Wondering how to be sure about a decision?

I want to talk about the downsides of freedom. 

Many times in conversations with clients, I will hear, “But how am I supposed to be sure that he's right for me?” This is usually in reference to a guy that they've gone on a few dates with and things are starting to look like they're moving in a good direction. 

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In today's day of dating apps with seemingly endless swipes and TikTok videos of couples being reunited after months of international long distance, there's a lot of possibilities. Your partner could be anywhere. This is really the expression of our romantic freedom. We are free to meet so many more people than two generations ago when you met someone in your hometown and settled down. We are more free to move cities, which extends the number of possibilities. Society has shifted so women feel more free to wait until their late 20s or early 30s to get married, giving them more time to stay selective and keep looking. 

But freedom comes at the cost of certainty. 

The more free we are, the harder it is to be certain about anything. With more options, more factors, more time to decide, more flexibility, each decision becomes much more complicated. And what decision could be more significant and complicated than choosing who might be your long term partner?

So when I have these conversations with clients, I don't blame them for wondering how to be sure, certain, about him. But I explain to them the connection between freedom and certainty - the more you have of one, the less you have of the other. So they have two real paths forward - reduce the amount of freedom in their decision (i.e. decide that they're only dating in their city and they're going to pick someone by the end of the year) or change their threshold of certainty, to start to accept that they might not reach 100% sure about him, but 85% is pretty darn good!  

Psychologists ran an experiment to demonstrate this “paradox of choice” - they studied customer behavior at a stand in a local food market, comparing how often consumers made a choice when there were 24 jam options vs. 6. The larger selection generated more interest but with the smaller selection, customers were 10x as likely to make a purchase. TEN TIMES. 

Obviously, my clients rarely choose the first option (to decide to only date in their city for 1 more year) because it sounds arbitrarily limiting. But if you're not going to limit yourself down to 6 jams, you're going to look at a 24 jam table and either keep sampling forever or after sampling a few, but without sampling them all, just decide that apricot is the one you like the best and commit. 

At some point, you decide that you are sure. 

“Sure” is something that comes from inside us, not from the world around us. Because when it comes to romantic partners, there's no objectively correct decision, like knowing you've got the correct shoe size when it just fits. 

But here's the good news - deciding feels good. Logan Ury, in her book How to Not Die Alone, describes a type of dater called The Maximizer, a type who is always looking for the objectively best in everything, best coffee maker (extensively researched on Wirecutter and meticulously examined), best hotel for their next trip, etc. The Maximizer really struggles to be sure unless they know they have the “best” - which obviously will never be explicitly clear in their dating life. The alternative is to become what's described as The Satisficer - a dater who has a clear set of standards (to use the coffee maker example, can make 5 cups at a time, isn't too loud, comes in a fun color) but once those standards are met, is willing to commit to the decision (or person). They evaluated these personalities (using product purchase decisions) and the Satisficer were overall happier with their decisions than the Maximizers, even when they select an objectively worse option. Because once they made a decision, they stopped the second guessing and just enjoyed the product.

In a dating context, this does not mean that you should stay with someone when you're unhappy because you “already decided.” But if this post has resonated with you, you might benefit from reducing your quantity of escape hatches (or if you are currently dating and deciding whether or not to commit, by reducing the quantity of times you have to decide you like him enough).

Give yourself a decision point - I will continue seeing him for 1 more week and on Sunday, I'm going to decide yes or no. Then once you make that decision, you decide you're sure. Believe that you made the right call. And then enjoy being with this person that you've decided to be with.

(If something egregious comes up, I promise it will be apparent enough that you can separate that from the minor doubts and questions. If you are constantly looking for a sign you might not have found the “best” option for you, you will always eventually find it. )


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