You're right - you're overthinking it.
You appear pretty nervous about coming across as desperate - I'd try not to worry. If you're just interested in him, and he sounds interested in you, neither of you will look desperate.
Desperate would be like... "OMFG, Y U NO TEXT ME BACK IN LIKE 5 SECONDS!!!" lol
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Have you met him or haven't you?
Why are you waiting until after the holidays?
Just text him and talk to him! You won't seem desperate unless you do it all the time and start listing the names of your future children.
Uhm.. he probably just decided to send you a picture just in case you forgot he was cute lol.
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