Male (from SE Asia) in late twenties who moved to Chicago last year. Finding it really hard to make friends since moving here. Not extroverted by any means.
I tried the usual – going to bars, Meetup groups, trivia, sports but I can’t make my mind up to do things that I am not intentional about. One because I am really competitive which doesn’t help when I lose at sports or trivia and extremely busy during the week (think finance). And two I find it difficult to genuinely connect with people who I have nothing in common with (exactly those kinds of people you find in bars). At this point, I have exhausted all my options that I’m just thinking about going to the museums or parks alone. But if I decide to do that another part of my mind thinks of all the more objective things I can be doing on the weekends (get another workout, meal prep, shopping, real estate investments, etc.) and my mind asks what do you expect to get by going to a museum or park because there’s less than 1% chance you make friends just by going there and talking to random strangers.

Basically, I have forgotten how to have fun because of my career making my thought process more regimented and ruthlessly efficient to think about objective gains (money, health) rather than subjective gains (friends, relationships, happiness).

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