So how could I get him to do that?
I don't know you will just have to talk to him, make him feel comfortable, let it subtlety be known you are single (if he doesn't know already), maybe ask him if there are any girls he likes, or maybe ask him what he likes in a girl. Stuff like that, your a girl you have a lot of power over him (as much as most men would hate to admit it lol) if he really likes you it shouldn't take much, if he thinks its a sure bet he may just ask you out. I am a shy guy myself and unless i know with out of a doubt a girl is interested i almost never ask them out (a bit of personality flaw in myself that i am working on) the thing is asking a girl out and putting yourself there can be one of the most terrifying things for a man, some men are good at hiding it but even confident men are at least a little nervous when asking out women.
Good advice. By "ask out" do you mean ask if I want to be his girlfriend?
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Over a year
what about texting?
I guess the same