alt Hacker NewsI found mixed results given underlying anxiety that hadn't been diagnosed at the point I was trying this. Talking to new people at work, while out pursuing hobbies, and around town, all accrued to more and better conversations.
It was a much bigger struggle with conversations where I was putting extra pressure on myself. Being able to have those other conversations was helpful though. Eventually, I found a therapist and am in a better place with this.
Letting curiosity be the motivator behind starting these conversations and cultivating curiosity more broadly can help -- or at least I have found it to be helpful in making initiating feel less forced. I wonder about people's jobs or the reasons they are visiting a place or what they think about what's happening nearby, or just generally who they are.
One antipattern I've encountered with this approach tho is that sometimes anxious people will exhaust their conversation partners with a battery of questions. Even if thoughtful, this can sometimes have the effect of exhausting your partner, and tends to keep the conversation steered away from actual connection. YMMV, but either way be mindful and make it a point to share yourself