My situation is this: Been single for a year after leaving somebody and starting afresh on my own with my son. I am at college and have been friends with a guy who is a fair bit younger than me for ages. He has been to my house many times alone and with other friends of ours. He has stayed over on my sofa several times after having wine at the weekends. We have never had sex or really mentioned it much.

Is he inexperienced with women? 

I have started to develop feelings for him because I have realised how sweet he is. I haven't told him incase it's not reciprocated and I would feel a fool as well as make our friendship awkward. We are in touch constantly and I have told him all about my past relationship which included violence to me and my son. I am not sure if he fancies me. When we go out he will automatically pay for things and he bought my son a couple of nintendo games for xmas that he wanted as well as other things.

He certainly seems to value you and your son, to go to that much effort and expense.  The question is, is he a lonely guy that's looking for some friendship or is he a lonely guy looking for someone like you.  I don't know so far. 

He sent me an ecard and bought me a most haunted boxed set that I really wanted. I also got him something that he wanted. The thing is he has a place at med school this september in Wales. We are in the Midlands at the moment and as far as I know he is going there. He has also applied to Birmingham which is close and got a place there but he said he was accepting the place in Wales but this was 12 months ago. He never mentions other women, I know he dosen't have a girlfriend and isn't gay.

If you really and truely know he isn't gay, then this suggests to me he is not used to women and lacks a bit of confidence with women.  Usually if your friends with a woman for a while you will open up and start talking about other women and getting advice.  The fact that he hasn't, suggests he maybe avoiding doing this because he fancies you and doesn't want to make you think, he is thinking about other women which would give you a clear sign he is not interested in you.

He has talked about going on holiday in July and asked if I fancied a trip away. He made it clear that my son could go too then went off to play with him. He only met my son in the first place because we were friends. I would normally only want to introduce someone that I had seen on my own for sometime and it was clear I saw them as a permanent thing. I wouldn't want my son to get attached to him if he goes off in September and who knows when I would see him. Would he be doing these kinds of things if he wasn't interested in a long term future with me?

It is very unlikely that a guy would go to this much effort for you and especially for your child unless he was interested in a relationship with you.  The only other circumstance is with a very rare kind of guy, where he will see this situation as a practice for getting married, having a relationship and having kids. 

This has been going on for over a year and I think if he was just trying to get into my knickers he would have made moves ages ago.

I do think you have a strong basis for a long term relationship if he does fancy you.  The fact that he hasn't tried to get into your knickers demonstrates he is willing to take things slowly and have a proper relationship on a proper basis. 

He makes arrangements with me for every weekend now and I meet up with him after my lessons finish at college. I haven't met any of his family nor him mine but we spend a lot of time together when he could be off with mates or doing his own stuff. He is 23 whereas I am 33 but I do look about 25, he thought I was this age when we first met.

I would have thought he was definitely unlikely to fancy you with that sort of age difference.  However, it sounds like he thought you were younger for a long part of the relationship and that will have given him chance to become attracted to you before thinking about your age.  I always say that men usually don't fancy women that are significantly older than them.  But the truth of the matter it's not just a matter of age, if a woman is 40 and still looks 18, then he will find her attractive.  He will think she is that age and when he's walking down the street hand in hand with you, other people will think he's in the arms of a young woman. 

So the truth of the matter is maybe age isn't as important, it's more the age that you look, that's important.  I say when women say men are too old for them, that age is just a number, I think maybe I should say the same about women.  Age is just a number and what really matters is what age you look.  Some famous celebrities are in their 40s and still look great, there is even a minority in their 50s that look great.  And even bigger minority in their 60s that look great.

The more time you spend together the more likely he is start to start thinking, maybe this is the woman for me. 

So shall I say something to him to see whats going on? If so what? And if he does like me then why is he doing all this stuff but not making more of a move? I am really confused.

From what you have said, you don't really give me any conclusive evidence that he fancies you.  There are some positive things, that make it more likely, but nothing that says he definitely does fancy you.  Like does he flirt with you, does he touch you in anyway, does he say anything sexual to you, does he mention anything to do with relationships.  If not maybe you should try off with some light flirting, gradually build up the flirting if he is comfortable with it, then if you are comfortable about having sex maybe you could start making some hint towards sex.

Maybe it might be useful if you read something posted by my visitors in the forums. 12 steps to Pair bonding.