She looks up from a story about vibrators. “Maybe Victoria and Graham’s housewarming party.”
And so the post-NYU migration to Brooklyn begins. Victoria and Graham aren’t a couple in the traditional way (he was the president of Delta Lambda Phi, the gay frat), but you never see one without the other.
“What about dinner at Hotel Tortuga first?” I ask.
“You know I wouldn’t show up to that party without pregaming.”
“I want you to meet Adam. Tonight at Tortuga.”
She raises her eyebrows. “Wow. Sure, invite him along.”
With Caroline’s encouragement, I carefully type out an invitation designed to sound as casual as possible.
“Caroline and I are getting dinner tonight at our fave Mexican place. Join us before the concert?”
Before I can lose my nerve, I hit send. I’m too antsy to return to my writing while I wait for his response. Instead, I wait and watch for the three gray dots to pop up that indicate Adam is texting me back. They disappear and I panic. Is it asking too much to introduce Adam to Caroline? Ten seconds later, the dots reappear, and Adam’s text slows my pounding heart.
“Sure thing. Just text me the address.”
That’s how, seven hours later, Caroline and I wind up in our usual booth in the back of Tortuga. I sit on the far side, my back to the wall, so I can watch the door for Adam’s arrival. Caroline sits across from me. Her cheeks are pink from the sun. The ponytailed waiter knows to bring us a pitcher of frozen margaritas before we even ask for one. I focus on ladling the slushy drinks into three yellow plastic cups to distract from my nerves.
“Just relax,” Caroline whispers, watching me frantically lift the cups to eye level to check if I poured them evenly. “Your stress is stressing me out.”
“Sorry,” I say.
I set the drinks on the table and fidget with my half-healed hangnail instead.
“It’s just me, some bomb-ass Mexican food, and a hot guy who’s already obsessed with you,” she reassures me. “Chill.”
“I just hope you guys get along—” I begin, but cut myself off abruptly as I see Adam enter the tiny restaurant.
He makes his way to the back, ducks down to give me a chaste peck on the cheek, then straightens up and extends his hand to shake Caroline’s.
“I’ve heard so much about you,” he says warmly.
“Yeah, same. I mean, obviously,” Caroline replies.
Adam slides into the booth next to me.
“Thanks for coming,” I say.
He shrugs. “Of course.”
To date a guy who shows up when he says he will—it’s refreshing.
He takes in the walls papered with crayon drawings, the orange speckled tables, the yellow hanging lanterns. The tables are close together, packed with people who feel comfortable enough here to slip their shoes off and sit cross-legged and barefoot.
“It’s like home,” I explain.
There’s a short lull in the conversation as Adam glances down at his menu. Caroline and I could recite the whole thing by memory, so we stare at him, then at each other, attempting to figure out what to say. I want this to go well so badly. It feels like so much is at stake.
“You know, Caroline probably deserves a finder’s fee or something,” I blurt out.
“For what? For me?” Adam looks up, amused.
“She sent you that first message on Tinder,” I clarify.
“You’re a matchmaker who doesn’t even make her own matches?” he asks.
“Oh, come on. I make enough. Caroline was just showing me how to use Tinder, and there you were,” I explain.
“So I was talking to . . . her?” he puzzles out.
That night feels like it took place years ago. So much has happened.
“Well, then me. And then, actually, my coworker Georgie. But then me, in person.”
“After you hunted me down like an animal,” he says, grinning.
If only he knew the full extent of my stalking. Caroline and I already looked up his parents’ house on Zillow (yellow ranch, three bedrooms, two bathrooms) and found his college ex-girlfriend’s Pinterest board themed around decorating her infant son’s nursery.
“Don’t complain. I got you here, to the best pitcher of margaritas in Manhattan.”
“Cheers to that,” Adam says, lifting his cup.
We all clink drinks. Later, the waiter comes by to take our order, and Adam asks Caroline about her pilot. He says he tried to write one years ago—I had no idea. Their conversation turns to the screenwriting software Final Draft, writers’ groups, querying agents. I sit back to watch them find common ground. I can tell when Caroline is bullshitting a guy; it’s imperceptible to whichever dude she’s nodding and mhming along to, but I know her too well to be fooled. She looks sincerely interested in what Adam has to say. Her smiles actually reach her eyes. I get a little high on the vision of my favorite person and this new guy in my life beginning to kinda-sorta-maybe get along.
The waiter drops off our plates, each piled precariously with entrées surrounded by pools of guacamole and sour cream.
When Adam looks down at his plate, the waiter mouths a comment behind his hand: “New guy?”
I blush. I can’t respond without drawing Adam’s attention.
But the waiter isn’t done. “He’s cute.”
For four years now, Tortuga has been my place with Caroline. It didn’t matter if we were living together in the dorms or our apartment. Tortuga has always felt like our home away from home. I don’t know what they put in the margaritas, but this place has good vibes only. Jonathan would eat here sometimes with us—and later, Mary-Kate and Toby, too—but there was no question who got custody of this place in the breakup. It’s eerie to see Adam eating his beef-topped nachos where Jonathan once ate his carnitas quesadillas.
It could work, though. I can see Adam fitting into my life the way Jonathan once did. He’s performing the role of Potential Boyfriend with charm and ease; Caroline’s dates—like Wesley, the melted-cheese artist at the rooftop party—typically fall flat, leaving me to wonder what she sees in any of them. They embarrass her. But Adam is carrying the conversation, asking Caroline all the right questions, and behaving like a gentleman. I’m proud to have him here. As he eats and talks next to me, he slings his arm around my shoulders and stretches his legs out under the table, like he’s getting comfortable.
After dinner, we linger outside the restaurant. Adam has his arm wrapped around my waist; Caroline’s a foot away.
“So, there’s this band playing at Rockwood Music Hall tonight,” he says. “Think The Strokes, but new. Seriously good guitar. I covered them a while ago and the publicist says I can swing by with a few people.”
“Great,” I say.
“Caroline, coming? I’m sure I could get a third ticket, no problem.”
She hesitates and runs a hand through her hair. “I’m going to head over to Victoria and Graham’s housewarming. I’ll catch you later?”
“Yeah, I’ll see you,” I say.
“See you soon,” Adam says, breaking away from me to give her a hug.
I hope he means it.
Caroline heads east toward the subway as Adam and I round the corner to walk to the Lower East Side. When I thank him for meeting her, he shrugs.
“Yeah, of course. She’s cool. And I know how important she is to you.”
“Like a sister.”
“I got that.”
There’s a beat of silence. I’m embarrassed by how happy I am that he accepted my invitation to meet Caroline. I want to read into it and assume he must really like me—but I also don’t want to get my hopes up and then be wrong. I can’t be crushed by two men in one summer.
The publicist, a woman dressed in black wielding a clipboard, is standing behind the bouncer in the doorway of the venue. She calls Adam’s name as he approaches.
“You made it!” she squeals. Then, to the bouncer, she explains, “It’s fine, they’re with
me.”
I’m not much of a music junkie, but even I have to admit it doesn’t suck to be pulled into a hot concert spot by a hot guy on a hot New York summer night. There’s already a crowd at the base of the stage where a four-piece band sets up against a red wall—three guys in Adam’s mold of white T-shirt and black leather jacket and a girl in a long gauzy dress, clutching a microphone. I’m tall, but not quite tall enough to enjoy the view from the back of the crowd. I rise up on my toes to get a better view.
“Let’s watch from the balcony,” Adam says, pointing to a staircase leading up to a second floor.
I follow him through the crowd, up the stairs, and to a two-top overlooking the stage. It’s perfect. A cocktail waitress drops off two beers.
“From Sara,” she says.
“The publicist,” Adam tells me.
The beer is refreshingly cold—and free.
“You know, I never thought this would be my life,” he says, leaning in close so I can hear him over the din. “I still feel like a nobody from Atlanta who snuck into this dream life.”
“I get it,” I say. “Trust me, I get it.”
Five years ago, I could barely imagine living in New York. And I certainly couldn’t imagine the sweet jolt of tracking down a promising match for a Bliss client, or the comfortable silence that comes on a quiet night in with Caroline, or the satisfaction of leaning my head against Adam’s shoulder as the band below crackles to life and begins to play.
— Chapter 19 —
Three weeks later, my first column publishes on Esquire.com. I didn’t think anything could top the thrill of seeing my name stamped across the top of the column—that is, until I saw my name printed across a check. At $200 a pop, the column proved more lucrative than setting up a single date. It felt more rewarding, too. It even garnered enough online traffic that Diego asked for a second one.
For column number two, I gave Eddie and Diane pseudonyms and told their story, which was becoming more adorable by the day. I wouldn’t exactly describe their first date as smooth—he choked on his mozzarella stick when she called him “brainy” and had to go stand outside the bar, hacking and wheezing, until he coughed up the fried cheese and regained his composure. But by some miracle, they both wanted to see each other again, traversing borough lines for a dinner on Staten Island. And again, when they took a ferry and a subway and a bus to meet for a Mets game in Queens.
“Unbelievable. She . . . wants me?” he asked breathily over the phone one night.
Against all odds, she did.
He sounded like a sixteen-year-old girl gushing about a date. They were a long way off from officially calling themselves boyfriend and girlfriend, he told me, but they liked each other enough to go on multiple dates, which is more than I could say for most of my other matches. I had assumed Eddie would be my toughest client, but he turned out to be the easiest. The happiest. He went into his date with Diane without expectations or a checklist, so he was able to appreciate her for exactly who she was. Maybe that’s the key to it all—rolling with what life gives you, rather than seeking something that isn’t there.
I’m still figuring out what my third column will be about. There’s Mindy, of course, who had seen Gordon for a second and third date, but still wanted to see other men on the side. There’s Chrissy, the banker who loudly asked to be set up with men interested in bondage and domination (the cardigan-wearing group of moms planning their private-school kids’ charity auction at the next café table turned to gape). There’s Brett, the gay political consultant with the used-car-salesman smile and impressive speaking gig at the last DNC, who wants a revolving door of buff guys to help him blow off steam after a long day of campaigning. And then there’s Margot, the socialite who only dates musicians, who bragged about her long-ago fling with Kanye West and dropped vague references to her friendship with Beyoncé. I set her up with Anna Wintour’s favorite DJ, a hunky former model, but she rejected him when he revealed his favorite book is merely The Da Vinci Code. “I date intellectuals,” she seethed.
And there’s Wretched Gretchen, as I think of her these days, who wants an accomplished tennis player who spent significant time traveling abroad and happens to be blessed with Jon Hamm’s fine bone structure and a whole pile of money; I gave her a private wealth manager who taught tennis lessons at a Swiss boarding school after college and lived in Buenos Aires for a year. She trilled his faults to me over the phone the morning after her date with a perverse note of pleasure in her voice: yes, he played tennis, but he hadn’t played regularly since the ’90s; yes, he had lived abroad and spoke three languages, but didn’t seem passionate about traveling to her favorite countries.
She sent me an updated, annotated version of her checklist explaining how Mr. Hedge Fund failed to meet her specifications. And another annotated version when Date #2 failed (she’s appalled by his table manners and posture), and another annotated version when Date #3 failed (she said the dark circles under his eyes were “distracting”), and another annotated version when Date #4 failed (she disliked his “aura of negativity”). Lately, I’ve been fielding daily phone calls from Wretched Gretchen, in addition to highly detailed emails that require thousand-word responses to adequately answer her list of questions. For fun, Caroline calculated my hourly wage when working with Gretchen, and found that I would have made eight times more money flipping burgers at McDonald’s. Delightful.
Not all my clients are so memorable. Most of them are what Adam called “Sex and the City women.” We all know the type: mid- to late thirties, brilliant, tons of friends, high-powered career, schedule packed with boozy brunches and Hamptons weekends and SoulCycle classes. Almost all are Jewish and had intended to get married and have kids five years ago. I scooped up a few particularly dashing specimens on JDate and rotated them through my Sex and the City women until I found a match that worked. I set these women up with Mitchell, the pediatrician who actually volunteered with the homeless on the weekends; Ari, the graphic designer with impeccable bone structure; Noah, the CFO with a disgustingly cute terrier, who’d be married by now if he were just two inches taller.
Adam would have fit the bill, but I didn’t send him out with anyone anymore. I added a note to his profile in the Bliss database explaining that he was “seeing someone” and should not be contacted by any of the matchmakers.
So. Adam. Adam, Adam, Adam. Paris may be the city of love, but I swear there’s nothing more magical than getting to know someone new under the glittering lights of New York City. The West Village was meant for long, winding walks hand in hand, lingering in front of lingerie stores, kissing along the waterfront. His rooftop in Chelsea was made for savoring wine under the stars. Central Park was crafted for lolling about in bathing suits in the grass on sun-drenched Saturdays, and the whole borough of Manhattan was designed expressly for popping into bagel shops to order everything-and-a-schmear piping hot out of the oven.
We spend a lot of time together blushing, insisting how lucky we are to have found each other. When we went uptown to Serendipity for frozen hot chocolate and had that particular discussion all over again, the girl at the next table actually rolled her eyes and coughed loudly in our direction. We switched to a more mundane conversation topic while playing footsie under the table. Infatuation like this happens once in a lifetime.
Here is how New York tests your love, or at least your lust: if you are willing to brave the smell of hot, rotting garbage wafting through Union Square on a ninety-degree summer day in order to cross town to have sex in a cramped apartment without central air-conditioning, you know it’s real. You’ve made it. Congratulations, you may pass Go, collect $200, and head straight to Kleinfeld’s to pick out your big white wedding dress. Mazel.
And that’s how the rest of my summer goes—a frenzy of matchmaking by day, a whirlwind romance by night. By September, I no longer sleep in my own bed. Caroline doesn’t mind; she’s been seeing her Bumble match Owen at nearly the same pace. I stay at Adam’s place almost ev
ery night. He offers me one of his white button-downs to sleep in, under the condition that I wear it without anything underneath, but I opt to sleep naked instead. Stiff white shirts, just like the Financial District, Midtown skyscrapers, and spreadsheets, still remind me of Jonathan in a painful way.
Jonathan tried to get back in touch with me. In the weeks after the wedding, we were tagged in a dozen photos together on Facebook, which made my stomach turn. Next, he tried calling me. I didn’t pick up, so he texted repeatedly asking to get coffee and talk things over. I ignored those, too, and got a rush from how good it felt to blow him off. Was this how he felt every time he stayed late at the office when we had plans?
The more experience I rack up as a matchmaker, the worse I feel about men as a whole. I talk to dozens a week, and so many of them are just plain awful. The finance types refer to dating multiple women at once in terms of “diversifying their portfolios.” But across every profession, they’re all bad. They shoot off texts riddled with spelling errors, demand to be set up with the hottest physical specimens available no matter what kind of garbage they look like, and assume that no matter how often I mention my client, I’m really just out to score ass on Tinder for myself.
By contrast, Adam is a dream. He’s easygoing, makes me laugh, and brims with stories of his adventurous twenties. He shows up to hang out with me when he says he will. He pays attention. Even if I have to trudge through the depressing singles scene all day at work, I get to leave it behind when I’m with him.
As my thoughts ping between Adam and Jonathan—as they do daily—Diego emails with news. He has an opening on staff for an entry-level writer to cover dating and relationships. Do I want to apply? I send him my résumé immediately. I’m shocked when he replies a few hours later and asks me to do an edit test—industry-speak for a packet of ideas and writing samples.
I slave over the edit test for four days, barely emerging to flick through Tinder during meals, and send it off to Diego before I can second-guess myself out of applying for the job.
Playing with Matches Page 19