"entertain me" ??? 10 pts?

There is this guy whio i have "talked" to for about two or so years now.He is now in college with my brother,and they are long time friends from football and such.We mostly text,but have gotten together 4 or 5 times late at night..3 times we have hooked up.never .he is shy,and never had a girlfriend.But so good looking,and i know he has a good personality just won't show it to me.He isn't mean,just quiet. Anyway he is texting me again now and i'm tryinng to subtly give him the impression that i am not just a toy for hook ups. and i actually am a good girl,and want a realationship.we are far from,but i will be seeing him alot when my brother rooms with him next year so it's possible. How do i act towards him?while we are texting? he always tells me to "entertain him". Do i just say no??? ahh help,i like him...alot