I'll second what some of the others have said; ask him in person. Maybe he's just worried he annoyed you and is avoiding your texts in the hopes of an easy way out. Not very mature, but nobody is all the time.
Also, I doubt he realised that you were thinking of this in a romantic way. I know I wouldn't, in his place, so maybe you could be a little bit clearer if you talk to him and things go well.
Erm, no offence or anything, but he doesnt sound like the sort of person you'd want to spend a part of your life with, let alone the rest of it. And by the sounds of it your not just looking for a one timer. You may not be looking for a partner for life, but still. Also, you mentioned that he isnt as much of an ass around you as he is around other people? Does that mean that he's an ass around your friends/family (if he knows them XD). If he is, then thats another reason you may want to rethink this whole 'crush'. Would you be willing to go out with someone who acted like a jerk towards your friends?
Er... after re-reading this I kinda seem quite intense, dont I. XD
Mh, sounds like he's pulling your chain a bit. Hot and cold. Bait and switch. At the very least, he sounds incredibly unthoughtful of your feelings. I'd look somewhere else for a romantic partner. Chances are that even if it was a "misunderstanding" when he flaked on you, it would be a reoccurring one. He could have easily sent you to a text to clear up anything that needed to be cleared up right away, but he didn't. He's probably just not that into you and doesn't want to hurt your feelings, and/or likes the power trip. If it makes you feel any better, it happens to almost everyone.
I don't think you're being too forward at all but chances are while you were considering your arrangements to be a date, he was just thinking of it as exactly what it was - a plan to get together with a friend and study for a while. It doesn't make it ok that he didn't show up, but he had no way of knowing how much it meant to you. It's really difficult to try and guess what someone else is thinking so I reckon mention it the next time you see him in person. It doesn't have to be a big confrontation, just a "Hey, I was waiting for you on (whatever day) but you didn't show up. What happened?".
Yeah, I thought about that. I guess I just don't get the avoiding part. He seems to shy or would get to flustered in asking me himself, so I feel like I would have to do it myself. I just can't seem to find him when he's not with his friends.
When you show too much interest guys seem to close down. I'm not gonna say you were acting desperate. You gotta play the game and seem aloof sometimes. You really should have not gotten mad though. Maybe he was a little too shy or who knows why he stood you up. But constant texting is like stalking. One should be sufficient. You should have just said something like "I missed you at the study hall/ library. What happened?" kind of non-chalantly like it was ok if he didn't come and It was his loss, not yours. By not saying anything you gave him the power to play games and enabling it. If I were you and the way he acts I'd write him off.
You were considering this the first step toward a more intimate relationship, but did not portray it as such to him. You said you were looking for scholastic help. And it sounds like he was not really comfortable with his abilities there, "He wondered about being able to help me, but I told him I'd take all the help I could get"
Sooooo if he liked you, and felt he could not help, or possibly thinks that HE is stupid and bad at school, and does not want to either let you down by not helping you or does not want to appear stupid what would he do? Probably something about like he did.
"Forget" realize you are mad, figure he has blown his chances with you no matter what, so ignores you.
Not saying he likes you, there could be other scenarios. And some of those could be he realized that you were viewing this as the beggining of a romantic relationship, but did not want one, so he ditched you.
But you did not say "hey, I would like to go to the movies with you" or "there is a dance coming up at school, would you like to go with me?" or even the very honest, and scary "I think I like you as more than a school friend, would you like to go out?"
If you do not ask for what you want, then do not get what you want, you should not really be surprised.
And it sounds like the only way to find out why he did not show is to talk to him in person.
What was for you a big deal as if you had asked him out on a big date, was for him probably just a study date. He probably never second-guessed your intentions. It seems more likely to me that he forgot than that he blew you off. It's still rude of course, but there's no reason to look for bad intentions where he probably just acted the way he did 'cause he's a bonehead.
I would just ask him if he forgot, and then ask if he wants to hang out after school some time. Less study date-y and more date date-y but still not something that puts too much pressure on either of you.
And you don't need to turn this into a big issue, and not being too confrontative about it is really the best for the both of you, too. Just ask him why he didn't show up on the study date last week, if he forgot or something.