

It’s not weird to think about the other paths you could have gone down. But I would avoiding feeling too much regret. If something genuinely seems interesting to you, make it part of your current life, even just as a hobby or side project. Remembering that we are more than just our current selves is important for not getting swallowed by the grind.
If it’s feeling envy about the better life some alternate you has, try to keep in mind that nothing is simple. Although other choices might seem appealing in abstract, maybe they’d also lead to more problems. Sure, you could have been a doctor, but maybe the stress would have driven you to burnout and opiate addiction (69% of doctors misuse prescription substances).
I’d also say, that as I get older, I feel like I hit different “Save Points” that prevent to much regret. I chose to study philosophy instead of law, which means I’m a lot less rich than I might have been, but I would trade my weird, chilled friends from uni for the bunch of competitive over achievers I would have been “friends” with if I’d gone down that route. I met my spouse during a stressful period in my life, completing a degree for a profession I no longer work in. I could see that whole period of study as a complete waste of time, but if I’d never met the person I married the my life would be incomparably poorer.



Meeting other people’s friends groups (as you described meeting your partner’s friends) is a great way to shortcut that awkwardness. Its not just that someone else has done the hard work of filtering folks out, but that people are just on better form when with friends. Part of the problem of making friends in random social events is most people are either a bit awkward or putting on a social ‘mask’, which makes it harder to actually identify the people you’d like once you got past that.
My wife social circle has a bunch of people who entered as someone’s partner for a whole, but stayed friends with us after they broke up (even if there was a delicate period post-split where we hung out with them both, but never together).