If he texts you back all the time, texts you every day all day and you can still talk comfortably in person, does that mean anything? My belief is that if a guy isn't interested he won't text you back.Especially not stay up with texting you until one of us passes out.
Most Helpful Guy
I text with my sisters late into the night all the time, but I don't want to date them.
If you want MORE than just casual chatting then you're going to have to push the issue.
Try increasing the flirting to see if he flirts back, or if he backs off.
If he's shy then he's worried about making a move, so give him more indicators of your interest and make it obvious that you're not going to freak out if he tries to cuddle or kiss.
And get him alone. Isolate and escalate.
When in doubt ask his friends. Ha!