Valentines day is about taking bold risks. Should I take one with my crush?

kirsten_kangaroo
Alright, so I'm a freshman in high school, and there's this junior that I like. We're both in the marching band, and on the way back from competitions (this was around midnight) I would end up sleeping on his shoulder, and he didn't mind. Aww, cute. I know. So Valentine's day is coming up, and I want to either find out if he likes me, or do something to build our "friendship." Any advice? I'm really shy, so it's gonna be hard for me to get the courage to do ANYTHING. Thanks! :)
Valentines day is about taking bold risks. Should I take one with my crush?
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