Playing with Matches

by Hannah Orenstein

  “Ladies, ideas?” Penelope asks.

  The matchmakers spring into action, with fingers flying over keyboards. One calls out a five-digit ID code, adding, “She’s a surgeon who went to Stanford.” Allison enters the code into her own computer, pulling up her photo and information, and shakes her head. “Too old for Craig.” One person points at another, snapping her fingers repeatedly, struggling to recall the name of “the therapist who went out with the startup guy to that karaoke bar in Brooklyn Heights the day it was raining.” The other person somehow knows exactly who she means and shakes her head no, explaining that the therapist is now seeing someone else. Another matchmaker drums her fingers on the table and suggests her own client, whom Allison kindly dismisses as not smart enough for Craig. There’s a silence, and Penelope admonishes the group.

  “Most of your clients went to Ivy League schools. Some of you went to Ivy League schools. Surely there’s someone out there for Craig. Think!”

  Another flurry of activity: the matchmakers recommend their sorority sisters, friends of friends, and former clients who might be single again. An idea dawns on me.

  “I might know someone.” Everyone looks over. “My roommate Caroline’s older sister Grace might work. She went to Brown and works at a non-profit. She’s twenty-six, if that’s not too young for Craig. But she’s new to the city and brilliant and looking to meet people.”

  “Is she pretty?” Allison asks. “Craig is a snob about looks, even though he claims to be a sapiosexual—only attracted to people’s intelligence.” She looks as if she is trying extremely hard to avoid rolling her eyes.

  “Very pretty.” I pull up her Instagram on my laptop, scroll past some unflattering, artsy close-ups, and click on a lovely photo of Grace taken at Caroline’s graduation party a couple of months ago. I turn the laptop around for Allison to see. Grace looks a lot like her sister except she has rounder features and would never pierce her nose like Caroline did.

  “Hmmm. She might work. Does she date outside her race?”

  “I’m not sure. I mean, why not?”

  “A lot of people don’t. The two demographics that receive the fewest messages on dating sites and apps are black women and Asian men. That puts Craig at a disadvantage.”

  It seems as if people cease to be people here. Instead, they fit into boxes: age, race, neighborhood, height, pretty or not pretty, what school they went to, how much money they earn. I tell Allison that race doesn’t matter to Grace.

  “And she wouldn’t be put off by a guy like Craig?” Allison asks, concerned. “He’s an odd duck. Stubborn, ultra-analytical, a little shy.”

  “She hasn’t gone out with anyone in a long time. I think she could be into him.”

  I haven’t exactly answered Allison’s question, but it’s probably better not to. I’ll beg Grace to do it later. If she needs to be bribed with a bottle of wine, so be it. I need Allison and the rest of the matchmakers to like me. Allison asks me to text her Grace’s contact info, and I can’t help but smile.

  The rest of the meeting passes in a rush. I’m impressed by how much the matchmakers know about the people in the database:

  Alex can’t date Katie because he’s allergic to cats and she has two.

  Julian won’t find Polly attractive because he’s exclusively into Latina and Asian women.

  Marla shouldn’t be set up with Norm because he looks too much like her awful ex-husband.

  Harris isn’t successful enough for Tom, unless he got that promotion he was hinting at the last time Zoe spoke to him.

  Vanessa once might have gone out with Charlie, but she’s gotten much pickier since she made Forbes 30 Under 30.

  Nick is blacklisted after the very rude, sexually explicit voicemail he left for Penelope.

  The matchmakers conjure up strings of names in a row, recall a dozen ID numbers off the top of their heads, and remember tiny, precise details about hundreds of strangers’ lives. And when the possible database options seem exhausted, they keep going. They shout out names of people they met at dinner parties and music festivals and indie movie screenings. People who once dated their best friend’s summer fling’s coworker but are now single. People who followed them on Twitter last week who might be attractive in real life. My own social circle suddenly seems so small.

  When it’s my turn to share, I recap my lunch with Mindy, coffee with Mark, and exploration of the database and Tinder.

  “You should check out Sam in the database,” Penelope suggests.

  Georgie snaps her head up so fast, I’m surprised her thin neck doesn’t break. “Sam Nolan?”

  “Sam Weinstein.”

  “Penelopeeeee,” Georgie whines. Her lower lip sticks out and her spine sags into a curve. “You know I want him for myself.”

  I look back and forth from Georgie to Penelope to Georgie again. From the head of the table, Penelope sits up straight and purses her lips.

  “He’s off-limits. He’s in our database,” she says firmly.

  “Come on,” Georgie protests. “You know I’m obsessed with him.”

  “Georgie, I said no. You know the rules.”

  Georgie glares furiously at Penelope across the table. “Fine.”

  Head down, I type Sam’s name into the database, trying to tap the keyboard as lightly as possible to avoid disturbing the meeting further. There’s a note in his profile that he’s been dating someone named Kerry for the past month.

  “We’re professionals here,” Penelope continues, “and we don’t mix business with pleasure.”

  Georgie is still glowering, arms crossed.

  “Well, there’s one guy who seems pretty perfect for Mindy,” I say, desperate to cut through the tension in the room. “Adam. Thirty-three. He’s an editor at Esquire and takes photos with his cute, little old lady grandma, and apparently has this sexy southerner thing going for him. But I haven’t told him yet that I’m a matchmaker.”

  “Do it now!” Georgie says. Her fury seems to evaporate. She turns her megawatt smile on me for the first time and leans over the table to reach me. “Here, give me your phone.”

  I open Tinder on my phone and take a second to read over Adam’s last message to me. My stomach tightens into a knot, but I hand my phone to Georgie anyway. She glances at it, types out a message without hesitating, and slides my phone back to me for my approval.

  Adam, you’re a delight. I’m so glad we connected. But I’m afraid I have a bit of a secret: I’m not single. And I’m not cheating on my boyfriend, either. I’m a matchmaker for a dating service, and I’ve been hoping that you would be a perfect match for one of my clients. She’s beautiful and vivacious and witty and I know she’s dying to meet a gentleman such as yourself. Could we meet for drinks sometime? I’d love to tell you more . . . xoxo Sasha.

  It sounds nothing like anything I would ever say—ever—but Georgie probably knows what she’s doing. I hesitate over the intimate “xoxo Sasha,” but hit send anyway. My heart is racing. What if the message is so crazy, he doesn’t respond? I guess there are more fish in the sea, but there’s something about this particular catch. I don’t know what it is—just a gut feeling that tells me he’s the right guy for Mindy. Maybe it’s my newfound matchmaker intuition coming in strong.

  When the meeting ends ten minutes later, the matchmakers disperse: some spread out into the study to chill, others dash out the door for meetings. I scoot my chair back and gather my laptop and purse. I know I shouldn’t be nervous about joining them in the other room, but butterflies form anyway. They’re all just so polished and opinionated—I wouldn’t even know where to begin to connect with them. Even though Elizabeth has been friendly to me, it doesn’t mean they’ll all be like that.

  That’s when my phone lights up with a Tinder message from Adam.

  Sorry, but I was interested in you, not your “client.” I don’t think this is going to work out.

  — Chapter 6 —

  Here’s what I wish I had known before Jonathan took hi
s job: when you date a finance guy, you have to be okay with getting neglected. I am now, most of the time. They don’t mean to eff you over like that—it’s just that the job comes first and everything else comes, well, dead last. But I’ve been waiting outside Ruchi, the Indian restaurant near his office, for nearly a half hour, and my neck is starting to ache from craning down at my phone to pass the time. I’m bored and annoyed. Jonathan was supposed to pop by for a bite to eat with me, then run back to finish up his work. My phone rings. Jonathan only calls when it’s bad news.

  “Hey,” he whispers, “I’m so sorry I’m running late. I know I told you I’d try to be better about this.”

  I exhale just loudly enough to let him know I’m not thrilled. “No, it’s fine.”

  “I feel really bad for having you trek down here, but Mitch sprung this fire drill on me at the last minute and I can’t get out right now.”

  I got used to this a long time ago. A fire drill is when a boss throws an urgent task at a junior banker and sees how quickly he can get it done. It’s not Jonathan’s fault, but this is the second time he’s canceled last minute this month. He wasn’t like this when we first met. His job changed everything.

  “I mean, I’m already at the restaurant. You can’t leave the office just for a half hour? You’ll need to eat something.”

  I’m pleading. I hate pleading. It makes me sound needy. There’s a long pause on the other end of the line.

  “I’m so sorry, babe. Tonight’s not gonna work.” At least his voice sounds tender as he shuts me down. “I have to go.”

  The phone clicks off. It’s been a shitty day: Mark disappointed me, Adam disappointed me, and now, completing the trifecta, Jonathan is disappointing me, too. Men are the worst.

  Ruchi is overpriced, and so even though I could kill for some chicken tikka masala right now, I cross the street and pick up a slice of dollar pizza instead. The pizza guy hands it to me on a paper plate and I sit at one of the low gray tables under harsh fluorescent lights. A late-2000s pop song blares from the speakers. I open Tinder, go through twenty-five profiles, swipe right on five, and match with three. I copy and paste identical messages to each of them, taking care to personalize them with names so each man feels special—a tip gleaned from our staff meeting this afternoon.

  Hi Jason! I know this might sound unusual, but I’m actually not on Tinder for myself. I work as a matchmaker for a dating service called Bliss, and I think you could be an amazing match for one of my clients. Would you be interested in learning more? I’d love to hear from you.

  Although I’m sending a ton of messages, my inbox is frustratingly empty. I double-check just to be sure; no new messages from Adam.

  I’m curious if I can find him outside Tinder, which turns out to be surprisingly easy. Researching potential matches for Bliss uses the same skill set I honed as a freshman reporter at NYU Local. I Google “Adam + Esquire + editor” and up pops his page on the website—Adam Rubin. (Rubin! So, he is Jewish.) He writes about music: album reviews, industry news, interviews with rock bands and rappers I’ve actually listened to. I get sucked into reading his work. Then I type his name into Instagram and scroll till I find his profile. The most recent photo is of a dimly lit drink on the rocks, posted twenty minutes ago. Guys never know how to properly edit photos. Hello, saturation and brightness filters.

  “The usual watering hole never fails,” the caption reads. I tap open the location tag: Tanner Smith’s, a bar on West Fifty-Fifth Street.

  I flip back through Adam’s photos. I’ll admit it: he’s a hunk. I have a crush—a work-sanctioned, totally productive crush that I want to spin into a match for my client. So sue me. Georgie goes out to pursue matches in person all the time. Maybe I can, too.

  Before I lose my nerve, I scarf down the rest of the pizza, dump the plate into the trash, and speed-walk to the subway, darting between workers filing out of office buildings. You can do this, you can do this, you can do this, I tell myself with every step. This is your job now, this is your job now, this is your job. I hop on the train uptown. I realize that Adam might have already left the bar, or maybe that was an old photo he just posted now. It’s not like real life is a Law & Order: SVU episode, where the bad guy is always at the same neighborhood pub that the cops just so happen to visit. New York is sprawling, and Adam could be anywhere by now. I don’t want to sit alone in that pizza shop all night. I want to be bold, like a real matchmaker would be. I don’t have a plan for what happens when I find Adam; I just know that I have to win him over for Mindy. When I get off the subway and reach the bar, I take a deep breath and push open the door.

  It’s darker inside than I expected, and it takes my eyes a second to adjust. The bar is all gleaming wood and old-fashioned black-and-white tile and swirling wallpaper. It looks like the kind of place where cocktails are 80 percent elderflower liqueur and cost a minimum of fifteen dollars. Pretension aside, it looks comfortable, like everyone here just happened to drop by their hippest friend’s place for a drink after work.

  I take a few hesitant steps forward, scanning the row of people at the bar. There’s a guy with a dumb handlebar mustache reading from a Kindle, two women in off-the-shoulder tops clinking wineglasses, and a pack of four dudes who probably work in marketing who are all wearing identical blue button-downs with light sweat stains under their arms. Every stool is taken, and from what I can tell, Adam isn’t anywhere. He could be at the back of the bar, I guess, but I’m too self-conscious to poke around. That’s when I lose my nerve. I shouldn’t be here. Adam doesn’t want to be bothered. He doesn’t want to be tracked—fine, stalked—via social media. What am I doing?

  I leave the bar. I slump against a wall and feel embarrassed. I really thought I could do this job—be bold and flirty and fabulous. Instead, I’m chasing down a dude I’ve exchanged three messages with on Tinder on the slim chance he’s actually down to date Mindy. But I’m not brave enough to pursue Adam. I want to go home. I’m only a half block from the N train. I trudge toward it, but stop at the top of the stairs leading down to the station.

  I didn’t come all the way to the bar just to turn around and go home. I’m already here, and even if I feel silly and self-conscious, I’d feel even worse going home on the subway without making a real effort to find Adam. I turn around and walk the half block back to the bar. I pull myself up to my fullest height, take a deep breath, and head back inside. I have to do this.

  I walk along the bar. Same Kindle guy, wine women, marketing bros. No Adam. The bartender, a guy with a slight build in a tight vest, catches my eye.

  “Can I get you something?” he asks, picking up a cocktail menu and offering it to me.

  I smile and shake my head. “Maybe later.”

  I move toward the back of the room, where tables line a rosy brick wall. And there he is: Adam, alone at a two-top, nursing what looks like whiskey and hunched over a black Moleskine notebook. At least, I think it’s Adam. He has dark curls, an olive tan, and two days’ worth of stubble. I pull my phone out of my purse, open up his profile on Tinder, and swipe quickly through his photos to confirm his identity. It’s definitely him.

  I have never approached a guy in my entire life. Like, not even once. I rack my brain for an opening line, but I’m coming up with nothing. I know if Caroline were here, she’d tell me I don’t need an opening line—because I’m hot (according to her), guys will talk to me no matter what. I don’t really believe her, but right now I need some advice. I take five quick steps in Adam’s direction.

  “Adam, hi!” I wave.

  He looks up from his notebook, startled. His dark hair sticks up in the front, like he recently ran his hands through his hair. “Hi!” Then a short pause. “Er, do I know you?”

  “Sort of. Well, no. I guess you don’t. I’m Sasha. From Tinder.” I can feel my face turning bright red.

  He tilts his head and gives me a blank look.

  “The matchmaker.”

  His expression changes as it sinks in.
He runs a hand over his stubble. “Jesus Christ.”

  “I swear I’m not stalking you.”

  “I don’t know if I believe you.” A hint of southern drawl laces through his vowels. “How’d you know I was here?”

  Time to think fast. I can’t let him slip away. “How about I tell you over a drink?”

  “Don’t you have a boyfriend?” he says, a hint of a challenge in his voice. His eyes gleam. He’s cuter in person, should that even be possible.

  “I mean, yes. But that’s not the point. I just want to get to know you. I really think you’d hit it off with my client.”

  “You know, the more you use the word ‘client,’ the more this sounds like an escort service gone wrong.”

  “I promise it’s not. Let me buy you a drink?” I will him to not reject me in public.

  Adam scratches his chin and looks around, then gives an exasperated sigh. He closes his notebook and stands up from his chair. He’s massive—six foot three, a wingspan like a basketball player’s, shoulders that slope endlessly under his worn-in charcoal gray T-shirt, and an aura that extends a good two or three inches beyond that. He moves to the open chair and pulls it out from the table.

  “All right, take a seat.”

  I’m shocked, half by my bravery and half by his chivalry. I sit; he waves over a waiter.

  “Could we get a cocktail menu?” he asks.

  “Oh, I don’t need anything special,” I say. I don’t want to waste his time. “Just a vodka tonic, please. Thank you.”

  “I’ll do another bourbon, neat,” he tells the waiter. He’s close to finishing his drink.

  Adam takes a sip from his glass. “So, Sasha—Sasha, is it?—you should probably start by explaining how you found me here.”

  “It wasn’t rocket science. You’re easy to find on Google, and from there, your Instagram told me where you were.”

  “That’s creepy.” He cocks an eyebrow.

  “Yeah, maybe, but I wouldn’t have tracked you down if I didn’t think you’d be the perfect match for my client.”