I didn't actually date this guy, but not for lack of him trying. This guy randomly started talking to me on Facebook. I didn't/don't have many friends, so I talked to him occasionally. It didn't take too long for him to start messaging me pretty frequently, and getting weird about it too. He always talked about how rich his family was, what a nice house he lives in with them, and how much extra money he has (he was in his thirties and worked for his dad). I guess he thought it was cool to be "wounded" or something so he kept telling me how he used to party all the time and experiment with drugs, which for some reason made him weep on voice calls.
But what really irked me was how innapropriate he'd get. He would tell me how pretty I was, how he wanted a girl like me, yada yada. I tried to ignore it. Then he started asking me for pictures of me, then nudes. I was beyond uncomfortable with that, because 1. I have a boyfriend and 2. I'm only 23. I told him this numerous times. He'd apologize, grovel,complain that no one understands him, and then repeat the same thing the next day.
So, about a month into talking to him, I got my laptop we're, and it was destroyed. When I mentioned this to him, he started insisting that he would send me a new laptop. When I declined, politely telling him I felt uncomfortable receiving such a gift from him, he freaked the fuck out, insulting my family, my mental wellbeing (I had told him I suffer from anxiety) and ranting about what a nice guy he was, I never cared about him, he was just being nice by talking to me because he's actuay too good for me, ect. I didn't respond.
For the next week, he send many messages apologizing, so I decided to accept his apology, but didn't rely message him much anymore.
He asked for nudes again. I politely told him that I was sorry, but if he asked again I would have to unfriendly him, because I am in a relationship. He ramted all the same things again, this time with extra emphasis on what a nice guy he's been to me. I blocked him, because fuck that.