how to compliment a woman

the best possible response to “Nice ass!” is “Thanks, I use it for pooping.”

Do you mind if I say this? You look great.

You are a very pretty girl. I mean, that’s not the only thing I care about in a person. But, yes, I do appreciate a good-looking… whoever you are.

One evening in August, I made the fateful decision to treat myself to a dinner in my own company after a long day of train rides. As it were, I found myself sitting next to Benevolent Sexism himself.

The man was a few bar stools away from me. He had a leathery square-jawed face and the kind of smile that closed business deals. He shook a bottle of tabasco vigorously over his platter of oysters, then proceeded to interrupt my communion with my steak. Leaning over, using a gravelly indoor voice, he gave me… a series of compliments.

As if he hadn’t already formed a convincing proposition, he then proceeded to slowly slurp an oyster off its shell while maintaining steady eye contact.

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I’d like to follow a column about women’s body image with one about the sense of entitlement many men have around women’s bodies.

What is the difference between a compliment and harassment?

Whether or not men should compliment women they have no acquaintance with is tricky business. Compliments are rarely given without vested interest. To pay a compliment is to introduce a currency, to suggest an exchange of social capital, of approval for time or flesh. To abuse this currency is to assert power, i.e. when a creep at a bar makes an unwelcome and offensive advance. In such cases, the seemingly innocent compliment becomes but another indicator of gender inequality.

In my last column, I spoke about the constant societal pressure inflicted on women to feel ashamed of and to want to change their bodies. In a world that offers a beauty ideal too thin to spread around, a woman who decides to love her own body does so against an overwhelming number of social forces.

This is why, when a man praises the beauty of a woman he barely knows, regardless of his intentions, he is tapping into the old patriarchal strategy that preys upon this serious vulnerability. The flipside of validating one woman’s body is the institutionalized policing of all female bodies as a whole.

To men: A compliment about appearance to a woman you’ve just met—if your social relations are defined by your broad status as strangers of the opposite gender, and not anything more substantial—risks becoming an insidious flaunting of social currency and power.

If society tells women that the end goal of the feminine performance is Looking Hot while Accomplishing Everything Else, it can be hard to shake the feeling that perhaps it’s the performance that’s being complimented, not the person. You are pretty, in the wrong context, sounds like That’s good, keep on being pretty. It becomes a reminder to the woman that she is being looked at instead of interacted with as a cohesive being.

How then, can a man say something nice to a woman who he wants to get to know better?

Complimenting Women—in Simple, Actionable Terms:

  1. If you don’t know each other, never use a compliment about her body as a conversation starter. Never on the street. Never on public transport. And especially never if she’s wearing headphones. This will never achieve the desired effect.

Compliments are intimate. For most women, their reaction to an unknown man commenting on their appearance, whether positive or negative, is repulsion.

  1. Telling a woman she is attractive can go either way, depending mostly on whether she’s already attracted to you. This sounds obvious, but it is actually counterintuitive.

Men have been taught that compliments open the door to romantic or sexual interest. In truth, telling a woman you find her attractive only works in your favor if she’s already interested. If she isn’t, you’ll pretty much ruin your chances.

  1. Unless you are completely, completely sure that she would like it (or, to err on the safe side, unless she has given you permission), a compliment accompanied by touching or intimate proximity is worse. For example, the classic hand on knee, or lean in maneuver. According to an informal survey conducted by sex educator Dr. Emily Nagoski, 25% of women will be squicked out by touching from the get go, while 50% says their approval depends highly on their level of attraction.

In general, shut up about her appearance. Which brings us to …

  1. The best compliments are genuine (!), specific, non-appearance based. Talk about something substantive. Something you have in common. Admire her for something real—her mind, her sense of humor, her work ethic—and talk to her about it. Pay a compliment only if it’s relevant to the conversation you’re having.

You always need a reason for talking to her other than the fact that you want to talk to her. Which, alas, means that very often there will be no reason for you to talk to someone you want to talk to, and therefore you don’t talk to her. Sorry.

  1. Lastly, only offer something positive about a person’s body or belongings after you’ve said something positive about their other attributes that you can only know by having a conversation with them.

The number one focus of compliments between loving partners is neither appearance, skill, nor personality, but the experience of being with them. In other words, not You look amazing, but You make me feel amazing. And that’s what a compliment should be—not a proposition, but a statement of admiration, appreciation, and plain old liking.

The short of it is that there is no secret trick to delivering a sexual or romantic compliment to a woman you’ve just met. It is not possible to do so. Women deserve to be treated as individuals, not as potential girlfriends or partners. The vast majority of women will never be your partner, and they should be treated according to these odds—unless their behavior communicates otherwise.