[JulianMorrison]

The rule is: don't assert your situational power. A woman alone or outnumbered among men is going to feel pressured. Comments you make won't be well received even if she is worried enough by the pressure to smile and hide her discomfort. She'll just curse your name to her friends after work.

Contrast: if you're the only man in a room of women, and the boss is a woman, would you dare speak up with your "nice dress" type comment? That's what it feels like to be on the downside of a power gap.

[chunkybacon]

Believe it or not, I would dare speak up, even to my boss, if I thought she would appreciate the comment.

[sp332]

Yeah, why not? In a room full of men, the comment would be made to the other men, but for the benefit of that woman. It would be flippant and funny. In a room full of women, the comment would be more personal, and I would have to keep the tone extremely light because the more serious I am, the more vulnerable I am.

[ajross]

Seriously? You're saying that standing alone in a room full of women of uniformly equal or higher social standing (suggestion: if you have kids, take a day off and bring them to any local parent/child activity -- it's likely to be 100% mothers) you'd feel comfortable blurting out "You're wearing a low cut dress! I know where I'm sitting!".

Please (please!) try this. And bring a camera. I suspect you'll be very surprised at the results.

[sp332]

Of course I've done it. I was at an all-mothers event mostly by accident. She glared at me and kind of laughed. My mother gave me a dirty look lol. Pretty much expected. Did you expect something bad to happen? Maybe it would be different if she were single and available?

[ajross]

So I guess the lesson is that because sp332 feels no shame in deeply embarrassing situations that no one else would. Yikes. I'd be bright red and backing slowly toward the door if that came out of my mouth. You, sir, are weird.

[sp332]

Well I felt pretty bad about it at the time, and left the room after a minute. But later she told me (when I asked her about it) that it wasn't a big deal and I shouldn't have taken it so hard. My mom doesn't remember the incident but she tells me that no one would have cared much.

[ajross]

OK, but that's a really telling detail: she was gracious about it, because she could be (she was in a position of social power), and because you were visibly embarrassed. In the anecdote above, the guy wasn't apparently embarrassed, and Katie didn't have the social power to tell him "it's OK" even if he was (and why should she have to, if she was the one who was embarassed?).

See the point? These are critical details, and they change the moral calculus. You can't wave away an incident like this just because you can imagine something similar which wasn't a problem.

Like I said way up-thread: someone (you) is going to point out that not all women would react like Katie did. So what? Context matters!