If only peer pressure didn't exist

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I seem to think that had there not been things like clubs, bars, parties when you're young, man-made deadlines or expectations to have to start by a certain stage in life having relationships, sex, marriage and kids etc I seem to feel I wouldn't be having these comparison thoughts or missing out as though I "should" be doing these things because it's "expected" of us otherwise we are "losers" or feeling regrets for not doing it when I didn't want to do certain things.

I seem to think that if I turned into an extroverted, party-going person and ended up getting with someone that it rid me of the negative comparing thoughts, start feeling more content and be free of any regrets.

Your main problem doesn't seem to be peer pressure so much as internalized expectations. The difference being peer pressure is external, whereas what you engage in is internal.