I also have a hard time in social situations. I've started noting how many times a conversation ends with something I say. . . way too many for comfort. My problem is that I don't feel like what I have to say is important or interesting. I cover it up by saying that I'm better at listening than talking, convenient excuse.
What you might want to do is pick someone you trust to practice with. It could be someone different with different topics. Know someone who really likes a certain TV show (some people really LIKE talking about their favorite characters and story lines)? Anyone you know really into a certain sport? Is there a neighbor that you can chat about what's going on with a local event? Conversations that start out with trivial things could lead to deeper ideas. And there's nothing wrong with a trivial conversation now and again anyway.
The most important thing (which I'm also working on) is patience. Good friendships with real connections happen over time. NOT EASY I know, but the friendship could be worth the wait.
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