What could explain this guy's weird behavior? Insecurity? Immaturity? Something else?

I'd say he'd like a relationship but doesn't think you'd agree.
Some guys are also incredibly dense to signals. While there's the guys who think a woman who accidentally makes eye contact wants them. On the other side. All the compliments, hair flipping, touches, excuses to sit close and smiling. Go flying right over their heads.
So, if you do want a relationship and have been giving signals. You may have to ask him out point blank or ask "Hey! Why haven't you asked me out yet?". I like the second one more. As it's more a challenge of throwing down the gauntlet. If you put a little oomph behind it.
You broke his heart, but he still loves you, so he's conflicted.
BOTH...
he is not confident enough to pursue you...
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