How To: Compliment Women Without Being A Creep


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Well, you guys, we have really done it now. We as men have successfully destroyed the concept of actually approaching women and paying them a genuine compliment. Guys yell out of car windows, cat-call women on the street (and insult them when they don’t answer), and leave ridiculous comments on Facebook photos.

Unfortunately, the words “hot,” “sexy,” and “beautiful” have been nearly destroyed and terribly watered down by these slobbering dogs. And honestly, it comes across a little try-hard, creepy, and unoriginal when you use them – especially if you don’t know her.


So needless to say, if we ever hope to pay a genuine compliment or approach a woman to start a conversation, we have some serious adjustments to make in order to not be met with a brick wall of an attitude.

First of all, learn to read signals. It’s honestly not that hard. If she is walking along the street and her head is down at the ground, don’t say anything. If she is on her cell phone, don’t say anything. If she has a baseball cap pulled over her eyes, she is hiding from you. Don’t say anything. We need to be able to take simple non-verbal cues and act (or not act) upon them accordingly.

If a woman is walking towards you on the street and you make eye contact, smile. Casually. Maybe say hello. Casually. And keep moving. As human beings we are naturally social creatures, and I do believe most people will respond positively to kindness, but it is absolutely imperative you don’t overdo it. You don’t need to start a conversation with everyone you see – just smile and say hi. I do this with both men and women, and nobody seems to mind.

The other night I had just parked to pick up take-out. There was a girl walking out of the restaurant next door going to her car, which happened to be parked next to mine. She glanced over at me a couple of times, so I smiled at her and said ‘nice boots’ which she enthusiastically thanked me for saying, flashed a big smile, and we went our separate ways.

No harm, no foul.

Some guys might be reading this thinking to themselves: What’s the point of this? What am I getting out of this deal if I just compliment a woman and then walk away?


By asking this question – we are uncovering the very problem. The “what’s in it for me?” mindset is precisely what causes problems when it comes to not only relationships, but approaching people in the first place. If you always have a motive other than simply making a woman feel good about themselves, she will know. Every time.

She will know by your body language. If your shoulders are directly pointed at her, you will appear too aggressive and immediately put her on guard. She will know by the tone of voice you say things in. She will know by the expression on your face. She will know, especially, by what you say.

The more comfortable you get with simple things like smiling and eye contact, the more you will realize that people actually do usually respond well to these innocent, friendly gestures. This will help you pick up on cues from women when you notice who smiles back, who doesn’t, and what they had in common. It will then help you identify situations where it is welcome for you to move past a simple smile, and actually start a conversation.

If you are in a coffee shop, or a bookstore, or even at a bar (anywhere that doesn’t require you to stop her in her tracks in the middle of the street), then pay attention to your surroundings. Ask a question. Pay for her coffee. Hell, pay for her book. Most men don’t think twice about asking a random girl at the bar if they can buy her a drink, but when was the last time a man saw a woman looking at a book in a bookstore, started a conversation with her about it, and offered to buy her the book?

Here is one last statement I am going to make that will probably get me some backlash from some of you, but it is undeniable in the world we live in: Be attractive.


I am certainly not saying that if you did not get lucky in the gene pool, you are out of luck. We’ve all seen beautiful women with average looking men and wondered “How did that happen?” It happened because he presented himself well. He worked with what he had. He walked, talked, dressed, and acted like a gentleman. He stood out from the crowd. He treated her with respect. He carried himself with respect.

To a mature woman, this is what makes a man attractive. Of course they swoon over models and movie stars just like men do, but they understand that if they are not made to feel comfortable, if they are not made to feel respected, if they are not made to feel safe, if they are not made to feel wanted and desired – no level of good looks will make up for it.

If you want to be seen as a mature man who is different than the rest of the Desperate Dans that women are approached by every day, you are going to have to act like it. Master the skill of conversation. Work to transform yourself into the man who a woman would want to talk to. Define yourself. Be the flame, not the moth.

The bottom line is this: If men want women to stop complaining about guys being creepy, then guys should just stop being creepy. If we want to be taken seriously, we need to act seriously.

Simple as that.

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  1. Amanda Carter on October 29, 2014 at 10:14 pm

    YES! I loved this. So many times men will use the excuse “I was just giving her a compliment.. it’s not my fault she took it the wrong way”. I’m glad someone finally explained it!

  2. Sae Sae Norris on October 29, 2014 at 10:23 pm

    Wow, a guy that was genuinely confused by women’s behavior (reaction), asked women what their take on the problem/solution was, endured a zillion conflicting responses, and then RE-STRATEGIZED his tactics? Men, take a leaf. That’s a helluva lot hotter than any “hey there” you could toss our way.

  3. Melissa on October 29, 2014 at 10:37 pm

    It would be AWESOME if someone bought me a book! Let alone actually talked about it

  4. Donna Cruz on October 29, 2014 at 11:09 pm

    As a woman in a VERY public career, I’ve experienced the “cat call”. But aside from the ONE CREEPY guy that followed her for 5 min in this video (and yes, he was a creep) I think she should have said, “thank you” a few times. #class Donna

    Sent from my iPhone


  5. aee8 on October 30, 2014 at 12:49 am

    Thats pretty good article! That would be nice if the guy bought me a book.

  6. Nancy Cokinda on October 30, 2014 at 1:26 am

    Another much needed and perfectly stated blog, James! Re-posting this on my Face book page so Generation Y can read this. Sorry, too late for Generation X-the bitter generation—the moms and dads who failed to teach these basic skills to their Generation Y kids. I love connecting with older Baby Boomer and Formal Generation gentlemen who are adept at these social skills, and have been honing them for many years. One of my favorite moments was running into a French bistro while still in my white fencing knickers and hair braids, walking past a table of 4 Frenchmen in their 80’s who were having coffee at an outside table, and stopping in my tracks. They greeted me in French, started a conversation, and I spent an entertaining hour having coffee with these 4 charming gentlemen. They were intelligent, educated, polished, witty,well-traveled, and had mastered the old European art of flirtation. And all they wanted was a lady’s presence and good conversation for an hour. It was delightful.

  7. […] Some of that results in articles like ‘15 Signs You’re With A Good Man‘ or ‘How To: Compliment Women Without Being A Creep‘ which are often met with resistance…from, you guessed it, men. If you read an article […]

  8. Claire Heaslip on October 30, 2014 at 1:06 pm

    That book idea really needs to become a thing! Plus comparing books you’re both buying is an amazing conversation starter

    • anonymous on October 30, 2014 at 8:02 pm

      As a guy I do have to ask about the book thing to women. A guy buying you anything wouldn’t make you feel pressured? If somebody buys me something I feel compelled to pay it back. You guys don’t feel that? Or is it something like you can sense the intention of why he is buying it?

      • Sae Sae Norris on October 30, 2014 at 8:25 pm

        Feminine instinct. For me, it’d be up to sensing the guy’s intent. And YES I absolutely would feel like returning the favor –and maybe treating the guy to lunch or something.

      • Claire Heaslip on October 30, 2014 at 10:50 pm

        It all depends on the intention with me. If I sense a guy, or anyone for that matter, is paying for something with the intention of making me owe them… I usually decline the offer. However if its done in the same spirit as paying for coffee while on a first date then I just consider it as something nice someone has done. Not something I have to worry about “paying back”.

        As for buying someone a book at a book store, men buy girls drinks at bars all the time. This is exactly like that, expect instead of trying to get a girl drunk, you end up getting to know her.

  9. anonymous on October 30, 2014 at 8:41 pm

    That is kind of my point though. From my perspective as a guy, therefore don’t know the female perspective, I would take that as quid pro quo rather than a generous act. If I talk to a girl quid pro quo isn’t my idea of romantic. I actually avoid buying stuff because I find that it hinders her judgement of my personality.

    • Sae Sae Norris on October 30, 2014 at 8:53 pm

      That’s fair enough. To clarify, for me, I wouldn’t shoot a guy down for trying something like that. But, if that’s not your style, how about observing what she’s buying and initiate a conversation about it and take things from there?

      I think most of the women here simply appreciate James’s idea of not trying to pick us up while we’re walking on the street (it’s just not the right place), and getting creative with initiating contact in a setting that is a little more easy to have a conversation. I think it has more to do with that than the idea of someone spending money on us.

      I also like the idea that you don’t have to be in a bar/club to pick up girls. We’re everywhere. As a rule, we typically just don’t like being approached on the street.

      Does that make more sense?

      • anonymous on October 30, 2014 at 9:03 pm

        Yeah that makes more sense. I read this because a friend on facebook posted it and the first thing I hadn’t heard from a million other places was “buy her stuff” so that initially just sent up a red flag. If I am interested in the girl and what she is reading than I will initiate a conversation if I am in the mood. To me I think I come across as desperate trying to buy stuff for a girl. I just hope that the author wasn’t stating it as a necessity in order to establish some sort of connection. The not buying rule actually extends to bars as well as when I was younger I had experiences with women who would take it and walk off without a thank you, you live and you learn though. The exceptions to me are girls on their birthdays, other than that I just get the sense that I am coming across like I expect something back and vis a vis self-fulfilling prophecy that is exactly the vibe she gets.

      • protocol417 on October 31, 2014 at 2:07 pm

        Anonymous: I think the point that the author was trying to make is that FIRST you have the conversation, and, if things are going well, THEN you buy the book. I don’t think you start with the offer… that would be very weird… and I don’t think it was “mandatory”. Nothing is.

        So far as buying drinks: It’s rude that you weren’t thanked, but a drink is not payment for “something more” (conversation, relationship, sex). It’s a gift. So if she walks away, it’s her right to do so. She doesn’t owe you, and it would be a bit disturbing if she did.
        That said, I wish more women bought drinks (or coffee, or books) for men. When I was dating, I would’ve loved to do that, but in my experience some men see that as an affront to their masculinity. Even my husband sometimes has a LOT of difficulty with me paying for things.

  10. anonymous on October 31, 2014 at 2:13 pm

    I never said anything mandatory had to be returned for me paying for a drink. The point was that it doesn’t work for me to meet people. I find just talking to a girl does. Personally to me paying for anything for a woman who is a stranger is odd to me. It just isn’t me. If other guys can do it and feel comfortable, fine. I can’t. I find other ways to connect. Maybe because I really don’t associate economics to any sort of gender binary.

  11. thesteadfastsoldier on October 31, 2014 at 10:48 pm

    I just posted an abbreviated blog post similar to the part about becoming a man. I ventured off to another topic, which was more about being single and ‘becoming’ the right man. I discussed being a ‘hopeful romantic’, and being patient for when I will meet a woman.

    I really love your stuff!

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