12/09/2010 05:23 pm ET Updated Nov 17, 2011

Charming or Creepy? The Art of Complimenting Women

Dear Jen,

There are many times when I'm buying a cup of coffee or a sandwich or something, and the girl at the cash register has some stunningly beautiful feature -- eyes usually -- and I feel compelled to compliment her. I never say anything, though, because I don't know if that would be awkward. So I'm wondering, am I right in keeping it to myself? Would most women be flattered or creeped out, and what does it depend on?

--The Sound of Silence

Dear Silence,

I am pleased to report that I am friends with the Funniest Person in the World. I can't be at his house for more than 10 minutes without finding myself clinging helplessly to furniture, banging my head against the wall or doubled over as if I'm begging someone to kick me. He's been happily married to the same person for over 20 years, and although she is as sweet as pie, the woman has the sense of humor of a bowl of pudding. While the rest of us are teary-eyed, red-faced and stumbling around screaming for help, she sits there, nervously smiling, as if she's just sat in something wet.

"Oh, the waste!" I think as I drive away. All that precious hilarity that goes soaring over her head only to land in a stinking, rotting pile in the corner when they're alone.

So many people starving for laughter in the world, and there he is, feeding caviar to the flies. I can't stand it. I really just can't.

I feel the same way about undelivered compliments, the ones we don't give to each other or to ourselves. We are on this planet but once, and to spend it holding back our gushing appreciation of the things that light us up is a shameful waste.

If you say something to the cashier of your dreams and wind up rubbing her the wrong way, she'll probably think, "That guy was weird, but cool, he thinks I'm hot!" Getting a compliment, even if you need a cooty shot afterwards, is still a compliment. So the way I see it, it's a win/win situation: whether she finds you creepy or charming, you still made her feel special and appreciated, and you should be proud of yourself for conjuring up the cojones to put yourself out there.

In an attempt to help you err on the charming side, however, here, are some pointers:

Charming: Complimenting her while looking in her eyes and smiling.
Creepy: Complimenting her while staring at the floor -- or worse, her chest.

Charming: Smiling, no-big-dealing, and walking away.
Creepy: Lingering, staring, wiggling your fingers, wanting something in return.

Charming: Following up with a lovely chat.
Creepy: Touching her.

It's about who you're being and how you say it, not what you say, so be light and fun and happy about it, and so will she. And practice makes perfect, so do it as much as you can. And lastly, to paraphrase Eleanor Roosevelt, no one can make you feel like a dick-twiddling pervert without your permission, so give yourself a break, be brave and let the compliments fly.