Girls, you start dating a guy who wears hats 24/7, is it a big deal?

This is one of my biggest fears since I'm going bald and therefore I always wear a baseball hat. It makes me look better and younger. When you're 21 and have a receding hairline, you can easily look like a 30 year old. Cover it up, you look youthful again.

My question is what happens if you're going on a few dates with a guy and he always shows up with a hat and when you ask him about it he tells you he's balding and a bit insecure about it? Will you leave him and hurt his feelings by stomping on his insecurity or will you be understanding?

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  • 24/7 yeah. But on a couple of dates wouldn't bother me.

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  • A bald head would confuse me way less than someone who sleeps with a hat... xD

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    • Should've mentioned, we're talking about the first 1-3 dates

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    • Consider this scenario, a young guy and girl meet to hang out and on 3 occasions. They keep it simple, walks in the park, cinemas, coffee shops, no fancy restaurants. The girl casually asks the guy if he always wears hats and he tells her the truth. "I'm balding and insecure about it so I prefer to cover it up". Is he screwed?

    • Depends on the girl I'd say. Doesn't matter for me tbh.

  • Nah, wouldn't bother me, my brother-in-law has the same problem and wears hats lol

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