both sides of a breakup

Reality Hit After He Proposed

A weeklong series dedicated to skewering the traditions, expectations, and psychodrama that surround wedding season.

In “Both Sides of a Breakup,” the Cut talks to exes about how they got together and why they split up. Emily and Curtis, both 32, met right after Emily went through a difficult breakup. They fell in love quickly and got engaged just six weeks into their relationship. This is the story of why they never made it down the aisle.

Curtis: She was a little bit of a wounded bird when I met her. Coming off a few bad breakups, a little lost, really wanting marriage and kids but looking in all the wrong places …

Emily: I had just suffered the hardest breakup ever. Like, the one that did me in for life. My ex had some kind of meltdown and turned into a different person and everything fell apart … it’s a long story. Anyway: And here comes this guy — handsome, sweet, funny, honest — who just wanted to love me, treat me right, and be with me forever.

Curtis: I knew she was a little bit of a wild card, but I can’t say that didn’t seduce me all the more. That, plus whiskey, a lot of whiskey.

Emily: We had like three wasted dates at really great bars and restaurants, where the music was just right and the food was amazing — all of which ended in dancing and then superhot sex — and then we were both just like, “Let’s do this! Let’s choose each other. Let’s just be with each other! Yay! Roar! Get it!” It was a crazy romance, but the good kind of crazy.

Curtis: I loved her right away. Not at first sight, because at first sight, I thought she was a little … what’s the nice way to put it? She was a lot. Funny, outgoing, but a lot. Regardless, I did fall in love with her by approximately our third date. I told her I loved her during sex that night.

Emily: He said something really cheesy but very endearing on our second date. He said, “I’m falling in love with you, Emily Jane.” (My middle name is Jane.) I was like, “Um. Okay. Hmmm. Actually, I’m okay with that.” And then, he took it to a new level on date five or six. He was like, “What’s your ring size?” I told him my size and was like (to myself): I’m partially in shock over that question and what it could mean, but partially floating on a cloud about it all. I never told anyone we were getting so serious because rationality played no part in any of this. I didn’t want to hear anything rational or logical from anyone. My friends who’d met him liked him a lot, and my family lives in California so they never had a chance to meet him. I was just so manic and high on life. And high on … not getting hurt by a man.

Curtis: I can’t remember how I knew her ring size. But my sister, who works for a very popular jewelry company, suggested a certain ring for her. My sister was excited that I was so head-over-heels for Emily. Our parents are pretty removed from our lives, so it’s just us, and we’re always excited at the prospect of growing “us.” After knowing Emily for six weeks, I proposed. I did it on her front stoop over our morning coffee together, a favorite ritual.

Emily: It was pretty picture-perfect: two cups of great coffee in big white mugs. A Brooklyn stoop on a warm spring morning. I said, “Yes!” I was thrilled … I think? We kissed. We went upstairs and had sex. Then we both went to work. But on the subway, for the first time since I met Curtis, a sliver of reality sunk in. Anxiety … pure anxiety. I mean, we had been drunk, high on love, or in a sex-fog for six weeks. Could that possibly last? Was any of it real? All day at work, I was more panicky than overjoyed.

Curtis: I don’t know. I’m a guy. I was just happy I got the girl. There was no anxiety for me. I proposed, she said yes, I went to work, and I couldn’t wait to come home and see her (we were basically living at her place, though I still had my apartment). It was simple and sweet for me. But I remember that night, she was like, “We gotta talk.” Uh-oh. She told me she felt really panicked about everything. We blew it off as just an overwhelming day. But I couldn’t sleep that night though … I felt rattled. We didn’t have sex for like the first time ever and I was like, Not good. This is not good.

Emily: I couldn’t stop being anxious. And I didn’t want to tell anyone we got engaged, which was weird. I was a little embarrassed — and I guess deep in my gut I knew this wedding wouldn’t see the light of day. For a month, I placated myself by telling myself that there was no rush to have a wedding, maybe we didn’t even need to have a wedding. The idea of City Hall helped me feel a little less anxious. But even with that, I was like, Ughhh I don’t know. It’s not like anyone was breathing down my neck about it. Curtis was wonderful and patient.

Curtis: I’d say a month after I put the ring on her finger, she was like, “I can’t.” And I was like, “I know.” I wasn’t going to force her to marry me. It was a sad night. We both cried a little. She said she needed some space.

Emily: It just didn’t feel right. I can’t articulate why. I had to listen to my heart. I don’t know if I wanted to be alone, for once, or if it was that we just weren’t soul mates. But I felt a tremendous relief when I went to give the ring back …

Curtis: She kept the ring.

Emily: … but he insisted I keep it. Sometimes I wear it when I know I won’t see him. Wearing it in front of him would just be too insensitive, I think.

Curtis: It’s been a year since we broke up. We’re still good friends; we hang every few weeks, go to brunch and such. We laugh about it now, our great fling. I still love her, but I’m okay to love her as a friend. She can have me back whenever and she knows it! I’m just kidding. Kind of.

Emily: I’m still single. Curtis has become one of my best friends. I enjoy my time with him. We don’t hook up, but we still laugh a lot and it always feels great. Unfortunately, he’s not “the one” — I wish he was. But my heart still says, “Sorry, babe. Nope.”

Both Sides of a Breakup: Reality Hit After He Proposed