Finding Love Digitally, Losing It IRL

A dating coach’s experience with “’til death do them part”

I started my business bootstrapped. I had $50, a Twitter account … and that’s basically it. To “market” my “company,” I created Craigslist postings with headlines like Online Dating Guru Will Write Your Profile and Digital Dating Coach For Hire. Interns plastered the city with photocopied flyers while I trolled message boards and searched hashtags on Twitter, looking for users complaining about online dating. I’d creepily join conversations, inject some advice and ask a question to continue chatting. One hundred percent of the time it elicited a “?!?!?!” reaction but 89 percent of the time, people would comment back or follow me.

We’ll call one of my very first clients Joe White. He was moving from the East Coast to the Deep South and wanted help adjusting to the dating scene and new dating sites. From the comfort of my couch I wrote a Match.com profile that would attract his version of a Southern belle, recommended he join OkCupid, where I thought he’d find more matches he’d like, and tweaked his Facebook page from a potential partner’s perspective. As he selected cuties online, I’d ghostwrite messages to them as the silent partner in Joe’s love life who kept his side of the screen warm.

As Joe settled into his new place, his perspective on dating evolved. “I wouldn’t say I’m looking for something serious,” he said on one of our calls. “But the more I think about the idea of someone special, the more open to it I become. Maybe someone will come along.”

A few months later, someone did. Amanda’s first words to Joe were: “I’ve never written to a guy before, but your profile was so compelling that I just had to say HI!” When they met up, drinks turned into dinner, which turned into talking all night. Soon after, Joe made their relationship exclusive and deleted his profiles.

Fast forward to one year later when Joe called to share the news of their engagement. I danced wildly around my teeny New York City apartment, squealing with joy, asking him question after question about his OkCupid bride-to-be — how he proposed and the details of the upcoming wedding. We were giddy, laughing together, sharing a moment of pure joy. My student was about to graduate from the school of online dating with a PhD in matrimony. I literally jumped up and down and told him how ecstatic I was for this major milestone in his life, something he’d never forget. And I’d never forget either — Joe’s engagement and wedding was the first of my professional career.

Yes, I’m in the business of love, but with that inevitably comes loss.

I have to be honest and say that when I created a company that would connect hearts I (perhaps naively) never considered the other extreme that the people whose lives’ I touch might face: Death.When I first heard that Joe’s wife passed away suddenly in her sleep at the age of 32 — after only one year of marriage together — I couldn’t do anything except sit speechless. This news meant my first married client became the first widow of my work.

My mind whirred, trying to think of what I could have done to protect Joe and Amanda’s union, but there were no answers. While I found Joe his right click, I ultimately couldn’t troubleshoot their marriage’s fate. For someone whose professional livelihood is to sync heartbeats, I was at a loss for helping Joe’s heart pump again — this time, on its own, without it’s other half. I attempted to write my condolences, but for possibly the first time in my entire life, found myself at a typing standstill. How could I put an “I’m sorry for your loss” message into words when I was the one who wrote the profile that attracted Joe’s wife?

I barely moved the entire weekend. While my heart was breaking for a client I’ve known so long and mourning the loss of his soul mate, my mind went to some pretty dark places about my place in their relationship. It’s rare that I question the decision to make love my life’s work but for two days my head and heart battled. My vocation, which usually exists to me only in Technicolor glory, was suddenly pixilated. Tissue in one hand and a pen in the other, I asked myself some of the heaviest questions I’ll likely encounter as a love-preneur.

• Am I meddling with fate? What if I’m not part of the plan?
• Will my work just ultimately lead people into crisis?
• Does being a catalyst for love outweigh the loss that people stand to feel?

I came close to shutting my business down for good. Joe’s loss rocked not only my soul but also tested my entrepreneurial mission in a way I didn't know existed. Scrawling furiously on page upon page of a journal, I took stock of every crippling fear, hesitation and frustration. By Sunday night, I had an epiphany.

I tried imagining a world without my fiancé. After all, existence without Thomas and I’s first tweets to each other would be similar to Joe’s life sans his profile that attracted his late wife. While I wouldn’t necessarily know what I was missing had my fiancé and I’s cyber-paths not crossed, I wouldn’t be complete. Part of that is of course because there wouldn’t be an “us,” but there also wouldn’t be a “me.” I’d still exist, but I wouldn’t be this me that I am today, at this very moment — the person who has grown alongside the love of her life. Through emotions, experiences, decisions, sacrifices, love, life, and death, we’ve both become enriched versions of ourselves, together.

I know the same can be said for Joe. Despite his loss, he would have never been the enhanced him that led him to marry the love of his life after a two-year courtship. Though his clarity was temporarily removed, she left a light inside him that couldn’t be dimmed.

And with that, I found the words to type to Joe. We spoke a week later. It was certainly nothing I felt trained for (luckily he was also working with a therapist) but Joe trusted me with his heart and I was honored to be included in the conversation. He was confused by what happened. One moment she was there and the next, she was gone.

What’s more is that his own life seemed to suddenly feel uncomfortable to him. He questioned everything: Was he living in the right place? Is his work meaningful enough? Should he make new friends? Would he ever find love again? Loss, especially so young, meant a major shift for him. Despite the grief, one thing was certain: he wanted to honor her for the rest of his time on this earth by dedicating his life to creating a charity that would make her proud.

I won’t pretend to know what losing a life companion feels like, particularly so suddenly and soon into a union. But I do know that Joe’s wife has never truly left him, not simply due to memories he (and other loved ones) have, but because he’s changed after his life with her as a couple. Joe is now an evolved version of himself. And though he’s without what he expected to be his lifelong partner, the love they shared will always exist.

While contemplating this, Joe’s Facebook status updated on my laptop screen. He wrote how he learned that love lives on beyond the body and concluded as a tagged update: “with Amanda White.”

Feeling suddenly solid in that moment, I recommitted myself to the mission of helping singles find their love at first click. Had I not worked with Joe, it’s likely that they may have never had any time in each other’s arms. So each day, I wake up and continue to help online daters follow their heart’s hard drive. That’s the best way I know how to honor Amanda and Joe’s love … and their loss.