Cas is a lot of things, but popular isn't one of them. He's what you'd call a geek or nerd, or Crowleys favorite 'fag'.
But when Castiel is up on stage, with his base guitar, his lyrics, his band, his fans, his siblings, and his signature outfit, he's in his domain. So at school when he invites people to his concert it surprises him as well.
Dean is a lot of things, but perfect is not one of them. His family isn't in the best shape, his friends talk about him behind his back and lie to him, he has trust issues, and his dad is never home and when he is he's drunk. So when the guy he's had a crush on sconce he saw him invited him to a concert, he thought it'd be like a cello concert or piano, not base guitar.