Kent Hernandez/FUSION

Of all the ups and downs that I've had in my dating life, the most humiliating moment was having to explain to Siri that I got dumped.

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"Siri, John isn't my boyfriend anymore," I confided to my iPhone, between sobs.

“Do you want me to remember that John is not your boyfriend anymore?” Siri responded, in the stilted, masculine British robot dialect I'd selected in "settings."

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Callously, Siri then prompted me to tap either “yes” or “no.”

A few months into the relationship I'd asked Siri to remember which of the many Johns* in my contacts was the one I was dating. At the time, divulging this information to Siri seemed like a big step — at long last, we were “Siri Official!” Now, though, we were Siri-Separated. Having to break the news to my iPhone—my non-human, but still intimate companion—surprisingly stung.

Siri wasn't the only screen-based trial of my break-up. Our relationships now exist across networked webs of digital connections, webs that we build up each time we begin a new romance and then must painfully break down when one ends. When I flicked open my laptop at work, the bottom-right corner was empty where a Google chat had previously sat waiting for me. Notifications of unread Snapchat messages used to lead to goofy photos of John, but now they're just, disappointingly, announcements from Team Snapchat. Every time I send a note to a particular group of friends, Google's algorithm suggests I add John to the e-mail thread.

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Our relationship was the digital equivalent of moving in together, and now painful memories of him were scattered all over my online home. Technology was making my heartache worse, but that's not how these things are supposed to work: Technology is supposed make our lives easier, so I sought out tech fixes for a broken heart.


Google chat had been our most frequent method of communication (he was an Android guy). I wanted to reduce the temptation to send him an informal hello and prevent one from him sending me spiraling at the buzz of a notification. After telling Siri it was over, I uninstalled the Google Hangouts app from my phone, archived our conversations and muted notifications for any messages my ex might send me.

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Then I deleted Instagram from my phone, to keep myself from browsing through old photos of the mini vacation we'd taken just two weeks before our split. Snapchat, too, got booted from my screen.

“We now have all these technologies that are urging us to connect all the time and the built-in assumption is that you want to connect,” Ilana Gershon, a digital anthropologist at Indiana University who has studied breakups, told me. “When you’re breaking up, all of the sudden you are trying to do something that the technologies are just not built for.”

In other words, how do you disconnect from someone when he is just one click away on every platform you visit on a regular basis?

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An hour after we broke up, I wandered over to Facebook and noticed that John had just "liked" a story of mine I'd posted earlier that day. Ugh. What did that mean?

In a study published last year, 62 percent of daters said they spent a lot of time reanalyzing Facebook wall posts and messages from exes after a breakup. This, the researchers said, doesn’t exactly help with the whole moving-on thing.

To avoid falling into that trap, I unfollowed my ex on Facebook, to keep his posts from showing up in my feed. And then I installed Block Your Ex, a browser extension for Chrome and Safari that will prevent you from compulsively visiting someone's Facebook profile, Twitter or blog.

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In the past, if all your exes lived in Texas, you could just move to Tennessee, but now, all of our exes are our virtual next door neighbors. What I needed was the digital equivalent of a very long holiday in Tennessee, a way to escape our relationship's digital detritus and the compulsion to navigate my browser to memories of our past every time I found my mind wandering.

A browser extension, KillSwitch, promised to permanently purge all past interactions with an ex from Facebook, but that seemed too extreme. I didn't want to sever our connections entirely. I just needed some distance to grieve, and then, eventually, to move on. (Plus the KillSwitch no longer seemed to work; like many of the apps for broken hearts I tried out, it seemed neglected by its creator, who I can only assume got into a new relationship and lost a passion for it.)

In the time before smartphones and Snapchat, I might have stuffed all reminders of our relationship in a box under my bed until I was ready to revisit them. Instead, I upgraded to StayFocused, a Chrome extension that allowed me to limit my time on sites like Facebook to only 10 minutes a day, lest I find myself browsing through posts from our mutual friends, engaged in a self-defeating search for traces of John.

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Gershon told me that some people find it easier to just quit social media altogether when dealing with a split, but I didn't want to give up my connections with family and friends, especially now.

In researching her book “The Breakup 2.0: Disconnecting Over New Media,” Gershon found that part of what makes modern breakups so crazy-making is the lack of uniform etiquette for how to use different kinds of technology in the aftermath of a split. What a breakup means in real life is usually fairly clear. You stop texting 10 times a day, staying over at each other's houses, calling just to say hi. But should you stop liking stories your ex posts on Facebook? Should you unfriend them altogether?

"There’s no agreed upon etiquette," Gershon told me. Liking an ex's Facebook post can be a casual gesture for one person, like a wave hello when you pass them on the street. For someone else, it could be loaded with meaning.

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I kept purging. I searched for "breakup" in the iTunes store to see what kinds of solutions lovelorn programmers had dreamed up to help heal my broken heart.

I found an app called Picture to Burn that aims to digitally reproduce the cathartic act of burning an ex's photo (for free!). The app syncs up with your phone's camera roll, from which you select images to "burn."

But setting a pixelated flame to our digital relics only felt like I had turned our relationship into some kind of venture-backed gimmick. Not to mention, most of those photos were still on iCloud and Instagram, anyway.

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Another app, Drunk Dial, the most useful of the bunch, forced me to do math if I broke down and tried to dial my ex.

And for $3.99, Breakup Medicine, offered suggestions for daily exercises and inspirational advice to get me through the sadness. The advice was approximately the same as the motivational posters on the walls of a therapist's waiting room. "Let confusion guide you," it soothed. "Go for a walk and find something beautiful." Most other apps seemed to offer similar strains of comfort — they sought to turn my phone into a confidante, something I turned to in need of a friend.


I was ultimately disappointed in what technology had to offer when it comes to heartache. This is one of the problems that Silicon Valley doesn't seem to care about.

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The truth is, there isn't (yet) a quick tech fix for a breakup. Even if you unfollow, unfriend and restrain yourself from the temptation of cyberstalking, our technologies still hold onto traces of our relationships.

I logged into Instacart the other day and on checkout realized it had defaulted to a store in John's zipcode. Once, when boarding a flight, instead of my boarding pass, the iPhone's Passbook app served up the tickets for an event my ex and I had gone to the night before we broke up. In an instant I went from totally fine to completely unglued. Around every corner of our digital worlds lurks a new opportunity for heartache. Algorithms never forget.

“These little tiny bits of pain add up to this much bigger thing," said Sarah K. Hallacher, a Brooklyn-based artist and UX designer, who explored the web’s memories of heartbreak last year with a project she called “User Experience of Heartbreak.”

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Even years later, Hallacher told me that every time she creates a new transaction in the payments app Venmo, it still automatically fills in the name of the ex that inspired her work.

“No one at Venmo could have ever predicted they needed to consider emotional protection when building their algorithm,” said Hallacher. "Maybe our emotions will evolve to get used to the way algorithms handle our relationships, but right now there’s a big clash. It could be the stupidest thing that sets you off.”

The problem, said Steve Whittaker, a scientist who studies human-computer interaction at U.C. Santa Cruz, is that our digital information is simply not well organized. It's one thing to round up a box of mementos from around the house, but corralling all of the pieces of a relationship that exist across our digital life is an impossible task.

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"You’ve got all of these places where you have records of this person," he said. "These things can become very evocative triggers.”

Eventually, Whittaker imagines that technology will catch up to the problems it’s created. Maybe, for example, software could track and harvest all of a couple’s shared digital content, then store it in one less-accessible place after a breakup. Google Photos could use its facial recognition feature to put all of your photos of an ex in the digital equivalent of a shoebox of memories.

Perhaps, in the future, if I tell Siri I've just gotten dumped, it will know how to handle things more gently, offering me some sort of pre-programmed comfort, rather than algorithms that constantly surface reminders of the person who is no longer a "favorite" contact in my phone.

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*This name has been changed.