Thanks for all the responses and free therapy.
I have come to the conclusion that I think its more than his looks. I have dated men that weren't good looking, but I found them sexy. i don't know if I find him sexy and I think that is the problem. I can handle not being the best looking, I actually prefer it, its the lack of sex appeal. I'm not shy (if you can't tell) so I have no problem with saying lets hit the barber shop.
Right now I think I'm going to lay low in the cut and see what happens.