Looking for a little bit of advice

Too many contradictions to even begin to digest this. Maybe re-edit it?

I would say that 2 months is definetly long enough to ask him if you're feeling comfortable with it and feel like he might be too.

One thing you should understand is that not all people are like your last partner. If you feel comfortable with him, discuss what he thinks about what's going on and try to open up to him and share your feelings.

Are you still talking?

Well the person from your "computer-dating" experience already had a game plan. To get with you and honestly it sounds like random roulette. Honest to gosh any website where you meet people is going to yield that result. My brother did the same thing, and the girl he met is not open to conversation and has a messed up mentality when it comes to people, along with girls literally trying to runaway/escape ( who are +18 ) from home like my sister did. You did that for-fill normality.

This guy from grade-school level actually knows you. Is actually attempting to plan his future ( he has no idea of where to go or what to do ). My advice to him would be to study to become a surgeon. If you like him or want him, you should also be more physical with him, and massage him. You could be his back-bone that keeps him on the straight and narrow path of having a normal life. This could lead to a traditionalist life where he could be a bred-winner. There is nothing wrong with planning out your life rather then having mindless random sex. Those are the majority of people who makes up that work. He has a head on his shoulders, but lacks direction.

Other guy is random sex, you went out with him three times, which could mean he could have other people he associates with as well.

I would put the moves on the guy who has his future ahead of him rather then the random guy. If I had somebody working my body while I was studying, actually makes more sense then some predator.