The endeavor seemed, at first, like a joke on Silicon Valley: An online start-up was crowdfunding a shipment of single women from New York to San Francisco, so the nerd-kings of tech could finally get dates. “Cross-Country Love: Help Fly NYC Women to SF” was the brainchild of Lauren Kay, the 24-year-old CEO and founder of dating start-up the Dating Ring. She launched the service in New York City, then expanded to San Francisco when the company gained entry to prestigious (and notoriously male-dominated) tech incubator Y Combinator. But the New York network had two women for every man, and the San Francisco network three men for every two women. So she filmed a video for the crowdfunding site Crowdtilt in which female New Yorkers and male San Franciscans plead to be brought together. “Would you please pay for me to go meet boys?” a pretty blonde asks the camera.
The backlash was swift. Valleywag called participants “comfort women,” prompting a commenter to correct: “Slight difference. The comfort women of WWII were slaves. These women are just skanks who want to marry a millionaire.”
One-hundred twenty-nine donors and $10,222 later, plans were in motion. Fifteen lucky women were selected to make the trip; each would go on two “curated” dates selected and planned by the Dating Ring. There would be a cocktail party where the New York women would meet their Crowdtilt benefactors, and a rager open to all Dating Ring members of both genders. At the last minute, Lauren agreed to add a 16th woman: me.
Here's what happened next.
DAY 1: MY JETLAGGED DATE WITH A PICKUP ARTIST
I arrive at Newark airport to find a circle of young women seated cross-legged by our gate, while a Nightline producer films them. “Is this a bachelorette party?” a stranger asks. Over the course of the weekend, I will resort to describing us as “a travel club,” “a sorority,” “a reality TV show,” and “a prostitution ring.” Dating Ring co-founder Emma Tessler hands me an itinerary and travel kit with everything a single-girl traveler could need: lip balm, condoms, and makeup remover.
We’re a telegenic group, attractive and diverse, with ages ranging from early 20s to late 30s. Melissa, a drop-dead gorgeous Notre Dame–educated firefighter who provides counseling for survivors of 9/11, seems to have been designed in a laboratory for perfect women. Galadriel, a radiant speech therapist with curly blonde hair, was named for the elf queen in Lord of the Rings.
On the plane, my seatmate flirts with the dashing Qatari journalist sitting between us. I eavesdrop, then ostentatiously put my earbuds in, but in fact I am still eavesdropping. When we land, they exchange business cards. This girl is not messing around.
At the hotel we are four to a room, splitting double beds, college-spring-break-style. My roommates are Susannah, a 24-year-old who works in fashion; Renée, a 32-year-old who works in fine art and teaches yoga therapy on the side; and Lisa, a tattooed 26-year-old writer who supports herself by ghostwriting online dating profiles. My new friends and I primp and give each other wardrobe advice, then summon cars to take us to our first dates. Our transport for the weekend is provided by Lyft, which is sort of the hipster version of Uber: The cars wear hot-pink mustaches, rides begin with a fist bump, and passengers are encouraged to chat with drivers.
All 16 dates are occurring simultaneously at the same bar, which is a blessing, since gossiping about dates is more fun than actually going on them. The Dating Ring is basically a tech-enhanced yenta; they combine one-on-one matchmaker meetings with algorithms, feedback, and a sizable database of singles to supercharge blind dates. My first date is Greg, a tall, dark, and handsome 37-year-old Yahoo employee who used to support himself as a professional pickup artist, though he prefers the term "social coach." Moved by a character in The Game known as "Juggler," a young Greg sought Juggler out and apprenticed with him, eventually working full-time for Juggler’s company, Charisma Arts. “Honestly, most of the guys I coached just needed to practice eye contact and basic stuff like smiling,” he says. Did it work? “Well, a bunch of them have girlfriends now. And I don’t.”
We drink and talk on our own, then mingle with other couples. Lisa is wearing a microphone, which we use to shout gossip into the Nightline producer’s ear. “We’re doing shots! This will be great B-roll!” I scream into Lisa’s boob. Greg leaves early; he has to get up at 8 a.m. to ride the Yahoo bus. He does not attempt hanky-panky. I return to the hotel and crawl into bed with Renée. This is not the stranger I imagined sharing intimacy with in The Land of Single Men, but when I wake up jetlagged before sunrise, I realize our butts are touching.
DAY 2: SORORITY SISTERS
Already, my New York friends are ridiculing me. “Do you love your pledge class sisters SO SO MUCH?” one snarks by text. “You’ve gone too far,” another says after reviewing a photo in which I am performing a sorority squat with such gusto that it doubles as a high-intensity workout for my glutes.
I don’t care about their cynicism. I am in California, land of the earnest. My social euphoria is that of a middle-schooler at summer camp. My sister wives and I do everything together. We eat together, sleep together, dress together, group-text one another incessantly, and visit tourist traps. If we were in New York and ran into a shrieking bachelorette party of women like us, we’d hate them. But at BFF camp, we are free.
Tonight’s date is another man named Greg. This one is tall, blond, handsome, and a programmer. Greg 2.0 agreed to participate in our bicoastal dating experiment because he loves San Francisco so much, he wants to evangelize. He’s looking for a serious girlfriend, and while he talks about these deeply personal matters, I exercise my peripheral vision in search of Greg 1.0. He's with firefighter Melissa.
Greg 2.0 drops me off at a bar with the girls. I watch one make out with her date while another flirts with strangers. Alexa, a 24-year-old pop singer who has a song called "Twitter (Spaces in Between My Heart)," summons a bunch of jocks she met that morning at the gym. (Alexa’s first date offered to take her and the female friend of her choice to Napa Valley. She declined.) When the guys offer to take us to a hip-hop club, Alexa bends over and announces, “I’m gonna twerk my little thang!” A few drinks later at the club, my thang gets into a few undignified positions, too.
Outside the hotel at 2 a.m., yet another New Yorker is passionately making out with her date. “It was just the craziest chemistry I’ve ever experienced in my life,” she will later say. They're seeing each other again in two weeks.
DAY 3: MEN IN THE WILD
On Saturday, we have two parties: A two-hour cocktail party for our Crowdtilt benefactors and the men we’ve dated so far, followed by a larger party for all Dating Ring members in the area. “Time to go be geishas!” Susannah sings brightly as we take Lyft to a bar called Skylark.
This is the night things get dark.
Some of the men at this party are more eccentric than those we received as matches. A programmer who donated “several hundred dollars” to the Crowdtilt likens the donation to “giving $2 to a homeless person.” In an affectless voice, he analyzes the relative Asian-ness of each of my facial features, then explains his frustration with online dating: “I prefer to use reality as my platform. There’s zero latency, no lag. Do you know what lag is? When you do something online, you don’t get a response right away. Meeting women in reality — boom! — fully responsive.” As he says this, he begins to touch me. I flee. Soon thereafter, Emma Tessler points out a different man she believes to be “obsessed with” me. She offers to run interference, and I do not see him again.
I meet an angel investor who admits he gave to the Crowdtilt to butter up CEO Lauren Kay so she’d accept his money. “With these Y Combinator companies, sometimes so many people want to invest that they end up turning down money,” he explained. He’d given money to the Dating Ring to secure the chance to give even more money to the Dating Ring. He wouldn’t tell me how much he invested, but did mention a desire to buy an airplane.
As the party grows, we become inundated with men. We are experiencing gender imbalance in the wild, and it is chaos. Every time I turn, there are men lined up waiting to deliver carefully rehearsed greetings or to initiate repartee. At this point, I am so exhausted from constant socializing — even Lyft rides feel like first dates — that I feel a breakdown coming on.
DAY 4: CRYING GIRLS
Today’s daytime activity is a picnic in the park. I find Lisa and tell her it’s time to do as the San Franciscans have done since before the dawn of personal computing: get high. She goes to Dolores Park to seek weed from strangers, while I return to the hotel and initiate a texting phone tree. Twenty minutes later, as a white guy with dreadlocks is dumping vegan brownies onto the bed, there is a knock on the door and the Nightline film crew is standing there with a camera and a giant light. “Just a minute!” I shout through a crack in the door. When the dealer exits, I wonder if Nightline thinks I boned him.
We use Lisa’s bounty first, rolling joints and smoking them one by one in our hotel room. In the spirit of sisterly sharing, I have given pot brownies to everyone who's asked for them. Around midnight, I am informed that half of those girls are curled up in the fetal position, crying. I report to the triage room, where I stroke a woman's hair while trying to hide how excited I am to eat my brownie, now that I know it is strong enough to make grown women cry. This is also a good way to evaluate men, if you’re into sexy bad boys.
DAY 5: ‘FULLY WIRED’
We report to CEO Lauren Kay’s apartment for brunch. She lives in a residential tower billed as “a design-driven lifestyle pioneer,” “efficient, engaged, and fully wired.” The elevator speaks to us.
As I stand on a terrace dotted with flat-screen TVs, watching a beautiful couple making out in a swimming pool below, I have a revelation about why the Cross-Country Love Crowdtilt met its fund-raising goal: For every tech guy struggling to find love in San Francisco, there is one struggling harder to find novel ways to spend his money. The funds necessary to fly 16 girls cross-country so they can sleep four to a room is nothing compared to the sums that disappear when hotly anticipated start-ups go bust. Here, money is weightless. Social connections, on the other hand, are commodified: Fist bumps are mandated, “friends” are declared, and Dating Ring members provide feedback after every date to help laser-focus the next. The company's algorithm may one day know your desires better, even, than you do. That technology has allowed us to so thoroughly interrogate, define, and perhaps redefine our feelings is simultaneously exhilarating and exhausting — much like spending a weekend with strangers in a new time zone.
As the airplane takes off that afternoon, I eat some brownie, then curl up in a ball and stare out the window in silent bliss. After five days of nonstop meeting and greeting, the tacit permission to ignore everyone is a sweet relief. A 32-inch seat in economy class has never felt so private.
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