The Art of Planning a Date

In my last post, I wrote about asking a woman out.  Today, I’d like to talk about actually planning your date.

Good dates are not random events.  Planning a date is a skill that gentlemen master – a skill that can significantly increase the likelihood that you and your date connect.  Here are a few of my tips for planning dates:

  • Think of a date as an event you’re hosting.  You’ll want to plan, think things through, and make sure your guest is comfortable.
  • Choose somewhere that gives a glimpse into your life:  since women are always interpreting, choose a place that says something about you.  Choose a bar you enjoy, a bookstore you love, an activity that is your hobby.  Make sure your date planning says something about you and that it’s something attractive.  It’s better to show her who you are than to plan something fancy that doesn’t resemble your everyday life.
  • Take her somewhere she’s never been before. If you take her to the same place other men have taken her, you’re already appearing to be like every other guy she’s dated.  This means that, in your spare time, you should find a handful of spots that women you date probably haven’t been to.
  • Set a very clear and easy meeting place.
  • Have a nearby place to hang out while you wait for her to arrive.  You should be ready for your date to be late – and you don’t want to be waiting there for her. Instead, tell her you’ll be nearby and that she should text you when she arrives. Hang out at a nearby place where you can kill time.  Then, when she texts, you will be at a conveniently close location and can walk or drive over in a few minutes; this shows that you have your own life you’re living and, if she’s late, she’s not going to see you as the guy who’s been waiting there for 15 minutes with nothing better to do.
  • Plan three locations over the course of the night.  Psychology studies report that people feel much closer when they’ve been to multiple locations together.  How long you spend at each is not as important.  You could start with an art gallery (free, plenty to discuss, can be done in 20 minutes), then go for a drink, and then switch locations for a nightcap. By the end of the night, it almost feels like three dates.
  • Choose places that allow you to sit side-by-side or diagonal.  Don’t take a date somewhere you must sit across the table from her. It makes it difficult to touch her playfully and practically impossible to kiss her. Find venues that have couches where you can sit comfortably side by side.
  • Your locations should be arranged chronologically to increase intimacy.  Don’t start at a dark candlelit bar sitting next to each other and then transition to a bright public space with lots of people around.  The idea of a date is to sink into each other.  As you’ll see in the next post on the date itself, you’ll want to make sure that the last location is conducive to the two of you kissing discretely.
  • Last, think of what the woman will need to wear.  If you’re taking her somewhere fancy where she may be wearing heels, don’t then plan something where she needs to walk around a museum in uncomfortable shoes.  Women think about this.  You should too.

With these basics, you should be able to plan a three-venue date that increases intimacy, gets you talking and touching, and leads to the kind of date you’ll both want more of.