Great dates don’t just happen. They take immense planning. And then you have to act like you didn’t spend much time on them at all. Plan on three parts (and have a backup!).
Part 1: The Food
A meal is a good starting point. During summer, it could mean a picnic. In the winter, it usually means a restaurant. Pick something with a good hook, like Cheddars, the all-mac-and-cheese place on the West Side, or Empress Taytu, the great Ethiopian joint on the East Side. The restaurant should match the tenor of the rest of the date. You’re setting a tone here. And make reservations if they’ll take them.
Part 2: The Event
Ideally, find something happening around town that’s not always going on. This shows that you care enough to think it through, rather than slouch through the dinner-and-a-movie route. Flip through our On the Town listings, the Plain Dealer’s Friday Magazine and the alternative weeklies (and look at the ads, too, since they sometimes cover things the media don’t). Find a festival or a show — anything quirky and different. One of my best dates included going to a candy factory to learn how to make candy canes.
Part 3: The Finale
Part three should be something that can be abandoned without notice. I never mention it early. If your date is a stinker, end after part two — you still seem like a gentleman. Then go meet up with your buddies. But if the date is going well, you don’t want to finish up asking, “What do we do now?” Look for something that seems like an afterthought, but is special. Find out where that great jazz act is playing, and keep it in your pocket. “Hey, you know, I heard Blue Lunch is playing at Wilberts ...”
Oh, and pretend it’s not 2008: Open the door, pick up the tab.