If you're ready then get out there and do it, brotha! Your sense of humor is definitely the golden ticket!
I'm currently VERY casually seeing (dating?) two very different women (30 and 31) and just enjoying my time with them. However, I think my 23 yr old trainer (yeah, baby!) from the gym dropped a pretty big hint yesterday about being interested in me. An older guy came over and began talking with my trainer. He told her how cute she was, and that this is probably why she gets the good looking guys to work out with (nodding at me). She replied with, "Yeah, unfortunately it's always through work." The guy then says, "Fortunately?" and she answers with, "Unfortunately."
We get along pretty well and laugh/joke a lot during the workout, and I'm about to finish working with trainers in general and to just workout on my own from here on out. Maybe I'll ask her out sometime, too!
I'm also quite sure my daughter's preschool teacher is interested too (as is the now 20 yr old from dance that I had the drunken night with during Halloween).
Apparently the old saying, "When it rains, it pours," can be positively applied to women too!