Dinner, movies, bowling and catching a game together are classic, tried-and-true date activities that guarantee a good time if you like your date. However, you won't get a true picture of who the person you are dating really is without delving a deeper. Once you find yourself becoming really interested in someone you are dating, plan dates that are fun but that will put you in situations where you can get to know your date on a more personal level.
Take your date with you to different social events, such as a friend's house party, a co-worker's birthday celebration or a casual game night at your place This will give you an opportunity to see how your date acts in various social settings. You might discover that she's a pretty great dancer at the club, or she hates to dance and is a wallflower. You could find out that he is super-competitive and a sore loser at board games. You could see how she interacts with your friends and if she keeps her focus on you, or if she has wandering eyes.
Take a walk with your date with no particular destination. This will give you an opportunity to talk and discover shops and other places together that you might not have noticed before. You can see how spontaneous he is: stop in at an art gallery you run across or pop into an open house and pretend to be potential buyers. If you live in or near the area where you grew up, take your date to your old stomping grounds, such as your childhood home, your high school and the pizza spot you and your friends used to hang out at. Have him do the same for you so you can learn about his past and how he grew up.
Being put in a high-pressure situation can bring out someone's true colors. Join a local competition together, such as a city-wide scavenger hunt, a couples dance competition, a country fair cook-off or a geo-caching competition. The two of you will have to work together to prepare for the competition and come up with a good strategy. This could be the ultimate test to see if you are in sync in terms of approach and ideas. You might discover that your partner is super-supportive and cool under pressure. On the other hand, you might learn that one of you is far more competitive than the other, or that your partner gets really flustered or mean under pressure.
If giving back and helping out in the community means a lot to you, see how your date feels about that and if she would like to join you when you volunteer. Take her with you to a soup kitchen to see how she is around homeless or otherwise struggling folks. Take her with you when you read to kids at a local youth center's and see how she interacts with the kids. Help build a house together with a volunteer home-building program. You'll soon be able to tell if your date really enjoys volunteering with you or if she is just doing it because you asked and she is trying to impress you.