Male Employee Constantly Flirts with Female Manager, Making Her Feel Incredibly Uncomfortable

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Emmy Pratt • Writer and Editor
Jun 7, 2026 12:30 PM EDT

What should she do in this situation? 

Back in the day, office romances were much more common. A ton of people met their future wife or husband at work, but this method of matchmaking has decreased over the past 50 years for several different reasons. People's social lives are much less intertwined with their work lives than they used to be. It's much more common for employees to go to the office, do their work, and leave without ever taking time to socialize with their coworkers. There are some offices where coworkers go out for happy hour Monday through Friday, and all of their coworkers are their best friends, but that is more the exception than it is the rule. If coworkers can't even find the desire to be friends with each other, there's literally no way they're going to date each other. 

Another reason coworkers are unwilling to date each other is that harassment policies can be somewhat unclear about what constitutes workplace harassment. They usually define harassment as making unwanted advances, but how are you supposed to know that the advances are unwanted until you make them? One employee might see unreciprocated flirting as harassment, while another might reciprocate the flirting, start a relationship with the flirter, and get married to them! It all depends on the person, and most employees would rather not risk their careers by flirting with coworkers if they think it might get them in trouble. 

The manager in this story has not reciprocated her direct report's flirtatious behavior. He's clearly not getting the message that she's not interested in him in this way, and she doesn't know what to do about it. He hasn't asked her out, but he clearly has a crush on her. 

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  • Models representing a male employee flirting with his female manager when she's trying to get work done by herself.
    via Walls.io

    Models representing a male employee flirting with his female manager when she's trying to get work done by herself. 

  • My male direct report has a crush on me, his female manager, and his behavior is making me uncomfortable. I am seeking advice.

    Not sure if anyone has experienced this. But it's very clear that a man reporting to me has a crush on me and is now becoming a bit more obsessive. He seems
    via u/EnvironmentalAd2110
  • openly needy for my attention (why did you move our 1:1 by one hour? You don't want to talk to me anymore, do you? lol. Winky face). Ans there are several other clear signs that it's the case. Body language. Choice of words. Etc.
    via u/EnvironmentalAd2110
  • ΠΙΛ
    via Walls.io

    A representation of a male employee, leaning in to flirt with his female manager, who is not interested in him romantically in the slightest. 

  • I know this can happen and often nothing to worry about, but in thus case I am feeling incredibly uncomfortable. I don't know how to address it, as it would be easy for him to deny.
    via u/EnvironmentalAd2110
  • Are there any tips on continuing to work together? Any insights will be deeply appreciated.
    via u/EnvironmentalAd2110
  • CoffeeCrispDaBest My suggestion would be to address some of the unprofessional behavior in a way that doesn't suggest he has a crush on you. For example, when you rescheduled the meeting and he responded with a wink, I would just matter-of-factly explain why you had to reschedule and then ask him to not use the wink emoji in his communication with you. Hopefully, he will get the point that you know what he's doing and that he needs to stop. If he doesn't, at least you have a record to show HR of
    via u/CoffeeCrispDaBest
  • Cheezburger Image 10636688640
    via Andrej Lišakov (Unsplash+)

    Models pretending to be HR employees documenting a case of an employee behaving inappropriately with his manager.

  • FatDaddyMushroom So I work in HR and I have a few recommendations that depend on your comfort level and the severity of your reports behavior. 1. Have a serious discussion about your expectations of professionalism. You want to be direct that you are not interested in socializing and that communication stays job relevant. Then send a follow up email going over what you discussed. 2. Save any texts or emails that make you uncomfortable in case you have to escalate to HR. HR needs some kind of doc
    via u/FatDaddyMushroom
  • 3. It is perfectly fine to communicate that a tone or using certain language makes you uncomfortable. Its not about being accusatory, it's about setting your boundaries and expectations. If you are direct, set boundaries and expectations and he improves then it shows some maturity. If he pouts or gets dramatic at first then improves after the weekend, then he is manageable. If he does not improve or gets worse then you may need to escalate.
    via u/FatDaddyMushroom
  • PhulHouze Avoid mind reading and focus on facts. You can't prove that he has a crush on you. You CAN prove that he is communicating with you in a way that is not professional. Address the professionalism. The fact that you are keeping it about professional behavior should send the hint. If it doesn't improve, document.
    via u/PhulHouze
  • sjwit This is so tricky because, in my experience and observations, anything you say to him will be met with "Oh, you misunderstood", or "wow, I didn't mean anything at all, I was being friendly". I think if I were you I would document 2-3 specific incidents, like the email with the winky face, or a conversation, comment, etc., and meet one on one with him and HR (or someone else in management if you don;t have HR)
    via u/sjwit
  • I'd approach it like this: "I realize that you may not have intended these comments in an inappropriate manner, but it's important for you to understand that what matters is how these kinds of comments feel or sound to others. It is not professional or appropriate to send emails with winky faces to your boss, or to say things like X or Y, and I need you to be mindful of this going forward." Also mention that these are the kinds of situations that can result in harassment claims in the workplace
    via u/sjwit
  • Hollywoode Yup this has happened to me and you just need to be direct and professional, after ignoring multiple text messages with winky faces etc (ignoring was a mistake) he then escalated and when something positive happened he asked me out for a drink and dinner to celebrate and I shut it down and said sorry I don't socialise with direct reports outside of work. But this only works if you genuinely do not socialise with any of your direct reports outside of work
    via u/Hollywoode
  • red4scare Heads up to your boss and HR, cos the first person to talk and get their version out there is much more likely to be believed. You do not need to ask them to get involved, just a "FYI this is happening and I'm handling it". As for handling I'd go the uber-professional way. Winky emoji? I dont think this ia the way you should be using to communicate with your manager.
    via u/red4scare
  • You dont want to talk to me anymore? I'm busy, I'm giving you the same time as I give all my other direct reports. He will say that you are a b or some other mysoginistic cr p cos guys that do not know how to take him. Again, HR must know in a hint are like that, but f advance in case he tries to retaliate.
    via u/red4scare
  • MrsFrugalNoodle I'm a woman working in tech, when I was younger it happened more, now I'm old it doesn't happen as often. Colleagues: those that touch my hand, put their arm on my shoulders, pat me on the back, offer me a massage. I say I'm not comfortable with anyone in my personal space, it reminds me of the sual harassment i experienced as a graduate. That shuts that sh down.
    via u/MrsFrugalNoodle
  • Direct reports: I say clearly that we have a professional relationship that I'll be the one evaluating their performance, put people up for promotions, training and learning opportunities, be responsible for firing. Any appearance of special favours or preferences is unethical for the team. While we are friendly, we are not friends and interactions needs to align with that line so the managerial responsibility can be maintained
    via u/MrsFrugalNoodle

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harassment employee flirting manager message uncomfortable crush
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