I decided I needed a new shade of nail polish so I walked into one of my local beauty supply stores while in guy mode. Usually I have no problem buying nail polish (or makeup in general), as I'm sure I'm not the only guy who goes in to that particular store to buy some (or maybe not). I also needed a hardening clear top, so I asked one of the ladies working there. She pointed me to it, and even mentioned which one was on sale. The weird moment came when the lady asked me who it was for - I didn't lie - and I got a weird look. So I just grabbed the nail polish and moved on to look at the eyeshadow palettes.
While doing so, the lady (talking to herself) started complaining about how someone had swept up something sticky with the broom, then passed the conversation over to me "these girls complain about being tired all the time and look at me, I'm twice their age with twice their energy."
"It's all about the attitude" I said. "You stay young because you feel young."
From there, we ended up having a wonderful five minute conversation about staying young while aging (though I'm 28, she was 65). Maybe it was the fact that I told her she looked 15 years younger (she really did)... while ringing me up she said a light eyeshadow would contrast well with my long eyelashes. She didn't ask if the palette was for me, but she assumed so, and with an accepting attitude.
I have now bought makeup several times and this is the only time I received any sort of odd looks, but I guess complimenting a woman never goes wrong, regardless of gender.