The Neurotic's Guide to Complimenting Women

This post comes from Roger Wingstrom.  Roger is either a guest contributor to the Sandbox, or a fictitious persona created by Steve.

Here’s Roger:

Hi everybody.  I’m Roger, and this post is all about how to compliment women on their looks.  Knowing how to give a great compliment to a woman is a very delicate matter, and is three parts art, two parts science, and one part luck.  Only attempt to compliment a woman if you really know what you’re doing.  Trust me, I spend a lot of time thinking about the best way to compliment women.  Just so you don’t think I’m pompous, however, I readily admit that other ways to interact with women are way beyond my expertise.  If you want to, say, suggest that you and a female coworker get some coffee without making it seem like a come-on, you’ll have to look elsewhere because that one just leaves me baffled.  Also, I should probably disclose that my knowledge is mostly academic.  But it’s still good advice because, as I’ve already mentioned, I spend a lot of time thinking about this.

Let’s get started:  There are seven primary types of compliment.  The seven types are listed below, along with examples and explanations of when to use them.

1.   The Descriptive Compliment

Example:  “Your lipstick matches your hair ribbons.”

You cannot find a worse type of compliment.  The descriptive compliment consists of describing the physical characteristics which make a woman beautiful.  It also strips all humanity from the art of the compliment, rendering a compliment soulless and clinical.  Pointing out the specifics which make a woman beautiful merely exposes the superficiality, hollowness, and transience of conventional notions of beauty.  No woman will feel better about herself after hearing about the symmetry of her eyebrows. 

2.   The Suggestive Compliment

Example:  “You’re looking great today.  It really perks me up.”

There is no worse compliment.  To reveal your sexual desires, even subtly, is to treat women as objects and is demeaning to both women and men.  Never, ever disclose that the sight of a beautiful woman causes all your rational thoughts to be supplanted by a burning hunger for sex.  Never hint at the Herculean effort required to refocus your mind onto anything other than the woman’s body while you're in her presence.  Never divulge that, even after she leaves, the lingering effects cause you to—

You know what?  Let's just move on.

3.   The Gay Compliment

Example:  “Wow!  Who does your nails?!”

This is the ultimate in bad compliments.  A gay compliment is one which requires a working knowledge of women’s style.  Now, a man who offers a gay compliment is not necessarily gay himself.  But try telling that to a woman right after someone with chest hair approves her taste in d’Orsays.  If she doesn’t find the compliment jarring, that means she thinks of you as someone who actually follows women’s fashion.  That’s even worse because it means you’re more interested in how the purse looks on her than how she looks with the purse.  The best you can hope for with a gay compliment is to make her feel like a faceless mannequin.

4.   The Poetic Compliment

Example:  “The only thing that lifts my heart more than seeing your face is watching your smile.”

This compliment is the absolute worst.  First of all, once she notices the hyperbole, she’ll wonder whether every other compliment she’s received was also an overstatement.  Second, the compliment draws so much attention to itself that it totally derails the conversation, and is embarrassing to both you and her.  And finally, it shows that you’re more interested in showing off your eloquence than in making her feel good about herself.  The poetic compliment is downright egotistical.

5.   The Self-effacing Compliment

Example:  “Not that my opinion matters, but I think you’re rather pretty.”

It doesn’t get any worse than this type of compliment.  If you disqualify a compliment before even offering it, then why should she listen to the compliment?  Furthermore, by prefacing a compliment with self-deprecation, you practically scream that you’re only giving the compliment for the sake of giving a compliment, and clearly signal that the compliment is insincere.  You might as well insult her to her face.

6.   The Straightforward Compliment

Example:  “You’re beautiful.”

Of all the types of compliments you could make, this is definitely the worst.  A straightforward compliment describes a woman with bare adjectives like “cute,” “fine,” or “stunning.”  Straightforward compliments may or may not include intensifying adverbs like "highly," “quite,” or “very.”  If you think this grammar lesson is dull, just think about how she feels after hearing a cliché like “You’re so gorgeous” again.

7.   The Perfect Compliment

You may notice that I haven’t provided an example of the perfect compliment.  That’s because, just as all women are unique individuals, the perfect compliment will vary with individual circumstances.  Because the perfect compliment is so context-specific, any example would only apply to its own circumstances, and would only be misleading. 

In any case, the perfect compliment is the worst type of compliment.  If you do actually figure out the perfect compliment, it will only be through hours and hours of reflection, coupled with months of waiting and watching for the opportune moment.  If you manage to pull it off, the perfection of the compliment will be so apparent that she’ll instantly realize that it’s the result of extensive scheming.  She’ll also realize, even more disturbingly, that you were only able to pull it off by biding your time and following her around for who-knows-how-long.  You might as well draw up the restraining order right now.

As you can see, each and every type of compliment is the worst compliment you could possibly make.  If you want to compliment a woman on how she looks, the only viable thing you can do is forget about the whole thing, and avoid her as much as possible.  In fact, it’s not a bad idea to just keep away from women generally.  That will give you the time and clarity you need to meditate upon the hard questions in life.  Who knows, you might even figure out the least awkward way to ask that coworker out for coffee.

And if you do, please tell me what it is.

--Roger