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My coworker - who is a very talkative person - suddenly came to me and told me that he is off the following day and asked me whether I was off the next day, too. I told him that I would be working. Then he asked me when am I'd be going to take him on a date. I brushed it off, since I assumed that he was joking, which I told him, reminding him that I had already told I that I had a boyfried when he asked me earlier. However, he insisted that he was not joking.

I ignored him, but he kept asking over and over again when I'd be taking him out on a date. I said that this would never happen. He said "stop it", but the next day he told me, not to make any rush decision, but rather think about it. I said that there was nothing for me to think about. The answer will still be no. He asked me whether I have someone? I told him that I indeed have someone to which he replied that I should have just said that. I said that I thought that he was joking since I had already told him that I'm not single. Hence I didn't take the request seriously. Then later on he asked me again and I asked him whether he was deaf, for I already told him I had a boyfriend, but he accused me of lying and asked me where I lived, since he wanted to come over? I told him that I would not tell him where I lived and that even if I was single, I would not want him around, since I prefer to keep work and pleasure apart. Then he said that we won't pleasure ourselves here at work. I still said NO and he was like "alright I guess it's no then". I thought that was the end of that until I saw him the following week.

He came to me, winked at me and asked me whether I did miss him. I bluntly said NO, but he insisted that I would have missed him and just lied to myself. Another time I told him that I only liked him as a coworker. He asked me why I was so mean to him and told me to smile for him then.

I never said anything to encourage or lead him on but he is being weirdly aggressive about it. And it's hard to tell whether he's just joking. It was brought to my attention that there are other people who overheard him talking about his girlfriend. And another coworker that I confided in insist that he must be joking. When I asked him he din't outright deny it but he said he never told anyone about his private life so there's no way anyone would know if he's single or not. He's making me uncomfortable, should I report him?

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    Country tag is pretty important, can you please add that? Dec 17 '19 at 23:46
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    The title is misleading, this behavior is no longer "flirting".
    – usr1234567
    Dec 18 '19 at 10:15
  • OP, I have edited the title and tags of the question. The behavior you are referring to in the question body goes well beyond what people usually associate with "flirting" and the key fact that you have rejected him previously is materially important to the context.
    – magisch
    Dec 18 '19 at 12:29
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    Whether you have a boyfriend or not is none of this guy's business. You don't need an excuse to tell him to get lost.
    – henning
    Aug 19 at 22:09
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You can report him right now if you want. You have more than enough to make a solid case.

But if I were you, I'd give him an ultimatum via email.

If you ask me out one more time, I will report you to HR for harassment. Do you understand?

The same goes for any joke or flirty comment. If those continue too, I will report you right away as well. Again, I am not interested in you in any way shape or form. Don't make me repeat this. I do not want to go out with you. I do not want to flirt with you.

And please don't try to soften the blow by saying that you're in a relationship. That time for niceties has long passed. And saying that you have a boyfriend can imply that you would go out with him if you didn't have one. If you say that, you'd have opened the door to him asking you "Have you left your boyfriend yet? Have you left him yet? How is so and so? Is there trouble in paradise?"

And giving that ultimatum via email is better than doing it in person. It creates a written record and timestamps it. If you do it in person, he might try to preempt you and accuse you first to HR.

And of course, an ultimatum is no good if you don't enforce it. If he replies by denying his behavior, or saying that he was joking, or anything of that nature, without actually saying that he's going to stop, go ahead and report him.

The same goes if he follows you home, or anything like that. Call the police if he does that. After you send out that email, do no longer try to reason with him. Some people crave negative attention. Do not even give him that. If he doesn't respect your boundaries after this email, let HR or the police be your intermediaries.

And if he still wants to be friends, please say "no" to that as well. Do not leave any wiggle room for misunderstanding.

No, we can't be friends. All my friends can take "no" for an answer without the threat of HR hanging over their head. For that reason, you can't be my friend, and you'll have to find friends elsewhere.

You can be my work colleague. When we have to work with each other, we can be civil and cordial to each other, but that's it. I offer nothing more and I want nothing more.

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    Plus, immediately write down all these interactions with as exact times and details as you can remember; include any emails or texts or other recordable items, so that when you go to HR it's not "first strike" there's a lot of backing documentation.
    – mxyzplk
    Dec 18 '19 at 4:43
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    Also, if possible, OP should see if there is coworkers who witnessed the behavior and asks them if they'd be willing to back them up if things escalate.
    – user3399
    Dec 18 '19 at 8:21
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    I disagree with a small part of this. Don't tell him you're uncomfortable. Don't play the victim in any way. Take the upper hand. Tell him his attentions are not required and unwanted and will have severe consequences if continued.
    – user207421
    Dec 18 '19 at 8:33
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    @Martijn, I suppose "Do you understand?" is enough, but I don't get why you want to include "If you have any questions, feel free to ask". Dec 18 '19 at 12:47
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    I have had to deal with personalities described by the author, best leave them no path, to weasel out of their responsibilities.
    – Donald
    Dec 23 '19 at 23:51
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Then he says where do you live? I want to come over at your house.

You can ask once. You can ask twice, to make sure. (And some people would even disagree there). At that point any sensible man (or woman) would stop. But that sentence, that is deep into worryingly creepy territory. This is a situation where you should go straight to HR. Then find out where you can buy some pepper spray. This isn't flirting, this is harassment.

PS. The question has changed since, the quoted line isn't there anymore.

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    And don't rule out going straight to the police, or a lawyer. There are such things as Apprehended Violence Orders in some jurisdictions, or at least maybe the cops will have a little chat with him that should scare the bejeezus out of him.
    – user207421
    Dec 19 '19 at 23:48
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    PPS. The question is still there, just worded differently: "[He] asked me where I lived, since he wanted to come over?"
    – Belhenix
    Dec 20 '19 at 23:33
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I ignored him, but he kept asking over and over again

With individuals like this, you cannot ignore, you must demand. That demand should be with a serious demeanor. Often such a response right at the start prevents such follow-up trouble.

If you are forced to talk to him now, do not explain things giving lists of this and where we can and cannot interact (which is where I disagree with other answers). Instead, with FIRE tell him to back off, warning if he does not he will be reported to HR immediately. If he does not back off report him. Hopefully he will be removed and then make sure you protect yourself like gnasher729 mentions. This is creepy/stalker behavior, so don't take any chances.

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    Not only demand, demand LOUDLY. In front of other people. The OP has no reason to be embarrassed about this. Make sure there are witnesses so there isn't any question what's going on.
    – DaveG
    Aug 19 at 0:07
  • I wouldn't recommend making a scene in a professional environment. though. I think reporting would be the correct way to go, a warning might be a good addition though.
    – Mathijs
    Aug 19 at 6:06
  • @Mathijs the OP needs to make the harasser's behavior visible to other people. Politely saying "no" isn't working. The harasser needs to understand that there's going to be consequences in the workplace if he keeps this up.
    – DaveG
    Aug 20 at 3:37
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IMO you are dealing with a borderline or full blown high conflict personality. Most likely a narcissist. To assess this, you should do a WEB analysis, WEB standing for Words, Emotions, Behaviour.

Do they use all-or-nothing words ("my way or the highway")? Do they evoke powerful emotions (you feel like he's a wonderful human being, too good to be true, or an absolute creep, he makes your skin crawl)? Does his behaviour seem out of place? Would 9 out of 10 people behave like him in a similar situation?

The key characteristics of narcissists are a hyper-inflated self-image (they are superior to everyone else, especially your significant other), they feel entitled to special treatment so normal rules don't apply to them (they just ignore office politics, internal regulations or social norms in general), and usually they lack empathy, so they can be very pushy, insulting or demeaning to others in public. Narcissists don't have significant relationships with anyone but themselves, they use relationships with other for their own gain. They also act the way they do because that's who they are, no conscious intent.

The best way to deal with a narcissistic HCP is to stay off their radar. Unfortunately that's too late now.

Dealing with narcissistic personalities at the workplace usually involves avoiding them, not trying to prove them wrong, not trying to provoke them by setting ultimatums, not pointing out their lies or deception in front of others, not responding with funny comments or putdowns. Just being calm, nonreactive and disengaging from the conversation usually stops them from paying attention to you.

If you have to talk to him, use empathic, respectful statements. They seem to crave respect most, so statements like "I respect our working relationship very much, but unfortunately I'm not ready for a new commitment" might do the trick.

Talk about other options or choices to avoid becoming the narcissist's target. Turn their ultimatums into choices. They demand a date, you turn that demand into a choice. "I can't date you because I am in a relationship. You're a charming individual and I'm flattered by your attention, how about we talk about this when I'm no longer with someone." You must be very careful as they are very bad at handling rejection. Seeking revenge for being rejected is the most common trait of a narcissist. You do not want to become the target of blame for a high conflict personality.

Setting boundaries is very important. Do note that setting boundaries with narcissistic personalities might result in you getting fired or otherwise hindered in your career path if they are your superior. Use empathy, attention and respect when setting boundaries. Respond with accurate statements to all incoming criticism.

Ultimately, the best way to deal with this person IMO is getting off their radar. Avoid being their interest. Involving HR might just make you their target of blame.

@Jenny99: Please read up on managing narcissists at the workplace for yourself and decide if my advice is worth taking or if you want to aggro this person even more on yourself.

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    Strongly disagree to everything here — I literally cannot comprehend telling the OP that they should be "calm", "respectful", "stay off the radar" and avoid becoming the "target of blame" and trying to rationalise the behaviour of other person as having "no conscious intent". Would downvote this more than once if I could Aug 19 at 8:42
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    BoboDarph showcasing a bit of a high conflict personality themselves.
    – user72058
    Aug 19 at 9:18
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    "I respect our working relationship very much, but unfortunately I'm not ready for a new commitment" - This is shockingly bad advice.
    – Eric Nolan
    Aug 19 at 9:37
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    I regret that I have but one downvote to give.
    – Unfair-Ban
    Aug 19 at 15:04
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    -1. This advice only applies if you want to keep that narcissist in the workplace, but it's not up to OP to change the way she behaves to better deal with her harasser. The harasser needs to learn how to stop acting like this or be taken out of the workplace by HR/police. Your answer only benefits the person who is in the wrong. Aug 19 at 18:13

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