I'm 35 and my 17 year old niece's best friend comes over with her to my house a lot. He's 18. I know a lot about him because we chat a lot. He recently just moved out of his mom's house because she was using belts, shoes to hit/discipline him when he was 17. He always talks about how he'll never talk to her again and all of that. My niece went home last week but he stayed longer which I didn't mind. I asked him if he needed to talk about something but he said he's good and just asked if he could watch TV for a little. I said sure and sat next to him. Out of nowhere he told me that he thinks I'm pretty and looks good for my age and I awkwardly said thank you. Then he asked me what I think of him and I said you're a nice young man, putting emphasis on the young. He sucked his teeth at that and a few minutes later asked if we could go out sometime. I told him no and he got upset but said okay & left it alone. After that he got up to leave and I told him bye but he didn't respond. Yesterday he came over with my niece and I had a friend over. He was flirting with her and she actually flirted back. I pulled her aside and was basically like what the hell are you doing? After that I dismissed her but he stopped her to get her # before she left. I really think this kid has mommy issues. I mean there's a possibility he just likes older women but I see him and my niece as my children so you guys can really imagine how I felt last week.