The Freedom of Expiration Dating

Several years ago, I did a project called 20 Dates in 20 Weekends: A Craigslist Dating Experiment. It was an epic adventure where I took 20 random dates from Craigslist and turned them into comedy gold. Well, okay, maybe not exactly, but in retrospect, it was funny. At the time it felt grueling and slightly uncomfortable. 

Anyway, I went out with people I would normally never consider going out with, and focused on being present during the dates; asking questions, trying to figure out what made these men tick. Most of the time, I was surprised. I ended up learning a lot about myself the more I listened to and understood the people I went out with. It was a real turning point in my development as a human.

Of the many things that I learned, the lesson that has helped me the most is that when I let go of my expectations, I have way more fun. I was never looking for any of these men to fill any of my specific needs, desires, or gaping chasms in my emotional life, I was just hoping to have something interesting to write about at the end of the night. This approach kept me open to appreciating who they were. People are really very entertaining if you let them be.

I call it expiration dating. When you go out with a person without any pre-conceived notions of a long-term commitment, you end up having way more fun because there is no pressure to turn it into something. You are free to enjoy because you have no stake in making it last. You can be yourself, and you don't have to ask them any leading questions or figure out whether or not they will be a good long-term earner. In the end, you really just need to prepare to meet someone who could be interesting, or, best of all, challenging. I love a good challenge.

Just yesterday I was speaking to a friend of mine and he told me that he and his lovely wife of fifteen? sixteen? years were initially expiration daters. He said that in effect, it allowed them to just be themselves, no pretense, no bullshit. Don't get me wrong, I am not telling you to use this strategy to hook someone into a long-term relationship. I am not a fan of LTRs, nor would I ever suggest that anyone use any particular strategy in order to get one. I am simply saying that when you let go of control and expectations, your dating experience is more enjoyable, no matter where it leads you.

I talk to a lot of people about dating and they seem to loathe it.  They tend to see relationships as something that will spare them from an incredibly unpleasant and horrible series of events. This is too bad and violates one of my biggest rules in dating and in life. Do not look for rescue from your present horror. The choice you make is very often made in desperation and in many cases will produce an out-of-the-frying-pan-and-into-the-fire-type effect. How many times have I seen people make bad choices in love simply because their singledom/dating life was less than fulfilling? Too many to recount, and I bet if you thought for a minute, you might realize that you know someone in this very situation.

Unpleasant experiences are opportunities to turn something bad into something truly great. Once that thing, event, experience is something we love, we are bound to make better choices for ourselves. Having a life that consists of choosing the lesser of two evils is a depressing way to live. All you need to do is look to the US political system to know that.

This is my challenge to you on this Friday morning. If you happen to find yourself single, go out with someone this weekend who you are not really interested in, someone who you might not typically date. Find out what their world view is all about. Prepare to be entertained. Set your focus to "razor sharp" and be curious. Put your expectations, your needs, desires and desperation aside, and you just might have a lot of fun. You might laugh. You might learn a little about yourself. If you take this challenge, leave your results in the comments section below. Or, if you need to work up to this challenge, let me know how it goes when you can manage it. 

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