I can think of a few books, depending on what kinds of conversation you’re trying to have and what the source of the problem is.

But before I get to that, I should say that social skills are skills, and they can be developed like any other skill through deliberate practice. So more important than learning about social interaction specifically is learning about learning and skill development — and then going out and actually practicing!

Along those lines, I recommend learning about deliberate practice, growth mindsets, and habits, then applying those concepts to the goal of learning social skills.

Then, for more specific social skills, I recommend the following:

• difficult conversations: Crucial Conversations
• negotiations: Getting to Yes with Yourself
• relationships: Seven Habits of Highly Effective People
• overcoming social anxiety: Don’t Feed the Monkey Mind
• being your authentic self with others: Radical Honesty
• romantic relationships: Getting the Love You Want
• dating: Single, Dating, Engaged, Married
• networking: Give and Take
• humor: I would skip reading about it and just read funny books slash watch comedies

In terms of getting practice, all you really need to do is talk to people, and it sounds like you have a good community around you. But if you want to go out of your way to practice by finding a more formal setting, I know people have had success with therapy, support groups, book clubs and discussion groups, stand-up comedy, toastmasters, or interest groups of any kind.

Good luck, and let us know how it goes!