How to Plan a First Date

Given how much it takes out of a person simply to approach a stranger at a bar, let alone get their number or ask them out, it seems unfair that you’ve then got to plan the perfect date, too. Unfortunately going to Disneyland isn’t usually a viable option — and neither’s Dollywood, which is too bad, because we think that would make an awesome first date.

  1. The most important rule of first dates is to keep it simple. A date that is too long or too complicated or overly planned is likely to put off your companion for any number of reasons –you’ll seem desperate or pushy or controlling or just plain weird. Plus, you’ve got to save something for later.
  2. Second, it’s mean and underhanded to to make the first date some kind of “challenge” in order to figure out how daring your date is or how hot they look in a bathing suit or how intelligently they can comment on abstract art — save that for the third or fourth date. However, it’s perfectly acceptable to choose a first date that highlights one of your own skills — on the pool table, in a museum, navigating a certain neighborhood (e.g. dim sum in Chinatown followed by bubble tea at a little tea shop around the corner).
  3. Third, the date should not involve some activity that precludes conversation (for example, the opera, the library, a deafening rock concert, or an obnoxiously loud bar). But nobody wants to spend an entire evening in an empty room with nothing but conversation to fill the space, either — that’s not a date, that’s a police interrogation! Instead, find activities that offer a mild distraction and some potential to spark conversation. For example, a mosh pit hardly screams “romance,” but a low-key concert in a small local bar is ideal. (Just avoid folk music — that’d kill even John Mayer’s sex drive.)
  4. On a final note, when making plans together, don’t be bossy about your suggestions, but don’t be wishy-washy either: “I don’t care, whatever you want” is never a good answer to any question.

This column also appeared in print in Metro


  1. A movie and dinner is a classic, and it gives you something to talk about so there’s not that awkward silence.

  2. An invitation to coffee (or tea) at a cafe is the absolut standard in Germany. If both are pleased with that, usually a walk together will follow.

  3. Great article but it should be called how not to plan a first date. You give great things to avoid, but what about actual suggestions?

  4. Love this! I actually just wrote an article on what to expect on a first date (ever). Dating in college is dead so a lot of students have never been on a first date! Check it out 🙂

    We also added this to our “Links we Love this Week” roll!

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