“Why We Didn’t Work”

One cozy December evening, I (Jacqueline) was out drinking martinis with pastry chef friend Paulette Goto, talking about past loves. We dug into the nitty gritty around breakups: Do you remember the reasons for them clearly? Do those reasons change with some hindsight? Did your ex really tell you all they were thinking and feeling at the time? Do you have any regrets? Might they?

That night, using the radio show and my job as a writer as an excuse, I came up with five questions I’d ask some of my exes, as a little social experiment of sorts. Why did we break up? What didn’t work about us over the course of our relationship? What did? When they think about me now (as Paulette assured me they obviously do), what do they think of? And do they have any regrets? 

When we discussed this idea  on the show, Ben jumped on to participate with his own exes and own curiosities.  We sent out the questions and details, gave it time, and got some answers. Then, we scheduled two shows where a licensed therapist was to guide us through the communications (click here for Ben’s and mine). We were both nervous before our segments. We both had fabulous women supporting and coaching us. And we both we a bit surprised by some of what we were told about ourselves.

We were both nervous before our segments. We both had fabulous women supporting and coaching us. And we both we a bit surprised by some of what we were told about ourselves.

Since our show is a quick, live beast, we often find ourselves dazed afterward, discussing what felt great, what didn’t sit right, and what we need to improve upon for the future. The last two shows prompted much more reflection than our collective average. Ben spoke a little on his greatest takeaways before my session with Diana last week, and I’ve been chewing on a good amount of my own. Rather than take more precious air time to dive in deeper (we have current dating conundrums and beautiful people to speak with, obviously!), we’ve put pen to paper (well, fingers to keyboard), and articulated where the Why We Didn’t Work experiment has left us now.

Read Jacqueline’s Takeaways on All The Feelings

Read Ben’s Takeaways on The Examined Life

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