How do I compliment a woman I've just met?

Guests enjoy Grey Goose cocktails at a Soho House Chicago pre-opening with Grey Goose on Aug. 3 in Chicago.

Guests enjoy Grey Goose cocktails at a Soho House Chicago pre-opening with Grey Goose on Aug. 3 in Chicago. (Jeff Schear / Getty Images for Soho House Chic / August 2, 2014)

Dear Anna,

I’m a single man in my mid-20s and am wondering if there’s a way to tell a woman she’s attractive without coming off as a creep or offending her. I’ve told women they were beautiful and been sneered at or ignored, even though I meant no disrespect! How can a man respectfully compliment a woman he’s just met? —Nice Shoes.

Dear Nice Shoes,

Thanks for noticing! I just ran my summer Crocs through the dishwasher, so it’s nice to know my efforts are being appreciated.

Based on a very scientific poll I conducted on Facebook and Twitter, the overwhelming consensus for how to compliment a woman you’ve just met is to comment on what she has control over—e.g. something she’s chosen to wear or rock (“What a fetching fedora/Nicolas Cage tattoo!”), or an activity she does well. The latter is a little harder, unless she’s, like, walking down the street on her hands or something, but not impossible. Perhaps she taps a keg with aplomb or dances as well as this gal.

In addition to complimenting sass rather than ass, Caitlin adds: “Give a compliment and back off, expect nothing in return. It’s a gift, not a transaction.”

Remarks based purely on physical appearance were considered less welcome than on, say, a woman’s style, but not always. Devon says, “I personally love it when I’m complimented on my appearance. I also try to go out of my way to give sincere compliments because if you don’t like them something is wrong with you.” Lydian agreed that sincere compliments were the way to go: “Compliments should be tailored to the individual, and the ‘You seem ... I hope ...’ format could avoid making the person feel uncomfortable. For example, ‘You seem like an awesome person. Hope I’ll see you around.’ It’s genuine enough for someone to feel good about, but also gives the person some room to breathe.”

If that fails, never underestimate a comment on intelligence. As Sarah notes, “Recently I got ‘You have such a sexy brain.’ And then all of my clothing fell off.” Jolie offers the advice that you should compliment a woman the way a woman would. “I compliment women on the street all the time. ‘Lady, you are absolutely rocking that teal hair.’ Or, ‘You just look so pulled together, head to toe—thought you should know!’”

Tristan relies on the straightforward and always sound approach: “Listen to her and actually pay attention to what she says.”

And perhaps my favorite, from the aptly handled @Mocha_Jesus: “You look like you deserve equal pay and the right to do whatever you want with your body.”

Get in my coupe this instant, sir!

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