I Broke Up With Someone Over Text & It Wound Up Stretching Out For Months

All’s fair in love and war. Or is it? In this age of digital romance, where breadcrumbing, ghosting and benching are enabled by our iPhones, it’s only natural that the text message break-up is a popular phenomenon. To quote Kanye West: “Text message break up, the casualty of tour / How she gonna wake up and not love me no more?" In the eight years since he penned those lyrics, the devices might have changed, but the sentiment hasn't. Indeed, when I attempted to break up with someone over text, it didn't go well.

I'd been dating this guy for three months — the three loneliest, most depressing months of the year, right after Christmas when New York City becomes a barren wasteland of dirty snow and loneliness. So perhaps things progressed a bit faster than they normally would have. We had gone on many dinner dates, discussed upcoming plans, and texted often. The reason I elected to breakup via text was because I felt the relationship didn’t have a long enough duration to mandate an in-person conversation. I’d been in year-long relationships that ended properly, with public tears on a park bench and aftermath drinks discussing what went wrong. But those were more serious. Here was a classic case of she’s just not that into you.

I’d resolved to end the relationship before the bus ride was over. That gave me roughly five hours. Turns out, I would need even longer than that.

After evading dinner dates for two weeks, I finally decided to terminate the relationship while on a Bolt Bus back home to New York from Rhode Island. After seeking the romantic counsel of my younger brother (never ask a 19-year-old boy for advice), I’d resolved to end the relationship before the bus ride was over. That gave me roughly five hours. Turns out, I would need even longer than that. Word to the wise: do not embark on a text message break up while riding a crowded bus alone on a Sunday evening. The Sunday Scaries were out of control.

I drafted and edited what I thought was an immaculate iMessage.

Hey, yes my weekend was great! I actually can’t get together on Wednesday, but also wanted to let you know that I’ve loved getting to know you better, and have so enjoyed our dates, but I’m not really in a place to be in a relationship right now. I’m so busy with work and school, and I feel like you deserve better. But I’d love to stay friends.

Was I busy with work? Yes. Was grad school killing my social life? Also, yes. Would any of this matter if I wanted to date him? No.

I recognized the line about "staying friends" seemed cliché, but it was the truth. I genuinely believe you can only stay friends with an ex if you were never emotionally invested in the first place, which, luckily (or unluckily) was the case for me.

I was satisfied with my message. So I sent it. But I wasn't prepared for any of the follow-up questions that soon flooded my screen.

"Why can't we work around your schedule?" "What do you mean, you aren't ready for a relationship?" "Why did we have so much fun last week, then? Didn't we have so much fun last week?" "What are you actually looking for?" I felt like I was in a divorce proceeding, justifying my points. It was like talking to a lawyer. One that I had kissed only a week prior.

I felt guilty and unprepared to answer any of his questions. One difference between texting and talking is the response time; the stilted pacing of our iMessages opened up a floodgate of (unrequested) feedback that I feel confident my recipient would have felt less inclined to say in person. Crucially, dumping someone via text gives your would-be partner more time to plan a response — time they will likely make good use of, as they’ve just been spurned. The paragraphs of text messages that I received were overwhelming. While five minutes of awkward silence in a restaurant can leave both parties feeling sheepish, uncomfortable, and eager for the check, five minutes while texting is no time at all.

By hiding behind a screen, I’d inadvertently left the door open for negotiation.

Delivering the news via text actually prolonged the discussion and made it more uncomfortable than I could have possibly imagined. By hiding behind a screen, I’d inadvertently left the door open for negotiation. He simply refused to be broken up with—a move that was quite successful for Chrissy Teigen, though it ultimately couldn’t save our fledgling relationship.

In the days that followed, he would alternate between sending long, imploring messages to get together or shooting off brief, casual texts about my weekend as if nothing had happened. The messages came for weeks. Months. At first, I reiterated the points of the breakup. Eventually, I stopped responding altogether.

Though we share some mutual friends, I hadn’t expected to keep in touch, considering the way things ended. But when I saw him later that year, at a rooftop party on a hopeful Saturday in May, I actually enjoyed his company. Maybe it was because the temperature was above 20 degrees, and life didn’t feel so dire, but we were able to laugh about our short-lived, tactlessly discarded romance. I liked him as a friend, and was open to that possibility, though I’d soon learn that, for him, the romantic possibility never really ended. He told me (again, of course, via text) that things didn’t really feel over for him. He was certain that we could pick up where we left off. I tried to sound casual and self-deprecating that night; I wanted to apologize and then move forward. But my eagerness to avoid any awkwardness somehow was mistaken for flirtation — which turned out to be the most awkward situation of all.

After two more weeks of his persistent texting, I agreed to get drinks in our neighborhood. Sidling up to the bar, I ordered a martini. I needed some liquid courage to deliver my prepared speech. I took a long sip before looking him in the eye and telling him I didn’t share his feelings. Our chemistry was platonic. I didn’t want to be in a relationship with him. He tried to protest, but I shut him down.

Then, magically, after 15 more minutes (and, honestly, another round of martinis), the tension dissipated. We speculated about possible endings to Game Of Thrones and shared our theories about Kanye West. After we parted ways that night, he stopped texting me for good. I ran into him at another party and we were fine. My lesson? Woman up and dump people in person.

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