Playing with Matches

by Hannah Orenstein

  The only person who knows about the breakup is fucking Tim at Dean & DeLuca, which means I have to tell people, one by one, that the relationship I was so proud of is over. Mary-Kate’s wedding is in four days. That is, if I’m still going—I’m not sure if I’m still invited. My skull aches. My eyelids are glued shut with goopy mascara schmutz and the dry, crusty remains of tears. My eyeballs are swollen like grapefruits.

  I want to feel better, not worse, but I don’t know how to do that. So, instead, I pour myself a double or triple or quadruple vodka tonic from the kitchen. Jonathan’s Columbia sweatshirt is still draped over the back of a chair; I hurl it toward the living room wall. Then I sit down, open my laptop, and click over to Facebook. I search Jonathan’s list of friends for the name Cassidy, and exactly one result pops up: Cassidy Greer. Her profile is locked away under privacy settings, so all I can see is a small square photo of a laughing blonde. Of course he went for a blonde.

  I Google Cassidy and instantly wish I hadn’t. Her name appears in a gushy feature titled “The It Girls of Instagram,” published last year on The Cut. I’m simultaneously engrossed and repulsed. I skim past the sections featuring the Instagram-famous DJ and the leggy redhead who scored a modeling contract, and land on Cassidy, a food blogger with more than 250,000 followers. She’s a bottle blonde, obviously. Her eyebrows are two shades too dark for her buttery Blake Lively hair. And her pale pink, carefully lipsticked mouth is too big for her face. But I can’t delude myself into thinking she’s not attractive—she’s beautiful. The reporter reveals she maintains her slender frame at Pure Barre, and that her father happens to be a retired vice president at Bain Capital and a close personal friend of Mitt Romney’s. She went to Yale. Of course she did.

  It gets even worse once I pull up her Instagram. Every photo features a mouthwatering meal bathed in bright white light. There’s the açai bowl topped with juicy red strawberries, the avocado toast sprinkled with black pepper, the kale salad drizzled in olive oil. Her delicate, long-fingered hands sit at the edge of each photo, holding a fork or cupping a latte. Her face is always just tantalizingly out of view. If I didn’t hate her on principle, I would’ve followed her, too. I scroll back through six months of photos before I slam my laptop shut.

  Orlando is meowing on the floor, wrestling with Jonathan’s limp sweatshirt. He has the sleeve caught in his daggerlike claws, and he’s batting it into the corner of the living room. The sweatshirt will be ripe with dust bunnies, and I don’t feel like rescuing it.

  My phone buzzes with an incoming text. It must be Jonathan; my fingers fly to my phone so fast, I’d be mortified if anyone were around to see. My stomach drops at the sight of a different name on the screen.

  “Just sent out a bunch of new messages on Tinder. Very nerve-racking. Don’t know how you do this all day for work, but I’m impressed,” Adam writes.

  His text is the first thing in hours that’s made me not want to kill myself or somebody else. I start to type back a response, but I realize I have no idea what I want to say. I delete the whole thing, then impulsively hit the call button.

  “Hello?”

  “Skip the Tinder dates,” I hear myself say. “Would you want to go out with me sometime?”

  I feel like I’m at the top of a roller coaster, right before I plummet a thousand feet toward the pavement. This is the worst idea I’ve ever had.

  “I thought you had a boyfriend.”

  “So did I.”

  “Oh, jeez. I’m so sorry.”

  “Don’t be,” I reply.

  I should hang up and go live in a post-apocalyptic Siberian cave where I can’t embarrass myself like this in front of other human beings, but it’s too late for that.

  “Well, in that case, yeah. We should get drinks sometime.”

  “Drinks! Yeah. Tonight?”

  “Tonight, uh, let me think. Um . . . I actually have plans.”

  “Oh.” Could I have sounded like more of a desperate loser? I’m tempted to Sylvia Plath myself, but I don’t really know how to turn on the oven.

  He rushes to fill the stretched-out lull in the conversation. “Next week, then?”

  “Yeah. Next week.”

  “I’ll text you,” he promises.

  We do that awkward thing where he starts to talk, then I start to talk, and then we say goodbye. My cheeks are burning and I feel like I’ve had a triple espresso shot. If Jonathan can sleep with other people, so can I.

  — Chapter 13 —

  None of the traditional post-breakup options appealed to me. I didn’t want to chop off my hair (too unflattering), or wallow forever (too depressing), or get a sick revenge body (too much effort). So, instead, I threw myself into work.

  Bliss matchmakers work on commission: clients pay $700 a month for two dates, and I get to keep 35 percent of that, or just over $120 per date. That had sounded like a lot when Penelope had first explained it, but now that I’m seeing how much work goes into every pairing, I’m realizing exactly how much work I need to do to stay afloat. Patti Stanger made this look easy and lucrative on The Millionaire Matchmaker, but she had me fooled on both counts.

  That’s why, on my first morning as a single person, I actually iron my most professional-looking white button-down, pat concealer onto the bags beneath my eyes, and walk to the Bliss brownstone to talk to Penelope. I find her in the dining room, tethered to her usual array: laptop, iPhone, and extra-large iced coffee. Her nails clack rapid-fire over the keyboard and I see a Bumble conversation in progress on her phone.

  “Hi,” she says, eventually making eye contact after pausing mid-word to check her phone. If she notices that not even Maybelline’s finest could disguise the puffiness around my eyes, she doesn’t say anything.

  “Hi. I’ve been thinking—I’d love to take on more clients. If possible. I just feel like I’m finally getting the hang of this.”

  “It’s going well with Mindy?”

  “Well, she says she had a great time on her first date. I don’t think they’re going to go out again, but I’m searching for other matches for her.”

  “She went out with Adam, the Esquire editor, right? Tall, Jewish, thirty-three?”

  There are more than five thousand people in Bliss’s database. Penelope is truly frightening. Almost as frightening as the tiny jolt of electricity in my stomach when she says his name.

  “Yeah, that’s Adam.”

  “Not a bad start. I can give you more clients. But are you up for a challenge?”

  I need the money. “Sure.” I sit down.

  Penelope opens our database on her laptop and pulls up a client’s profile.

  “So, he’s not quite as ‘cool’ as Mindy,” Penelope begins slowly, making sharp air quotes around the world “cool.” “But don’t let that scare you.”

  Then I take in what’s on the screen. His name is Eddie Hyman. He’s five foot four and lives an hour away in the Bronx. His database photo is a selfie taken against the backdrop of a ratty couch. His shiny bald spot, uneven smile, and massive gut are not promising. He says he’s an accountant and “has minimal relationship experience.”

  “I’m not scared,” I lie.

  “Let this scare you, then.” Her voice goes flat. “He’s forty years old, just moved out of his mother’s house last year, and has never had sex.”

  Oh, dear god. And his last name is Hyman?

  “He’s the sweetest guy you’ll ever meet, I swear. He was working with Bella, one of the other matchmakers, but they just didn’t have the right chemistry. He asked to be transferred to someone a little more sympathetic.” She pauses. “And Bella doesn’t work here anymore, of course.”

  I’m not ballsy enough to ask why.

  Penelope sends me his contact info, then flits out of the dining room, citing a meeting with an investor. I slump over the cool surface of the table and press my forehead to the lacquered wood. I can find Eddie a girlfriend. Sure, no problem. Tons of women want sweet, smart, sensitive men. Sexual experience i
sn’t necessarily a deal-breaker. Height isn’t necessarily a deal-breaker. Right? Ugh. I’m not even able to convince myself.

  I borrow Georgie’s fake-flirty tone and type out an email to Eddie, explaining that I’m so excited to work with him and that I’d “love to arrange a cocktail or coffee meeting” at his earliest convenience to introduce myself.

  Eddie’s earliest convenience, it turns out, is that afternoon. It’s his idea to meet for coffee rather than drinks; it’s my idea to travel to his neighborhood, Riverdale in the Bronx, which is so far from my apartment I might as well be somewhere in the Atlantic Ocean. I just want to be polite. My subway ride to meet the forty-year-old virgin extraordinaire takes an hour.

  I arrive at his chosen coffee shop and spot him instantly—he’s hard to miss. I chose to wear my flattest flats so I don’t tower over him, but there isn’t a pair of shoes in the world that would make our four-inch height difference less awkward. The coffee shop is cute, with windows draped in cheery gingham curtains and glass pastry cases holding mouthwatering cheesecakes.

  Fifteen minutes have passed since we introduced ourselves, and despite amping my practiced charm up to eleven, I was having trouble breaking the ice. Eddie is flustered. He pushes up his glasses, fixes the collar of his shirt, clears his throat. A thin bead of sweat rolls down from underneath his sparse brown hairline toward his temple, and he mops it up with a wrinkled handkerchief. I pretend to fiddle with the clasp on my bracelet to avoid staring and making him feel even more uncomfortable.

  “Let’s talk about your previous dates with Bliss,” I suggest. “Any feedback on what wasn’t working with Bella would be so helpful, so we don’t run into the same problems again.”

  “I did not find Bella very professional.” His voice is stiff and a little nasal.

  I prod him for more information. Jesus, I’ve had more forthcoming conversations with my cat.

  “She sent me on a date to walk around Chelsea, which is extremely far from me,” he began slowly. “Which I didn’t mind. But when I got there and found my date, we ended up in the middle of the Pride Parade. Now, I don’t have a problem with that, but it was . . . a bit loud. Bella said she didn’t realize the parade was that weekend.”

  I love the Pride Parade, but it’s the last place I’d ever send a date. Picture literally two million people flooding the city, half of them in rainbow-striped jockstraps dancing on floats. Add in sweltering summer heat, booming Mariah Carey and Britney Spears songs, and street vendors selling flags and glitter, and it’s a lot. It’s hilarious to imagine Eddie trying to carry on a real date there, but it’s also kind of sad.

  “And then Bella disappeared. Never set up another date, even though I had paid for a second one already. I mean, I get it, I’m not the easiest person to match. But there has to be someone out there for me. I’m not asking for much. I’m just a little socially awkward. Meeting people makes me anxious.”

  He looks at me with weary eyes, then looks away.

  “I get it, Eddie, I do. I get anxious when I meet new people, too.” I make a fluttering motion by my stomach. “Butterflies, nerves, you know.”

  “How could you possibly know what this feels like?”

  He gives me a withering glare, and suddenly, I hate myself for what I said. He leans back in his seat and crosses his arms over his chest. I feel acutely aware of the sugar in my voice and the bright smiles I’ve been sending him across the table. He must think I’m the biggest simpering fake in the world.

  Time for a new tactic. I ask him to tell me more about himself. When he falters, I lead him through the conversation one question at a time. Eventually, he describes a quiet life to me. He works as an accountant. He goes bowling once a week with the same league he’s been playing in for a decade, roots for the Mets, and has been considering getting a dog. Maybe a beagle. He doesn’t have many friends.

  “But a few months ago, well, I . . . I was sort of dating a girl. She taught high school marching band,” he says, dropping his voice to a whisper and blushing furiously, “and made ends meet by writing erotica on the side. We were together for three weeks.”

  Well, well! I can’t bring myself to ask if he’s actually a forty-year-old virgin after all, so I smile maniacally and tell him that sounds very, um, exciting. He doesn’t look like he wants to offer any more information. Instead, I push for details on his ideal match. Eddie tells me he’s looking for a girl—“er, sorry, a woman”—who’s smart, extroverted (“to balance me out”), wants a family, and likes sports. He’s shy about describing his physical preferences.

  “Pretty, I guess,” he says, looking down at the table. “Blondes or brunettes, doesn’t matter to me. And, um, petite would be nice. You’ve probably noticed I’m not the tallest guy.”

  After we drain our coffees and scrape the last of our pies from our plates, Eddie walks me four blocks to the subway. On the way, I catch our reflection in the window of a Barnes & Noble. We make a jarring pair, but my hour with Eddie has softened me. He’s awkwardly lovable. At the entrance to the subway, he goes for a handshake and I give him a quick hug.

  “I’m going to find someone for you,” I tell him. “I promise.”

  Back at home, I get into Serious Work Mode (translation: hair up, bra off, sweats on) to find Eddie a date.

  I open Bliss’s database and set the search parameters for straight women ages 30 to 40 in New York City. Two thousand results pop up, and I groan. I start by reading through every profile, but after three that are way off-base, I realize there’s a faster way to do this, even if it feels mean. I scroll through the results in search of the least attractive photos. Within fifteen minutes, I have three potential options to review. Finally, I have hope!

  But that hope is short-lived. As I delve further into their profiles, I have to cross each one off my list. Nell, a thirty-one-year-old accountant, says that she’s new to dating and wants a more experienced partner—that’s definitely not Eddie. Marie, the thirty-seven-year-old special education teacher, is 5'11". Liz, a thirty-three-year-old nurse, specifically requests “no bald men, please,” although personally, I think she could stand to be less picky. So I’m back where I started. I email Penelope to see if she has any ideas. She responds quickly.

  Eddie is a tough one. I don’t have any women in mind off the top of my head, but you might want to try creating a dummy profile on OkCupid as a man. You can fill in a little of his information if you’d like. Reach out to women and explain that you’d like to set them up with a friend of yours. Whatever you do, don’t use the word “matchmaker” in your message, because that tips off OkCupid that you’re a professional and they can shut down your account. I’ve been kicked off the site seven or eight times already—they don’t like us poaching their users. Good luck!

  I spend the next hour glued to OkCupid. It’s something to do other than wait for Jonathan to text (he won’t) or refresh Cassidy’s Instagram (I shouldn’t). First, I create a fake email address, which I then use to create a fake OkCupid account. The site’s interface doesn’t feel half as current as swipe-based apps like Tinder do. Now that you can search for a husband using just a few photos and an optional one-liner bio, anything more than that feels like you’re trying too hard. I fill out the bare minimum of biographical information about Eddie—just enough for it to feel like a real profile and not a front for a serial killer. Then I dive into the pool of available women.

  One profile jumps out at me immediately. Hilary86’s photo shows a woman with enormous brown eyes. She describes her life as a travel reporter, which has taken her hang gliding in Brazil, on a kayaking tour of Indonesia, and to a safari in Kenya . . . and that’s only this year. “If you have a passport and a sense of adventure, you might be able to keep up with me,” she writes. “Keyword: might.” I’m jealous of her confidence. She’s approximately eleven thousand light-years out of Eddie’s league. I click back to the list of potential matches and start to browse. I keep getting lost down rabbit holes like Hilary’s, but aft
er an hour, I’ve sent identical messages to three women.

  Hi! I know this sounds weird, but I’m actually a woman. My friend Eddie here asked me to help him out. He loved your profile and I think you’d really get along. He’s a gentleman with a heart of gold, smart but not show-offy, and would sincerely enjoy meeting a kind, down-to-earth woman such as yourself. I know this is far-fetched, but is there any chance you might be interested?—Sasha

  Of course, the problem with this method is that women typically receive more messages than men do. The numbers point to a grim reality: none of these women will even open my message, much less write back to me. It hurts to imagine that someday soon, I might have to sift through OkCupid—or some other site or app—for myself, not just for Eddie. I’m not ready for that yet. I’m barely ready to get a drink with Adam.

  My phone pings with a new email. It’s an OkCupid message from one of the women I was interested in for Eddie—thank god! In my haste to read it, I knock an old coffee cup onto my laptop. Luckily, it’s empty and there’s no harm . . . but even if I did spill coffee, it would be a small price to pay if it means Eddie the forty-year-old virgin will not die alone.

  Hi. I’m not sure if you messaged the right person. Are you sure he would want to meet me?—Diane

  Diane’s profile reveals a drawn face, prematurely lined, with small, beady eyes behind outdated square glasses. Caroline has a similar pair she bought at a vintage store, but she wears them ironically. “I’m a little shy. I don’t have much relationship experience. Just waiting to meet the right person,” Diane’s profile says. If Eddie had a female replica, Diane would be it.