I've just woken up to a whole load of comments on this thread and I have been reading them all. I want to thank everyone for their input and their decision to spend time helping strangers like me out on the internet, because it truly has made me realise some things. I know I am immature, I'm still finding my place in this big scary world. This guy is very intelligent, compared to me anyway, and has helped me out a lot and that's a reason why I like him. If I'm ever upset or stuck, he'll give me good advice and comfort me, I mean he wrote my CV and cover letter which landed me a decent job! I realise I'm becoming quite dependent on him and sometimes feel scared that if he's ever to leave me I won't know how to navigate in the 'adult' world. It is a very sad mind-frame and I need to get out of it and grow up. I would like to meet him alone in a public area before NY, so I will definitely make sure to arrange that. In the past I have asked him to meet with me, but he never follows through with his plans. I don't really understand why he'd make a leap from not wanting to see me at all to going to NY, but I think it's because he's lonely and has no one else to go with. NY is his favourite place and he goes every year at Christmas. Last year he went with his ex, who I was friends with (yikes that did not end well). Him and I do occasionally speak sexually, which I enjoy and don't feel pressured into as he's never asked me for pictures and if I don't feel like chatting about it he'll stop. We've discussed the situation in NY, and he's told me if I don't like him romantically in person then it's totally fine and we can just going as friends and can still have a good time even if nothing more comes of it. What I have concluded from all of your comments is that because his last girlfriend was mentally and physically abusive, he spoke to me because I was young and much more accommodating. I don't judge him for living with his parents, or not having a job at the moment, whereas anyone his age would immediately label him as a loser and move on. He's admitted to me that he feels his life isn't going anywhere, so there's certainly a lot of emotional baggage there too. All in all, I know he isn't a good fit. I am going to meet him, probably go to NY, and if it doesn't work out then I won't be distraught and hey, I will have a cautionary tale to tell my future children.