How to give a woman a compliment on her looks: Advice for Obama and other men

President Obama got in a spot of trouble this week when he gave a compliment to Kamala Harris, the Attorney General of California, calling her "the best looking attorney general." He later apologized to her. It seems odd that Obama, who has an excellent history of supporting women's rights, and is clearly very comfortable with powerful, highly accomplished women, would have made such a simple mistake.

My issue with the entire affair is that reactions seem to fall into two camps: "it's not that big of a deal, why can't men give women compliments?" and "he was a jerk who made a demeaning comment." I'm here to offer a more nuanced perspective.

Before I do so, however, I would like to point out that, if the worst thing that happens during Obama's presidency in terms of his personal relations with women is that he gets into 5 minutes of trouble for giving a good friend a compliment, he's doing really well. And so are we.

Obviously, there are times when it is appropriate to give a woman a compliment on her appearance. Most women at some point put a great deal of effort into how they look - they buy expensive clothes, they put on makeup, they might work out. Even women who spend most of their time in jeans and t-shirts occasionally like to dress up. But there are also times when giving a woman a compliment is rude and inappropriate. How to tell the difference? Here are three guidelines:

1. Professional vs. social environment. It's generally not a good idea to give a woman a compliment on her looks in a professional environment; it's far more acceptable to do so in a social environment. The exception to the professional rule is if the woman has a job in which her looks are important professionally; model, singer, or actress, for example. Why is this? 2 reasons. First, if you comment on her looks, it means that you think her looks are more important, at least at that moment, than her intelligence or her abilities. Which means that you aren't paying attention to those. Which means that, at least for that moment, you aren't taking her seriously. If there are other men with you, you probably aren't paying attention to their looks. So you are taking her male colleagues seriously in terms of their abilities, but not her. The second reason is that most professional relationships have at least some adversarial aspect to them. Even if you have the nicest boss in the world, you still have some interests in conflict with her. But giving a woman a compliment on her appearance is an act of intimacy, even if it's a very mild intimacy, and you are asking her to be emotionally vulnerable as she accepts your compliment. That may interfere with the adversarial nature of your relationship.
In a social setting, it's much more acceptable to make an emotionally intimate connection with a woman, because those situations are generally not adversarial, and there's probably a much higher level of trust. Obama's mistake was confusing the social and the professional. Apparently he and Kamala Harris are good friends personally, and have known each other for a long time. So he felt free to give her a compliment as a friend. If he had done so in a private setting, like at a fundraising dinner with only other Democrats present, he might have gotten away with it. But Kamala Harris, as Attorney General of California, has LOTS of adversarial professional relationships, more so than almost anyone else in the country. The issue is not that she doesn't want to be emotionally intimate with people; she's also a politician. But she wants to be the one in control of when she is. See #3 below.
There are some situations where people who know each other professionally interact in a social setting, for example at a conference. Err on the side of being professional, but, again, see #3 below.

2. It's generally OK to give a woman a compliment if she is getting - and wants - lots of attention. At a wedding, the bride will be getting lots of attention, particularly for her appearance. She wants that attention in that setting. So give it to her. The bridesmaids, and even most of the other women, will feel the same. If a woman or girl is at a formal dance (like a prom), she probably wants attention paid to her appearance. If she is receiving some kind of award or special recognition, and has dressed up for the occasion, it may be appropriate to compliment her appearance, as long as you also recognize her accomplishments. This may be one of those situations where the professional and the personal mix.

3. The most important factor in deciding whether or not to give a woman a compliment is: take your cues from her.  Repeat: take your cues from her. If there is any question in your mind about whether or not she wants the compliment, first, stop and think. Try to put yourself in her shoes. Is there anything unusual about this situation that would indicate that it's either appropriate or not? Did she clearly make an effort to look particularly good on this occasion? How well do you know her? Are you equals, or are you her superior, or her inferior, professionally? Are you giving more attention to her than to other women in the room? Are you giving attention to her that you would not give to men around you? Maybe not OK. Or are you at a bar late on a Saturday night, and she's been checking you out for the last 10 minutes? Are you at a party and she's wearing a tight skirt and a low-cut blouse? Probably OK.

Taking your cues from her means that you are listening to her, maybe even before she has said anything. And the best way to get a woman to listen to you is to show her, first, that you are listening to her.