Sorta reminds me about the time I worked to J41's, one had an all female crew (CA, FO, FA) and the other an all male crew. I told that to the all guys flight and they just about blew a gasket.
ACA has a fairly hot blonde who is a CA on the CRJ, I think out of ORD, I'm not sure. When I was at ORD once during the winter, there was either light snow or light frost, I can't remember. I asked her, "Do you want the trucks?" She told me she thought I said, "Are you in charge?"
Later, I heard the FA telling her that some guy asked if the CA was female, and almost fell over when he found out she was pretty hot. I told her, "Ma'am, you don't want to know what I was going to say to you when you thought I asked if you were in charge." The FA said, "You can tell me if it's not obscene." I said, "OK, it doesn't matter how many stripes you wear, it's always the man who is in charge." The FO just sat there and said nothing (good boy) and the CA replied w/o skipping a beat, "It's obvious you have never been married."
NW has a fairly butchy DC9 CA. My supervisor looked at me and said, "You know that's a man, right?"
I think my favorite (and most embarassing) stories occur on the corporate sides. There are a lot of corporate flight crews that have no uniform, and there are very very few female pilots. This one chick in a challenger walked up to me, handed me a pair of chocks, and gave me a list of things like she was the flight attendant. I walked out to the aircraft, and there was a pretty fairy looking guy in the galley. "Sir," I asked, "Can I see your FA?" "I am the FA." "No, I want to speak to your other FA." "I am the only FA." "You mean to tell me the hot chick in the sleeveless red top is a PILOT?" "Yeah. She's up front."
Then she turned around and waived. **CENSORED****CENSORED****CENSORED****CENSORED**, was I embarassed.