"Are you having trouble dating?"
So begins the pitch of almost every dating self-help book ever written. This particular iteration of the question, however, came from the website of a Hollywood dating coach whom I'd found because she had posted on Craigslist seeking a "part-time writer" and "personal assistant." My boyfriend had dumped me that week—my first week after moving to Los Angeles—because we'd argued over Kanye West. So, yeah. I was having some trouble dating. I was also unemployed.
The website continued: "Millions of people today are struggling to find an amazing life partner who can really commit, but with my help, you can have the love of your dreams." Elsewhere on the site, there was a clip of her guest starring on Millionaire Matchmaker.
Needless to say, I was sold. I replied to her post, got an email back, and told her my availability for an interview: literally whenever and as soon as possible. The next day, I drove five minutes from my 7-Eleven-adjacent apartment to her house, which was nestled atop a lush green lawn and a jungle of pricey looking plants. This was a house that broken relationships and desperate single people built.
I'd spend the next three months researching the "dating advice" world, watching reruns of The Bachelor, writing blog posts about how long grown women should wait for sex, and using the failures of my own love life to give my boss fodder for her own blogs. Mainly, I ghostwrote her clients' dating profiles. I pretended to be everyone from a 34-year-old male Filipino software salesman to the 57-year-old female head of a production studio. My personal tragedies were another man's Match.com profile.
The way I saw it, love wasn't free for everyone. For some people, it could be bought—but they'd need help from me and Kelly* to write the check.
"So this blog is more about getting 'naked' emotionally—do you see what I'm saying?"
"Getting naked" was the terminology Kelly used in real life and in her e-book on dating, which she made available for free on her website. It was the way she described being emotionally honest with someone before "getting into bed" with them. That might seem dated, but it's essentially in line with the current media we consume on courtship. On The Bachelor, for instance, no one is supposed to sleep with the guy until a week before the series finale, and maybe not even then. (On season 11 of Bachelorette, Kaitlyn Bristowe slept with one of the contestants during a trip to Dublin on week six, which caused actual outrage, due in large to the fact that no one traditionally has sex on the show until the finale.) Dr. Laura says that sleeping with someone on the first date is a no-no. Even asshole pickup artists contend that the longer you put women off, the more they'll want to fuck you.
"What if you do get naked before getting emotionally naked?" I asked Kelly on my first week. "Like, hypothetically, let's say I slept with this guy on the second date. And say he told me he couldn't stop thinking about me—"
"Crissy," she sipped her coffee and stared at her laptop screen. "Sex first is what people do at your age. Well, I mean, I used to jump into bed with some guys. I literally had hundreds of first dates before I met David*."
I literally heard her say this hundreds of times. She'd been in the trenches of online dating in the 90s, when it was strange to use the Internet to meet anyone at all. In spite of this, she was convinced that it would be the way she'd find love after her first marriage fell apart—and it was. She met her second husband, David, on a dating site before she even had a cellphone. He'd been late to the restaurant they agreed to meet at, and in a scene that took place like a romantic comedy in my mind, she waited there for him by the restaurant's phone, cord and all. The experience she had with online dating that made her suspect in the 90s made her an incredible dating coach in 2014.
She was everything you'd want in a dating coach: blissfully happy in her second marriage, in her 50's, mentally stable, a certified counselor, and a talented photographer. Not only did she do one-on-one and couples counseling to help people get their shit together, but she also made sure your profile pictures didn't make you look horrific, pixelated, or insane.
Her coaching broke the surface, too. One man, age 42, came in and said he only dated 25-year-olds, all of whom he referred to as "girls." After six sessions, Kelly made him understand that he was being very immature. Slowly but surely, she convinced him to date in his own age bracket and to never again refer to women as "chicks" on his profile. She also got an insane, Heidi and Spencer-esque celebrity couple to agree to get individual professional help outside of couples counseling. Not every single one of her clients ended up in a relationship; in fact, few people were able to resolve their issues as fast as they wanted them fixed. But they came in one way and left another, more healthy way. And wasn't that, I reasoned with myself, the mark of a good relationship?
Getting into Bed
On my first day, Kelly had emailed me over fifteen pages of notes from interviews with her clients. She told me to turn each client's file into a one-page, first person profile. The information ranged from mundane to strange. "I failed a gardening class," read one note. "Classes at the sex addiction center were really helpful," said another.
I always started small, plucking out seemingly insignificant details and stretching them to seem like they meant something about a person's character. "I'm a nurturing person in every way… except for when it comes to plants. I took an indoor gardening class, which was great! Until I killed all of my plants, even the cactus." Smiley faces were essential, and so were exclamation points. One guy's notes said that he was okay at baking, so I wrote the ending of his profile accordingly: "I like to plan things out so that they are even better. I don't do anything half-baked…so to speak ;)"
I enjoyed pretending to be a divorced older man with commitment issues or a problematically emotional lingerie saleswoman, but I found other parts of the job frustrating and uncomfortable. By month two, I had grown to loathe helping Kelly write her "expert" blog posts for a popular dating website, in which I had to discuss what women should and shouldn't do in the dating game. She would provide the information and advice in the posts, and I would help her format them in a way that suited the advice website. We picked topics together that gave me pause, but that I knew to be the most popular angles: when to get into bed with a guy, why confidence is sexy, and how to be confident without being too confident. Wasn't it misogynistic to pander to women like this? Didn't she hate it too?
"Well, what's a major problem for women to deal with in dating?" Kelly asked me.
"Urinary tract infections," I said.
Kelly laughed but rolled her eyes. "There's nothing new under the sun," she retorted. "It's pretty simple. You put yourself out there, and you learn from every date and relationship, bad or good. And you date like an adult!"
However, when I browsed Tinder after work, the corny blogs and dating profiles I'd written earlier haunted me. What if people my age wrote their profiles as artificially as I did when I was pretending to be other people? While the profiles I wrote for Kelly's clients were intimately personal, the advice blogs I helped generate seemed almost monstrously faceless. The editors of the advice site often titled the pieces with click bait headlines that made them even worse, like "Why Guys Don't Actually Like Sexy Girls." Both Kelly and I hated the way they ended up, especially since they enforced sexist stereotypes that we both actively fought against in our daily lives. She would never tell a female client not to damper her confidence in a dating profile, and I would never shy away from coming off as self-assured on my own.
The most successful dating profiles that I wrote for Kelly's clients were the ones that verged on saying too much—like one that talked about a woman having taken care of her mother while she passed away, or another where a guy lamented his inability to enjoy masculine traditions like football. Both resulted in great dates with likeminded people, people that may have never swiped right if the profile had been pithy and impersonal.
Conversely, the most trafficked blogs I wrote, both for Kelly and on my then on my own, were the ones that painted with giant, broad, gender trope-heavy strokes: sex moves girls wish guys would stop doing, what guys hate that girls do on a date, and so on. Even the words I used in the titles—"guys" and "girls" instead of men and women, for example—felt stunted in their maturity. These hyperbolic, zeitgest-y titles were the most popular, in spite of the fact that the best dating profiles seemed to be hyper-specific. In this way, it seemed to me that personal honesty and the intimacy of realness could only exist in the private space of the profile, at the dater's own risk. Maybe this was why people needed coaching, I thought, waxing at my most Carrie Bradshaw conclusions: love really was a gory spectator sport or a tedious game of emotional chess.
The Walk of Shame
After three months of working for her, I had to tell Kelly I needed to leave my post as her assistant to take a different writing job. At that job, I'd published an article that went viral about "sex moves that girls wish guys would stop doing," and it went viral. While telling Kelly that I was quitting, I got a text from the guy I was seeing: "Hey…that article you just wrote—is that about me?" He was doubting "us." Days later, he dumped me with a "let's be friends" text.
"Oh, he's a dick!" Kelly said when I told her on the phone. I was still new in town, and she was as good a friend as any that I'd call for counseling in a situation like this. I'd slept with him on the first date, though, I said. By her standards, I'd fucked it up from the jump.
She sighed into her phone. "Sometimes," she said, giving me her best understanding tone, "you think it is, but love isn't real all the time. Sometimes, it's shitty. And over time you learn how to tell one from the other, and, uh—" She fumbled, sounding unsatisfied without a clever ending for her sentence. "Well, that's all it is."