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Oregon Date

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Here’s a new way to meet someone: have a friend who is on the same dating site as you recommend a guy she’s already been out with and connect via said dating site. That’s exactly how I met Jon, who lives in Portland, Oregon. Our profiles said we were a 95% match, but percentages aside, I still would have wanted to date him. He wears glasses (I’m a sucker for spectacles and freckles), is well versed in the art of traveling and had a sense of whimsy in his summation of self.

As if to prove all of the above reasons why he was just my type, Jon decided to plan the Portland date knowing only that I’m a bit adventurous and wanted to see his town through his lens. What developed was a game he titled Dateopoly. Just hearing the name of the game made me clap and bounce with excitement.

To start, you’ll need a neighborhood stuffed with a variety of shops, cafes and little places of interest, and one half of a set of dice, also known as a die. You’ll also need a set of questions that you’ve either developed on your own, or perhaps from a game such as Would You Rather or Loaded Questions.  We used a six-sided die, but feel free to go wild and grab something else, modifying as necessary.


1. Each player takes a turn rolling the die.
2. After each roll, the number you’ve rolled dictates what happens next.

Roll a one: Ask a question.
Roll a two: Ask a question.
Roll a three: Travel three businesses down and stop in.
Roll a four: Travel four businesses down and stop in.
Roll a five:  Travel five businesses down and stop in.
Roll a six: Travel six businesses down and stop in.

3. Enjoy!

This was a rad first date for so many reasons. First, it gave us a task to complete together, meaning we’d learn more about each other than if we were just to sit and talk. And if all conversation failed, at least we had to chat about the rules, or wherever we were. We were constantly offered a new environment to interact with.

So away we rolled. The next four hours had us drinking coffee, taking silly photos in a fabric store, exploring a dilapidated garden, scenario dancing (okay, that was of our own accord), talking about our favorite childhood memories, sipping beer, stopping into the Portlandia-famous “Put a Bird On It” store, and yes, going into Shebop — the famous female-friendly sex store. Plus sharing a stout, an order of fried macaroni and cheese and an order of collard greens. It was an incredible way to see the hipster-cool hood while getting to know each other.

3 Responses so far.

  1. How fun is that?! I would love that! Awesome start to the trip. :)

  2. […] Half an hour before our date, I realized we hold wildly different beliefs on religion, politics, fiscal responsibility and social matters. As I scatteredly began making sloppy mental lists of “okay” topics and “off the table” topics, I started to really make myself a little batty and decided I’d just be myself and talk. But that didn’t mean I wasn’t supremely anxious and thus was fiddling with the red die leftover from Dateopoly. […]

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