The object of a first date is to get a sense of the person to determine if you'd want to meet again. Often times people meeting for the first time are also nervous, so the conversation starts with something like the weather and continues on with subjects that are either bland or inappropriate. A better strategy is to ask open-ended questions that will allow your date to show their personality.
Here are some conversation starters to help you decide if your date is worth a second meeting:
Find out what your date likes to do after work and on Saturdays. This will help you figure out if you two have similar interests on a general level. For example, if one of you heads for the couch after your day at the office, and the other can only relax after a long walk, this will help you determine if your preferred method of down time corresponds with your date's.
While this question is similar to the one above, phrasing it this way may give you insight into one of two things: your date's religious beliefs and preferred activity level. For example, if your date prefers to spend an entire day reading the Sunday paper and drinking coffee, while you prefer to get out to some of the local sites, this could be a source of conflict for you going forward. Chances are any mention of the word "Sunday" will also invoke a response about religious beliefs if your date generally spends time attending church services.
You don't need the whole family history, but by asking this question you're bound to find other details that have influenced your date's quirks and habits.
Vacation time either becomes a way for a couple to bond, or acts as a source of irritation. Note that vacations are different than the way you spend your average free time. If you had the time and resources to make an official "getaway," and one of you opted for uninterrupted time on the beach while the other shunned prolonged sun exposure, you may have a problem.
This is kind of like the "where do you see yourself in five years" question we're often asked on job interviews. Finding out about life goals and desires can give you a clue as to your long-term compatibility.