How to Compliment a Woman and Not Seem Like a Creep

How to Compliment a Woman and Not Seem Like a Creep

Know this. I’m writing this post with nothing but the best of intentions. However, in working on this, I've realized it's a much more sensitive issue than I had initially imagined. In fact, I feel like I can't even bring the subject up without feeling uncomfortable. But I don't see the the issue with telling someone, "that looks great on you," or, "you look good. Have you been working out?" or, "I like the way your hair has looked lately.”

My first step in researching this post was to reach out to a few female bloggers to gain their perspective. This also happened to be my first clue that I had stumbled into something stickier than originally anticipated. One responded that she didn’t have any concrete ideas, but warned me that the difference between between being complimentary and being creepy was a “fine line”. Another told me she had to think about it because it’s really easy to come across as a creep. I haven’t heard back. And the third? Well, she didn’t even respond.

My goal with this is to help guys that seem to have trouble knowing what to say. I want to bridge the gap between what men want to say and saying it in a way that women will want to hear. I was one of those guys who had trouble with this growing up. I had no older siblings and parents who didn't quite know how to communicate either, so I stumbled. A lot. I wish I had had someone show me the ropes, to tell me the rules. With that in mind, here are my five rules for complimenting a woman without coming across like a creep:

1. Criticism is NEVER ok, even if followed up with a compliment.

No backhanded compliments. No critiques. No suggestions. No advice. No “help”. This is about appreciation, recognition, and praise. Like your mother probably told you, “if you can’t say something nice (and ONLY something nice), don’t say anything at all.”

2. No comments on anything specific.

Chances are if you’re noticing something about her, she is too. She may be self-conscious about what you’re noticing. She may not like that people are noticing. I suggest sticking to general compliments or pointing out something that she obviously chose like clothes, shoes, an accessory, etc.

3. Sincerity is the key. No ulterior motives.

This is also about being a gentleman. Manipulation is not cool. A compliment should exist solely for the sake of being a compliment. You’re selling yourself short if you think the only way to get what you want is by deceiving someone else. I would bet you’re more resourceful than that. Be honest, be genuine, and commit to only telling people things you believe are true.

4. Read the relationship.

For me this is the hardest part. Are you and this woman people who share compliments and moments? How intimate are you and she allowed to be with one another? Unfortunately, if she “friend-zoned” you, that’s where the relationship is. Don’t push. Accept it, and respect those boundaries.

5. Don't overdo it. One and done.

Laying it on thick is a sign of desperation or insecurity, and is extremely easy to read. Say something nice and move on to other conversation.

Look, I know this is a delicate issue to write about, but we should be discussing it. Human interaction is part of life. As we move so much more towards texting, snapping, and tagging, I think we lose those interpersonal skills that help us handle real situations which are never going to go away, no matter how digital life gets.

I really want to start a conversation on this. Leave a comment. Let me know what you think.


Tailor & Barber