Playing with Matches

by Hannah Orenstein

  “You have profiles on all of them?” I ask, incredulous.

  “All of them. And you will, too. That’s one of the reasons we hire matchmakers in their twenties. Young faces are the best bait on dating apps.”

  “And the other reason?”

  She laughs. “We try to hire girls who have actually had sex in the past decade. Our competitors are all women in their sixties.”

  “Oh.” I don’t know what to say to that. I have, in fact, had sex in the past decade. As in, like, yesterday. “I almost wonder, though . . . wouldn’t it be easier to meet people in person?”

  “I mean, I guess you could run around the city all day trying to meet men,” she concedes, tilting her head to the side like she’s unconvinced. “But that’s what our clients are doing, and clearly it’s not working for them, either. Dating sites and apps expedite the process. I was chatting with a dozen guys at once when you came in this morning.”

  “A dozen?!”

  “There’s Joey, the pro-tennis player with a fetish for older women,” Penelope begins, ticking him off on her finger. “That’s a definite no. We don’t want our ladies to feel objectified. Andrew, a lawyer. He seems promising. Maybe a little dull. Raphael might work out for somebody, but it seems like he only goes for real beauties. I’m still sussing out his type, but the size-zero models hanging off his arm in every photo aren’t a good sign. Hold on, I need to get to these,” she says, gesturing to her phone.

  She bites her lip, thinks for a second, then taps out rapid-fire messages on an app I don’t recognize. I watch her grin and purse her lips, as if she’s actually flirting in real life. Between her pinup look for a casual Thursday at the office and her quick, dry appraisal of these randos, I feel as if I’ve briefly left planet Earth. Is this my life now? The brownstone is quiet, and suddenly I have visions of lounging for hours a day on this insane velvet couch, typing out messages to older men I don’t know. I can’t believe this is a real job. I run my hand over the velvet and feel the fibers prickle the wrong way.

  She cackles loudly over a message. “Raphael claims to have slept with two Victoria’s Secret models. Not with that hairline he didn’t.” She tilts the screen toward me, and sure enough, the top of his head is covered with sparse wisps of dark hair. He’s twenty-seven.

  “Ouch.”

  “Don’t feel guilty, you can laugh,” Penelope says. “Most of them are assholes anyway.”

  “Don’t we talk to any women?”

  “Sure. Our clients are sixty/forty—more women than men—but straight women are harder to reach on online dating sites because all of our matchmakers are women. So the female matches we find tend to be through our own personal networks.”

  “Can’t you make a profile as a man and look for women that way?”

  “Technically, yes. But we don’t do fake profiles often. When you’re searching for matches, you’re searching as yourself. Your own name, your own face, your own bio. The more real it is, the more authentic it feels.”

  She goes back to typing. I hear the front door open and a voice coo “Hello,” then the clacking of heels on the hardwood floor. A few seconds later, two girls appear in the living room. Penelope looks up from her phone and stands up, sauntering over to hug each one. They all exchange greetings. I stand awkwardly, waiting to be introduced.

  “Ladies, this is Sasha, our new hire. This is Georgie and Elizabeth.”

  Georgie is a tiny pixie of a thing in a men’s pinstriped white button-down—rumpled, like she had picked it up off a guy’s floor that morning—that falls mid-thigh, revealing just the flirty hem of black silk and lace tap shorts underneath, and a messy topknot. She gives me a brief once-over and a half grin—“Nice to meet you”—then turns back to her conversation with Penelope.

  Elizabeth is Georgie’s polar opposite: she welcomes me with a firm handshake and a genuine smile. Her coral red sheath dress reminds me of something Anna Wintour would wear to terrify some underfed assistant. Unlike Georgie, she actually speaks to me.

  “You’re going to have so much fun here,” she says with the instant ease of a person who knows how to make small talk.

  I’m embarrassed to tell her I’ve never actually done this before, but I do anyway. I babble when I’m nervous. She doesn’t seem to care—not about the babbling, not about my lack of experience.

  “Look, I dropped out of law school for this. I’ve never looked back.”

  “Really?”

  “Less money, sure,” she concedes. “But way more fun.”

  She’s friendly right away, the way that drunk girls always are at parties, except I get the odd sense she’s actually like this all the time. Georgie gossips with Penelope in a low, throaty voice. Out of the corner of my eye, I see Georgie hold her hands eight or nine inches apart and hear a low giggle. Penelope’s eyebrows shoot up.

  The training continues for the rest of the afternoon—we cover how to use the database, what to write to people on dating apps, how to grill each potential match to determine compatibility with clients. Georgie perches on the arm of the couch behind Penelope, and Elizabeth sits with her ankles crossed on the paisley loveseat across the room. They chime in with tips as Penelope talks. By the time I leave, my notepad is full of scribbles and my mind is racing. Penelope tells me she’ll be in touch soon to arrange my first meeting with Mindy.

  “She’ll love you, darling,” Penelope calls to me as she leans out the doorframe over the stoop. “Nothing to worry about!”

  Nothing to worry about. I can do this. Right? As I leave the brownstone and walk uptown to my apartment, it occurs to me that this whole matchmaking venture could be a total failure. This job requires schmoozing, and I’m not exactly a people person. But I have to make this work, or else it’s back to Mom and my stepdad Steve’s house in Jersey.

  — Chapter 2 —

  “I just want a guy who knows what he wants,” Mindy says, wrapping up her breathless rant about the abysmal state of the thirty-something dating scene in Manhattan and stabbing a leaf of kale with her fork.

  She chews in silence—the first silence that’s fallen over the table since I complimented her blouse as an icebreaker fifteen minutes ago. I’m grateful that she’s been doing the heavy lifting in the conversation, since Penelope’s training session yesterday feels like a blur. Everything seemed so simple when she explained how to run these introductory client meetings, but actually putting those skills into practice now is terrifying. It’s like that required science course I had to take in college. I could follow along when the professor explained how to calculate the distance between two planets using some complicated formula, but when I had to do it myself on the exam, I blanked.

  I’m relieved that I like Mindy a lot so far. She’s delightful, really. She arrived at Sant Ambroeus twelve minutes after we were scheduled to meet, but texted me an apology in advance: “Running late. My doctor’s appt ran long. (Consultation for freezing my eggs.) In a cab now. Sorry . . . see you soon!!! xoxo!!!” She’s personable and energetic and doesn’t seem to notice that I’m woefully underqualified to find her a husband.

  I had suggested this place to Mindy because I know she lives around the corner in the West Village, but also because Jonathan had once brought me here on a date. He hadn’t told me that he was a regular, and I got weirded out when the waiters kept clapping him on the arm and calling him Johnny Boy. That day, I had ordered the cheapest thing on the menu, a nine-dollar tiramisu, in case I ended up paying my own half. I didn’t want him to think I was using him as a free meal ticket, even though that was occasionally true.

  Mindy and I sit in the back at a table crammed between two others. Around us, Ladies Who Lunch types recline on red-leather-tufted banquettes, eat open-faced tartines with foie gras or tuna, and drink tiny espressos. The restaurant hums with chatter in English and Italian and the clatter of silverware against white ceramic plates. Chanel bags hang over the back of almost every chair in the joint. My black Michael Kors tote from Beacon’s Clo
set is stuffed under the table. Mindy’s purse is the faintest baby pink and made out of buttery leather. I can’t identify the designer, which means it probably costs more than a month’s rent.

  Mindy finishes chewing her bite of kale and leans forward in her seat, elbows on the table and hands primly tucked under her chin.

  “I can’t express enough how important it is that he feels very masculine,” she says. “He should be strong, decisive, deep voice, broad shoulders. I don’t want anyone who’s wishy-washy.”

  “Got it.” I nod.

  “But the thing is, he’s got to be Jewish. That wasn’t so important to me when I was younger,” she says. She lingers over the word “younger,” her eyes widening ever so slightly over the top of her lifted coffee cup. I haven’t told her how old I am and don’t intend to. “But it is now. I want my kids to grow up the same way that I did.”

  “Not a problem.”

  “Some Jewish guys are too soft-spoken for me, too whiny, too close to their moms,” she says. “That’s not right for me. I mean, of course they should love their moms. But not love-love their moms all the time, you know?”

  “You’re looking for someone who’s family-oriented but independent,” I rephrase. This was a tip from Elizabeth yesterday—churning out the exact same concept in different words makes the client feel like you’re on the same wavelength.

  “Yes!”

  I never got the same you must marry a Jewish guy or else schtick from my family. I’m only half Jewish on Dad’s side, and it’s not like he ever went for Jewish girls. He likes blondes—Mom, of course, and then his string of girlfriends named Stacey and Tracy and Laci once he moved to Miami. Any Jewish girl claiming to be a natural blonde is just a liar with a good colorist. I’ve never dated a Jewish guy. I imagine it must be simpler to be born with specific rules about who is available and who is off-limits. It must keep you laser-focused on exactly who you’re looking for, the way Mindy is. I didn’t exactly have criteria when I met Jonathan—I just wanted someone normal, because that was not exactly in great supply when I was growing up.

  Mindy’s rose-gold iPhone starts to ring.

  “Do you need to get that?” I ask.

  She barely glances at the screen before sending the call to voicemail. “No, what would be more important than this?”

  But, like, no pressure or anything.

  “I just . . .” She stops and sighs heavily. “I just feel like I’ve tried everything. I’ve dated everyone, tried online dating, the dating apps, let my friends set me up, went to therapy to get all my baggage sorted out, joined a running club to meet new people, saw psychics, lost weight, did juice cleanses to suck the toxins out of my dating life. . . . I’ve been banging my head against the wall for fifteen years trying to find my person. I just want to be a mom. I’m almost coming to terms with having a baby on my own—but I’m not ready to stop looking for a husband just yet.”

  It feels disrespectful to keep eating while she says all this, so I put my fork down. I want to reassure her that I’ll find her guy, but I have no idea where to even begin. Instead, I open up the iPhone Note I’ve been adding to throughout lunch and rattle off what she’s looking for. Anything to make myself sound capable.

  Her dream guy is in his mid-thirties to mid-forties, I recite, maybe a banker or a lawyer, and hot in a Ryan Reynolds kind of way without being a gym nut. (“Because it’s not like I have a perfect SoulCycle attendance record, you know?” she points out.) He should be Jewish and smart and want kids. He should work hard but not so hard that she never sees him; he should be funny but not in a snarky, sarcastic way; he should be kind and thoughtful and considerate. Most of all, he should be excited to settle down and start a family.

  “You got it,” she says, beaming. But the smile doesn’t last long. “And that’s not too much? You don’t think that’s too difficult?”

  I shake my head and reassure her that I know exactly what I’m doing. I mean, yes, okay, matchmaking sounds crazy hard. But on the other hand, I’m the only one of my friends with a boyfriend, and I think I did a pretty fabulous job finding and keeping him. Girls at NYU couldn’t believe that I had found a hot, successful, cool straight guy who willingly wanted to be my boyfriend. (Before I moved here, I had assumed the city would have a Mr. Big living on every block. Imagine my surprise when I discovered every guy at NYU was either a gay theater major or a player who moved through a new girl every week. Straight, single guys in the city know they’re a hot commodity, and so they typically turn into assholes.) If I landed myself a boyfriend, I can land anyone a boyfriend. Right?

  “I got this. Promise.”

  I try to push the butterflies out of my stomach. We get the check and I put down my card to expense to Bliss later, praying I haven’t hit my credit limit. I don’t want to think too hard about failing my way back to Jersey. Outside the restaurant, Mindy initiates a dramatic double-cheek kiss and we part ways. Time to find Mindy’s husband. Let’s go.

  — Chapter 3 —

  I pop in my earbuds and walk east through the West Village. The city is sunlit and stunning. Lush rows of trees give shade to brownstone stoops adorned with black wrought-iron railings. I stroll past the throngs of sunbathers and jazz musicians in Washington Square Park to arrive at Think Coffee near NYU. They have iced coffee that chills my ribs from inside out and enough students with lavender hair and septum rings milling about to make me feel as if I’m still in school. I came here every week in college to work on my pitches and stories for NYU Local, the independent student-run blog. The coffee shop is cozy—the menu boards behind the counter are hand-drawn in colorful chalk, the couches are overstuffed, and the walls are papered in flyers explaining the differences between Ethiopian and Tanzanian coffee beans.

  When I get to the front of the line, I place my usual order with the barista for a large iced coffee. Our eyes meet and my cheeks flush. He isn’t my type at all—he wears his thick red hair in a man bun and his forearms are covered in intricate geometric tattoos—but there’s something appealing in the warmth of his eyes and his even, straight teeth. I suppose that’s a prerequisite for matchmaking, falling just a little bit in love with everyone you meet.

  The barista hands me the coffee. I toss him a brief smile and circle the crowded shop until I find an open table. I pull my laptop out of my bag. It latches onto the WiFi right away, even though I haven’t been here since I graduated. Home is where the WiFi connects automatically. I find the link to Bliss’s private database in my email. Penelope had positioned this—working remotely—as a major perk of the job during my training.

  “Just think, you can work while getting a pedicure!” she had crowed.

  I refrained from telling her that I’ve never gotten a professional pedicure in my life. When I was a kid, I used to watch Mom at the kitchen table with a paper towel spread under her hands while she did her own nails. She always filed them into long points and painted them cherry red. She never splurged on a salon. I thought home mani-pedis were the height of glamour and beauty. I thought she was prettier than all the other moms who picked up their kids from school in sneakers and ponytails.

  By middle school, I realized that different wasn’t necessarily better. Tom Braddock, the hulking jock who was the captain of basically every sports team ever, mimicked Mom’s walk as she came to pick me up from school one day when we were twelve. He stepped gingerly on his tiptoes, miming her walk in platform sandals, and wiggled his hips from side to side. His hands dripped from limp wrists and he put on a thick accent to say, “Baby, don’t hug me, my nails are wet.” I ran to the car and bit my lip to keep from crying.

  I dive into the Bliss database for Mindy by setting the parameters to straight men ages thirty to forty-five who live in New York; it spits out 2,087 results. The choices are dizzying. I suddenly feel self-conscious—I know that this is New York and weirdos abound, but there’s still something ever so slightly embarrassing about online shopping for dudes more than a decade my senior. I hunch ov
er my laptop and pull the screen closer to me, then begin combing through the men’s profiles one at a time.

  No.

  No.

  No.

  No.

  No.

  No.

  No, no, no, no, no.

  Oh my god, no.

  And so on, and so forth, for, like, a half hour.

  None of the men are complete garbage trolls. A lot of them come close to what Mindy is looking for. But something is always off. One guy checks almost every box on her list, except for the largest one: he has two kids from a previous marriage and no interest in having any more. Another guy sounds totally sweet and family-oriented just like her, but he works for a non-profit and makes only $40K a year.

  I’m on the verge of losing hope when I find Mark’s profile. He’s number 506 in my results. He looks like a grown-up frat boy with soft brown eyes, ruddy cheeks, and a boyish smile. He works in finance, likes to run along the Hudson River on weekends, and has traveled to three countries in the past year. There’s something vaguely Ryan Reynolds–like about his jaw. Mindy might go for him. His profile doesn’t give me warm fuzzy butterflies the way I hoped it would when I stumbled across the right match, but reaching out to him is worth a shot.

  I dig the notes from the training session out of my bag and copy what Penelope had told me to write in an email from my new Bliss account.

  Hey Mark!

  I’m Sasha, a matchmaker with Bliss. Your profile stood out to me for one of my clients in particular because you’re both well-traveled and have a similar sense of humor. I’d love to learn more about you and see if you’re a good match for my client. If you are, I’d be happy to set you up for free. Hope to hear from you soon!