Find out if you like doing the same things. If you enjoy watching a movie at home with a big bucket of popcorn when he'd rather be out hiking a trail, that's a clue that you have different hobbies. The more activities you enjoy in common, the more you'll have to do when you're together.
Inquire about her faith. It may not seem that important at the beginning when you're just deciding who to date, but dating someone who believes much as you do will help a future relationship. If your faith is important to you, this is an especially pertinent piece of information to have before asking her out.
Share similar family values. You spend every holiday surrounded by family and can't wait to open presents on Christmas Eve, but he flies to Aspen to ski Christmas week. The differences in your life may attract you to him now but may cause problems when your family asks for him next Christmas.
Watch how she treats others. When you go out on your first date, pay attention to how she interacts with and treats other people. You can tell a lot about her by whether she berates the wait staff for small infractions or treats others with respect.
Consider your past relationships. If you see a familiar unsuccessful pattern emerging, think twice before saying "yes" to dinner and a movie with another high-powered executive. You might think you need to be dating a certain type, but it may be time to redefine the type for you.
Resist giving in to a dry spell. Your friends may mean well by trying to send you out on blind dates with all of their girlfriends' girlfriends, but don't ask someone out just for the sake of going out. If you know ahead of time that she just doesn't interest you, then head off any future complications by passing.
Evaluate whether your goals are compatible. If you see yourself in 10 years with the four-bedroom, two and a half-bath colonial with two kids, a dog and a picket fence, but he's talking about backpacking through Europe before touring the Outback, forgo a second date.
- Use the first date as a chance to really listen to what she's saying, how she says it and if she's really paying attention to you to get a sense of how she communicates.