There's a guy at work that I only see a few times a year at social functions. We've never spoken because we have no reason to and I would like to change that. The little that I know about him from other people is that he's in his late 20's, has never had a girlfriend, is shy, very smart and nice. Although he is not considered what would be conventionally attractive, the first time I saw him I was instantly attracted to him and have always wanted to approach him. I'm very shy myself, but I have decided that I need to get over my shyness and just do it; however, I'm worried that I won't be pretty enough, interesting enough, coherent enough, etc. Yes, I know I will have to fake a little confidence. In short, I'm looking for some advice on how to do this. Is it too weird and uncomfortable to just randomly approach him out of the blue? Is using work as a topic of conversation a good ice breaker? If it goes good and I like him, is it too forward to ask him to hang out some time? I've only ever asked out two guys before in my life (years ago) and it didn't go well. The rejection was obviously crippling to me since I have not done it since. Thank you for reading and I appreciate any advice given.
Most Helpful Guy
Yes go for it, start off with asking about his job and tell him about yours. Don't worry about being good enough.1