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A Gentleman’s Guide to Giving Women Compliments

“You have the prettiest eyes I’ve ever seen,” a man once told me after sidling up to me at a bar on a sweltering summer night in my twenties. “Really?” I replied. “Look, I’m sure you mean it and all, but don’t you think that by now I’ve been told my eyes are pretty by every man I’ve met since I was 12? Try again.”

“I have steaks and air conditioning at my apartment,” he said in response, not missing a beat.

Reader, I slept with him.

Just kidding! I tell this story to demonstrate that complimenting a woman’s eyes is probably one of the most obvious things you can do, because if it’s the first thing you notice, it’s probably the first thing every man has ever noticed about this woman since she was born.

This is really the first and main thing you need in order to understand how to compliment a woman: Most women have been relentlessly “complimented” their entire lives, beginning with girlhood, peaking in puberty through their early twenties, only to slowly drop off as they age into decrepit unfuckability at 31. By “complimented,” I mean “commented on,” meaning our bodies have been annotated our entire lives by complete strangers who’ve anointed themselves as amateur model scouts moonlighting as sports commentators.

We’ve been told by complete strangers if our tits are big, our faces are right, our are eyes good, our smile welcoming, our hair sexy, our posture okay, our asses resembling enticingly drummable bongos. Over a lifetime, it’s tiresome, and depressing, and yet, strangely revealing.

Ask any woman you know what men find physically appealing about her, and she’ll list a slew of things men have pointed out to her unsolicited, sometimes without even using complete sentences. “Hey, legs!” a man yelled at me at a Howard Johnson’s swimming pool in the 8th grade. “Big tits,” a guy coughed out once as he passed me on the street in the ‘90s.

So, if you really want to impress us and not be a complete asshole, follow these rules when complimenting a woman:

Consider the Point of the Compliment

I know it’s to tell her she has a bangin’ bod. But what do you want from this woman you’re about to drop some knowledge on? The first thing you should ask yourself before you blurt out a compliment to a woman is why you’re actually complimenting her. Are you trying to be nice? Or are you trying to get laid? Do you want to get to know her or are you just trying to boost her confidence? Do you want something out of this woman or do you just give compliments to anyone, willy nilly? This is important, because men often dole out compliments in a scattershot haphazard way that leave women with absolutely no real understanding of what you want. We assume if you’re complimenting us at all, you are probably willing to fuck us or trying to. Barring that, it’s anyone’s guess.

Highlight What’s Unique, Not What’s Obvious

Compliments that stand out don’t notice the same things every man has; They acknowledge the things every man hasn’t. As MEL deputy editor Alana Levinson told me, “A great compliment should be to highlight someone’s unique qualities, what makes them different. Too many men see it as a way to tell a woman she meets society’s standards. I get why they do it — everyone wants to be told they are pretty. But pretty girls know they are pretty; they figured it out at age 5. I’d rather be told I’m different in some way.” Her examples: Instead of you have pretty eyes, say “I like the way your eyes change color in the sun” or “I like the way your lips purse when you’ve had something sour.”

Compliment Her Choices, Not Her Actual Body

We can take some pointers from a recent Reddit thread on the Ask Women subreddit where user Varl_Bolverk asked the women in the group what men can do to make a woman feel comfortable on a first date. A number of women chimed in with suggestions about how to comment on a woman’s appearance.

“If you want to compliment her, try to stick with complimenting things that she’s made a choice about,” one commenter wrote. “To a lot of people, ‘That dress really looks amazing on you’ rings as less objectifying (and therefore less creepy) than ‘Your body is amazing.’”

This is a good point, but it isn’t a hard and fast rule. You may actually compliment her body, but it’s important to do it in a sincere way. See the next rule.

Always Be Sincere (And Accurate)

If you really need to tell a woman she has the greatest ass in the world, consider that she knows there is objectively a better ass. That doesn’t mean you can’t mean that she really has a perfect ass in your view. But make it clear that you aren’t pretending she’s actually perfect, but that she’s just perfect for you.

In conclusion, real compliments — good ones — stand out because they demonstrate that the compliment giver sees us in a new, attentive, thoughtful way that’s clearly distinguished from the relentless scrutiny we’re used to about our bodies.

A great demonstration of this is John Legend’s song about wife Chrissy Teigen, a legit supermodel he could wax all day about how great her face and body are. Instead, he wrote her a song about how beautiful she is in every other way — her smart mouth, when she’s crying, her “perfect imperfections.”