Search Results: guys make fun of pretty girls

My boyfriend's friends keep saying he's lucky as hell he has me, but he doesn't think so. I'm curious what you guys think.

-Short / very petite
-Dresses cute (Thigh highs and neck ribbons are a staple)
-Cancels our own plans so you can have a guy's night
-Makes baked treat snack boxes for guy's night
-Plans fun dates, even after three years (Go karting, paintball, shooting range, ect) out of own pocket
-Pays for pretty much every date, actually
-Pays attention to everything you like, so you can have a happy birthday/christmas/whatever presents
-Likes watching anime/playing JRPGs
-Does oral 90% of the time when asked
-Doesn't mind cleaning up after you / you come home to a clean house with laundry done
-Makes lunch/dinner and drop it off for you every weekend while doing overtime/working
-Only gets a little disapointed for cancelled dates, doesn't actually yell
-Can't actually yell, my voice is too quiet
-I haven't gotten a birthday present in two years and don't mind
-Baking, baking, baking. Always cookies and cupcakes.
-On special days, breakfast in bed
-Adventures are fun!

I'm a senior in HS and looking for a date to Prom, and I immediately thought of this guy (Junior, by the way) who I interact a lot with on social media & rarely in person. We seem to find a lot of the same things funny and have really similar views.
However, I did not want to be too forward with this guy and wanted to get to know him before I asked to go to prom (as friends). I decided to have one of our mutual friends set up a day for us three to all hang out together. So, on Friday a week ago we all hung out for a couple hours and we all had a lot of fun. This guy even made a point to go up to my younger brother and tell him how much fun it was to hang out with me because they are in an upcoming play together for my school.
So during the week after we hang out and I notice he seems to be making more eye contact with me and noticing me more (nothing that screams I LIKE YOU, but a little more flirty than usual). After school I finally decide to go up and talk to him right before he leaves. I sparked the conversation and he seemed pleasantly surprised, relaxed and smiled a lot. We had a very short conversation before he said he had to go and I ended with "I liked hanging out with you Friday", he said "Yeah, same" (or something of that nature).
A couple days and he seems to be acting the same towards me on social media. But yesterday I DM'd him on Twitter (I don't have his number) asking which nights he was in the upcoming play. Nothing else, and no smiley faces or anything flirty. He has yet to respond but I've seen him tweet things so I can be positive he has seen it.
Other things I know about him would be that based on his Twitter accounts (and he lets me follow his private twitter) he seems pretty insecure and I heard from his friend and ex-gf that he can be awkward around girls he does not know that well, however he seems confident in his friend group.
My question is, what is going on that would make him ignore a simple question? And what should I do?