One of the dangers of dating a lot is the tendency to move toward the trap of the ritual. The stereotypes have expanded, but keep their general shape:

• Watch a movie–This has taken new forms as live music, plays, and speakers become more common. They’re all pretty bad options unless you’ve got something planned alongside the activity that allows you to get to know your date better. Even if you were just planning to have sex after the movie, knowing the other person better can make your heartless copulation a more fulfilling experience. At the same time, if you like to keep things vague and enjoy spending extra time finding out if you’re compatible with somebody, just watch that movie!
• Go to dinner–I love food so I can’t knock this too much. But sometimes its good to break away from the evening date. Places like lunchdates.com have tried to access this with a site that pairs up singles for short afternoon dates. I like evening dates after date #3 (See Recycled Dates) when I already know somebody a bit. Otherwise, never waste a weekend evening on somebody you don’t know. A failed afternoon or morning date just fuels the conversation that night with friends. An evening date gone bad and you’ve just put yourself to bed alone and in a bad mood! Save the romantic dinners for date #4 or better when you known your efforts won’t go wasted.
  
• Hang out with a group of friends belonging to either of you. This might seem like it would make it easier to get to know the other person, except you may be allowing yourself to get lost in the relational shuffle. I remember one time I hung out with a girl for the first time while at a party she was hosting with her housemates. Apparently, she’d told all her buddies that I was probably the funniest guy they’d ever meet. I showed up tired and unwilling to chase the laughs of complete strangers. Not a fun evening!

As a subtext: if you get the chance, find out if your intended SigOt is the pretty boy/girl of their social group. Guys can be easier to deal with because they often accept that their buff buddy may get more dates…not the same with the ladies. Do not expect the friends of your new perfection to allow you access to their princess without first submitting to a critique fit for a presidential candidate!

That said, stay away from obvious fires and try to mix things up! You’ll have more fun and will subsequently present a more attractive side to your date. A few suggestions?

1. Take a cooking class. Most high schools have evening classes that are often very inexpensive while still being very informative.
2. Find a street fair. Crazy people lurk at these and it can be fun to watch them while eating highly suspect oily food. This sort of thing will appeal more to the cowboy boot-wearing girl who laughed in your face at the suggestion of taking a vegan cooking class. 
   

   Photo by Ed Reardon

3. Make up a story about needing to do community service…plant some flowers with the local garden club…then admit that you didn’t want her to think that you were playing an angle, that you don’t actually have community service as a felon, and that you just really like flowers. On second thought, only say the part about being a felon if you have a sense of humor, timing, and delivery.

Good luck!

Seth