Playing with Matches

by Hannah Orenstein

  “I broke up with my boyfriend last month after Georgie found him on Tinder, but he apologized and wants to get back together. For good.”

  A silence falls over the room for a moment, then it explodes into a cacophony of cheers and whoops. A few of the girls scramble over to my seat to see the ring up close. It’s exciting, but terrifying. With every “Oh my god” and “Congrats!” this whole mess feels more real. The girls ask if we’ve set a wedding date and accuse me of hiding my engagement on Instagram, and I feel sick. The flurry of attention should be exhilarating, but it feels all wrong.

  “I didn’t say yes,” I admit, swallowing. “Things are complicated between us right now.”

  The noise dies down. Georgie gives me a knowing nod.

  “Say yes for the rock alone,” Zoe encourages.

  “Seriously,” another matchmaker chimes in.

  “I think it’s super romantic,” Allison says. “I wish my ex would come back like that.”

  Penelope looks amused. “Ladies, let’s get back to work. We have so much to get through today.”

  I zone out for the rest of the meeting. If I really were engaged, that would happen over and over again, on Facebook and with my high school friends and at family reunions. I’d be treated like the girl who has it all: the hot, successful fiancé, the sparkling ring, the fabulous job, the perfect life—when that’s only what it would look like on the surface. The fear that Jonathan and I might not last would lurk underneath. I understand now how Gretchen must have felt when she got engaged—and I never expected to find any common ground with her.

  When the meeting wraps, I try to hustle out the door, but Georgie catches up with me on the stoop.

  “Hey, wait!” she calls.

  I spin around.

  Her usual obnoxious confidence is gone, and I notice for the first time how childlike her petite frame really is. She looks embarrassed to have chased me out here.

  “I just . . . You’re not really engaged to him, are you?”

  “Not really. Maybe? I’m still figuring it out.” I know I sound stupid, but what else can I say?

  A group of other matchmakers stream out the door past us, straining to hear our conversation. Georgie, god bless her, waits till they’re out of earshot before speaking.

  “I know it’s not my place, but you can’t marry him, Sasha.”

  “You’re right, it’s not your place at all,” I retort, crossing my arms over my chest.

  It’s one thing for Caroline to weigh in on my potential engagement, but Georgie—the only girl on the planet besides Chrissy Teigen who can actually pull off sex hair—doesn’t know the first thing about my life.

  She backs away, palms up. “Look, I’m sure I don’t know the full story. But I remember when we found him on Tinder. We’re matchmakers, Sasha. We know how to read men’s intentions.”

  I snort. “Yeah, right.”

  “Tinder is full of guys like Jonathan. They’re all slimeballs. I’ve been in your shoes, remember? I know what it’s like to think you can’t do any better than the guy right in front of you, even if he sucks.”

  She gives me a sad smile. I lean back against the wrought-iron railing of the stoop.

  “He doesn’t suck. He just made a mistake.”

  “Look, I’ve never met the guy, but it sounds like he sucks. If you set, say, Mindy up with a guy, they hit it off, started dating, and then a couple of weeks later you found him on Tinder, wouldn’t you warn her?”

  “It’s not the same.” Georgie is pissing me off.

  “Why not?”

  “Because I love him, all right?”

  The words burst out and hang there. It’s the first time I’ve let myself acknowledge that I love him since we broke up. I hide my hands in my pockets.

  “Just because you love him doesn’t mean you shouldn’t leave him.”

  She says this like her twenty-six to my twenty-two makes her some fountain of wisdom. Across the street, a twenty-something guy in a dark suit hustles down the stairs of a brownstone and into a waiting Uber. He checks his phone as he ducks into the car. Another Jonathan. The city is full of them.

  “I have to go,” I say, stepping around her tiny frame. “I have work to do.”

  “I know you’re going to make the right decision!” she calls.

  Yeah, yeah. Like that’s so easy.

  To get my mind off my train wreck of a life, I head to The Bean, a coffee shop up the street, to churn out matches. At The Bean, the baristas all have bad chest tattoos, the customers own tiny adorable dogs they tie to their tables, and the cold brew is double the price it should be. I order a coffee and sit down with my laptop to tackle my inboxes.

  I message back some dudes on Tinder, Bumble, and FetLife.com for Chrissy, the BDSM-loving banker. Her first two dates were less than ideal: she thought one guy was too short and slight for her plus-sized frame, and the next was a guy she called “the most arrogant idiot she’s ever had the misfortune of meeting.” Her third match needs to be totally baller.

  “It sounds like you’ve been to some incredible places,” I type back to the advertising guy who bragged about his vacations to Thailand, Iceland, and Morocco in his profile. I’ve been chasing him for three days now, but I’m not totally sure why. It’s not like there’s anything particularly special about him, other than the fact that he’s single and is responding to my messages at a timely clip. Every online dater on the fucking planet claims they love to travel.

  “Where do you want to go next?” I ask him.

  “Age is just a number. I don’t think you’re too old for me at all,” I lie to the forty-seven-year-old I’m wooing. I haven’t told him I’m chatting him up on Chrissy’s behalf yet, since I get the vibe he might not be into a plus-sized girl. (He keeps stressing he likes “fit” girls, as if there is no way any girl above a size twelve has ever entered a gym.) I note that he has a baseball cap jammed firmly on his head in every photo. “Bald?” I jot into my spreadsheet where I track potential matches.

  I coax a Bumble guy into agreeing to a phone call so I can learn more about him. His name is Vince, he’s a forty-two-year-old chemist, and he’s not scared off by the concept of a blind date. I need to suss out if he’s potentially interested in tying up Chrissy or throwing her around. There are zero non-awkward ways to do this, so I futz around with softball questions about what kind of personalities he’s attracted to and what he does on the weekends before asking about his preferences in the bedroom in a straight monotone. He fumbles.

  “Excuse me?”

  “Like, are you into rough sex, or are you more gentle, or do you have any particular fetishes?”

  I flush pink, but pretend this is a very normal question to ask a stranger just ten minutes after first speaking on the phone. If I act casual, so will he. The guy at the table next to me stops typing on his laptop and cocks his head an extra five degrees toward me to listen. Bro, chill.

  “Oh, uh, just, um, normal stuff, I guess,” Vince says.

  “Normal stuff. I see.” I don’t bother hiding the disappointment in my voice. I stop typing notes on my laptop.

  “I mean, most of the time,” he confesses, his voice dropping low. “Give me one moment. Let me close the door to my office.”

  I get an earful of his interest in role-playing, taking “classy, intimate black-and-white portraits,” and, yes, dominating women. I feel a lot like I imagine an OB-GYN might—I know way too much about the sex lives of people I’m not having sex with. In addition to passing Chrissy’s requirements in the bedroom, he also seems tall and broad enough to make her feel dainty, and he appears to have hobbies other than bragging about his international vacations to single girls online. Phenomenal. When I’ve heard enough to check off my boxes, I tell him I’ll be in touch soon.

  Next, I dive into my email, fending off Wretched Gretchen with another thousand-word email, reassuring her that no, I’m definitely not using any online dating sites or apps to locate men for her (I definitely am), and ye
s, I’ve reviewed the most recent version of her checklist (I skimmed it; I want to kill her), and yes, I’m quite confident that the next match will be better (ugh), and that yes, I understand that if I can’t deliver a fantastic match next time, she’ll have to be transferred to a new matchmaker (please!). I should spend a good chunk of time tracking down a new guy for her this afternoon, but I’ve hit a wall. Sometimes, matchmakers need to help their clients figure out what they want. But that’s clearly not the case here. I know what Wretched Gretchen wants—I just have no clue where to find a 5'10" half marathoner with zero baggage from past relationships and a passion for parasailing, or whatever she thinks she needs. I need to talk to Penelope about developing a new strategy for working with her, since clearly, what I’m doing isn’t working.

  Dwelling on Wretched Gretchen stresses me out, but the perfect antidote waits in my text messages. Eddie sends me a selfie of him and Diane. Their heads press together into the frame and they wear matching toothy grins. “We’re calling each other boyfriend and girlfriend now. Thank you so much. Can you please cancel my Bliss membership?”

  I’m still beaming from Eddie’s good news—fine, and also mourning the lack of income—when I get an email from Diego, the Esquire editor. For a short message, it packs a dizzying punch.

  “Sasha, I liked your edit test. When can you come in for an interview?”

  I jam my clenched fist over my mouth to stifle a shriek.

  “Did you do this?” I text Adam frantically, adding a screenshot of the email.

  “Nope. That’s all you,” he writes back.

  I’ve never been to Adam’s office, but I wonder how close he and Diego sit. Close enough that they’re laughing over my texts together?

  “Seriously,” I text.

  “I’m serious,” he responds.

  If Adam didn’t ask Diego to offer me an interview, that means I earned it on my own. I had pitched stories culled entirely from my real life, about online dating and cheating and age gaps in relationships. Miraculously, Diego had liked them. A chill runs down my spine. I write him back a ridiculously earnest and polite email, expressing gratitude that he had even considered my edit test and letting him know that my matchmaking schedule is flexible. I could be in his office at any time.

  I’m not even sure that I want to leave Bliss. I haven’t even been matchmaking for two full months; the high of holding people’s love lives in my own two hands hasn’t worn off yet. But the daily rigor of the job is sinking in. My thumbs ache from swiping; my feet are blistered from running between neighborhoods; there’s a crick in my neck from spending so much time on the phone. I’m beginning to feel like a robot who sees people as strings of database numbers; I’m too emotionally exhausted from dealing with clients to give my fullest attention to Caroline; and I can feel myself hating men—truly despising them—with a vitriol I’ve never felt before. Given all that, I’m still barely making enough money to get by. It’s not that I want to leave matchmaking, but I can’t stay at Bliss forever and retain a grip on who I am.

  Diego confirms an interview slot for tomorrow afternoon. I enter it in my calendar and try to relax, but I can’t. The stupid diamond ring is staring me in the face, like it’s taunting me to make a decision. I take the subway downtown to Tiffany on Wall Street. Tiffany is a soaring granite building with a majestic, robin’s-egg blue flag out front and a lanky doorman in a black suit with a matching blue satin tie. I look disgusting (unwashed hair, grubby jeans, flip-flops) but the doorman gives a gallant smile. I suppose he’s seen tourists look worse. I have a hunch that this is where Jonathan bought the ring. Just being here makes my stomach churn.

  I approach a salesman and ask whom I could speak to about diamonds. He directs me to the diamond department on the second floor. I wind through a group of preteens fawning over the Elsa Peretti Bat Mitzvah jewelry and take the elevator up one level. Upstairs, it’s serene, empty save for one couple poring over a case of rings and two saleswomen. One, a fifty-something blond woman with a Farrah Fawcett cut and a name tag that reads DEB, greets me with a cheery hello.

  “Is there anything I can help you with today?” she chirps.

  “Actually, yes. I . . .”

  Jesus, how do I even begin to explain this?

  “I . . . was recently given a ring that I believe may have been purchased at your store.”

  I awkwardly splay out my fingers like engaged girls do to show off their rings, and Deb takes my hand. She peers at the ring and coos.

  “Ooh, yes, beautiful. I believe I sold that to a gentleman just yesterday. You’re a lucky girl!”

  I emit a sound that could possibly be considered a laugh. A display case of diamond rings rests between me and Deb; a dozen rings for a dozen happily-in-love couples who will probably get married with no drama, and maybe ten or fifteen years down the road, they’ll fall out of love, have a nasty divorce, and take off the rings for good.

  Deb has kind, dark eyes rimmed by fine lines. She wears a thick strand of pearls around her neck and looks like the mom who always had homemade sugar cookies lying around her kitchen. Meanwhile, my hair has frizzed in the humidity and I’ve been hovering on the edge of a panic attack for the past twenty-four hours.

  “I don’t know exactly why I’m here.” I don’t even feel like I’m inside my own body.

  “Do you want to exchange your engagement ring? You know, some girls do that after the proposal. They go for a bigger diamond.” She actually winks.

  “You know, I’m not even really sure if I’m engaged,” I mumble. “I didn’t say yes. My ex-boyfriend proposed to me yesterday.”

  Deb’s eyes go wide.

  “We were together for more than two years, but when I found out he cheated, I dumped him,” I explain. “And I’ve been seeing this new guy, who I’m really falling for, and I can’t help but wonder if I’m missing the opportunity of a lifetime if I say no to my ex. He really could be the one, although I’m not even sure I believe in ‘the one’ as a concept at all, you know? Well, maybe you don’t. You work here. I guess I’d hoped that you could give me some advice. Ha. I’m sure this all seems ridiculous to you.”

  I take a deep breath and slide my hand off the glass counter. I sound unhinged.

  “Oh my goodness.” Deb covers her mouth and shakes her head. “I don’t know what to tell you, hon.”

  “So you were here when he bought this?” I ask, probing for any useful scrap of information that might help me make a decision.

  “I was. Young guy, dark blond hair, in a suit—that’s him?” Deb confirms.

  “Yeah. Did he say anything about me?”

  She tilts her head, like she’s trying to recall. “I don’t know if he said anything that stood out specifically. He seemed excited. Maybe a little nervous. I assumed it was typical pre-proposal jitters.”

  My hangover is returning with a vengeance. The couple at the other end of the counter is now trying on rings: he has a dark crew cut and glasses; she looks like an Anthropologie catalog model, with a wispy bob and floral A-line dress. I stare up at the ceiling and try to breathe, willing my heart rate to return to normal. Deb looks concerned.

  “Do you ever get guys in here who need to return rings? I mean, if the girl says no.”

  “I suppose it could happen.”

  “But it doesn’t. Not really, does it?”

  “No,” she concedes. “It doesn’t.”

  I slump my elbows onto the counter and bury my face in my hands. If I give Jonathan the ring back, I make him the most pathetic man in the world. I don’t want to do that to him. I try to explain this all to Deb, and she gives me a sad smile.

  “You know, it’s very kind of you to consider his feelings,” she tells me. “Some girls might be tempted to exchange the ring for store credit and go on a wild shopping spree.”

  “I couldn’t do that.”

  She raises an eyebrow. “He splurged. You could exchange this for several pretty pieces.”

  I examine the ring a
gain. “How much is this?”

  She pulls up the electronic receipt on the computer behind her and writes out the number on a small slip of paper. She slides it across the counter.

  Instantly, I’m nauseous. A cold sweat breaks out along my spine. The ring costs what I spend on rent in a year—and I live in Manhattan. Everything spills out: I tell Deb about our perfect start in Paris; my job as a matchmaker; the horror of finding him on Tinder; that Instagram bitch Cassidy; my infatuation with Adam; how confident Jonathan looked outside my building yesterday. By the time I’ve finished, Deb is glassy-eyed, carefully dabbing at the corner of her eye with the back of one finger.

  Nothing screams train wreck quite like making the Tiffany saleswoman cry.

  I pinch the ring between my middle finger and thumb and slide it off my finger. It leaves two millimeter-wide indents on my skin.

  “Do you have a box for this? I don’t want to wear it home.”

  “You’re giving it back to him?” she says, a note of alarm in her voice.

  I sigh.

  “I don’t know. Maybe. Wearing it just makes me feel uncomfortable, so I’d rather put it away till I make a decision.”

  “I have a feeling that your story isn’t over,” Deb says, reaching across the counter to squeeze my hand. “You’re both just so lovely.”

  I give her the ring. She nestles it inside a new black velvet box and drops it into that little blue bag that every girl in the world is supposed to want. I don’t know at what point my life derailed into a rom-com (rom-com gone wrong?), but none of this feels right anymore. Three months ago, my life was simple. I wasn’t a matchmaker. I wasn’t having a covert affair. I wasn’t wandering around Manhattan with ten thousand dollars’ worth of bling from a guy who fucks other women. I miss goofing off late at night in pajamas with Caroline over cheap wine. Married women don’t do that, do they?

  Before I leave, Deb steps out from behind the display case to give me a hug.

  “I know you’re going to make the right decision,” she says softly. “I just don’t know what that is. Only you do.”

  If only I knew.