Advice

It sounds like this guy really cares for you. He seems nice and playful, and it seems that he likes you. 1

If and when you ask him out, do it when it's just the two of you doing something fun, like playing video games or... well, you get the picture. Remember that's it's perfectly okay for you to ask him. You should ask casually, "Have you ever thought about going out?" or something like that.2

If you don't want to do that, you could test how much he likes you. You could sit at a table with people he doesn't like/know, or invite him to a party where you're doing something not of his interest. Do not overuse this, for it will seem strange.3

And if it doesn't work out, you can always remain friends.4

ALSO! Don't try to make him jealous. I mean, getting with another guy just for a certain guy is not the right way to go. And wearing revealing clothes, like super mini miniskirts or tight tube tops won't get you anywhere.5

If you really want to date him, hang out with him more. Do fun stuff. Make him laugh. Tease him. Guys can never resist a challenge, so challenge him to a game of something. 6

Do's and Don'ts7

DO8

Act kind, playful, etc.9

Laugh at his jokes, but not the unfunny ones10

Flirt occasionally11

Call him your nickname12

Tease him (PLAYFULLY!)13

Go to his important events - such as a basketball tournament or a chess competition and cheer him on14

DON'T15

Try to make him jealous16

Become somebody you're not17

Try too hard18

Try too hard to impress him19

Badger him about dating20

Hope this helps!