Dating Drama

I met this guy about a year ago and we've been good friends for a while. We both admitted to each other at one point that we had an interest in each other, but due to complications we couldn't make it official. So we both have been flirting and stuff and now there isn't anymore complications, but he still hasn't asked me out. I would do it myself but he is a bit insecure about his masculinity and I know it would mean the world to him if I let him do it instead. I am a very patient person when it comes to romance, but I'm now nearing the end of the school year and I've been through a situation like this before that messed me up emotionally. I try to get closer but now sometimes I wonder whether I'm becoming a bother to him and if he even still likes me. I really don't know wha to do anymore, and I just want some advice here.