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So many guys are truly clueless when it comes to complimenting a woman. How many of you have said any version of the following:

“Wow, you’re totally gorgeous. Let me buy you a drink”

“God broke the mold the day he made you!”

“You are fine! I gotta take you to dinner sometime girl! Gimme your phone number!”

It’s a sad moment when any man lets rip with any of the above. Can you see how insulting these are? Cool guys never waste their time with “compliments” like these.

Not only is it blatantly obvious that the only thing you are thinking about is sex, but it is also painfully clear that you lack imagination and any ability to actually pay attention to anything other than her looks. That’s three strikes against you, and you have only said one thing!

Women don’t like to be treated as sex objects by men -clear? When you “compliment” her with any of the above, you give yourself exactly zero chance of meeting the actual person, and having a real conversation.

Let’s take a minute now and talk about how to compliment a woman, in a way that doesn’t insult her.

First of all, people (not only women), prefer to be complimented about things that they have actually done. So, in the case of complimenting a woman’s appearance, why not consider her selection of clothing and style?

“Let me say, you look terrific, your sense of style is spot-on. Are you a designer of some sort?”

“Are you an athlete? You walk with such grace and composure – not easy in heels on the concrete sidewalk”

Your chances of flattering her are very high with statements like these. You could even initiate a conversation with a woman using these.

Again, you are talking about the choices she made around her clothing selections for the day or the grace with which she carries herself (something she has undoubtedly worked hard for). You are complimenting the person, rather than her God-given looks.

If you are in conversation with her, and feel the desire to compliment her, again, try to stay away from her looks:

“Wow, I am impressed. You are a great conversationalist. This is really interesting. Let me ask you, how were the dinner table discussions when you were younger – pretty involved I’d bet.”

“You’re clearly well read – a characteristic I really respect. Where did you get that quality? My mom and dad were avid readers when I was growing up, so I naturally became one too in my adult years.”

If you ever do feel compelled to remark on a woman’s beauty, be sure not to do it when you first meet. This just places you in the age-old category of a guy who is only interested in sex, and can’t think of anything original to say. SERIOUSLY. It is far more powerful to do so later in the conversation, as she will feel more comfortable around you and thusly more able to be flattered.

“You know, I haven’t said so until now because I didn’t want to make you uncomfortable – but you are a very beautiful woman. It must be both a burden and a luxury for you in life. Do you ever feel that people are often speaking to the face or the body, and not the person?”

Ultimately, you want the compliment to indicate that you are able to pay attention to more than just her pretty face. It also indicates that you have some knowledge of what it means to be a beautiful woman in the world. This helps her to relax around you even more, allowing her to open up more to you.

That’s how you really reach her guys, not by barking at her out your car window…

Feel free to send me your comments or questions. I am always eager to hear from guys in the real world, facing real challenges. You might be surprised to know that many guys suffer the same challenges as you – so go ahead and ask. Just be sure to put “Mailbag” in the subject line.