He shakes his head. “There you go again with that word—‘client.’ You’re gonna have to explain that to me. This whole ‘matchmaking’ deal.” He actually makes air quotes. “I don’t want to buy anything, if that’s what you’re after.”
“No, that’s not what I want to do at all,” I counter quickly. “I work with a company called Bliss. Our clients tend to be too busy or too high profile to go out and find dates themselves, so they turn to us to help find suitable matches. Clients pay for personalized matches, but recruits like yourself don’t pay a dime.”
The more often I churn out Penelope’s words from training, the more they feel like my own. Every conversation I have on Bliss’s behalf makes me feel a sliver more like a bona fide matchmaker and less like a kid faking her way through a grown-up, glamorous person’s life. The waiter returns with our drinks.
Adam leans back in his chair, stretching his arms up and interlocking his fingers behind his head. I can see a hint of his stomach and the trail of hair leading into his jeans. I snap my eyes back up to his before he can notice.
“You know, what the hell?” He laughs and leans his elbows forward onto the table. “It’s not like I’m meeting my dream woman on Tinder.”
“God, it’s the worst.”
“Oh, yeah? How long have you been on it?”
I bite my lip and consider lying. “Three days?”
“Come on.” He groans. “That’s nothing.”
I can feel my cheeks flush again, and I know it’s not just the first sip of my drink. There’s a tiny spark between us that needs to be extinguished.
“So, um, can I ask you a few questions about yourself? To see if you’re compatible with my . . .” What’s another word for client? “With the woman I’m working with?”
He laughs, spreading his elbows wide and resting his chin on his knuckles. “Shoot.”
“Are you looking for a serious relationship, or something more casual?”
It sounds so clinical when I ask it like that. But I have to say it—I mean, I met him on Tinder, so for all I know, he could just be looking for a casual hookup.
He rolls the edge of his glass on the table, avoiding eye contact. “It’s probably time for something serious. That’s one of the reasons I left the South. I grew up and went to school in Georgia, but everybody down there paired off years ago, and then it was just me. Third wheel extraordinaire.” He laughs, but in the way Caroline laughs about being single; it’s not funny anymore.
“You want marriage and kids?”
“I mean, I’m not opposed to having a little fun along the way.” He grins. “But yeah, a family would be nice eventually.”
I’m relieved to be on the right track.
“Cool. Can you tell me about the type of women you typically date?”
“Type?” His accent draws the word into two syllables. Ty-ype?
“Like, in terms of looks, personality, interests, age.” I feel like a creep probing him for this information—like it’s too personal for me to ask. But I have to stick it out. It’s my job now.
“Oh, I mean, I don’t know . . . smart, funny, pretty?”
I nod encouragingly, but that doesn’t actually give me anything to work with. It’s too vague.
“When you say ‘pretty,’ what specifically do you mean?” I try.
“Well, I swiped right on you, didn’t I? I’ve mostly dated brunettes with, uh, a few curves on them. I’ve dated petite girls in the past, but it’s not on purpose. It just worked out that way.” He gives me a sheepish smile. “Sorry, I know you’re tall.”
“No, no, I’m not offended at all.” Actually, I’m irritated on principle. It works out best for everyone to pair off by height. But whatever, Mindy’s Olsen-sized—five foot two.
I draw out the rest of the information slowly: he likes women who aren’t afraid to call him on his bullshit and put him in his place. He wants someone with a little fire in her personality, someone with a delicious laugh. The most romantic thing he’s ever done was back in college, when he crammed into a bus seat for ten hours overnight with a bouquet of sunflowers and a tub of chicken soup to surprise his long-distance girlfriend when she had the flu. (Mindy will die—that is too freaking cute.)
The conversation dances in lazy circles away from the subject at hand—the novel he’s working on, how he always felt out of place in the South, the creepy Pigeon Man with graying skin in Washington Square Park we’re both scared of—but every once in a while, he stumbles onto another note for me.
“I don’t always date Jewish girls, but I guess it could be nice. It would make my mom happy. But not a JAP. I’m done with those princessy types, you know?”
I nod and jot it down. No Jewish-American Princesses—he means girls who carry Rebecca Minkoff bags to brunch and spend Christmas eating Chinese food with their grandparents in Boca Raton. Mindy isn’t a princess.
“Oh, and you know what drives me crazy? I once went out with a girl who made the most disgusting noises when she chewed. This woman you have in mind for me, she doesn’t do that, does she?”
“She’s a perfect lady.”
He mimics the chewing noises, and they’re awful, like a trucker slurping down food in the front seat of his eighteen-wheeler.
“Ew, stop it!” I reach out and swat his arm.
His eyes flash to mine, and I suddenly pull back, embarrassed. I shouldn’t have touched him like that. Besides, he’s for Mindy. They’re perfect for each other—how could they not be? I adore her, he’s charming, and they both seem to like me. That’s how the transitive property works, right?
“I should probably get going,” I tell him.
“Of course.” He signals for the check. “Will I hear from you again? I mean, for Bliss.”
I’m surprised he remembered the company’s name. “I have to run the match by my boss, but I have a good feeling about this. From what you’ve told me, I think you two will really hit it off.”
The waiter comes by with the check and we both spring to give him our credit cards.
“Hey! I told you this one’s on me,” I say.
He shoos away my hand. “Come on. I can’t let a beautiful woman buy my drinks.”
I redden. “Seriously. It’s on my company.” I love that I can say that now.
“A southern gentleman would never let a woman pay her own way.”
It’s silly, because I know he can probably afford the tab with no problem. It’s just important that I keep this professional—and let Bliss cover the bill.
“Split it down the middle,” I tell the waiter after a tense beat.
Adam goes quiet. I think we both feel flustered. The steady lull of other people’s conversations fills the space between us.
He recovers from the awkwardness first, saying, “If your client is half as lovely as you are, I can’t wait to meet her.”
I break into a grin, but force myself to cut that shit out. “Oh, well . . . she’s really fantastic, I promise.”
We each sign the check and I follow him out of the bar. He holds the door open for me; he’s exceedingly well-mannered. I don’t know how to part appropriately. A hug seems too intimate, but a handshake would be too businesslike. He pauses, too, like he can’t figure it out, either. He steps forward, like he’s going for a hug, at the exact moment I give an awkward wave.
“Er, right, bye,” he says.
I turn and hurry down the street to the subway station. I take the stairs to the train two at a time. I happily swipe my yellow MetroCard through the machine—after all, I’m about to hit payday for Mindy and Adam’s date. The subway is humid and grimy, but there’s a four-piece jazz quartet on the platform playing “What a Wonderful World.” The trumpet player, an older man in a fedora, winks at me when he catches me listening. I let myself sway to the beat until the train pulls into the station.
— Chapter 7 —
Jonathan caved. He always does—eventually. Two and a half hours after Caroline and I popped open a bottle o
f victory pinot grigio to celebrate my successful stalking mission, Jonathan called. He was getting a cab home from work, he said, and did I want him to pick me up? It’s out of the way, but he wouldn’t mind. Caroline and I were in the middle of a deep dive through Adam’s Facebook photos dating back to 2007—it’s all we can see thanks to his privacy settings. But the minute Jonathan’s name popped up on my phone screen, I knew what he’d ask and that I’d say yes. I always do.
“I’m so sorry I couldn’t do dinner earlier,” he apologizes when I climb into the cab. I slide across the seat to give him a sloppy kiss. He pulls back a little too fast and I curl into the nook of his arm. “Oof, how’s the wine tonight?”
“Delicious, thank you very much.”
There’s a white plastic takeout bag in his lap that smells spicy and familiar.
“I brought you chicken tikka masala from Ruchi,” he says sheepishly. “I wound up ordering in.”
“For me?” I squeal. I cringe a little when I hear how drunk I sound.
“Just for you.”
The cab, the meal; it might sound special, but it’s not. Goldman Sachs lets even junior employees expense up to twenty-five dollars for dinner after 8 p.m. and any amount for a cab after 9 p.m. I’m not above enjoying his job’s perks. I almost feel entitled to them after all I put up with.
As the cab turns and zooms downtown, I tell Jonathan all about tracking down Adam and winning him over for Mindy. I amp up the parts where I really sold Adam on Bliss; I gloss over the stomach-churning chemistry between us and the way he called me “beautiful” in that languid, stretched-out accent.
“I wasn’t actually sure I was cut out for this matchmaking stuff, but I’m actually not . . . bad?”
“Of course you’re not bad.” He squeezes my thigh. “No guy in his right mind would say no to you.”
“But it’s not actually me, though. I’m just the . . .”
“Bait?” He turns to look at me, grinning, and his hand moves farther up my thigh.
I swat his hand away. “The middleman. The wingwoman.”
He smirks. “Call it whatever you want.”
My tongue still feels thick with cheap wine when Jonathan’s alarm blares the next morning.
“You can sleep in,” he says quietly as he shrugs into his suit jacket. “Just lock up on your way out.”
“Mmmrph.”
Eventually, the sunlight glinting off the glass office tower across the street makes it impossible to sleep. I get up, shower, savoring the ocean-scented bath products that leave me smelling like him, and tackle some work for Bliss. Penelope made it clear in training that I don’t have full autonomy—none of the matchmakers do. Before I can set up a date, I have to email Penelope a match proposal detailing why Mindy and Adam are compatible, including photos of each of them. (“Looks and status,” she had repeated. “Looks. And. Status.”)
Mindy Kaplan, 35, is a TV exec who hopes to settle down and start a family. She is bright, fun-loving, and hard-working. She seeks someone masculine and assertive, yet kind and considerate. Ideally, he’d be Jewish.
Adam Rubin, 33, is a writer who moved to New York from the South specifically because his friends had all settled down and he felt left out. He’s ready for a more serious relationship. He has impeccable manners, the broad shoulders and height that Mindy likes, and he’s Jewish.
They’re equally attractive and equally successful, and appear to be each other’s preferred physical types. (Her celebrity crush is Ryan Reynolds; he likes petite, curvy brunettes.)
I have a hunch they’ll click. He’s charming and suave; she wants someone assertive and masculine. She’s outgoing and he’s a little quieter. I think they’ll balance each other out nicely. I like the idea of them together!
I attach photos of Mindy and Adam and send the email off to Penelope. A jumble of energy and good nerves snakes through the pit of my stomach.
I pull on a pair of light-wash boyfriend jeans and a white eyelet top from the pile of things I keep at Jonathan’s place, and I’m in the middle of doing my makeup when Penelope emails back.
“Excellent work! You have wonderful instincts. Please schedule this date.”
I have wonderful instincts. I shoot off a text to Mindy.
“Good morning! Just wanted to let you know I had drinks last night with a handsome, charming gentleman for you. A. is an editor at a magazine and criminally attractive. When can you meet him?”
Penelope had taught me to never use people’s first names—initials only—before a first date. Bliss instituted that rule after a client Googled her match before a date, then stood him up because she didn’t find him attractive on Facebook. Plus, initials create mystery, and that only adds to the client experience, or so I’m told. Mindy writes back instantly.
“Sasha!!! I was just thinking about you. I was just reading my horoscope and apparently Venus’s return bodes well for my love life this month. CANNOT WAIT to meet A. Is Sunday night too soon? Any time after 6?”
“Let me check with him and get back to you.”
“Thanks, doll. BTW, do you know what sign he is? I’m a Cancer. Not that we have to be astrologically compatible. But it’s fun to think about.”
I look up Adam on Facebook. His birthday is in March. I Google his sign, then text Mindy that he’s a Pisces. This is so stupid.
“Phew!! I just really cannot date another Aquarius after what happened with my ex. Sorry, forgot to mention that earlier. K, can’t wait to see if he’s free Sunday.”
I start to text Adam, but another text pops up from Mindy.
“Sunday doesn’t sound like I’m too available, does it?”
I reassure her that it does not and finish my text to Adam. He takes longer to respond—enough time for me to finish my makeup and make coffee—but texts back to confirm Sunday evening. I wonder if he’s lounging around his apartment, or if he’s waking up in someone else’s, or if he’s already writing a story for Esquire.com. I stretch out on Jonathan’s beautiful brown leather couch intending to plan the date. But I wind up reading Adam’s stories on the site. There’s an interview with a producer on a highly anticipated upcoming indie album, a story mourning the loss of the famed New York City concert venue Webster Hall, and an essay defending country music from barbs thrown by what he calls “northern snobs” (guilty). I catch myself reading them each in his deep drawl before I close the site and force myself to get back to work.
Penelope had emailed me a Google Doc with creative date ideas, but they all seem too eclectic for Mindy’s tastes. One date involved pretending to be engaged and shopping for a diamond ring at Harry Winston together; another involved a scavenger hunt through Washington Square Park; a third sent the couple to an improv class on their first date. Those all sound absolutely mortifying to me. Instead, I call The Garret, a speakeasy in the West Village on top of a burger joint, to make a reservation for drinks. Simple.
I’m afraid of disappointing Penelope with my boring date. The job description for Bliss I had spotted on Craigslist had called drinks dates “dull.” I know she’s banned them because they turn dates into interviews, but I don’t think Mindy wants to play Truth or Dare while minigolfing, or whatever Penelope thinks would be exciting. She’s a pretty conventional girl. So to appease Penelope, when I enter the date into Bliss’s system online, I instruct both Mindy and Adam to bring a special object with which to identify each other. I decide that Adam should carry a single red rose and Mindy should bring a box of chocolates. Their icebreaker is to prepare a story about their first date ever, even if that was a sixth-grade outing to an ice cream shop. I hit send and the system emails both of them with the date information. Thirty seconds later, Mindy texts me a string of salsa-dancing lady emojis and “Thank you! Xoxoxoxo!!!”
It feels really, really good to have finally set up my first date. I set a calendar event in my phone for 7 p.m. on Sunday, when Mindy and Adam are supposed to meet. But I don’t feel self-congratulatory for long, because a few minutes later
, my phone lights up with another text from Mindy.
“Obviously very excited to meet A., but just curious—any leads on date #2?”
“I’m on the hunt,” I type back.
So I fibbed. But I’ll find the second date soon enough.
At 11 a.m., I head uptown to meet Mary-Kate at La Petite Coquette, the lingerie boutique in Greenwich Village, to shop for her wedding-night lingerie. She took a day off from work to iron out last-minute wedding details. I’m on the L train, squished between a college-aged guy loudly blasting Britney Spears from his headphones and an elderly woman shooting him disapproving frowns, when I spot a potential match for Mindy.
He’s in his late thirties with wire-rimmed glasses and a thick head of dark brown hair. He holds the subway pole in one hand and a copy of this week’s New Yorker in the other. He appears to be reading the articles rather than skipping to the cartoons.
Would Mindy like this guy? Probably. He looks like he’s cut from the same future-quasi-DILF-y cloth as the photos she sent me of her past two exes: tallish, dark hair, nice teeth. He wears that same J.Crew blue gingham shirt that every man in America owns. I would never say something to him for myself if I were single. But I said something to Adam first, didn’t I? And that (miraculously) turned out to be a success.
I decide it’s least awkward for me to say something to Subway Man right before I get off, in case he turns me down. I have one more stop, just one more minute, to make my move.
I maneuver past Britney Guy, who’s starting to groove and mouth along to the lyrics. No wimping out now. I stand firmly in front of Subway Man and try to use my steadiest voice.
“Hi.”
He looks up blankly from his magazine. New Yorkers do not speak to one another on the subway. Ever.
“Hi?”
“I know this is ridiculous, but I work as a matchmaker for a dating service, and I, well, I can’t help but wonder if you and my client would get along. I have a hunch that you would.”
I sound insane. Even Britney Guy stops dancing.
“Oh, jeez. Um, wow,” Subway Man says, grinning and running a hand through his hair.
Playing with Matches Page 7