Trolls, I unwittingly dated a "Nice Guy" and it ended in a restraining order. What is your best (worst) "Nice Guy" experience?

Not sure if this is considered 'nice guy' behavior.

Like... seven years ago, someone who I went to high school with messaged me very briefly on FB. Like, we might have exchanged 10-15 messages total. It was friendly. He was pretty popular/friendly in HS and has lots of friends, but never really dated anyone.

A year ago, he messages me on OKC. Says he has always really liked me and thought I was cute and his Dad (HS teacher) always spoke highly of me. We exchange numbers, and almost meet a few times. After a week or less, he started trending the messages toward sexual stuff, and I'm pretty much a prude about things until I'm in a relationship. I told him I didn't like it, and to stop. He apologized, and it was fine for about another week and it started in again, "Oh, you should hear about my dream from last night. I woke up so hard thinking about you. You're so sexy, I can't wait to fuck you." Seriously, bro. I told him again, to knock it off.

Two days later he did it again. So I just blocked him everywhere. (I know the 'right' thing to do is to message them, but he obviously doesn't respect boundaries so IDGAF.) I'm not sure how he wouldn't have gotten the point after I told him to stop twice already. He also had some other... different habits/hobbies and I wasn't really REALLY attracted to him anyway, so it wasn't much of a loss. I wrote it off.

The only place he wasn't blocked was POF (which I didn't really use/check). In the year since, he messaged me around 30 times asking for a second chance "I'm a good guy", "Please give me a second chance, it will be worth it", I've not responded to ANY of these messages. He's added me on Facebook. He's added me on Instagram. Blocked and blocked. We messaged for at most a month. I don't understand, and since we're from the same very small hometown, running into him is a real possibility and freaks me out a little bit. He's friends with people who know where my parents live. He knows where I live in my town. I have no reason to believe that he's stalking me or whatever, but his behavior since is just... unsettling.

/r/AskTrollX Thread Link - i.imgur.com