My advice? Date in bulk. Note I said DATE, not SLEEP WITH.
Like anything else, you get better with practice.
Coffee, at lunch is the best way to get your first date out of the way. It is shorter than lunch, it is much more informal, and she won't expect you to buy her coffee. Hell, it can be over as fast as you can drink a cup of coffee if it is really bad. Keep the conversation light, don't dwell on any one subject too long, and if she wants to drive the discussion, by all means LET HER TALK. Active listening is a key skill...women are experts at birth and can spot a "faker" a MILE away. Do not underestimate the power of this skill in your life.
