Answers
How to be more social
Short answer: don't try to be more social, design recurring frequency. One place per week, the same people, comments on the shared situation instead of the person. Familiarity does most of the work.
How do you become more social if it doesn't come naturally?
Stop trying to be more social in general and pick a frequency instead — one recurring thing per week where the same people show up. Pilates on Tuesdays, a wine bar on Thursdays, the same coffee shop on Sunday mornings. Familiarity does most of the heavy lifting; you don't have to be charming, you have to be there.
What do you say to start a conversation without it being awkward?
Comment on the shared situation, not the person. 'This line is wild.' 'Did you try the matcha?' 'How is everyone working on a Monday.' It's low-stakes because it's about the moment you're both in, and it gives the other person an easy on-ramp without feeling sized up.
How do you stop overthinking before going out?
Decide before you leave the house that you're going to enjoy two things and notice one detail. Tiny, achievable, specific. Overthinking thrives on vague goals like 'have fun' or 'be likeable' — concrete intentions starve it.
What if I'm just exhausted by socialising?
Then you probably haven't designed it to refill you. Shorter plans, fewer people, in places you actually like — a walk over a club, two friends over five. Being social isn't a volume metric; the people you light up around are the only ones that count.