I typically go to a male-oriented hair shop like SportsCuts. I don't know if any of you have any of these in the area, but it works out because its a very, very masculine atmosphere and almost all of the hairstylists are female (and usually eye candy). They specialize in all types and deviations of male haircuts (so they aren't going to suggest female styles), and never ask very many questions, also friendly. Most men don't chat it up in the chair, so they typically don't strike up any personal conversations. I'd say try looking for one of those places.
I also met this girl who was schooling for hair. She was great, and would do anything I asked just for the sake of learning. That may be a good route to go, usually the younger generation is more accepting and willing.