How should I ask him out?

I’ve asked guys out before! It’s a complete turn on to be approached by a confident woman - disregard all of that old fashioned nonsense. Unless he is a total wimp with self esteem issues - he will appreciate it. Since you have been friends with him for a long time, just start out by saying that you enjoy his friendship but would like to take it to the next level because you do in fact like him. Perhaps bring it up the next time you are both hanging out as friends…He should gleefully respond with, “Yeah, that sounds great!” You already know he likes you, so this should calm your nerves a bit. Plan a date with activities that you mutually like or that you can enjoy together. You know eachother well enough to understand eachother’s likes and dislikes…so that should be easy. Initiate and say everything with upmost confidence…hide your nervousness. Hope this helps!