Let’s be honest, giving compliments is a risky business. Even if you nail your delivery, its content could come off as clichéd, while less-than-optimal execution will merit, at best, an awkward laugh.
Invite warm conversation instead of a cold shoulder with thoughtful compliments she’ll actually appreciate, like remarks regarding her character, wits or intelligence. Flatter her family and friends and acknowledge style choices over physical attributes.
I can’t promise that’ll work 100 percent of the time but, whatever you do, don’t repeat any of the following failures. Trust me, these lines aren’t working on any women.
1. Shannon, 25: “ ‘You’re a very interesting woman, aren’t you?’ Like, is that a good thing or a bad thing?”
2. Caroline, 29: “ ‘How are you single?’ It’s like they’re insinuating I must be crazy.”
3. Sydney, 25: “ ‘Why do you wear all that shit on your face? You look so much better without makeup.’ It’s meant to be a compliment, sure, but it’s also like this shit on my face costs me half a paycheck and consumes a half hour of my morning every damn day.”
4. Kelsey, 25: “ ‘You have a really nice smile—you should do it more often.’ ”
5. Jessie, 27: “I hate when men compliment something physical about me. Compliment a choice I made, like the dress I decided to wear or the shoes I chose to put on this morning. It’s more personal than complimenting a physical attribute over which I had no control.”
6. Alaire, 28: “When I ask for his opinion on an outfit and he tells me that he likes everything. I just want the real answer. Be helpful.”
7. Paulina, 28: “I hate when men tell me that at least I’ve got a good sense of humor, unlike other women who are ‘easily offended.’ Stop being offensive because now I’m not laughing.”
8. Kerry, 26: “ ‘You’re asking for trouble in that outfit.’ That’s creepy, and you’re a predator.”
9. Sophie, 24: “ ‘You’re too pretty to be single.’ Maybe I’ve wanted to be single. Ever think it was a choice?”
10. Taryn, 26: “I hate when dudes assume I’m chill because I drink beer and watch football. I’m actually crazy AF—I just like watching large men in tight white pants tackle each other and cider gives me heartburn. But actually, a lot of women watch sports. Some of us even play them, too!”
11. Lesley, 27: “ ‘I like that you don’t wear a lot of makeup.’ It just insinuates that women who wear a lot of makeup are all high maintenance and, now, if I ever want to wear more makeup around you I’ll feel uncomfortable. So you better have meant that you genuinely like this bare face because it’s all you’re getting, boy.”
12. AnnaMarie, 25: “ ‘You ate that pizza like a motherfucker.’ I will never eat pizza in front of you again… at least not until you put it in front of me (in which case I’ll probably inhale it, again).”
13. Esther, 33: “ ‘How do you work full time as a mother? You’re impressive!’ How do you work full time as a father?”
14. Taylor, 31: “ ‘You kind of remind me of my ex, but not like that. She was cool. We’re cordial.’ I’m sorry… What?”
15. Cat, 26: “ ‘I love a girl who can eat. Most girls I go out with just order lettuce.’ Thank you for making me feel like a fat ass and also generalizing an entire species of human of which I’m a part.”
16. Julie, 25: “ ‘You’re too pretty to do X, Y, Z.’ Like you’re too pretty for that career, or you’re too pretty to be single, or you’re too pretty to be dealing with that drama, or you’re too pretty to subject yourself to that kind of behavior, or you’re too pretty for whatever. Being pretty is irrelevant.”
17. Kacey, 26: “Stop. Trying. To. Guess. My. Bra. Size. If you guess wrong, which you almost always do, you’re an asshole.”
18. Alex, 26: “Quit the unsolicited catcalls. Dry humping the air, licking your lips and yelling out ‘God bless’ isn’t enticing anybody.”
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