Context means a lot—the relationship (or lack thereof) you have with someone makes a big difference.

One example I can give you just to give you a frame of reference (but again this is different in some ways because of gender dynamics) is to imagine for a second that you have a gay male friend. Maybe you already do, but imagine in one reality this gay friend is a really nice guy you know really well who every once in awhile gives you a compliment like, “that color looks good on you” or “your hair looks really nice today” or “man, you look handsome this morning!” with a kind smile and in a casual way that clearly shows he means to boost your confidence and is being honest. I would think this would make you feel pretty good about yourself.

Now imagine an alternate reality where your gay friend is not such a great guy. He is constantly ogling you, especially when you bend over or when you reach for something and your shirt lifts up. He might even touch you without your permission and even when you pull away. The kind of compliments he gives you are demeaning, “the way your cock falls forward in your pants when you lean like that is so hot,” or “man your ass looks good in those jeans, makes me want to fuck you” etc. I’m guessing you wouldn’t feel so good at all. That would probably make you feel very, very uncomfortable and maybe unsafe. Especially if you’d made clear to him through body language or through words that you didn’t like it and if he kept doing it, even in public.

The first scenario = compliments. The second = sexualizing. But the main difference between this interaction and one with you and a woman is that the gender dynamics are very different. Women are constantly sexualized and objectified in a patriarchy and men are not. It’s fairly easy to imagine a scenario where you have a very close gay male friend and a level of comfort where the sexual comments would actually be ok as jokes where both of you have established comfort with that. But with a female friend or coworker—basically any woman you don’t have an established sexual/romantic relationship with, it’s VERY hard to imagine, in fact, I’d argue it’s next to impossible. Because women are constantly demeaned and thought of as sexual objects for men, and those words reinforce that system—even when the woman finds them funny or harmless.

The other thing to consider is even a well-intentioned compliment to a woman like, “I like your eyes” or, “that outfit looks good on you” can still do harm or be unwanted in many contexts. A good rule of thumb is if the woman is a stranger on the street, don’t talk to her unless she approaches you first (or a situation necessitates it). Compliments will be taken as threatening by us because most men use them as a means to hit on us or harass us. While that very well isn’t your intention, we have no way of knowing that! See here about the concept of Schrodinger’s Rapist. Another thing to consider is many women experience men approaching them ALL the time and don’t get time to themselves and part of a patriarchy is being expected to give up your time to men even when you don’t want to.

The other rule of thumb is that a positive comment about appearance that is wanted = a compliment, one that isn’t wanted = harassment. How do you know if she wants a compliment? It can be hard to know, which is another reason why I advise not approaching strangers because you have no relationship or context to establish what the woman is comfortable with or not.

I also think that compliments on appearance, even if very benign or well-meaning, can reinforce the importance of appearance for a woman, which is negative because in a patriarchy ALL that’s supposed to important about a woman is appearance. So I’d avoid those compliments on appearance with coworkers, for example, because that just reinforces to a woman that she exists for the male gaze and even though she is here to work, it’s her looks that matter, not her job performance or anything else.

Like once a coworker told me, “that outfit looks cute on you” and it made me very uncomfortable because, while I was flattered on one level, on another I felt like I was…brought down a peg? Like suddenly I wasn’t an editor like him, I was a cute girl in a skirt there for him to admire. Especially since he had seniority over me, authority over me and what could I say? If I had overtly reacted negatively to the comment, bad things could happen to me. And this is true in most cases when you give a coworker or woman you don’t know well a compliment: she has less power than you in a patriarchy and often feels she can’t reject it even if she wants to.

So then when CAN you give women compliments on appearance? I’d say with friends you know well, someone you’re dating, someone who is flirting with you like at a bar or established place for dating, someone who compliments you first, etc. You need to establish a context where you know the woman is comfortable with compliments on her appearance….

But you know what I’d advise? Trying to give compliments on something else for once! We’re so used to our appearance being emphasized all the time that if you complimented a woman on how articulate she was, or how smart she was, or how well she does her job, that would be a nice change and might mean more to her, and there’s much less of a risk of making her uncomfortable. Compliments like that, granted the woman isn’t a stranger and that you aren’t ogling her or anything, are pretty much always welcome. And think about it this way: how often are men complimented on this like that? A lot! And their appearance? Not so much right? Because men are valued for their skills and abilities more than women are… So idk, that’s something to think about.

Sorry this turned out so long! I’m glad you asked this question because it’s important for men to care about this. I think with an established relationship with a woman outside of a professional setting, nonsexual compliments on appearance are usually fine. It’s all in the delivery and in whether or not the context is appropriate, etc.