What Guys Said 0
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What Girls Said 2
He wouldn't get annoyed if you asked him to hang out. From what you've written, it sounds like he might even like to hang out over break. It sounds like he enjoys your company. A good rule of thumb when your texting someone you like is to treat the whole texting/asking to hang out thing like you would a friend. Would you worry about asking a friend to hang out? I wouldn't think so. Unless you text him multiple times during the day with nothing to say or if you text him repeatedly after he hasn't responded, you're not going to be seen as annoying. Best of luck!
If he gets annoyed than he is clearly not worth your time. Sure, he may not want to hang out, but any guy worth obsessing over would at least appreciate the thought. Good luck!