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First apartment (outside of college dorms) was fairly smooth. I had classmates who lived off-campus and that put the idea in my head that this was feasible, I checked the nearby student-oriented options and picked one that ended up being far cheaper than university housing.

First date was a stroke of luck. Right after move-in my first semester of college there was a sort of club that I joined, and one of the other new people there became my best friend and then, within a short time, my girlfriend.

First job of any sort (20) was a small number of hours per week and a shoe-in through college connections. First job that supported myself (mid-20s) was from responding to a classified ad in the paper, for something I had the physicality for and also some distantly-related experience.

The one thing I would belabor to my past self is to eradicate the sense of shame. Go out there and do the things that feel like they'd be humiliating, say the things that you don't feel comfortable speaking up about (as long as the intentions are good). This includes asking for help when you need it, which is probably before the point when you really feel like you need it. You don't get life experience by things going smoothly and according to plan; you get it by going into the weeds. Never be averse to being a beginner, this is part of what keeps you fresh. There are lots of kinds of discomfort that are very fruitful.