Most upvoted comment
Top Books on Reddit in 2018 rank no. 23
IWTL to be less boring on dates(r/IWantToLearn)
Read Dale Carnegie’s How to Win Friends and Influence People (not affiliate). Then read it again. It’s a classic book that’s required reading at almost every business school. Most of the topics are directly applicable to your problem, but more importantly they’re invaluable to other areas of life – which could indirectly improve your dates as well.
One of the key takeaways is that people are naturally self-centered. People tend to enjoy talking about themselves, so ask about them, their life, and their experiences.
Edit: turns out I own two copies of the book, so if you’re in the US, I’m happy to mail you some Reddit love (aka the book).