Do you have any guy friends you can ask about where they get their hair done?
This may be way too involved, but when I got my first "guy" cut, I asked my friend Josh where he went, and he gave me the specific name of the barber he went to.
I called ahead, made sure that he was working, and made an appointment (some shops take appts, some don't).
When I came in, because I specifically asked for that person, he asked me if he had cut my hair before, or how I was referred.
I told him that he cuts my friend Josh's hair, and I was looking to get a similar cut so I thought I'd try him out.
To me, this was kind of a safety net - if he did have a problem cutting a "woman's" hair into a guys style, he should know that he would loose one potential new customer as well as regular. I think when you can mention a current, regular customers name, you will probably have a better experience because referrals are important to those with a regular client base.
Again, maybe that's a little too much as it is just a haircut, but I felt the plan worked out well for me.