November 13, 2025 at 5:15 pm

A Bald Worker Was Asked Why He Wears Hats Every Day, And He Responded By Asking The Woman Why She Wears Makeup Every Day

by Matthew Gilligan

man sitting at desk

Shutterstock/Reddit

When are people gonna learn…?

When in doubt, don’t make comments about people look like OR what they’re wearing.

It just makes life a lot easier!

But I guess the woman in this story didn’t get the memo…

Check out what happened in this story from Reddit!

AITA For Asking Why My Co-Worker Wears Makeup Everyday?

“I (29M) was at work during a pretty long meeting with a few other co-workers.

One of my co-workers is new (late 30s F) and the conversation steered around our professional experiences and history. Pretty standard I guess.

Well, this was unexpected…

Midway during reviewing some boring stuff this co-worker asked me with a smirk, “Can I ask you a question?” Since we were talking about our professional lives I was like, “yeah sure what’s up?” and she followed up with, “Why do you always wear hats?”

Now, I’ll be honest I’m bald, however I like my baldness. I started balding at 21 and I was like, **** that, and just shaved it off instead of trying to style my hair in anyway to hide it.

Also since my hair is super curly and compact it just wasn’t gonna be an option. In college people loved it, said I had a good head shape and said I looked like Terry Crews, Shaquille O’Neal or The Rock (not sure about that last one lol) so I was pretty confident with it.

He has his reasons…

But when I turned 25 I started being mistaken for 30 cause of the bald cut so I started wearing hats pretty much everywhere. Grew a collection for all situations, work, gym, social life.

Anywhere besides weddings and funerals. And with hats on at 29 I’ve been mistaken to be as young as 22 (not the goal but yeah). The plan was to wear them until 30 and then cut back when my head matched my age.”

Anyways, this co-worker asks “Why do you wear hats every day?”

To be fair it’s a corporate setting but it’s also tech, we’re in marketing and it’s 2025 so smart-casual is the rule of thumb and my bosses don’t care and dress in hoodies and hats to work some days.

I responded, “I like hats,” and she said, “but every day?”

So I said “Yeah I’m bald, I like my head shape but I don’t wanna look like I’m 35 so I’ll wear hats for now, plus I look good in them.”

Now I wasn’t thinking and she’s probably around this 35 age or older so I may have offended her with that but she replied, “29 and wearing hats every day to hide? Wow.”

He let her have it.

This struck a nerve with me so I responded, “Well since joining I’ve seen you wear makeup every day, even casual Fridays or on your work from home team calls, so why do YOU wear makeup everyday?”

There was a muffled giggle but it’s clear the atmosphere was tense.

She got heated and said “That’s an inappropriate question.”

I said, “How? Other women in the office don’t wear makeup every day and my boyfriend sometimes wears makeup when we go out to a high class event. He just doesn’t do it everyday. So why do you wear makeup every day?”

She got heated and silent and one of the other co-workers went back to focusing on the deck. I feel like her and I not on the best of terms now as she will not talk to me now.

AITA for asking why my co-worker wears makeup every day?”

Let’s see what Reddit users had to say about this.

This person said they both SUCK.

Screenshot 2025 10 21 at 3.28.25 PM A Bald Worker Was Asked Why He Wears Hats Every Day, And He Responded By Asking The Woman Why She Wears Makeup Every Day

Another individual said he’s NTA.

Screenshot 2025 10 21 at 3.29.25 PM A Bald Worker Was Asked Why He Wears Hats Every Day, And He Responded By Asking The Woman Why She Wears Makeup Every Day

This reader agreed.

Screenshot 2025 10 21 at 3.29.32 PM A Bald Worker Was Asked Why He Wears Hats Every Day, And He Responded By Asking The Woman Why She Wears Makeup Every Day

Another Reddit user shared their thoughts.

Screenshot 2025 10 21 at 3.29.39 PM A Bald Worker Was Asked Why He Wears Hats Every Day, And He Responded By Asking The Woman Why She Wears Makeup Every Day

And this reader also said they both SUCK.

Screenshot 2025 10 21 at 3.29.49 PM A Bald Worker Was Asked Why He Wears Hats Every Day, And He Responded By Asking The Woman Why She Wears Makeup Every Day

Sometimes it’s better to just say nothing at all…

If you liked that post, check out this story about a guy who was forced to sleep on the couch at his wife’s family’s house, so he went to a hotel instead.