He's shy. Guys don't keep buyin' drinks for their girls if they're not interested. But then, only a guy who's new to the dating scene would keep spending $$ on drinks on a girl he just met. Plus, a pic of you and him on MySpace... ?

That's nice
With guys like that, if yer too aloof, he'll think yer not interested and he's gone. Looks like you'd have to lead him on. But not too much cuz you don't want his ego to shoot thru the roof.
Just text him the next time and pretend yer angry with him for not initiating....like.... "hey, it sucks to always be the one initiating. I'm pissed, so I'm now seriously considering not texting you for a while :-( :-) ;-) ". That should wake him up.