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?