Here's the first part of a two-part piece I wrote for my blog, http://www.richlifecleanspirit.com (originally posted to MaleLifestyle). I hope you enjoy it.

Motives

“You can easily judge the character of a man by how he treats those who can do nothing for him.”—Malcolm S. Forbes

This quote is the core principle of properly and eloquently delivering a compliment to a woman – speaking with the right heart. There is one reason and one alone to compliment a woman, and that is because you want to make her happy. One of the key differences between men and women is that women are better – MUCH better – than men in discerning motives. This awareness can be a source of tremendous anxiety for men, to feel that somehow she knows what you’re thinking. Well…it’s kind of true, so the only solution is have the right heart in the first place.

You can jujitsu this fact is by internalizing it and keeping it at the front of your mind when you talk with women. A while back, I’d read an article about how Steve Jobs conducted a meeting – if he looked around and saw someone who wasn’t really needed in the meeting, he’d tell them to hit the road. When I expressed admiration for this brutal efficiency, the woman I was talking to reacted in utter horror, imagining, correctly, the embarrassment and humiliation that the dismissed person felt. I’d totally missed that aspect of the exchange, and I admitted it, and complimented her on seeing what I’d overlooked. She deserved it – she’d done me a favor. Here’s the broad principle you can draw from this scenario – women can genuinely see things that we as men can’t:

“You know, I can’t believe I overlooked that. It didn’t occur to me to see it from the subordinate’s point of view…that is a stunning insight.”

Pro-tip: Avoid complimenting a woman when she’s mad at you. The worst time to compliment a woman is when we need the advantage of a complimented woman the most, of course. This goes back to the Forbes quote – the more impure our motives, the more transparent they tend to be:

My wife: I can’t believe you forgot about coming home early tonight.

Me: (thinking fast, but not fast enough) You look absolutely beautiful tonight.

My wife: (rolls eyes)Please. You fail at husband.

Match your compliment to your level of intimacy

“Proximality” is a fifty-dollar word that really just means “closeness”, but because it’s unfamiliar, it lacks some of the relationship-speak baggage that “closeness” has, so it’s useful.

The concept I’m getting here is that you’re more “proximal” to your mother/sister/wife than you are to the woman you just met at the dry cleaners. This proximality has important implications for how, when and why we compliment a woman.

For example, as a married man, it is only appropriate for me to ever deliver the following compliment to my wife, and her alone:

“I can’t take my eyes off of you in that dress.”

On the other hand, I deliver this compliment once every few weeks or so:

“That’s a lovely dress.”

They’re both about a woman wearing a dress, but once is vastly more intimate, more proximal – than the other. Consider these compliments at a dance studio:

“That was a beautiful waltz.” “You looked beautiful out there on the dance floor.” “You look beautiful on the dance floor.” “You look beautiful tonight.” “You’re beautiful.” The differences are subtle here, and illustrate increasing proximality:

“That was a beautiful waltz.” o A compliment to the act she performed, not directly to her.

“You looked beautiful out there on the dance floor.” o A compliment to her appearance in a limited scope of time, the moment just previous where she was dancing.

“You look beautiful on the dance floor.” o The same compliment without respect to time, and therefore broader in scope.

“You look beautiful tonight.” o The same compliment without respect to the context of her dancing, and therefore more intimate.

“You’re beautiful.” o An observation not on her appearance, but about her essential nature. In truth, it’s not about her at all, but rather an expression of the feelings she inspires in you. Serious talk.

The failure to appreciate proximality is what leads a man to stammer “you’re beautiful” to the beautiful girl he’s spoken to twice before, when he could have simply said “that’s a lovely necklace.” The failure to choose the right level of proximality for a compliment is the equivalent of asking a woman to marry him on the third date.

What’s happening here as the proximality scale ratchets up is that we’re talking less and less about her and more and more about the effect that she has on us. Higher proximality requires more vulnerability on BOTH sides to be successful, and that vulnerability has to be earned and constructed – again, on both sides.

Choosing Proximality

Avoid jumping levels – if this is the third compliment you’ve delivered, it should be level three (or lower, if you’re moving slowly). As a married guy, like I said, I get off the bus at level three with anybody but my wife, mother or daughter. But keep in mind that we’re not checking off boxes on a form (see Motives above) – proximality is not about what you feel, it’s about how you say it. You have to know the rules well enough to know when to break them.

For example, I was at a hotel with some people on a company trip and we commandeered a piano tucked away from the eyes of the staff. I hammered out a few songs on it and then handed it over to a woman I’d spoken to a few times but didn’t know terribly well. She had a drink or two in her, but she was still really nervous, and played a song for everyone. When she was done, I looked at her and told her “That song took my breath away.”

According to my rules above, I should have said something like “What a lovely song you just played!” or something else on Level 1. But she’d just laid out her soul on the keyboard in front of a bunch of people – that kind of vulnerability merited something bigger than a Level I.

To understand how to choose proximality, we have to understand why we need to. Being intimate and vulnerable successfully requires a counterpart in your partner – one-sided vulnerability is disastrous. An unwelcome compliment is worse – far worse – than no compliment at all.

Pro-tip: if you’re delivering a level 4 compliment, you should feel comfortable holding her hand. If you’re delivering a level 5, you’d better be comfortable holding HER.

Geez, where’s the romance here?

Don’t sweat it. What we’ve done here is applying a VERY clinical and nuts-and-bolts approach to a process that is organic and deeply human. All this stuff is training wheels until you internalize it…it eventually becomes instinct. One day you will deliver a level 2 and see in her eyes that she was hoping for a level 3.

Homework

For each of the following examples, you are talking to:

a bridesmaid at a wedding your child’s English teacher a woman you just sat next to the first day in class a woman you’re standing in line with to buy tickets to your favorite performer a woman you work with

Visualize the woman you’d like to be in the situation with. To kick the visualization up a notch, go to Google Images, search on “pretty girl in college class” or “beautiful woman English teacher” and pick an image from there. Imagine this woman the first time you meet, and then after you’ve been dating for six months. Once you’ve got a grip on this visualization, create compliments at all five levels of proximality.

It would be ridiculous (and hilarious) to pay a level five compliment to a woman you’d just met! Imagine this – rather than trying to avoid this uncomfortable feeling, turn it over in your head and laugh at it. Now imagine paying that compliment to the woman you’ve been seeing for six months. As you speak, she laughs nervously, looks down and touches her hair…she smiles.