How Not to Compliment a Woman

Sometimes, complimenting women feels like an important business meeting in another country. There's bound to be a miscommunication, and there's intense pressure not to say the wrong thing. A "complimentary" statement might be taken the wrong way. It's funny to think that one could ever go wrong with complimenting a woman, but actually it's quite easy to do (if you're me).

There are "slam-dunk" compliments that make women happy 100% of the time:

-Obviously, "You look great" works — but there are must-avoid words like "hot." "Pretty," "cute," and "beautiful" are acceptable.

-Recognizing a new outfit.

-Anything non-appearance-oriented like: "You're really intelligent," or "You sure are independent."

-Putting down her friend she's always annoyed with, indirectly complimenting her: "Wow, your friend Vanessa is a train wreck these days."

Most people think having sisters gives me insight into what women want, but it gives me too much of a glimpse into their world. So certain "insights" are like powerful forces that fall into the wrong hands (mine).

A memorable foot-in-mouth statement I've made to a girl occurred because of this "access" to female conversation that I grew up with.

After shopping, my sisters would get together and talk about the new outfit, one sister seeking approval from the other. On top of this approval, it seemed to be a badge of honor when the shopper found a deal, or avoided a traditionally expensive place. So the conversation goes:

Sister 1: "Hey, that's a great jacket."

Sister 2: "Thanks. Only $25 at Target." (Said in French accent "Tar-Jhay"; the French pronunciation in woman-speak seems to mean that Target supplied something that looked more expensive than it actually is.)

Sister 1: "Oh nice, girl!"

Such conversations remained in my demented file cabinet of "go-to" lines. I figured I had one up on other guys. Not only would I compliment a girl someday on how great she looked, but I'd layer on another compliment about how the girl must have found a deal on her outfit.

Of course, like most of my ideas, this plan did not have the effect I thought it would. One night out, this girl (Cara, one of the cutest girls I've ever seen in NYC) showed up with my friend Jane. I decided I'd make a move on Cara, using my tried, true, and tested "outfit" comment and then juice it up with my knowledge of what I thought she wanted to hear. I approached Cara, and said: "You look great. I love that outfit."

She smiled, glowed, and thanked me. Mission accomplished. Not quite. Remember, my "missions" must include the obligatory self-sabotaging comment or action:

"You look great. I love that outfit..." (a bit of silence as I generate the self-sabotaging verbiage in my head) "...and it looks like you didn't have to spend much money on it."

And with that, it was over. My friend Jane approached me later in the night asking me if I knew why Cara was crying. I was embarrassed to start my story with: "Well, I was trying to compliment her and..."

Another stupid "compliment" I attempted ended up alienating a friend. A co-worker asked me to describe the "perfect woman" physically. This was already asking for trouble. I talked about celebs with great figures: Heather Graham, Angelina Jolie. During my answer, my co-worker, Beth walked in. I decided to "throw her a bone" in a non-HR-threatening way: "Oh, Beth's height is perfect."

I then moved on to eyes, hair, and style but again referred to celebs. I didn't realize that my compliment was not so complimentary.

"Hold on. Hold on. Just my height? Thanks a lot," she said.

Once again, my intention of giving a compliment turned on its head.

In my next post, I'm going to present 11 "rules" for complimenting women based on my many errors.

Do you think I'm at fault here, or did the girls overreact — or both? What was my mistake with these? Including my friend in the "perfect description," applying my sister's conversations to the "real world"?

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