Thanks for Waiting

by Doree Shafrir

  But even though we were so different, as we grew older, we grew closer. By the time she got to law school, and I was at the Observer, we Gchatted almost every day. One day, over Gchat, she asked me if I thought it was “mandatory” to ask the groom’s sisters to be in your bridal party when you got married, and I responded that I thought it was a sign of respect. She had started dating her boyfriend, Steve, earlier that year, but he lived in Washington, D.C., while she was still in law school in Miami.

  Me: Are you and Steve getting married?

  Karen: Today? No.

  Me: Someday?

  Karen: We shall see.

  Me: !! Wowzers.

  Karen: You think I’d be doing this for nothing? All this travel and shit. Moving to D.C., etc.

  Me: Damn girl! You’re moving to D.C.?

  Karen: After graduation? Yeah, I mean if we are still together. You can’t have a long-distance relationship forever. I’m not sure why this comes as a surprise.

  Me: It’s not really a “surprise”; it’s more that you’re 23!!

  Karen: Well, we aren’t getting married tomorrow! And I turn 24 next week thank you very much!

  Me: Ahahaha.

  Karen: I don’t think 26 is too young to get engaged, married at 27.

  Would you be shocked to learn that Karen did indeed get engaged at twenty-six and married at twenty-seven? I, for one, was not. (When we had this conversation, I was almost thirty-one, with no engagement or wedding in sight.) How foreign it felt to have your life figured out at such a young age, to be completely confident in your choices, to choose a profession where you would actually make money, to be perfectly content with the guy you’d started dating at twenty-three!

  I had long told myself that we were so different, I wouldn’t want her life. Being a lawyer sounded horribly boring; my life was so much more exciting. I had never seen myself as someone who cared much about hitting “adult” milestones at a certain point—it felt so conventional, didn’t it? I was not conventional, I assured myself; if anything, I had always been a bit of a contrarian, taking pride in my ability to navigate the world on my own terms. I wasn’t going to be someone who bookmarked engagement rings before they’d even met a partner or obsessed about climbing up the corporate ladder. I was proud of my position as someone always slightly out of sync with the mainstream—that was why, I thought, as a journalist, I was so good at skewering it.

  But sometimes, I thought about my sister’s life, and I wondered: What would it be like to move through the world in the way that she did, to be that comfortable in your own skin, to have a completely unwavering confidence in yourself? I could barely fathom it.

  CHAPTER THREE

  In contrast to my sister’s direct line from high school to corporate law, my road to the Observer—and adulthood—had been circuitous. Starting in the fall of 2006, I’d been a writer for Gawker, a job I took after a summer of interning in the culture department at Slate, where I was a twenty-nine-year-old intern reporting to a twenty-five-year-old editorial assistant. I’d landed there after a patchwork of grad school and jobs: After a short stint in a PhD program in history (I dropped out after getting a master’s degree), I got hired at a local paper, Philadelphia Weekly, as the arts and entertainment editor. Toward the end of my second year there, I started getting restless. I loved Philly, but it also felt like my career options there were limited. One day, while reading a popular media blog, I saw a small item about a new subject-based journalism program at Columbia University that was admitting students who already had some work experience, and they were going to be offering generous financial aid. Since I was still paying off undergraduate loans, I wasn’t too stoked on the idea of taking on tens of thousands of dollars in additional loans, so this sounded perfect. That fall, I headed back to New York, where I’d lived for a year after graduating from college.

  I wasn’t sure what to expect from a new graduate program, especially since just a few years earlier, I had left graduate school. But now I was twenty-eight, I thought. Older and wiser. Still, at the end of the program, I didn’t have a job. I did, however, have an offer to be an intern at Slate, for $15 an hour. So now I was twenty-nine, and an intern—a paid intern, but still an intern. Maybe I shouldn’t have left Philly, I thought. I could still be working as the arts and entertainment editor at Philadelphia Weekly, drinking too much at the 700 Club, going to sweaty shows at the Khyber. It wasn’t a bad life at all.

  Was I just someone who was never satisfied with whatever she was doing? That was a grim thought. I didn’t want to be that person, but it was true that I did tire of things quickly. I’d never stayed at a job for more than two years; since breaking up with Jake, my college boyfriend, when I was twenty-four, I hadn’t dated anyone for longer than a year and a half. Or maybe this was just a part of growing up—trying things out and knowing enough about yourself to cut bait when it was clear it wasn’t going well. But if that was true, how long was this stage of trying things on for size going to last?

  In the meantime, the summer—and my internship at Slate—was nearing its end. One day I was sitting in an editorial meeting when the TV critic had an idea. “Chuck Klosterman has a new book coming out,” he said. “Has anyone ever noticed that his author photos are ridiculous? Like each one is just more pretentious than the next. We should do an analysis of Chuck Klosterman’s author photos.” Everyone laughed.

  “Great idea,” said the editor in chief.

  “That’s so funny,” another editor agreed.

  “Doree, you should write it,” the TV critic said.

  “Um, okay, sure,” I said. I was flattered that he had thought of me for the piece, and it seemed like something that I could run with and be funny, something that was a little outside of Slate’s generally self-serious articles and essays. I’d never actually read any of Chuck Klosterman’s books, but that, apparently, did not matter.

  The piece I wrote was pretty mean-spirited, and it didn’t dawn on me until much later that I’d been used—no one who was actually on staff wanted to put their name on an article trashing Chuck Klosterman, and I was too naïve to realize it. But the piece caught the eye of a couple of editors at Gawker, and they hired me as an associate editor, along with Emily Gould, a former publishing assistant with a pointedly funny blog, who was a few years younger than me. My boss for most of my time at Gawker was Choire Sicha, who had been the second-ever editor of the site and had been lured back to run it by Gawker founder and overlord Nick Denton.

  Denton sometimes seemed like a cartoonish supervillain. He was a forty-year-old Brit, very tall, with an enormous head but kind of pinched face, and closely cropped hair. After making millions selling an early internet business, he had moved to New York and launched the gadget blog Gizmodo in 2002 and followed it a few months later with Gawker. Over the course of four years, he had built it into a small network of other blogs. He was one of those bosses who would get completely fixated on one part of his company, and then suddenly move on to something else. But when you were in his sights, he was unrelenting. He deeply enjoyed tweaking the media establishment, and he had certain obsessions—the short-lived Condé Nast business magazine Portfolio being one of them, the micro-celebrity Julia Allison being another—that he insisted we cover constantly.

  Denton seemed to relish keeping his employees scared. We rarely heard from him directly; he communicated all his opinions about our work through Chris, my first boss at Gawker, and later Choire. When Denton was in the office—a storefront* on Crosby Street in SoHo, a block or so away from the luxury condominium building where he lived—a chill went through the room. It felt like he could sneak up behind you at any time and rip whatever you were doing to shreds. His attitude about almost everything was sneering, judgmental, caustic, and that was the posture we were expected to take with whatever we wrote about.

  At first, I actually found this perspec
tive refreshing. We were speaking truth to power! We were exposing hypocrisy! We were the scrappy underdogs who picked our targets carefully and exposed them for what they really were! And it was fun to write in a snide, snarky tone, to act like we knew better than everyone else reading. I especially loved when I managed to get into places or parties I wasn’t supposed to, like a book party for the author Christopher Hitchens that was held in the ridiculously over-the-top Upper East Side apartment of a Republican megadonor who had a photo album devoted to her dog’s trips to France on display in the library. I loved these little glimpses into a completely unfamiliar, but fascinating, world.

  But Gawker also played to my worst instincts, as though Harriet the Spy had been given permission to just run with everything mean she wrote in her notebook. Being mean, day in and day out, started to wear on me—I didn’t like that my default take on everything had to be so worthy of scorn. And when I stopped to think about it, just what was I doing at Gawker? Was my purpose in life cranking out multiple mocking blog posts a day?

  After a few months, I was tiring of the constant churn, and I was also tiring of the default stance that I had to take with each post—the assumption was that everyone and everything we wrote about was deserving of mockery. There was no room for empathy, no room for nuance. The point of view that I’d initially found alluring and fun was becoming altogether depressing. Was everyone an incompetent hypocrite? Certainly many wealthy people in positions of power are, in fact, incompetent hypocrites, but I started to feel like sometimes I was punching down. Should I care about an article that some underpaid assistant editor wrote in a lifestyle magazine just to mock it? Did it matter that the Park Slope Parents Listserv was up in arms about the gender of a hat? We writers were egged on by the site’s commenters, a crew of people who seemed to spend just as much time as we did on the internet, if not more, but who also were quick to turn on us if they felt we hadn’t upheld the covenant of the site. It was a vicious cycle, where we felt we were performing for an audience of mostly anonymous commenters, but who we also treated with some degree of scorn. After all, at least we were getting paid to be snarky on the internet; they were doing it for free.

  Denton encouraged us to turn people into characters, particularly anyone who had even the smallest desire for fame, and write about them repeatedly and relentlessly. When I stopped to think about it, I was sometimes a little worried about how easy I found it to be mean. But meanness was rewarded—by traffic, by commenters, by Choire and Denton.

  So when Peter Kaplan emailed me a couple of months later, it felt not just like my dream editor had noticed me, but I was getting a lifeline, a way out of the digital sweatshop. And now, just two years later, it had been taken away.

  * * *

  —

  AFTER THE LAYOFF, I tried to put on a brave face. I wrote posts on my Tumblr about all the things I was doing with my “funemployment”; I made a big show of getting together with other laid-off and freelance friends during the day, just because I could. But really, I was deeply hurt. I’d never been laid off before, and it made me second-guess everything. Like: Were there things I could have done differently at work? Did I act too entitled? Did I not make friends with the right people? If I’d made more of an effort with Tom, would he have kept me on? Had I thought of myself as above office politics, or had I just woefully misread the politics of the office? Or maybe it wasn’t about office politics at all; maybe I just wasn’t a good enough writer or reporter to stay on. Or maybe I was too expensive, since I was one of the better-paid reporters in the newsroom. Should I have asked for less money when I got hired? These questions replayed in my mind on a loop, as I sat at my desk in my apartment sending out freelance pitches. I was having trouble believing that I would ever work again.

  The day I’d gotten laid off, my friends Alison and Melissa, who were also writers, had informed me that they were taking me out for drinks that night at a bar we liked in Tribeca to drown my sorrows in alcohol.

  “They suck,” Alison said matter-of-factly, referring to the Observer.

  “Seriously,” Melissa said.

  “What if I never get another job?” I asked.

  “You’ll get another job,” Alison said. “I know you will.” I wasn’t sure I believed her, but it didn’t matter. In that moment, I just needed a friend who really got me to tell me everything was going to be okay.

  Alison, especially, was that friend. We’d met when I worked for Philadelphia Weekly and had been roommates briefly. People often said we looked like sisters, or at least, cousins, although I think people saw two white women with shoulder-length brown hair and the kinds of similar mannerisms and inside jokes that come with years of friendship and thought we looked more alike than we actually did.

  Like me, my close friends in New York mostly worked in media. Alison and Melissa were both bloggers, and then there was Tess, a newspaper editor; Lara, an art director at a Condé Nast magazine; Emily, whom I’d worked with at Gawker; Rebecca, an editor at Hearst; and Gabrielle, who also worked at Condé Nast. We were all in our late twenties or early thirties, not at the top of a masthead but not at the bottom, either, and none of us had kids yet. We were one another’s support systems, a place to vent when our bosses were being especially infuriating, when we got edits that made no sense, when we felt like we worked twice as hard as the men in our department for less recognition. (Most of us worked for men.) But we also celebrated one another’s promotions and new jobs and cover stories. I was grateful to have these women in my life.

  Skip Notes

  * The office was also next door to the unmarked door leading to a basement counterfeit handbags operation, so there were always groups of confused tourists peering through our windows wondering if this was where they could get their fake Louis Vuitton Carryalls.

  CHAPTER FOUR

  In my twenties, I had a tendency to fall into relationships without thinking too hard. I didn’t “date,” exactly; if I met someone, and we hung out, and made out or slept together, we usually ended up calling each other boyfriend and girlfriend. But I’d been a late bloomer in the relationships department. At college, surrounded by people who were always coupling off, and a Greek system that seemed to exist mostly so that people could hook up, I saw myself as a sad, lonely, unattractive outcast when it came to guys. I’d always had plenty of female friends, but I was so scared of rejection that I was reluctant to ever tell guys how I felt about them. Instead, I developed deep, unrequited crushes and never said anything, hoping that one day a lightbulb would go off in the brain of the object of my affection and they would realize, in perfect eighties teen movie fashion, that the right one had been there all along (the right one was, of course, me).

  I knew these were just Hollywood fantasies, but because I’d never been in an actual relationship, they were my only frame of reference. In the movies, the awkward girl or the tomboy or the outcast always ended up, miraculously, with the boy of her dreams. Surely someone would be able to pierce the armor I’d put up for myself and sweep me off my feet? It didn’t seem that far-fetched, but then again, I also had no idea what being in a relationship really entailed. It was like being so focused on the wedding that you forget that you have to actually be married afterward—I was so obsessed with the idea of “getting a boyfriend” that I had no concept of what happened next.

  I coped by becoming friends with my crushes. I could be the cool girl friend (but not the cool girlfriend), the confidante. If I couldn’t date them, then at least I could be in close proximity to them. But this could also be incredibly painful, and sometimes, it seemed like I was just setting myself up for more heartache. In college, instead of trying to get distance from my freshman crush, I agreed to live in a big off-campus house with him and six other people my sophomore year. When he promptly started dating one of our other roommates—my friend—I played it cool, as though I didn’t care at all, like I was totally over him. But act
ually, it sucked.

  I threw myself into my classes, double majoring in history and English and doing a minor in art history, and got involved in the school paper, where in the second semester of my sophomore year I became editor of the weekly arts and entertainment magazine. And I loved my motley crew of friends—at a school dominated by a Greek system, we were proudly, almost pretentiously outside of it. There was Daniel, an impossibly tall, impossibly handsome gay guy who’d been raised Orthodox Jewish; we bonded over our mutual love of Pavement and modern architecture, but also loved driving around Philly in his Saab (christened “Miss Saab”) blasting the Spice Girls. Jill was my first friend at school—we met in our economics class our freshman year and were both from the Boston area—and I was drawn to her Uma-Thurman-in-Pulp-Fiction haircut and obsession with Italy. I’d met Meera during our freshman orientation, playing Human Bingo in the quad; she complimented my turquoise nail polish and I complimented her patent-leather dog collar necklace. Senior year, Jill, Meera, and I lived with another friend, Liz, a chemistry major from Connecticut with whom I’d gone to dozens of concerts in Philly and New York. The four of us threw parties featuring our friends’ bands, cooked dinner together, and watched The X-Files. Down the block, Daniel hosted hours-long Shabbat dinners at his apartment that ended in impromptu dance parties. I had found my people, and I had resigned myself to the idea that a romantic relationship just might not be in the cards for me—not now, maybe not ever. Sex remained a foreign concept, something that everyone else seemed to instinctively understand how to make happen for themselves and that I just didn’t.