When should I complement a woman on her looks?

Here is the event that led to this question:

I’m with a friend. She’s wearing a new dress. She says, “I think this dress makes my waist look bigger. My daughter bought me this dress. It’s different from what I normally wear because [fashion terminology that goes over my head, but explains why her waist looks bigger.]” She looks at me. She’s gorgeous, her waist looks fine, her dress is nothing special. I shrug and tell her I know nothing about fashion.

I’m guessing she was insecure about her dress, and did not really want my fashion advice. I did not say anything because I thought she wanted an opinion on her dress, but I didn’t think the dress looked good and did not want to say that. I could have said, “Your waist looks normal. You look good in that dress.” Is this what I should have done?

What I worry about is losing credibility. If I always respond with a compliment, even when I don’t like something, then my complements would become meaningless. And I don’t like giving useless advice.

My second worry is sexual harassment, since my friend is also my coworker. I’m not worried about her. But I worry about being inappropriate with other female coworkers, so I error on the side of saying nothing about anyone’s looks at work. However, if I compliment my friend and not anyone else, then it would raise questions. Questions I can’t answer by telling everyone that I’m worried about sexual harassment from everyone but my friend.


I never thought a straight compliment would amount to sexual harassment. Our president has some of the best-looking legs in the company and people often compliment her on it (mainly female employees though, guys are too chicken to say it.)

Unless a co-worker is already a friend of yours, you should refrain from complimenting her body parts or making reference to how well or how poorly the clothing she is wearing fits around said body parts. It is probably okay to say that you like a new hat or bracelet, but be careful about commenting on necklaces that settle near cleavage.

When confronted with compliment fishing, “I don’t know much about fashion” is an excellent response.

You shouldn’t have to worry about losing credibility because friends shouldn’t fish for compliments very often. Everyone is insecure sometimes but you shouldn’t have to answer “does this make me look fat” questions as frequently as a significant other.

I don’t think when or how often you compliment people’s looks is nearly as important as how you compliment them. At work, “Your new hairstyle looks really nice” is a lot more appropriate than “You’re looking very busty today”

Hairy. (OP has already stated she’s a friend.) Maybe you could have said, “The dress is nothing special, but you look great.”

I like Becky2844’s advice just fine.

As a general rule, when a man is commenting on a woman’s appearance, he should go bland and avoid specifics.

“That dress really compliments your figure” is much better that “That dress makes your butt look great.”

For something to be “sexual harassment”, it needs to be sexual and harassing. As long as you aren’t make blatantly sexual comments on a repeated basis, you are fine. It’s okay to complement people. Just don’t yell out “Hey, why don’t you wiggle that ass more?” every time a woman walks by your desk.

If she’s fishing for compliments, there is no reason to get too analytical. Just say “Naw, you look great, as always” and move on with your day.

If you are straight, think about the kinds of compliments you’d appreciate from gay guys. You’d probably appreciate general comments, comments on your clothing or accessories, but not sexual comments or comments that imply they’ve been thinking about you sexually. That’s basically what women appreciate from men.

I didn’t explicitly read that she’s in effect asking a question in the OP but that may have been more clear in the moment. If I thought she was effectively asking a question I would have answered that her waist looks fine but I know nothing about fashion. If I felt familiar with her and was confident that straying slightly from the specific subject would not be a problem I might have added that she looks gorgeous, but this point has not quite been raised yet.

For ease of use: have “You look lovely” as your standard response. This would never be sexual harassment unless you’re doing something else at the time, like staring at her boobs.

She: Dress, difficult questions blah blah - “Do I look ok?”
You: “You look absolutely lovely” swiftly change topic “So Jodie Foster is gay huh…”

Nobody will notice that it’s your standard response. Then, as you get used to it, try to experiment. If your friend is wearing a bright colour, say “You look lovely, I like that the dress is so bright”. There is usually something you notice, different hair, big earrings, new boots. Saying “you look lovely, is that new?” is always good. You’ll be adored, easypeasy. Just a simple rule: do not compliment the body. Just don’t. It’s tricky, situations differ, people feel differently about it. Don’t go there.

ETA: I used to have a flatmate who had “you look lovely” as a standard thing to say. He’d yell it out the door as I was leaving, he would say it first thing if I came down stairs ready for a night out. Even though I knew, it was still nice that he always tried to remember to say it. Just kindness.

Complement = complete
Compliment = say a nice thing
Just in case anyone was wondering…

I agree. I worked in a female dominated worplace and NEVER commented on anything to do with their looks.
Personal comments can too easily be misconstrued in todays overly PC world.

If someone had asked about a dress or such I’d have just said it looked fine and changed the subject, or made an excuse and left.

So, what would you say if her waist didn’t look fine? Lie?
If you compliment one woman and not another, that could cause problems. Far better to say nothing to anyone and avoid potential problems.

I believe she was soliciting a comment from you. An appropriate reply would have been, “I think you look great in that dress and it doesn’t accentuate your waist in the least but it does make your fat ass look bigger!”

Standard question: “Does this dress make me look fat?”

Standard answer #1: “Does a bear shit in the woods?”

Standard answer #2: “No fatter than you usually look.”

You should complement a woman on her looks in the exact same circumstances that you would complement a man on their looks, and also when you are trying to chat up a woman (assuming that is your preferred gender).

I think what you said (about knowing nothing about fashion) was absolutely fine and appropriate for the circumstances.

If you do find yourself being directly asked to give feedback, stick with non-specific (and definitely non-sexual) terms, such as ‘I think you look lovely/beautiful/great/radiant.’ These are all compliments which don’t refer specifically to the body, or even worse, specific body parts (you know, those parts).

If you do get the type of workplace woman who asks questions like ‘Do my boobs look good in this dress?’ (and most workplaces I’ve worked in have had That Woman working there) then it’s safest to go with a jokey comment like ‘I couldn’t possibly comment!’ said with a smile, then removing yourself from the conversation or changing the topic to something safer.

The problem with saying “I know nothing about fashion” is that it is so obviously untrue that it could lead the person to think that they look so bad that you are trying to avoid telling the truth. It equates to telling a bad date that you “will call her”.
Far better to say something completely bland and change the subject, or leave.

So there’s no one in the world who can honestly say, “I know nothing about fashion”?

You know what you like.

I don’t want to appear harsh, but this seems like a very strange question for (what I assume is) a grown man to ask. I had made a comment in another thread about social cluelessness and this seems like a pretty good example. I don’t mean “cluelessness” like you’re a jerk or weirdo or anything. But it seems to me most people should know how to respond to a “does this dress make me look fat?” question without having to poll an anonymous message board.

The correct answer is “it looks lovely”. You don’t need to go into detail and she isn’t looking for a fashion critique. She just wants affirmation that she made a good purchase.
Worrying about “sexual harrassment” is nonsense. Sexual harassment is when you repeatedly make unwanted advances on another coworker, when your repeated offensive behavior makes someone uncomfortible (in certain cases), or when you use a position of power to coerce or threaten another employee.

Simply interacting with a female coworker does not set you up for a harassment case.

No, your ass does.

I don’t think it was necessarily fishing for compliments. It’s a question that a woman may ask ask another woman and get a helpful response. It sounds to me like she was treating you like “one of the girls” for a moment, without really realizing that you wouldn’t appreciate what she was asking.

Again, “You look great” is basically never out of place, unless you are also grabbing her boobs or pinching her ass.

To me, she seems to be asking for input in a rather indirect way, so I’d have to say if she’s at all reasonable, a politely worded response wouldn’t be a problem.