I Failed To Monetize My Life As A Dating Blogger

THE DARK DAYS OF 2009It had been six months since I quit, but I still managed to bring up the blog within 15 minutes of meeting Lauren.

We were at my go-to first date spot, a subterranean bar with shuffleboard and ping-pong in case the conversation flagged. When she asked what I did for a living, I dispatched with my day job in a few sentences before admitting, with false embarrassment, that I was also an aspiring writer.

The required follow-up question—”What kind of stuff do you write?”—was barely out of her mouth before I slipped into my spiel: “It’s a little embarrassing, but I used to be a dating blogger for Glamour magazine. Kind of like a male Carrie Bradshaw, but without the voiceovers.”

I hoped for a laugh; I got a thin smile. Undeterred, I soldiered on: “Now I’m writing a novel that explains what it was like to chronicle my love life for a bunch of strangers. Pretty corny, I know, but I figure it’s my best chance to get published.”

This was in 2010. The market for blog-to-book deals was still fairly hot, although I could practically feel it cooling, like a light bulb fresh out of the socket. Julie and Julia had recently been nominated for an Academy Award, and it seemed like every other book on the front pay-for-play table at Barnes and Noble was spawned on WordPress. I was holding tight to what was left of my micro-micro-fame, but its value was depreciating rapidly. Every day without an internet hit to my name brought me that much closer to being eclipsed on Google by Ryan Chrysler Dodge Jeep, the place to go for quality new and used vehicles in Bismarck, North Dakota.

Wait, it gets skeezier. My decision to base the novel on my time as a professional bachelor had as much to do with getting laid as it did with getting published. Prior to becoming a minor Internet personality, my love life had alternated between futile pursuits of women who weren’t interested in me and brief, disappointing flings with those who were. Being a dating blogger changed the equation. Suddenly I was more interesting to women, the type of guy they told their friends about the next day—”You’d never guess who hit on me last night.”

Like many bloggers, I put an immense amount of time and energy into creating an online persona that was more clever and charming than I could ever hope to be in real time. Although it certainly didn’t work on everyone, the blog won over many women before they actually met me, which dramatically shifted the power dynamics of our first encounter. It often felt like I was playing the dating game with a stacked deck, and writing a novel that capitalized on the blog provided an excuse to continue pulling the “male Carrie Bradshaw” card.

Lauren didn’t seem overly impressed with my literary ambitions, but she did agree to go on a second date with me and then a third, until we eventually stopped counting. She had a quiet intelligence and unshakeable optimism that were fascinating and alien to someone like me, who approaches every conversation like a scored debate and starts bracing for the end of every good experience from the moment it begins.

This isn’t to say I didn’t have reservations. Over the years I had developed a very specific vision of the woman who would make an honest man of me. Lauren, who had been in a sorority, wore Tory Burch sandals and used emoticons, wasn’t an exact match, and I used every deviation from the ideal as proof that it was too soon for me to fully commit.

I was, on the other hand, 100% committed to my book. I sent it out to agents eight months into my relationship with Lauren. My pitch, like the novel itself, put a premium on marketability:

During my two years as Glamour magazine’s dating blogger, the question I got most often was “What happens if you fall in love with one of the women you’re writing about?” I never met Ms. Right, but my fictional doppelgänger has and it ain’t pretty. “Riley Cull Falls In Blove” is the novel Nick Hornby might have written if he had been a dating blogger instead of a music critic.

A brief synopsis: Riley goes on a series of disastrous dates with women who are into him for all the wrong reasons before falling in blove (“blog love”) with Cassie, a second grade teacher at an inner-city school who rides a vintage bicycle, looks great in Keds and orgasms the first time they have sex. She’s initially skeptical of the blog but Riley wins her trust, only to betray it when a major magazine dangles a plum job in front of him. The Nick Hornby comparison verged on libel, but I hoped the story was good enough—or timely enough—to snag a book deal.

I ended up getting a wonderful agent, who sent the manuscript out to publishers and received a few nibbles but no bites. This was devastating news. More than anything, I regretted how eager I had been to tell people about the book, especially on Facebook (“Just finished the first draft of my novel. By the numbers: 90,214 words; 333 pages; 1.5 years of work; 1001 mistakes; 1 very confused main character; and 3 boudoir scenes, 2 awkward and 1 steamy. Let the editing begin!”). I imagined that every kindly aunt who had promised to buy five copies (“But only if you autograph them!”) and every virtual stranger who had liked one of my Facebook posts was simultaneously realizing they hadn’t heard anything about the book in a while and coming to the obvious conclusion: I had failed.

It was Lauren who brought me out of my self-induced pity coma. One of the editors said she’d be willing to give the novel another look if I told the story from the perspective of both Riley and Cassie, which would potentially make it more appealing to female readers. I wasn’t sure I could pull it off, but Lauren pushed me to give it a shot. Even if it didn’t work, at least I could move on without regrets. After much coaxing, I eventually realized she was right. I wasn’t ready to let go, not yet.

Lauren and I moved in together shortly after I began working on the second draft, but much of our time was still spent apart. Although I dismissively described the novel to friends as “chick lit by a dude,” the truth is I was putting everything I had into it. Every weeknight I wrote for two hours after getting home, and our Saturdays and Sundays were built around my extended writing sessions.

Lauren never begrudged me this huge investment of time and gamely indulged my regular bouts of despair, when I would collapse into bed and launch into an extended lament about how it was all a waste of time. With characteristic sincerity, she would tell me she believed in me, that I was destined to succeed.

I’d grumble something pessimistic into her armpit as she ran her fingers through my hair, but she made me feel better. Lauren almost always made me feel better. The fact that she rarely wore the Keds I bought her and counted “The Bachelor” among her guilty pleasures still bothered me, but it was getting harder to pin my lingering doubts about our compatibility on what were, in the end, nothing more than minor differences in taste.

The problem wasn’t Lauren. The problem was that my sense of self-worth still hinged on my ability to attract women. The novel served as my time machine, an excuse to revel in my bachelor triumphs on an almost daily basis, to roll around in them like a dog who’d just found something filthy in the park. When trying to nail the tone of a flirtatious exchange, I would rummage through the archives of my Gmail account in search of a message from an old lover, squandering entire writing sessions as I relived our fling, often turning to Facebook to see what she looked like now and whether she was in a relationship.

The feedback I got from my agent after sending her the second draft was mixed. The dual narration was working, but Cassie’s voice was off—she sounded too much like Riley. Which is to say, she sounded too much like me.

After another round of self-pity, I decided to give it one last shot. My strategy was to mask my inability to nail Cassie’s voice by switching the narrative perspective from first person to third. I thought it would be relatively easy, a simple matter of switching pronouns. But the longer I worked on the novel the more problems I saw, and every attempt at a fix knocked something else out of alignment.

Finally, after another seven months of work, I sent my agent the third draft. The first few weeks of waiting for her response were relatively painless, a welcome excuse to take a break from writing. Panic set in as the weeks stacked up to a month, and then two. My heart rate spiked every time the little envelope in the corner of my computer screen turned blue to signal a new message. It was the same jolt I felt when I was single and sending self-consciously clever emails to my latest crush. Far more than any of my oft-revisited triumphs, this sense of foreboding epitomized my single years, but I had forgotten all about it. I had blocked the bad parts out.

The decisive email finally came on a Wednesday afternoon. After taking a few cleansing breaths, I opened it and began to read, my eyes skipping over the introductory niceties until they thudded against the verdict: “I’m afraid I don’t have good news.”

In addition to various problems with the novel’s plot and voice, my agent worried we had “missed our window.” Not only was I apparently over, it was over. Traditional blogs had long ago been supplanted by platforms like Twitter and Tumblr; now I was just another guy trying to sell a debut novel.

I waited for the familiar sense of devastation to set in, but what I felt was relief. I was relieved to be done with a project I no longer believed in. On a more fundamental level, I was relieved to be done with a period of my life I had outgrown. I had fallen out of blove.

For all its contrivances, the one part of the novel that still rings true for me is the last chapter. Riley, who has broken up with Cassie in order to become a little more famous, finally realizes his folly in the middle of Times Square. He dashes off to the subway station to catch an uptown train and win back his one true love, leaving his unsigned magazine contract behind on 43rd Street.

My unwillingness to let go of a romanticized vision of my bachelorhood was sabotaging my future with Lauren, but unlike Riley I couldn’t leave it behind on my own; I needed someone to take it away from me. The death of that novel slammed shut a window that let in nothing but the past, freeing me from a nostalgia that was always teetering on the verge of regret.

After taking some time away from fiction, I recently started a new novel. It has nothing to do with the Internet, it’s not a love story, and the main character isn’t a doppelgänger for anyone. I also proposed to Lauren. Miraculously, she said yes.





Ryan Dodge is a freelance writer living in Brooklyn. The name of his first blog was “Exhibistentialism.” He has forgiven himself for most of the mistakes he made when he was 24, but that one still stings. Follow him @_Ryan_Dodge.