Caffeine Confidential: All The First Dates

I heard a podcast a few weeks ago about dating like an economist… and since I’m sort of technically maybe an economist, I thought I should give it a try in my own life. Considering I’m currently working an incredibly flexible schedule and can’t do anything in moderation, I blindly told my friends I would copy the woman in the podcast and go on 50 first dates, while cataloging a spreadsheet of data about them.


About 3 dates in, I realized 50 first dates would be a miserable, exhaustive experience. As of this writing, I sit at about 10 first dates. Each of them is cataloged, noting what I deemed relevant data points about each guy, and notes about him and the date. I never thought I would uncover some magical code to successfully finding love, but I was hoping to see if there were any patterns to my crushing, dating, and successes/failures.

In addition to these actual dates, I was on two dating apps (Tinder and Hinge), and ended up chatting with a number of additional guys. For various reasons, these chats never resulted in a physical meeting, so I didn’t count them… but they offered additional information that I’ve definitely pondered.

So, if I didn’t want to crack the code to looooove, why bother? Telling your “story” over and over sucks. Pretending to give three shits about some guy’s job sucks. Using your good mascara on a night that ends up being lame sucks. And, statistically speaking, considering I am in eventual pursuit of a monogamous relationship with a single guy, 99.9% of my dates are going to result in “failure” (aka not a serious relationship). Which, let me just jump in here and say, isn’t actually a failure… I could go on about why this is actually a benefit but that’s probably a separate post.

I did this to learn more about myself. Having been in back-to-back relationships that took so much out of me the past few years, I wanted to really explore what an unbridled version of myself was at 27 in the real world. I had this summer in 2010 where my college bestie and I didn’t take any classes, and didn’t take any work shifts, and just went on adventures and partied and contemplated life together (usually with lots of beer). Right now in my life, I have a brief opportunity to relive the Summer of 2010  for who I have grown into, and I took that opportunity by the horns.

It’s amazing what we learn about ourselves when we juxtapose with a stranger in an awkward situation. I practiced my “story” in different ways (not lied, let’s be clear). Did I call myself a consultant, a freelancer, or an economist? Did we do something sober during the day that put me out of my comfort zone, or retreat to drinks at a bar? And, probably the most important factors of all – how unfiltered and raw I can be about myself. How much is too much? How do I put myself out there… who am I, and how to I present that to the world?


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