I was looking through a friend’s OnlyFans page and saw where one of her subscribers left a comment under a photo of her in a leotard saying, “Wow, nice vagina.”

He might have been teasing her for choosing to wear a tight outfit and posing in such a way that her covered groin was visible, but something told me that it was (at least in his mind) a legitimate compliment. I shake my head when I see that happen and just want to take those guys to the side and say, “Dude…”


It reminded me of the scene in the movie “Taxi Driver” where DeNiro’s character takes Sibyl Sheppard’s character to a porno theater for a first date. She’s mortified, of course. But you can tell that, to him, it all seems normal and appropriate.

I thought I’d dedicate this blog to all of those guys who lack the skills to properly compliment a woman to get the response they want instead of a slap across the face.

This is NOT a how-to-get-laid advise article. If that’s the knowledge you’re seeking, look elsewhere. I simply know how to pay a compliment that actually resonates. Flattery may get your foot in the door with a woman, but I’m the last guy to give advice on how to charm your way into her bed. I have zero game, in that regard.

I’m talking to those of you who are, sadly, even more awkward around women than I am and can’t even compliment them without being clumsy or taking it to dark places.

How to NOT succeed when complimenting a woman

These days, paying a compliment is a minefield that could potentially blow up in your face.

First of all, women have caught on to the fact that when men compliment them on how they look with their clothes on, the unspoken subtext is that they’re attractive enough that we’re interested in seeing their clothes off. Thus, there’s no need to go there.

Sure, we might have pure intentions to make their day a little better by validating that they left their house making good choices on makeup and wardrobe choices. However, pretty women are constantly getting flattered by men who are hoping that the “buttering up” approach to engaging her self-esteem will get them conversational engagement that eventually leads to sex.

This is the human equivalent of animals sending signals for mating.

That’s a subtle distinction, but it’s the reason why a compliment from another girl carries more weight than what a pack of drooling boys heaves at her.

It’s easy to feel like the alien in “Star Wars” warping in to attack the Death Star and realizing the shield protecting it is still up, declaring, “It’s a Trap!”

Guys, don’t go splat on a woman’s defensive shields. Cause they’re always up. And anything you say is presumed to be manipulative bullshit unless you are complimenting a 12-year-old girl who just got her braces off and her boobs (eww, don’t do that unless you are a 12-year-old boy reading this).

An article on the website LovePanky puts it this way:

“A man can say one thing, intending nothing but a compliment, but the woman perceives a whole second area of interpretation that leads her to rightly or wrongly make her own decision on what it is you mean.”


The rules of complimenting a woman

Don’t objectify her

Whenever possible, don’t focus on her body and looks. The exception being if she’s a competitive fitness model who has been in the gym for months toning her body. Then it’s a compliment to her hard work rather than essentially saying, “God gave you great tits.”

Chattanooga model photographer

“That’s a nice shirt you aren’t wearing.”

Qualify any compliments about her looks

When you tell her she “looks really good today”, her brain goes into overdrive turning that into a negative where she’s pondering whether you’re actually telling her that she looks good compared to the disgusting wreck she must have been on other occasions you saw her.

How do you avoid that? By including words like, “You always look terrific, but there’s just something about you today that looks extra special.”

You might think you are safe by complimenting some features on her face like eyelashes or eyes since at least you aren’t focusing on her boobs, butt or crotch. But she might take this as saying that the rest of her must look bad. Particularly if she has poor self-esteem.

Beware of compliments that are actually veiled insults

“You look amazing since you lost weight” seems like a real confidence booster, but she might take it as you mean “You look so much better than you did when you were fat.”

Which may be true. Clothes probably do fit her better. She may be feeling self-confidence that radiates from her. But a better approach might be, “Tell me how you lost some weight. I need to lose a few pounds myself so I can feel more energetic and improve my health too.”

You’ve essentially said the same thing — thin > fat — but you’ve taken the focus off of her looking better skinny and put it onto the positive health and stamina benefits of weight loss.

This compliment is still fraught with peril. I asked one of my friends what diet plan she was on so I could try it and she replied, “Cancer.”

I promptly searched for a rock to crawl under.

People look fine when they’re carrying extra weight, but we’re all very sensitive to how others perceive us. Don’t just tell someone she looks great after she’s lost 20 pounds. Tell her when she’s gained 20 pounds so it balances out all of the pressure put on everyone to be physically fit instead of, you know, normal everyday us.

Age is another subject that is hazardous to get into because most of us over 50 are already feeling older than dirt. Telling us we “look great for our age” is both reassuring and terrifying because it means we likely aren’t going to look any better and just go downhill from here.

In reality, you can look great at any age or weight if you project confidence in your own skin. Being comfortable with yourself just the way you are is so sexy.

Don’t use a compliment just to fill an awkward silence during a conversation

This is when you might thoughtlessly blurt out something that comes out the wrong way. I’ve done this myself, and man, it’s not pretty when it backfires.

Be delicate when purposely trying to compliment something other than physical appearance

That’s right. You can’t even tell someone they have a great personality without it potentially getting turned around in their head. Use specifics rather than generalities: “You’re so easy to get along with” or “It’s so easy to have a conversation with you.”

Never compare your current partner to your ex

Never ask her if you’re the best lover she’s ever had. She might be honest and destroy your ego.

This can be devastating insecurity. Best to avoid comparisons entirely unless you are talking about emotional distinctions to reassure your wife or girlfriend that she makes you so much happier than your ex.

Saying you “traded up” while embracing her is a better way of sending the message that she’s hotter than your ex because you aren’t focusing specifically on physical characteristics. And for God’s sake, don’t say that in front of your ex unless you want to get your face clawed off.

Oh, and guys, don’t ask her how you compare to her past lovers or if your dick is the biggest she’s ever had. If she volunteers this information unsolicited, take the win, but never ask questions you don’t want to know the answer to.

Be confident and attractive

The same words spoken to the same person by two different men can have dramatically different effects. It’s kind of the same way that an exchange might be perceived as harmless flirting if the other person is attractive vs unwanted sexual harassment if they aren’t. Sad but true. Human sexuality is complicated.

Lower your expectations if you are a slob telling an elegant goddess that she’s beautiful. If she’s out of your league, accept that you’d have to make some life changes and work hard to realistically date her. Do your best to become the best possible version of yourself before you go around celebrating others achieving the same for themselves. Then your compliment will mean a lot more.

Be Polite

“Nice tits” may be stating a fact, but it’s rude. Don’t talk about her breasts at all. If a woman feels confident enough to share a photo of herself in a bikini on social media, don’t treat her like a slut or a sex object, even if you suspect she’s fishing for compliments and attention.

Being unnecessarily crude puts you on the level of a YouTube troll trying to deliberately make people feel like crap about themselves. Being a gentleman distinguishes you from all of the other guys being crude jackasses. In this day and age, it is appreciated.

Sharing a revealing photo does NOT mean someone is promiscuous in actual life. Models do it all the time to convey a lifestyle of physical fitness while displaying swimwear or lingerie. To treat them as the town bicycle in a comment is like assuming that Julia Roberts is a whore in real life because she played on in the movie “Pretty Woman.”

Compliment her in the spirit of “you go, girl!” encouragement or tell her that seeing her photos brightened your day when you had been feeling down. Then she feels as if she has performed a freakin’ public service!

And if your motives are to get her to post more revealing photos, the saying “you catch more flies with honey than you do with vinegar” applies.

Don’t send her an unsolicited dick pic.

Don’t be vulgar. Don’t share explicit details about how you pleasure yourself looking at her photos. It’s implied at a very subtle level, dude, and you just make her feel gross by sharing it so openly. Some women might get turned on knowing they made it into a guy’s spank bank, but it’s best left unsaid until you are intimate with a woman in real life. Then it becomes a fun game of phone sex or sexting.

Women understand that men are visual creatures. Before we had free porn all over the internet, there was the lingerie section of the JCPenney catalog, and before that, those topless tribal women shown in issues of National Geographic.

Keep the details to yourself, pal.

Rules for Compliments that work

Be genuine

Even if you are a bit clumsy, authenticity wins you points. Be sweet because you are actually a nice person – not a sleazy guy pretending to be decent to win points.

Don’t overdo it

You can appear “thirsty” if you lay it on too thick or share compliments too often. It means less if she feels like she doesn’t have to work for it.

Be situationally appropriate

Context and timing matter. Wait until you’ve charmed her into a relationship before saying how special she is to you. Start slow and follow your gut, even though your sex drive is telling you to find out quickly whether she needs to be sorted into the elimination pile. Wait until she gives you cues that she’s interested before you get too loving or sexual in your comments or you’ll shoot yourself in the foot.

Don’t let the other shoe drop

Don’t immediately follow up on your compliment with a romantic proposition. Leave it to marinate for a bit in her head. She may realize you weren’t just saying something sweet to get in her pants. Sure, you still are, but you’re not being obvious. Patience is a virtue lost on so many guys. Women appreciate a man who gets in their head a little bit rather than just going in for the jugular right away for the quick casual sex session.

Make a woman feel special

Women want to know that they aren’t just pieces of meat that a man will use and then throw away. They want security. Men can go around squirting our sperm into a different woman every night, but women crave commitment because it can be disastrous to become pregnant with the child of a man who has discarded them like last week’s garbage.

Telling a woman she looks “hot” can be a pleasing sentiment in terms of letting her know she’s visually pleasing, but choosing to instead use words like “beautiful” or “stunning” have more impact because they imply she has more value aesthetically and is worthy of more than a casual fling.

Once you are in a relationship, say things that let her know how much she means to you, emphasizing the effect she causes, the spell she has cast upon you. This makes her feel that sense of security she’s sought so she knows she isn’t going to be replaced by any of the women around her who are equally attractive.

I’ve heard married women complain about how they feel so undervalued by their husbands. Those dudes could absolutely turn things around by saying a few simple words like:

“I can’t imagine my life without you in it.”
“How do you look so beautiful all the time?”
“You look so cute when you laugh.”
“You brighten up my day every time I see you.”
“I could stare at you forever and I’d still feel like I haven’t had enough of you.”
“Spending time with you is the highlight of my day.”
“I feel so happy just spending time with you.”
“You could have any guy in the world, and yet you chose me. I’m so lucky to have you.”
“I wish I had met you years ago.”
“You’ve been on my mind all day.”
“You make me want to be a better man just so I can be more worthy of your love.”
“I don’t know exactly why, but you are so damn sexy.”

If you want to see a woman glow, those are the magic words to make her smile and make her happy. They make her feel loved and reassure her that she’s enough. If you say things like these and they aren’t met with enthusiasm, your relationship is in trouble, man.

If you are complimenting someone you are not already in a romantic relationship with, some good compliments might include:

“You’re smart. I learn so much from you.”
“You’re hilarious. Your Facebook posts are so smart and funny.”
“You’re not like everyone else. I am so lucky to know you.”
“You’re good at what you do.”
“I can’t quite put my finger on it, but there’s something about you that is SO attractive.”
“You’re awesome. I’m glad I met you.”
“I don’t know why, but I feel so comfortable around you.”
“I can see so much warmth and kindness in your eyes.” (only if she’s that kind of person)
“You have such good taste in music/clothes/food, etc.”
“Wow, I never thought someone so pretty could also be so smart.”
“You’re so smart, I could listen to you for hours.”
“You’ve got a great smile.”
“Your eyes are so expressive. I could get lost looking into them.”
“You’re even prettier (in real life) than your pictures.”
“Don’t listen to jerks trying to make you feel bad about yourself. You’re perfect just the way you are.”
“Aren’t you the sweetest?!”
“You light up any room that you walk into.”

In conclusion

Do your part to make the world a little nicer

In a simpler, less cynical world, flattering someone would be easy and showing someone that you are interested in them romantically wouldn’t be perceived as a negative thing. Making them feel nice would earn your way into a girl’s heart instead of being second-guessed.

Be the exception to the rule and let her know that you are one of the good ones worth giving a shot. Anything less just gives them more reason to presume that words are empty gestures.

Photo Copyright 2019 Steven Stiefel | Blog 2019 Stiefel Creative