I approached a guy a few weeks ago for the first time ever. We were leaving the restaurant at the same time.. made eye contact.. I got all the way into my car and decided I'd get out and hurry to see if I could catch him before he left.. as he was getting into his truck I walked up to him and said, "This is going to sound really strange, but um, are you single?"..and he said, "Yeah, actually I am"... and I said, "ah ok, I just thought you were a good looking guy, wanted to say hello"..and he said.. "Glad you did, I was wanting to approach you but chickened out".. we talked for a few min., exchanged number... He called me that very next day
...and we've been on quite a few dates since
But to answer your question, he'd have to be pretty freaking hot hehe
... I'd definitely do it again if I saw someone that I was extremely attracted to.