How to Tell a Flirtatious Boss to Stop Hitting on You

Flirtatious bossWhat should you do when a flirtatious colleague — one who’s kind of your boss — is hitting on you at work? Reader J wonders…

I am a (female) BigLaw associate, who has become the focus of flirtatious attention from a (male) partner, who (1) works in another, but near-ish office, (2) is on the Executive Committee, and (3) has quite a reputation for hitting on firm employees (attorneys and non-attorneys alike). My friends/colleagues’ advice has generally boiled down to: Don’t outright reject him, stroke his ego, etc., but continue to deflect invitations for dinner and drinks. A few have suggested telling him I am not comfortable dating someone at work (which is true). What is your and the readers’ advice re (1) how to handle his attentions and (2) whether I should report him to someone in the firm? FWIW, I have been aware of his reputation of flirting with other attorneys, but have learned of his recent shift to a staffer.

Yeouch. We’ve talked before about handling a flirting client, dealing with unwanted attention from older men while networking, and even about dating at the office — but not this particular situation. In my legal-eagle days, I would have considered any partner (even if he was in another office or another group) to be my “boss,” and someone who sits on the Executive Committee — presumably with firing powers — to especially be my boss. So I can see why Reader J is concerned, and I’m curious to hear what the readers say. (Pictured: Hey so I was wondering if maybe you might want to…, originally uploaded to Flickr by nate bolt.)

A few thoughts:

  • Be polite but direct. “Thank you for your interest, but I don’t date coworkers.” Period, full stop, end discussion. (Or EVEN: “I’m flattered, thank you — but I’m not interested.”) You can come up with another reason if there is one — you only date Roman Catholics whose birthdays fall under the sign of Aquarius, for example — but I think the answer here needs to be an outright, explicit NO. I actually totally disagree with your friends’ advice re: “stroking his ego” and “not outright rejecting him” — he’s a big boy, he can take it.
  • If the direct route is hard for you to do (and don’t beat yourself up too much if it is), you can always take a few other routes to “no.” What are you doing this weekend? Attending my boyfriend’s kickboxing competition, thanks! Yes, it’s a new relationship — we met at the gun show.

As far as reporting him goes — have you taken the steps above and been very clear with him that dinner and drinks are not on the table? Does he persist? Now we’re getting into territory that is less gray. Has he ever made physical advances toward you? Has he ever suggested your job might be somehow related to dating him? Do you feel like he might speak ill of you, without giving context, to other partners? All of these would nudge me more toward “tell HR.” I suppose the safe money would say to go ahead and tell HR regardless — perhaps a quick email after you have that “polite but direct” conversation we talked about, just to give them the heads up — readers, what do you think? How would you handle unwanted advances from a person of authority? 


  1. Anony-mouse :

    Document, document, document. Make sure he knows that you’re not interested. If he continues, keep a record of it. If you’ve ever made yourself clear to him that you were either uninterested or uncomfortable, and the behavior continues, get thee to HR or to any other reporting mechanism that your firm provides. This is more about protecting yourself at that point.

    • Just don't :


      Also +1 to: “I actually totally disagree with your friends’ advice re: “stroking his ego” and “not outright rejecting him” — he’s a big boy, he can take it.”

      Be polite, be direct, keep conversations and interactions strictly professional, and document. Let HR know if his behavior persists despite your stance.

      • S in Chicago :

        Don’t stroke his ego. While you may win points with him, you’re losing them with everyone else around you.

        • Word to your mother, Chicago. Every around you will know what you’re doing and may even understand why you’re doing it to some extent, since his reputation is known; however, people will still lose respect for you. Just sayin’ yo!

  2. I don’t think that HR needs to be involved unless (1) you say a polite no, and he persists, or (2) he does or says anything that smacks of your job success (or failure) being tied to your response to his advances.

    I agree that you don’t need to stroke his ego or not outright reject him. You do need to outright reject him. Once, politely, and then don’t escalate it unless he persists. But “I’m not interested” is a perfectly acceptable response.

  3. “If the direct route is hard for you to do (and don’t beat yourself up too much if it is), you can always take a few other routes to “no.” What are you doing this weekend? Attending my boyfriend’s kickboxing competition, thanks! Yes, it’s a new relationship — we met at the gun show.”

    I really dislike this approach. He should stop hitting on her because SHE said no. She shouldn’t have to invoke another dude just so that he’ll stop hitting on her because now he feels bad that he’s stepping on that other guy’s toes. This isn’t about some unspoken bro-code. It’s about her having agency and saying no for herself, and that being enough.

    • Senior Attorney :

      Amen to this!

      Although the very sad thing is that the “other dude” method is much more likely to be effective.

      • TO Lawyer :

        +2 I hate that I can’t tell a man I’m not interested and get him to back off, but the second I mention an imaginary boyfriend, it’s over.

    • Wildkitten :

      Amen. I hate this.

    • A professional woman :

      I definitely think the imaginary boyfriend is the way to go. While in a perfect world, saying “I’m not interested” should be the right approach, it could make him upset which could have a negative impact on you. The imaginary boyfriend at least lets him know that you’re not interested and from personal experience, many men tend to respect another man’s “turf” a whole lot more than they respect a “no, I’m not interested.” I think some men hear “I’m not interested” and take it as a challenge and become MORE persistent.

      • AAAAAARRRRRG tearing out my hair over here. No. Just, no. Do not entertain the notion that it is okay for a man to hear “no” and think “challenge! she must really mean ‘yes!’ or ‘be persistent!'”. Under no circumstances is that okay.

        • Blonde Lawyer :

          If you are trying to change the world I agree with you. I agree with you if OP were dealing with guys at the bar. But, if you are trying to survive in the workplace, where you are not going to change the world without first burning a few bridges, the path of least resistance might be best.

          • But if a female attorney in BigLaw can’t say “No” to an advance, on her own merits (not some imaginary boyfriend’s), then who CAN say that at work and have it be acceptable?

          • Blonde Lawyer :

            Law firms are the worst at following the laws.

        • AnonLawMom :

          I don’t think anyone is trying to say it’s okay that this is how men react, but it often is reality.

  4. Jumpingjack :

    This sounds like he might not be expressly asking her out, but is being inappropriately flirtatious. That would make it more difficult to reject, since there is no specific request to say no to. If that’s the case, how could that be handled? Dropping mentions of a boyfriend and being extremely formal and professional, are two ideas that spring to mind.

    • ExParalegal :

      A reminder to keep conversation professional or appropriate, or expressing a feeling of discomfort. I’ve done this. It helps.

  5. Taser?

    Sorry, this is a sore spot for me right now. I hate what women have to deal with in the workplace. (And in life.)

    • +1. Following up on my comment on the morning post a few weeks ago–still struggling with my boss, but thankful for everyone’s advice that I have not been overreacting to inappropriate behavior at work. It really stinks that women still have to deal with these issues in 2014!!

  6. Make expectations clear (that he should not have any), document contemporaneously, consult a lawyer, and avoid being alone with him. Complain to HR if it persists. Be explicit about the facts in your complaint. I am an employment discrimination lawyer. His behavior is not only inappropriate, but illegal if you make it clear that his attentions are unwelcome, and they impact your ability to do your job.

  7. ExParalegal at BigLaw :

    As an ExParalegal at BigLaw, THANK YOU for looking out for the “staffer”. She is NOT in the same position as you, and Kat did not address that part of your letter. Because you have the ability and freedom to say no as more of an equal to this partner, you MUST speak up for the staffer – please, take that part of it to HR, talk to staffer and let her know you’ve got her back, talk to the Staffer’s manager.

    THANK YOU. I saw this happen too many times…

    • This. Even if the LW can handle this a-hole, the paralegal has no recourse, no leverage. I would contact HR regarding his behavior towards the staffer. Depending on who exactly is HR (e.g., someone who isn’t sensitive to these complaints from women), consider asking a male ally to contact HR with his observations. I hate that HR might take a man more seriously than a woman, but it happens and protecting the paralegal has to be priority #1.

    • Anonymous :

      Although I feel for the staffer in this situation, I really really disagree that OP should do anything about the situation with staffer. OP said she “learned of” partner’s intentions toward a staffer. That suggests that she hasn’t directly witnessed anything. If you see a guy pinch a secretary’s rear in front of you, absolutely you should tell the DOOSH to knock it off. But OP is not the office sexual harassment police. She should not insert herself in a situation that has nothing to do with her. She needs to manage her own relationship with this guy and move on.

      • He has a reputation, & he’s doing it again to the OP. If he hasn’t been reported to HR for inappropriate behavior in the workplace yet, he should be. “Unwelcome sexual advances” in the workplace are considered sexual harassment by the EEOC. According to this post, this guy’s advances are of a sexual nature & they are not welcome.

        Report him.

  8. In a perfect world, you should be able to go to HR to get it to stop if your requests to make it stop are ignored. In BigLaw reality, you are likely to have your work taken away from you and HR is still likely to not be able to do anything despite it now affecting your ability to do your job. I don’t know what the right answer is because most of what I did was ineffective at getting such behavior to stop. I was lucky that my managing partner was a reasonable and good guy and very sternly spoke to the partner in the lobbying practice of our firm who referred to me as a dirty wh0re in an email where other lawyers were copied. You know, because I was dating a man he knew outside the firm and he thought it was HIGHlarious.

    This whole topic makes me so mad. UGH.

  9. It sounds like the guy is being annoyingly flirtatious, rather than making sexual advances. If this is the case, and you have long term career ambitions – don’t blow it by running to HR at this stage. You will be seen as a snitch and potential troublemaker. Sad but true – that’s the boys code!

    You need to strike a balance, which is professional, gets the message across, but gives him a graceful way out and maintains your place in the team.

    Next time he says something that makes you uncomfortable – why not just say lightly but directly “Are you flirting with me? I’m not sure that is appropriate, is it?”

    If he says “I was just having fun” – you could respond with ” actually it makes me feel a bit uncomfortable, especially as you are my senior”.

    That should get the message across without damaging the relationship – then you need to follow up with a great piece of work, to remind him what a valuable member of the team you are.

    • Wildkitten :

      I think the jerk would interpret this as flirting: “Are you flirting with me? I’m not sure that is appropriate, is it?”

  10. Ugh, how horrible. I just attended an ABA discussion on gender harassment and basically the system is super stacked against us. In a perfect world, (and maybe one we should strive for), you could say–without smiling or laughing–I’m not interested or I don’t think what you’re doing is appropriate. And that would be that. But in this non-perfect world, it’s extremely hard for women to be that forthright (for multiple reasons). You have to decide do you cringe and bear it or do you confront him? I don’t think there’s a real middle ground, and each option has negative side-effects. It’s just super crappy all around.

  11. MustangSally :

    Unfortunately, I was in a situation where my direct managing partner was openly hitting on me. He’s married. I’m married. I’m also 30 years his junior. We had lots of work-related travel together, and that is when the advances began. I am a litigator and generally a tough chick. I certainly thought if I ended up in this position I’d tell the guy to take a hike. In reality, it’s so incredibly hard when that person holds the keys to your future employment, receiving work, etc. I ultimately decided to be very cold/unfriendly toward this partner and would deflect any advances by changing the subject. I did finally stand up for myself when he began to try to touch my hair, touch my face, put his arm around my shoulders. I felt literally sick from the touch and told him very clearly not to touch me. Eventually, another male associate in the office saw/heard some of the advances and told another male equity partner. The equity offered to take the issue up the ladder, but I felt that I was dealing with the situation and did not want to be known as the woman that forced managing partner into retirement. I thought no one would want to work with me (even though I know that is so ridiculous). I now have no cases with creepy managing partner, and we generally don’t speak often. My career has since taken a huge upswing, and I am working with many attorneys from other offices on exciting cases. I’m not sure those opportunities would have occurred had I “made waves” within the firm. I think I made the right choice, but it was 18 months of hell. I don’t think there is one right way to handle this. I think you have to take care of yourself and trust yourself to know how to do it.