guys and it just makes me feel so awkward. I don't want to be rude or offend Bob because he means well, is a genuinely nice guy, and we get along really well otherwise (we both love football, are really into cooking, can talk about random stuff for ages), but I want the rest to stop.

How can I redirect the conversation/avoid discussing certain subjects without making things awkward or offending Bob?

  • 3
    What is wrong with "Bob I am uncomfortable with these conversation in general. let us talk about football instead" ?
    – PagMax
    Commented Feb 2, 2018 at 7:19
  • 2
    Which country is this?
    – gnasher729
    Commented Feb 2, 2018 at 8:06
  • Maybe take a look at IPS as well Commented Feb 2, 2018 at 12:08
  • 10
    This question should probably be tagged with sexual-harassment (or at least harassment). Even if Bob "means well" or is a "nice guy", his behavior is disrespectful and unprofessional.
    – MikeQ
    Commented Feb 2, 2018 at 16:20
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    The first the you need to do before you consider all of the advice in the answers below is to stop telling yourself that he is a nice guy. Nice guys do not behave this way. He is manipulating you and you know it even though you hope it’s not true because that would make life a heck of a lot easier. You don’t have to make it obvious to him that you know he’s not nice, but you really need to stop dismissing your intuition. Taking a self defense class is one way you can get more comfortable trusting that feeling and acting appropriately. Practice helps.
    – ColleenV
    Commented Feb 5, 2018 at 21:45

3 Answers 3


To put it bluntly this is sexual discrimination bordering on harassment. I don't think Bob is a genuinely nice guy, at all, as his behavior is so inappropriate, even simple cluelessness does not cut it as an "excuse".

To be clear, he is not harassing you in the typical "sexual" way but he is harassing you simply for being a woman. There is no reason to accept nor entertain this line of discussion, especially at work, in spite of the fact that he is "friendly" about it. This is so grossly out of line, I don't think you should worry too much about offending him - if he is offended, too bad. If he feels awkward, honestly he should!

OK rant over.

I would start by responding to these topics of conversation with something along the lines of "I know we have had a lot of conversations about my views "as a woman" and we have discussed my personal life in the past and I should have said something sooner, but this is really inappropriate conversation for the workplace and it makes me uncomfortable. It's very unprofessional to discuss these topics at work, and I don't want to have conversations like this anymore." You can be kind, you can be friendly when you say it, but be firm.

Do not get sucked into explaining/defending your reasons. If he asks, just reiterate that it's wholly inappropriate. If he says something in the direction of "but you never said anything before?" respond: "I am telling you now".

Be sure to not get into re-hashing past behavior - the point is to stop future behavior. Stay on point, stay "here and now" and make it clear you will not tolerate this going forward.

That may or may not end the behavior. If he really is a nice guy I think he will adjust and stop acting this way. Regardless, you should start documenting any incidents of this kind immediately as you may need to take this to HR.

The fact that he only talks about this stuff when no one is around leads me to believe he KNOWS it's inappropriate already.

No, not a "nice" guy.


First, I am in my sixties so I am older than he is and I know what people his age have already been exposed to. He would have been in the workforce the first time that sexual harassment became a big issue in the 1980s. So there is a good chance he was aware of what was defined to be acceptable and what was not. So yes, he is likely well aware he is being harassing. So don't buy any excuses that this was innocent or that he didn't know better. He did or he should have because sexual harassment rules in the workplace have been around for a long time. It would actually be more likely that he was unaware if he came into the workforce in the late 1990s or later when this type of training had fallen out of fashion. That fact that he pressures you on these uncomfortable topics only when others are not around indicates he is aware as well.

So there is no need to feel bad about confronting the issue. He knows he is out of line.

That said, I would likely leave the comments and questions alone until you resolve the most important problem - that of always pushing that you are a woman in front of clients. Start with this topic. The next time he does it, approach him in private as soon after the incident as possible and ask him why he did that and tell him it makes you uncomfortable. Note the date and the details of the discussion in a notebook or file. If he stops, fine no problem. If not, then remind him again after the next meeting where he does the same. Again document. Third time you talk to his boss or HR. Remember if he doesn't stop after being requested, this is not a nice man, no need to feel guilty for insisting he treat you professionally. A nice man would stop after the first request to stop.

This is the most important place to start because he is likely trying to trivialize your work in front of clients. This has more potential impact on your career than the private discussions.

Once this is fixed, then when he discusses a topic you don't want to discuss, change the subject. If he doesn't respond to that, then directly ask him to stop talking to you about these things and start documenting.


As a start, tell him in the strongest possible way that you find his subjects totally inappropriate, that he is creating a hostile working environment. Don’t give hints. It is obvious that Bob is no a person who understands hints.

Buy a notebook, and every time he says something that upsets you, you write it down, clearly visible to Bob. That serves two purposes: First, it gives you evidence. Second, it puts Bob on notice that you are not tolerating what he does and will take action.

Not offending Bob should not be your objective. His behaviour is something he can get fired for in many western countries. If it offends him to be told to stop such behaviour then he needs to be offended.

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    I feel like this is to harsh of an Approach since they have a friendly relationship. Commented Feb 2, 2018 at 12:06
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    IF it's too harsh, a variant is "please don't discuss this with me again; I don't want to have to start keeping notes." And then when it is discussed again, take a note. Commented Feb 5, 2018 at 22:03

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