[leeny]

My personal favorite of the ones that I've gotten...

"Normally, when a woman is dressed like that, I'm paying her to whip me."

(What I was wearing included but was not limited to a leather jacket and black shoes.)

[dzhiurgis]

Isn't that a self deprecating joke?

[leeny]

Sure. But just because something is self-deprecating and a (just barely funny) joke doesn't make it acceptable. Context matters, and this was literally the first thing the guy said to me.

[Archio]

It's not at all appropriate in a business setting.

[dzhiurgis]

I guess it depends whether you see tech events as business setting or social setting.

Also, wouldn't the aforementioned dress code be deemed inappropriate in a business setting?

[GFK_of_xmaspast]

If you're there for work it's business. (and what's so inappropriate about a leather coat and black shoes?)

[tptacek]

It is extraordinarily creepy.

[jsmeaton]

"Normally when I'm hanging out with someone that looks like you, I'm playing Dungeons and Dragons." Is that purely self-deprecating (assuming playing Dungeons and Dragons is such..)?

[dsuth]

No, it's an implication that the OP is dressed like a prostitute. That's not cool.