Should Men Compliment Female Friends and Coworkers on Their Hair?

Advice for a reader.

A reader sent in a question, again, seeking advice. I do not have an advice column.

Kelly —

As a dear sweet friend, there are two things you probably know about me: 1. I want to be nice or, at minimum, seem nice and/but 2. I am a man, a gender known for its shiftiness and size. My question is rooted in how #2 likely frames #1. Is it nice to compliment my female friends’ hair? Is it maybe too creepy to be worth it, like complimenting an outfit might be? I don’t know. I always liked complimenting hair because it’s the only physical compliment I’d like to receive. Now, there is some precedent with me complimenting men’s hair, as I have one friend (I was one of his groomsmen) whose friendship with me began because I asked him where he got haircuts. But mostly hair compliments are reserved for female friends, as female hair is cooler and women are more likely to undergo a big hair change — not like “big hair” as in all my friends follow Whitesnake on tour, but big hair as in significant hair (like bangs). Or sometimes they just put it up in a messy yet purposeful way and I think it looks cute! And what if this friend is a coworker and they come in and their hair looks like night time ocean? What about then!? Like, recently I complimented your new haircut and we had a conversation I enjoyed about it, but maybe you hated that and you waited for this moment to tell me. You can tell me now. It’s ok.

— Jesse David Fox

Jesse —

It is interesting to me that you emailed me another question.

My advice in general is: don’t talk to women. You should err on this side more often than not. However, if a woman has chosen to be your friend, I suppose you may compliment her hair, yes, as long as you stay away from phrases like “night time ocean” and instead just say something like, “Hey, nice haircut!” If I’m remembering correctly, you complimented my haircut with normal words, and it was certainly fine.

If your friend is a coworker, it probably depends on the degree of hair change. A haircut, sure, if you are careful and if you say it during a time when a conversation would happen naturally, like if you’re both in the kitchen. Do not say it in a Slack DM. “They just put it up in a messy yet purposeful way and I think it looks cute”? No.

Do not email me again.

— Kelly Conaboy