11 Rules for Complimenting a Woman

published 25 June 2010

This past weekend, I was at the beach with my parents and I watched my mom criticize my dad on his many ignorant moves. His only defense was: "It's my birthday so I am allowed to be ignorant."

It's tough to remember: Complimenting someone is more effective than criticizing. At work, you often hear about how you can improve more often than you hear: "You know what, you did a really good job on that project." We forget to compliment, but always remember to criticize.

The previous post highlights stories representing a fraction of the many times my compliments to women blew up in my face. I developed a list of rules for complimenting a significant other based on the multitude of mistakes I've made:

1. Go Out on Top.

Once I get a good reaction, I should stop the complimenting because chances are I'll screw it up. In my previous post, I complimented Cara's outfit, then tried to make it better and ended up wrecking everything else. I need to learn to leave things in good order, instead of leaving things destroyed. It doesn't have to make her jump for joy — it just has to make her smile.

2. Don't Try to Speak Their Language.

It's OK for me to notice a girl looks great, but saying something "makes her hips look great" or "looks like it's from Target," or " I love the new bag" will either upset her or make me look gay (and I don't need any more help with that).

3. If You Don't Know How to Compliment the Body, Avoid Complimenting the Body.

You can go too far, or not far enough. In the previous post, I said my friend had a great height, but it wasn't flattering because she must have other priorities about her body she wants to have complimented. But if I compliment a "sexualized" part of the body like legs, bust, or backside, it better be perfectly timed and perfectly delivered. Eyes, smile, and hair are good bets.

4. Avoid Tough Situations.

There are certain no-win situations when it's impossible to deliver a good compliment, like when I was describing the "perfect woman" in the previous post and decided to include my friend in the description. Also, complimenting a woman when she's mad might just make her more mad. It's not that easy to get out of trouble.

5. Avoid Impulsive Complimenting.

The debacle with Cara was premeditated, but my decision to blurt out my compliment about Beth's height flew through the (kind of nonexistent) "filter" I like to think I have. Stream of consciousness is good, but not for complimenting — an insult might slip out.

6. "Researched" Complimenting Is Good.

It might not be sincere, but if you discovered or are aware of something random that someone is proud of, compliment that.

7. The Golden Rule: Safety First.

This goes back to the business meeting in the foreign country. It's best to be reserved and refrain from pushing it too far. A nice compliment will bring a smile. But a poorly timed or badly delivered compliment could be misunderstood and ignite a storm.

8. My Intent Doesn't Matter.

In other words, her perception matters much more than my intent. So, I should pay more attention to how she will perceive a comment than what I intend to say. And that's a very hard thing to do.

9. Don't Do It All The Time.

It's just going to water down your compliments. It's special if you say it enough, but not all the time. And it's more sincere if you're not doing it all the time.

10. Keep It Diverse.

I wonder if anyone can ever get tired of hearing the same compliment all the time. Actually, if a girl kept telling me I was hot over and over, I don't think I would ever get tired of it. Maybe I mean: Find new things here and there to compliment someone on.

11. Don't Do It to Get Something.

That's just wrong. Guys who are out to get a girl in bed will shower her with insincere compliments as a means to an end. Or a guy might get "complimentary" to his girlfriend before he asks her if he's allowed to head to Vegas with his buddies for a week.

Have you ever reacted negatively to a compliment from a guy that meant to be positive? And has a guy ever been offended by any of your compliments? What's your advice for good complimenting? Are there certain subjects to avoid? Are the rules different for girls and guys?

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