If you’ve thumbed through an issue of Maxim magazine or Men’s Health anytime in the last twenty-five years, you’ve probably read a few pointers on how to properly compliment a woman. Personally, I think these lists can be a little too vague, and quite honestly, a little lame. For example, one list I read recently said, “When you meet someone interesting, commend her on her wit or intelligence—not her beautiful breasts.” That someone actually felt compelled to remind men not to compliment breasts at first sight shocked me. Don’t all guys know not to do this?
But then I remembered some of the “compliments” I’ve received over the years. I started to think that maybe what shouldn’t be said isn’t as obvious for some as it is for others. So I put together this list of “compliments,” all of which are real and were said to either me or one of my girlfriends. No urban legends, no made-up magazine quotes—these are (sadly) the real deal. Read ‘em and weep … and hopefully, learn a little from the not-so-savvy sector of bad complimenters out there.
1. “You look like Gregory Peck.”
Or Corey Haim. Or Janeane Garofalo when she was in her awkward, fat phase. Or Monica Lewinsky. Telling a woman that she looks like a man (or a woman who looks like a man, or a woman who wore a beret as a serious fashion statement to meet the President and then later gave said President a blowjob) is never good—even if you think the woman has an honest face like Gregory Peck’s, or a button nose similar to Corey Haim’s. Generally, women who are interested in men like men who are interested in women. It’s a simple formula, really. And trying to pick her up with the old “you look a little like Gene Hackman in his French Connection days” line will not only insult her, it might make her wonder why you’d want to get it on with Gene Hackman.
2. “I like women with a little gray in their hair.”
You can ignore the elephant in the room. Or you can bring peanuts to attempt to woo the elephant so you can climb up on it and ride for a while, maybe cruise around and jump it through a few fiery hoops of mockery. Let me be clear: gray hair is an elephant you should always choose to ignore. If you truly like gray hair, just say, “You have beautiful hair” and leave it at that.
Many of us in the gray-haired set are a little intimidated by the fact that most men would gladly drop even a youngster like Lindsay Lohan for a chance to hook up with her fourteen-year-old sister. Please don’t remind us that we’re aging and being trophy girled-out with every tick of the clock for younger, firmer models. Just give our grays the time-honored courtesy-ignore and proceed with your flirtation. It’s the polite thing to do.
3. “You have a very attractive labia.”
I first heard this from my ObGyn, a very professional straight woman who wasn’t hitting on me. I took her compliment and swaggered out of my appointment that day full of genital bravado. If it wouldn’t have caused a major HR violation, I probably would have even told my coworkers; I was just that proud. “Hey everyone, guess what? My doctor said my labia is pretty! Who’s up for Starbucks?”
A couple of years later, a boyfriend who was paying me a visit south of the border delivered a similar compliment, though this time in a huskier, sexier voice, “You have the most beautiful labia I’ve ever seen.” Um, what? Suddenly the compliment I’d been so proud of before seemed a little … creepy. Please, never say this to a woman. It’s nice that you appreciate the goods, but this is the one situation where it’s okay to opt for the dirtiest, most porn-worthy word possible over the very clinical “labia.” Please.
4. “I love your pedicure! Is your polish Cherries in the Snow?”
Sometime around 2003, Maxim must have run a story about how to deliver a more targeted compliment, because that summer was all about the details when it came to the initial approach. I heard a lot of, “That lipstick looks great with your skin” and “Your highlights are really fantastic.” Newsflash—women don’t have sweaty, naughty fantasies about getting naked with metrosexuals. (And why would they? Metro men don’t even like to sweat.) Maybe after a brief getting-to-know-you period, we’ll think the fact that you carry a murse is kind of cute (probably not) or we’ll learn to deal with your strictly regimented brow waxing schedule. But early on—especially as the initial pick-up line—these very specific compliments just come across as socially awkward, or downright gay. (Not that there’s anything wrong with that.)
In these situations, I think it’s best to channel an uber-manly man, like say, Clive Owen or maybe Harrison Ford—be general, but be genuine. “You have a really pretty smile” goes a lot further than, “Did you do BriteSmile? Your teeth are so white!”
5. “You can’t possibly weigh that much!”
Sometimes when we’re doing the courtesy reach into our wallet to pay for the drink that you should be offering to buy, you spy our driver’s license and ask to see it. For some reason (perhaps because driver’s licenses make for easy conversation?), the asking often turns into persistent but playful begging. Sometimes we give in and let you peek; other times you make a lunge for it and physically grab the license out of our wallet. In either case, never, under any circumstances, should you comment on the weight listed on the license. Because when you say, “Oh my GOD! There’s no WAY you weigh that much!” you’re absolutely right. WE WEIGH MORE! Everybody knows that women lie about the weight on their driver’s licenses, so you becoming incredulous over the fake fifteen- to twenty-pounds-lighter version of us is devastating. And god forbid, you let the, “Holy shit, you weigh more than ME!” slip. Women like to feel smaller than men, even if we’re not. It makes us feel more feminine. Playing along will get you a lot more action.
6. “You look a lot like my ex wife.”
The ex-wife or ex-girlfriend card is never what you want to lead with. When you say things like this, women assume three things: 1) You’re not over your ex. 2) There’s probably a restraining order against you. 3) You’re needy and will probably cry after we have sex for the first time and say something very Days of Our Lives-ish like, “I could make love to you every day for the rest of my life.” (Vomit.)
With over half of marriages ending in divorce, the days of judging people for a marriage that didn’t work are (hopefully) over. But that doesn’t mean you should trot out your divorce, ex-wife, kids, and alimony issues in the first conversation. Leave a little for her to learn later. The only thing worse you could say to a woman is …
7. “You remind me of my mom.”
Go ahead and cut your penis off, why don’t you? Because not only will you never, ever have sex with this woman, you’ll never touch her nor will you ever kiss her; in fact, it’ll be a miracle if she sticks around long enough to hear the first word of the next sentence. When you tell a woman she reminds you of your mom, this is what we hear: “You can plan on doing my laundry, cooking my meals, and basically taking care of all the shit I don’t want to do for the rest of my life. And we will have awkward, unsatisfying sex because I’ll always be wondering if this is what it was like for Dad.” Very. Very. Bad.It seems that men spend an inordinate amount of time trying to come up with the most genuine way to flatter women. But the best solution is so obvious: just walk up to her and say hello. You’d be surprised how rarely that happens, but how successful it actually is.