This will sound dumb, but just bear with me.

When I was younger, I always wanted to grow my hair out, but my parents never let me. So a few years ago, in my mid-20's, I decided "fuck it, I do what I want". Grew it out over about four years, and I honestly liked it. I felt more confident, more "me", I think. And while I'm straight, I got a lot of fellow dudes or older women would give me tons of compliments (older women constantly asked to touch my hair).

I got frequent comments, though, that I should cut it; whether it was to look more professional, or just look better. I eventually did, and to be honest, I got a lot of positive feedback about it. While my female coworkers are all married, they all said he was a relief when I did, and one even commented saying I was "really handsome with short hair".

So, I feel like I must look better with short hair.

Yet, I also feel like I'm worried about my appearance a lot more. Like, long hair is actually a lot of maintenance, but I always felt like I looked pretty good. With short hair, I feel like I'm constantly asking myself "does my hair look okay? how should I style it? what does it look like from different angles?".

I used to suffer from crippling social anxiety when I was younger, and since cutting my hair, I feel like I feel waves of that again, that I'd kind of "gotten over" when I was rocking the long hair.

So I'm not going to post pictures and ask "which looks better". But instead pose more of a fundamental question; is it better to try and objectively look your best, even if it means being uncomfortable or anxious sometimes? Or is it better to risk being less attractive, and feel like "hell yeah, I'm happy with how I look"?