Legitimately, the biggest thing that helped me was to join an RPG group. For me it was D&D. It made just talking to random people way easier, and I made a ton of friends throughout the years. Granted, I play exclusively online and join random games now and again, so I always have a new batch of people to talk to.

Otherwise, ask questions. Not boring, “how’s the weather” / “how are you” questions. But questions like “do you have any pets” or “do you have a favorite place/restaurant/hike/bookstore in the area”. Personal ish questions. People like to talk about their favorites or their things or their pets.

Also, mirroring questions. If someone asks you about your pets, asking them back is a good way to keep a conversation flowing, so I’ve found.

Is it unnatural to say hi and then ask “do you have any pets?”. Or am I overthinking it?