We met in a 12-step program. I was half-crazed and full of rage; Ella was crying about old wounds and what her life, at 22, had become. Afterward, over Mexican food with some other drunks, we talked about F. Scott Fitzgerald and climate change. Soon, we were inseparable.
When I took a job in California, she moved with me. We planned a future: engagement rings, children, moving back east. Then one night, after learning I’d gotten into graduate school in New York, I pulled out a little band of golden flowers. When I saw her face, I knew it was over. Her expression said no in a way she didn’t have to.
I wasn’t right after that. Grad school proved a blur of depression. Long before Tinder, I got into OKCupid and tried to screw my way out of sorrow. Then, about a year after the proposal, Ella and I met at a cafe in New York. She was going through a rough patch, too. She looked gaunt, her food issues in full flare-up. Sitting there—listening as she described her sadness and doubts about life and school—I suddenly felt grateful for what she said when I’d pulled out that ring, as much as it cut. We loved each other, but we shared a kind of pain that our love couldn’t help heal.
A few years later, when I married my wife, now the mother of my children, I called Ella; I regretted it immediately. She said she was glad for me. But I felt as if I’d slashed at her stitches. I guess I’d wanted to prove that I was worthy of love, which was its own kind of shortcoming.
I came to view our relationship, and everything after, as a series of small, instructive failures. I was angry back then. Pushy. Prideful. I made 1,001 little mistakes, and she was right to see us for how we were. She gave the gift of insight, and for that I’m forever thankful.
By all accounts, she has gotten her life together now. She’s a doctor, is married, has kids. Our lives have paralleled in a way. We both escaped our toxic selves and moved on to something healthy. But when I think about the moment I pulled out that ring and saw her face, it stings worse than anything I’ve ever felt. Growth can hurt like that.
This essay is part of our Art of the Fail series.