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Courtesy of Kayli Stollak

Internet Fame

How To Make It As A Millennial

Like many creatives in their 20's, Kayli Stollak's path to success lay through her blog. Now, "Granny is My Wingman"—on her double-dating adventures with her septagenarian grandmother—has morphed into a book deal and a TV gig.

At 26, Kayli Stollak has mastered her generation’s formula for creative success: start a blog that vaguely encapsulates the plight of all college-educated, urban Millennials; add a clever twist; and watch the publicity—and offers from Hollywood—flood in.

Such was the heady order of events in 2011 when Stollak launched grannyismywingman.com, a website chronicling her misadventures in the online dating world alongside her 75-year-old grandmother, Gail—whom Stollak describes as “part Larry David, part Joan Rivers… a shit-talking, straight-shooting, adventure-seeking, gossipy yenta."  The blog quickly went viral—Oprah.com reached out to Stollak after the very first post—and the television and book offers materialized soon thereafter (the tome of Granny Is My Wingman hit shelves Tuesday). In the book, Kayli and Gail whine to each other about their respective bad dates, gush about the good ones, and exchange non-sugarcoated—and occasionally unsolicited—advice. “You are definitely a girl who kisses on the first date,” Granny tells Stollak of her first OKCupid date. “You just weren’t that into him.” And it is, of course, an inspirational tale. As the book’s promotional materials assure readers, “The two women cheer each other on and become even closer as they share their dating exploits, learning that the hunt for happiness is the same whether you’re 25 or 75.”

Such ideas—quirky, unexpected—are catnip to producers and publishers in search of the next Lena Dunham. It's not an uncommon career arc for members of the Millennial creative class these days: countless book deals and television pilots have been extracted from blogs, Tumblrs, and Twitter feeds. The Twitter account ‘Shit My Dad Says’ become a (failed) television series with William Shatner; NBC’s “F*ck I’m In My Twenties” was born out of a Tumblr by 24-year-old writer Emma Koenig (she also has a book deal); and the CBS show “20-Nothings” is based on Lauren Bachelis’ “Hollywood Assistants” Tumblr.

Some of these success stories were happy accidents. But Stollak specifically set out to replicate the success of antecedents like Koenig and Bachelis. “Originally I wanted Granny to date online because I was taking writing classes and wanted some material to blog about,” Stollak tells me. “I had originally wanted to make a TV show about it—that’s where my heart was set to go in the first place. I started the blog and got press early on, which was from word of mouth, and then I started getting offers for TV, but they were like, ‘Hey little girl, here’s $2500. Give us your idea.’”

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Ultimately, she sold the concept to CBS. “We got to the pilot stage and then it was cancelled,” Stollak says. But the early onslaught of publicity gave her faith in the blog’s conceit. “We had obviously chosen the right topic to write about. There wasn’t even much content at that point; it was just the buzzwords—online dating, 'multigenerational'—and the title was catchy enough.”

Stollak studied film at New York University’s Tisch School of the Arts. After graduating in 2009, she moved to London with her then-boyfriend and worked as a production assistant for a commercial director—a safe entry-level job that she quit as soon as her relationship fell apart. She returned to Manhattan and the steady gig as a cocktail waitress she had maintained throughout college, enrolled in a writing class, and soon set to work on the Granny Is My Wingman blog.

Stollak’s book is fortuitously timed, as the culture of dating has shifted dramatically across recent generations. Those who were raised in front of computer screens are increasingly going online to meet someone—and their parents and grandparents aren’t too far behind on the trend. Sites like eHarmony say senior citizens are one of the fastest growing demographics, while other online dating magnates are finding ways to appeal to the Granny Gails out there. To wit: Match.com has developed OurTime.com, a site for singles over 50. (Match.com is owned by The Daily Beast's parent company, IAC.)

In this the brave new online world of dating—and failing at dating—Granny is at a competitive advantage. Unlike Stollak, she isn’t forced to watch former boyfriends and lovers, whose lives are still plastered all over her various social media feeds, move forward with their dating lives. Trolling Facebook one day, Stollak stumbles upon pictures of the new woman in her ex-boyfriend’s life: “Why didn’t I think to defriend all of his friends and family? (The obvious answer: I’m a masochistic stalker.)”

As Maureen O’Connor observed recently in New York Magazine, Millennials don’t really break up in the traditional sense anymore, and exes can been neatly divided into various categories informed by social media. “There’s the ex who ‘likes’ everything you post. The ex who appears in automated birthday reminders. The ex who appears in your OkCupid matches. The ex whose musical taste you heed on Spotify. The ex whose new girlfriend sent a friend request. The ex you follow so you know how to win him back. The ex you follow so you know how to avoid her in person...The ex whose new partner blogs about their sex life. The ex who still has your naked pictures. The ex who untagged every picture from your relationship.” This is the grim reality of dating in the age of Facebook and Instagram.

But Stollak, for one, has profited from her dating misadventures. Her blog was never as much about dating as it was about writing comedy and developing real-life characters that would appeal to a large audience. “The great thing about the TV stuff is that I got representation and so now I’m signed with an agency and a manager," she says. "There’s one about nightlife that I’m developing right now. I haven’t sold anything, but I’m working on it. That’s where I want to be right now.”

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