Honestly, I was never really cool but had ridiculous "being cool" beliefs to guide me if you know what I mean.
Totally know what you mean lol.
If you 'weren't cool' then you avoided a lot of misery and stupidity (hopefully).
I hate preppy, popular stuff, but at the same time, I was trying to be cool in the rock/metal kind of style. I would've done better just being a regular nerd, but I was sort of a mix of both. I used to smoke weed, but the nerds didn't do so. I wasn't a total burnout and did good in school too, so I didn't really fit in with the freak/metalhead crowd.
You were lucky that you never stopped being yourself, not totally.
I knew guys like you, people secretly admire and desire those things qualities.
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