Getting to the part where you ask someone out on a date is a sport. A serious fucking sport. It takes skill, emotional solidarity, and a keen sense of empathy. Ask, but don't be pushy; “let the game” come to you, but don't play games. Will they or won't they go out with you? Oh, wait! They decided to give you a chance! Hi-fives all-around, buck-a-roo!
The victory parade doesn't start with agreeing on a date. I'll tell you this: DO NOT BE WISHY WASHY. Have an idea of what you want to do, whatever it is. I won't begrudge any choice you make, just be confident and know what you want to do. Once you get to that point, don't falter by being a one-dimensional dater. Have a backup plan or several in mind.
Learn to improvise a little…
“The thing that a modern jazz musician does, which you should really keep in mind when you see him in concerts, or see him in jazz clubs, is somewhat similar to looking at a poet standing in the middle of a supermarket and improvising poetry. They are called upon by the discipline of this art form to go into public places where people are gathered informally, and to spontaneously create music. Unlike a poet, unlike the writer of a novel, unlike a painter, they have no opportunity to take this product that they have created and re-form it and correct the mistakes they might have made or change the way in which they approach it. What they do is done for all time, right then, when they do it. This is one of the unique things about jazz, and it's one of the things that gives it a particular quality of aliveness that makes it one of the most interesting and vital of all contemporary art forms.” ~ Ralph Gleason
Yes, in a sense, dating is an art form, a very, very subtle art form. You should know what bars and/or restaurants are in the area, bonus points if you know any nice walks in the area you're headed to. Sometimes, you show up at a place that just isn't as ideal as you thought it would be. You then have an option. Have a date at a shitty place, or salvage the date and pick another spot more ideal for you.
This is an area of strength for me, if I can be so bold. I had a date with a gal, we mutually agreed to go to a brewery, one that I knew was loud, but who knew? Maybe it wouldn't be. Well, it was. Thinking quickly, I knew of at least one other bar within a few miles away that would be perfect. It was dark, quiet, and had a great juke box. So we went to there and it was a big hit with my date, who commented “Nice audible, fella.”
Even if you don't know the area, you have technology at your fingertips; so have other spots in mind at all times. Not only will you become a better, sweller [sic] date, you'll certainly earn your date's appreciation. Additionally, you'll become a go-to resource among your friends who will be amazed at your ability to know all the great places.