The Subtle Art of Complimenting a Woman

I went on a first date recently where I spent five hours in my date’s uninterrupted company (dinner and a walk).  In all that time, not once did my date compliment anything about me.  Not my intelligence, my looks, my outfit.  Nothing.

Maybe this is my vanity showing, but that was enough of a reason for me not to see him again.  (Also, he was a mouth-breather.)  I just don’t know why it would have been so difficult for him to drop a, “You look good tonight.”  I mean, I worked really hard to look good for the date.  And I think I brought my A-game in the conversation arena; we never had a dull moment.  I would go so far as to say that I genuinely entertained him when I made him laugh every few minutes.  So where did I go wrong?

Am I really expecting too much when I require a man to take the time to notice that I’ve put effort into my appearance?  Am I using this as a cop-out when I want to be verbally appreciated by the guy who is supposed to be interested in me?  I wouldn’t mind it so much if it didn’t happen so often but I’ve found that a lot of guys are compliment-shy.

Perhaps it’s our faults, girls.  I know for a fact that I don’t have nearly enough class or grace when accepting a compliment.  But is my awkward acceptance speech enough of a deterrent for men to stop giving compliments as it is?  I’m calling foul on that one.

Gentlemen, compliments are a necessity.  I don’t need your approval, but I definitely want a little encouragement every now and then.  And when you’re starting a new dating relationship, it speaks volumes.  We of the Gentler Sex want to know what you enjoy about us.  Whether it be our hairstyle that evening, or the fact that we’re interested in the same topic, or just that you’re appreciating our company.  It’s an ego boost.  A reminder that all the prep work was worth it.  And, at least for me, is the most honest way to get to know someone.  You compliment me on my looks?  You’re probably on the more shallow end of the Dating Pool.  You compliment me on my intelligence or conversational prowess?  You’re probably a downright nerd.  And I like nerds.

All this work for nothing.


Tips for guys trying to drop the right lines:

Do compliment something I can control; my hobbies, my job, even my friends.  For example:

“I like that you’re into working out and being active.”  This opens you up to asking for a second date, “Maybe we can go hiking next time?”  Bam.  Winning.

“I like that you enjoy your work, even if you don’t like all the people you work with.”  This one demonstrates that you were paying attention to my whining.  Good job.

“You surround yourself with good people, I really like that about you.”  This one got me into an 8 month relationship with a really good guy.  I loved that he noticed my friends.  It meant so much to me.

Don’t compliment things I can’t control; my eye color, my height, my parents, etc.  For example:

“Your eyes are the prettiest color.”  Yes, most women swoon over this.  It’s the oldest trick in the book.  But guys, we’ve probably heard it before so it won’t make you stand out.  And, more importantly, I would rather hear you sound a little gay by complimenting my eye shadow, which I put on with the specific intention of making my eyes look so pretty in the first place.

“I love short girls.”  I will get up and walk away from you right at that moment.  Don’t tell me you’re attracted to me because I’m short; I hate being short!  All it says to me is that you would date any short girl, you don’t care who it is.  And, for the record, I’m only one inch under average.

“Your parents did a good job raising you.”  I’m a foster kid.  Fail.

Some of these examples are a little extreme but it’s a basic guideline to the very subtle art of complimenting women.  Make the compliment specific to the woman at hand.  Make it very clear that she is the woman you are interested in, not all women with that same attribute (even if you really are attracted to short women).

And ladies, put your Big Girl Panties on and take that compliment like a woman.  Show some class and act like you appreciate it, because underneath that indignant blush we all know that you do.

My name is Chelsey Mick, and this is how we take our compliments.

  • Shaggy

    honestly, I’m a married man but my wife lets me stare at other women, I don’t get her reasoning, but what i’m trying to say is that you are a beautiful woman and you should keep doing what you’re doing whether or not you get compliments because not everyone notices the true effort you put in, especially for a date that might not lead to further communication, i’m not saying there aren’t people that notice these things, it’s just (for a lot of guys i know) some men don’t like to be frowned upon for looking at and observing the women they’re interested in, they feel they can only look at your face until they get intimate with you, then and only then, will they feel they should notice your looks, your body, your appearance, your attire and dare i say it, your ass.

  • akidnameddroo

    I suck at complements.

    I used to try to keep it fresh and go for the slightly outside of the box attempt.

    Now I just go for flowers and “I think your really pretty”

    • akidnameddroo

      Nobody has ever given me flowers before… I’m not sure.

    • Járai Csaba

      Well, “You’re pretty” definitely won’t go for men (for various reasons) 😛 …. but “you are so strong”, or “I like how you control your emotions”, or “I liked how you played with that kid/baby” should do the job.

      As for flowers….yes, it works. That is something that nobody expects. For one, you would stand out. … Also giving a houseplant (obviously after a couple of dates), so that he needs to take care of it makes him think about you more often, and I believe, more gently.

  • davidfGuest

    Your fair visage gives rise to reveries of wearing you like a hat.

    (How am I doing?)

    • davidfGuest

      Love your writing! I’ll try not to be obnoxious.

      • davidfGuest

        Okay. Those eyes could make me forget where I left my goddamn boxers, you beautiful creature you.