Here is an answer from my last AMA that I think will apply to you about some of the books I think give a good base. Then, try speed dating a lot. Look at it as practice. Like you are a stand-up comic trying out new material. Try different things and see how people react to it, then try to better it. Basically, repetition will teach you and will remove anxiety.
No problem! I really enjoy helping people out with this. It’s a lot like pool/billiards. You just start playing and try and figure out the rules and strategies along the way with no real guidance. Umm, for books, to start with, try the original Men are From Mars, Women are From Venus. It can be pandering and simplistic at times, but it really gives a good base insight into men and women and how we communicate. That way you’ll have a good base moving forward. Others: How to Work a Room by Susan RoAne; Flirt Fearlessly by Rachel DeAlto is fun one on basic flirting; for great ideas on actual dates from lavish to free I absolutely love The Little Black Book of Dating Ideas by Buzz Boxx; for a very scientific but fascinating look at evolutionary psychology as it pertains to what is “natural, normal” for humans sexually, try Sex at Dawn by Christopher Ryan. I suggest these because they will build you a very comprehensive “base” of understanding that will make moving forward much less confusing and it’ll be much easier for you.