You learn by doing it.
Find someone you like (or who likes you) and start dating them!
Without dating apps:
* Join a few social/intellectual/school clubs or co-ed sports (e.g. running). Be a generally cool person and you'll find someone after a while. Or...
* Go to lots of low-key house-parties thrown by friends, or throw them yourself. See if there is any chemistry with "friends-of-friends." In these situations there is lower risk for each of you since you've been "vouched for" by mutual friends, and you've seen each other in a low-stakes setting. Bonus points if you are the one hosting/organizing the party.
With dating apps:
* Think of fun things you'd like to do if you had someone along: e.g. hiking, comedy show, exploring downtown, bar-hopping, etc.
* Use an app like "Coffee Meets Bagel" that limits how much time you spend on it each day.
* For each person you "like", mention one thing written in their profile and one thing from one of their more adventurous photos (generally one towards the back). Say something like "You look so excited in that photo with the ____, there must be a good story behind it!"
* This naturally starts the conversation on something and shows that you admire them in a way that other people may not comment on.
* Keep the back-and-forth relatively short (just within one day). Ask if they'd like to meet on "Thursday at 7 for drinks at ___. If it goes well we can take it from there." Suggesting a hard time and place before asking their schedule is easier for them to say "yes" or "No, how about Friday at 6" instead of asking "when are you free."
* To prepare for your date look at the map and make a short list of things to do / places to go depending on the mood of how the date is going: Chill, High Energy, Make-out spot, etc. Don't tell your date that you have additional options planned until you meet - just say "I have some ideas of additional places to go depending on how we feel later." She will generally be impressed. Thi
As a general thing, I believe dating falls into one of those category of things that are better improved by simply practicing it; I wouldn't really recommend any books on dating per se.
I can, however, recommend certain books that better explain the nature of social interaction in general that I personally found very helpful and have had a positive impact on my dating life:
Games People Play
Influence: Science and Practice
The Laws of Human Nature
I might have better suggestions for more specific topics...
So, in your opinion, what's the best way of learning how to date?