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Love story: When journalism and online dating combine

Good journalism skills can pay off in the unlikeliest of settings – including online dating.

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A few weeks ago, my phone lit up with the familiar flash of an incoming text.

“OK. I have a date,” came the message from a friend who was just in the beginning stages of getting over a bad breakup. Attached was a screenshot of a cute, 30-something woman’s Bumble profile: A few smiling photos, both solo and with pals, and those key, short but cryptic lines of self-description.

My phone pinged again: “So can you do your recon thing?”

Dating in the modern era is terrible: An endless string of high hopes and dashed expectations, countless hours spent browsing profiles on various sites, and recurring nightmares of winding up alone while all your friends, it seems, have paired off and are creating families of their own. So what is a modern person to do? Well, while I can’t speak to the situation of all modern people, I can speak to the situation of modern writers, whose job it is to literally find out everything they can about a person, place, or thing, and then create a story, hopefully a compelling one, out of what they uncover.

And so I texted my friend, a non-writer, back three short words: “I’m on it.”


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I didn’t start to date in earnest until after I’d finished my first-ever job in journalism. For two years I’d worked as a cub reporter at a very small-town weekly newspaper, covering everything from farming and agriculture to selectmen’s meetings (picture any scene from Parks & Rec) and high school musicals. Writing up to eight stories per week, work left little time for love, and in such a small town, the pickings were slim to begin with. When I moved to Boston to start a gig at a big city daily, leaving behind both a simpler way of life and an unrequited crush on a tall and bumbling British colleague, I found myself in a new place, with more free time but no network of friends. And so I started to date. At first I went out with men I met “in real life,” as I now call it. There was the bartender who asked for my number when I came in on a below-zero night in search of a stiff drink before a party where my college ex-boyfriend – the first to break my heart – would be in attendance. There was the restaurant owner who I met one night over a plate of perfect French fries. There was that other bartender – the one who worked at the same place as my best friend – who took me out for drinks at a dive bar, then to a five-star restaurant just before midnight to split a full tasting menu. My foray into online dating started soon afterward, first with a brief dabble on JDate, where I managed to find perhaps the site’s only red-headed Irish man, and later on OkCupid, where I met the man I thought I was going to marry. It was only after that breakup that apps like Tinder and Bumble and Hinge entered the picture.

Whether I met these men online or “in real life,” I realized right away that even awful dates with seemingly ill-fated matches (don’t get me started on the archeology professor who was arrested on a field trip for making a bomb threat in a cave), there was always the challenge of figuring out the facts about a person – and uncovering a good story in the process. It was this challenge, this discovery, that first drew me to writing, too. Only later on in my career did I come to appreciate the construction of a strong sentence, the beauty in a perfectly placed word, the beat of cadence; at first, I just fell in love with narrative.

And so, what I unintentionally found myself doing again and again was recreating my work life in my romantic one (to both good and bad effects), and utilizing the skills I had picked up interviewing sources, getting scoops, and finding material in the uncanniest of places.



Where reporting and dating collide


Do your research – but know when to stop.

While it is possible for good interviews to happen on the fly, going into one prepared is usually a key step to success. In journalism, that often means reading up on a source and researching small biographical details like where they went to school or grew up. While it can feel pretty creepy, doing a little bit of digging before a date can be helpful, too, especially in an era with overflowing options to swipe left or right. Knowing a few details about a person before meeting them can better prepare you to really listen to the good stuff, to ask the right questions, or to feel comfortable sharing your own story. At the same time, there’s definitely a risk of doing too much research, both in writing and in dating – so if you find yourself at 2 a.m. going down an Instagram rabbit hole of a potential date, power down and walk away.

Ask questions.

While writers aren’t the only ones who can ask questions, I’ve found that my writer friends are particularly adept at it in social settings. And when they do it, I see people – shop clerks, strangers at cocktail parties, Uber drivers – relax around them and open up. Writers know that asking questions and creating an atmosphere of interest and trust is crucial to getting a source to talk. But this also requires balance – part of earning that trust with someone you’re interviewing or writing about involves not just listening but also offering tidbits about yourself; asking questions, yes, but also knowing when to share. It’s in that sweet spot that connection begins. The same is true on a date – be interested, ask; be vulnerable, share.

Stay until the end – you never know when your story might present itself.

In my first newspaper job, my editor used to make me stay till the very end of any meeting I covered. Ideally, she would say, be the last one to walk out. “You never know when your story might present itself,” was her motto. This came true one night when I was thinking about skipping out early on a meeting that included things like shellfish licenses and stone wall regulations on the agenda. I decided to stay, and just as the meeting was about to wrap up, one of those “mundane” issues sparked outrage in an attendee, who began to toss chairs around the small room. There was my lede. On dates, I usually apply this rule. People are rarely at their best or most authentic in a first meeting or in the first hour of a meeting. You never know when or where your lede might come from, so stay for that second drink, walk that extra block, or go for that next date. If there’s no story after that, move on. At least you tried.


Find an editor you trust (or just a friend with good judgment).

My first stab at online dating was a three-month stint on JDate. I hated it. After an unsuccessful date with that Irish man (in which he pulled nail clippers out of his pocket after coming up to my apartment for the first time), I went out with only one other man – a sweet guy, but there was no spark. I took a break from online dating for a while, which translated into a full-on dating rut. Enter my friend and “dating editor,” Molly. One night, she’d had enough of my rut, just as any good editor will have enough of their reporter’s writing block. “Come over,” she said one day. “I’m going to cook, we’re going to get drunk, and I’m going to write your OkCupid profile.” Over the past several years, Molly, a fellow writer and editor, has continued to be my sounding board, listening to the stories I’ve told about dating and giving her thoughts on which material has legs. When she met the man she would ultimately marry, they became something of an editing team for me, with her now-husband offering his male take on my profile, dates, or current partners. Like any good writer, I don’t let my editor make my decisions or change my piece so that it no longer sounds like me. But it helps to have someone who can look at a bunch of details and see a picture emerge, a narrative that just might be worth telling.


A few minutes after receiving that text from my friend, I responded with my editor’s opinion: The gal from Bumble was definitely cute and smart – information deduced from a LinkedIn page I tracked down and a few articles – and she seemed to care about some of the same issues that my friend did.


“Wow,” came the return text. “You should be in the CIA.”


Julia Rappaport is the managing editor of a Northeast food and cooking magazine. You can follow her at @Julia_Rappaport.



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