Issue #250: I Regretted My Divorce for a Long Time (Here’s What Finally Changed)

On learning to live with regret.

I had planned to publish a Part 2 to my AMA today, until I came across this question from a reader, Alex M.: “Super personal so please feel free to skip! I’m also incredibly curious about what people regret, or how they think about regrets. What are yours? How do you?”

As I began writing, I realized I had so much to say about regret—including things I’ve never shared about my divorce—that I wanted to devote an entire post to answering it honestly. Let’s get to it. x

In the earliest days of my separation from my husband, I agonized over my decision to leave. I was operating entirely off of the intuitive sense that something wasn’t working, and that I needed to leave in order to understand what that something was. Back then, I grasped for answers—from books, from friends. When I called my mom for advice, she told me, “I’m afraid that you don’t really understand what regret is, since you’ve never had to experience it.”

Up until that point, I had never regretted anything, and why would I? Every leap I’d ever taken had paid off. And I knew that I could undo any of my choices if I needed to: I could transfer to a different college, move back to a city I’d left, switch careers. But, it turned out, I couldn’t go back to my husband.

When I left my husband in the summer of 2022, a part of me believed that I could go back to him if I needed to—he had been such a huge part of my life for eleven years, that, even as I left, I couldn’t wrap my head around the fact that there might someday come a day when he wasn’t. Throughout most of that summer and fall, we attended couple’s therapy together and explored the possibility of getting back together. That fall, at the advice of our therapist, I spent the night with him in the home we had once shared. I was supposed to stay for the week, but left after one night, writing in my journal as soon as I got back to my apartment, “Staying feels so much safer than leaving. Who’s to say which is better? If I stay, I feel like I will spend the rest of my life asking myself, But what if I had left?”

Still, two months later, I decided that I wanted to stay. When my husband came into my apartment to drop off our dog Toast, who we still shared custody of, I handed him a letter. He sat on my couch reading it: a heartfelt apology and entreaty to get back together. When he reached the end, my heart dropped when he told me he couldn’t do it. I had caused him too much pain, and he wanted to give the new relationship he had just started a chance.¹

Finally, I knew what regret felt like. What I didn’t yet understand was that regret, at its worst, is a verdict, but it can also be an important teacher.

At the time, regret felt like the deepest grief and shame I have ever experienced. It was as if my husband, all of his friends, and his family, who had felt like my own, had died and I was entirely responsible for their deaths. At the same time that I grieved losing them, I had to contend with my deep shame. I felt like a monster, like I would never be worthy of love again, like I might be the worst person to ever walk the planet. The pain was so deep that I woke up sobbing every single night.

At one point, early on, I Googled “divorce regret” and found myself on the saddest forum I have ever visited. In it, men wrote about their grief and regret around leaving their wives, or engaging in affairs that led their wives to leave them. They mostly wrote from small apartments, isolated from their families, only able to see now what they had lost. For a long time, I lived in the airless grief of my own small, post-divorce apartment until slowly, I began to wonder if my regret was trying to tell me something beyond, “You ruined everything.”