This is the first time I've felt compelled to post on Hacker News given this fits me so well, so thanks for that. I've definitely got a few thoughts on the steps I took that I feel correlated best with the confidence and satisfaction with my social life I've had for the past three years or so:
- Talk to strangers: This one goes against the age-old wisdom your parents taught you as a kid, but I now often work from cafes and occasionally bars, and generally I'll find an excuse to strike up one or two conversations per visit to a cafe with someone who seems interesting. I've found it incredibly helpful to feel socially connected with those around me, get comfortable practicing in a low-risk environment where you'll likely never see those around you again, and to remind myself that most people are good and friendly and open to communication
- Say yes to things: When offered a chance to go to a party, or to a work thing at a bar, or to a random ski trip someone just barely managed to snag a deal for, do it. These opportunities tend to build on each other
- Ask lots of people out: This one is specific to dating. I realized after a while that asking people out is incredibly low-risk. The worst thing that happens is they can say no, and you continue the conversation as if nothing had happened. Then actually go on the dates. Incredible confidence builder, because it works
- Seek out scary things: For my last tip, when friends suggest karaoke, do a shot and grab the mic. When you see someone pretty across the bar, remember that there's no real difference in outcome between not saying hi and getting turned down. An opportunity not taken isn't a middle-ground between success and failure, it's a failure. The more things you try, the more comfortable you get trying more things, and the more confident you get overall. Oh, and you also have a lot of fun along the way.