Playing with Matches

by Hannah Orenstein

  “You’re a stellar employee,” he deadpans. “No, really, I don’t want to get you into trouble or anything. But I also . . .” He falters. His next words are slow and measured, like he’s nervous and wants to be precise. “I really like you, Sasha. I know it’s only been a few days, but you’re phenomenal.”

  I try to keep breathing. It’s suddenly very hot in his apartment.

  “You’re not getting me into any trouble, as long as no one from Bliss finds out.”

  “Are you sure?”

  Goddamn, look at those big brown eyes. Like melted chocolate. The thing is, I don’t feel great about breaking the one rule Penelope has explicitly laid down. But with Adam right here in front of me, it’s impossible to seriously weigh the risks.

  “I’m sure,” I hear myself tell him. “I really like you, too.”

  He sets his wineglass on the table, then takes mine out of my hand and puts it down. He stands up and extends his hand to help me up off the couch, then pulls me into a kiss. He picks me up so I can wrap my legs around him. Normally, I’d feel self-conscious of my weight suspended in his arms like this, but he’s like a giant. He can handle me.

  “So, you’re sure this is completely forbidden?” he asks, his words hot on my ear.

  “Absolutely.”

  He carries me to his bedroom, kicks the door closed behind us, and throws me onto the bed.

  — Chapter 17 —

  The best part about dating Adam might be the texting. I know that’s not what I’m supposed to say—it’s supposed to be the sex, right?—but a week after our date in Greenpoint, Caroline has requested a girls’ night in and the banter over text all day has just been mouthwatering. Caroline and I sit cross-legged on the couch, passing a package of cold, sliced turkey between us, with white wine in plastic Solo cups on the floor. We’ve paused an episode of Broad City we’ve both already seen while Caroline catches me up on her date last night.

  “It was just weirdly . . . great?” she says. She looks both thrilled and confused. “He asked me questions about myself, paid for our drinks while I was in the bathroom, and texted me this morning to ask when he could see me again.”

  “That is shockingly normal.”

  She nods vigorously as she rolls another piece of turkey. “I know, right?”

  “Should I bother learning this one’s name?”

  “You know, you might. Owen.”

  “Do you think you like him? Or are you just marveling that he did all the things he’s supposed to do?”

  “I mean, I don’t know.” She tilts her head. “I haven’t really thought about it.”

  She pulls up Owen’s Bumble profile and hands her phone to me, and indeed, he appears shockingly normal. He went to school in Michigan. He works in advertising. His pictures suggest that he owns multiple nice-looking sweaters and has an array of equally normal-seeming friends. When I hand the phone back to her, she beams at the screen for a few seconds. I take that time to steal a glance at my own phone; just as I had hoped, a message from Adam waits for me.

  It sounds crazy, doesn’t it? Girl likes guy. Girl texts guy. Guy actually texts back right away. If Jonathan responded in under five hours, I considered that a success.

  “What are you up to later, miss?” Adam had written a minute ago.

  I can’t help my response: an instant grin, flushed cheeks, a pleasant drop in my stomach. I had forgotten what it was like to have a crush, but it’s this tornado of all-consuming physical sensations all the time. I crave his texts. It’s been a week since I’ve seen him last, and I miss being close to him. That’s what Caroline has been chasing all these years—the giddy joy of letting yourself fall for a person who actually deserves you.

  “That’s Adam?” Her tone is slightly sharp.

  I press my phone to my chest. “How’d you know?”

  She rolls her eyes, then picks up her phone with a breathy sigh, pouts, and bats her eyelashes in a cartoonish impression of me. “Come on, Sasha.”

  “I just . . . like him. I can’t help it.”

  Her face falls just the tiniest bit. “I thought—” She looks away, picks up her cup of wine, and takes a sip. “Never mind. It’s stupid.”

  “What?”

  “Never mind.”

  “No, what?”

  Her jaw sets in a hard line. “I just thought we’d finally be single together. You know, have fun with it. Like we used to.”

  I flash back to a night before I met Jonathan. A Tuesday—dollar-beer night at The 13th Step in the East Village, when hordes of NYU kids and twenty-something transplants who have yet to find better places to drink swarm the bar. It’s crowded wall to wall with people who slosh back pints between sticky wooden tables. One night, Caroline and I improvised fake names and stories for each new set of guys who stumbled by to slur pickup lines our way. We were Taylor and Danielle, pole dancers fresh off the plane from Indianapolis; or Ophelia and Constance, socialites slumming it at a dive bar à la The Simple Life; or Georgia and Marie, long-lost twin sisters separated at birth and adopted by different families, reuniting for the first time in the big city. We did it to meet men, but whenever I think back to that night, I barely remember the guys at all. I only remember feeling my stomach quake with half-suppressed laughter as I tried to keep it together as she reeled off these preposterous stories.

  I shift on the couch to face her straight on. “I’ll never stop wanting to be your friend,” I tell her. “Ever. Doesn’t matter if I’m single.”

  “I know, I know.” Caroline gets up from the couch to put the turkey back in the fridge, possibly to avoid looking at me. When her back is turned, I dash off a text to Adam.

  “Tonight’s girls’ night,” I type quickly. “Tomorrow?”

  Caroline comes back to the couch, brandishing the wine bottle in one hand and a pint of Ben & Jerry’s in the other.

  “I’ve seen Adam, like, three times, Caroline. That doesn’t change anything about our friendship.”

  She shrugs and resumes the episode on the TV.

  I stumble across the perfect date by accident the next morning. Gretchen emailed me a list of activities and events occurring around the city during the month of August, organized chronologically and then color-coded by theme (restaurants and bars in blue, outdoor activities in green, live music in red, theater in purple, and so on). “Just wanted to send over some suggestions while you’re planning my first date!” she wrote, complete with not one but two smiling emojis.

  Under the list for today, August 5: the book launch party for my new client Lily Chang, the writer living in Crown Heights, Brooklyn, who dates both men and women. She has a column about dating, which makes her possibly the one woman in the city whose job freaks out dates more than mine does. When we met for drinks last week, she explained that she didn’t really care about the quality or compatibility of her matches that much—she just wanted an entertaining story for her column. The mission was daunting, and so I kept putting it off. A week later, I didn’t really have any leads for Lily. But the book party would show my support for my client, and it’d be exactly the kind of date that would impress Adam.

  “Lily Chang’s book party tonight—you down?” I text him.

  “You know her?”

  I love that he texts back right away. He makes me feel wanted.

  “She’s a client.”

  “Whoa. I’ve heard she’s awesome. Let’s go.”

  That’s how we wind up in the basement of the ultra-hip bookstore WORD Brooklyn. Adam leads me down the staircase, beelines for the table with wine, and settles into the sea of folding chairs with an ease that makes me think this isn’t the first event he’s attended here. The crowd is very Brooklyn: the guys wear suede shoes and leather jackets even though it’s August, and the girls all have Parisian-looking bangs and carry canvas tote bags with the New Yorker’s logo or with a cutesy slogan about veganism (EAT BEANS, NOT BEINGS). I spot Lily at the front of the room, looking unbearably cool in a pair of ripped jeans and an
oversized vintage Rolling Stones tee. I want to say hi, but before I can, a thirty-something woman in dark lipstick squeezes into our row and perches on the chair next to Adam.

  “I thought that was you!” she exclaims, going in for a hug.

  “Hey! How’s it going?”

  “Ugh, you know. Working on a big piece right now. I didn’t know you knew Lily.” I can’t tell if I’m imagining the intimate, singsongy swing to her voice.

  “I don’t personally,” Adam says. He gestures to me. “Sasha works with her, actually.”

  The woman acknowledges me for the first time. “Oh, what do you write?”

  “I’m not a writer. I mean, I was. But it’s not, you know, my job right now.”

  “Oh.”

  If she had had the slightest sliver of interest in me before, it was gone now.

  “Sorry, I should’ve introduced you. Sasha, Katie, Katie, Sasha,” Adam says. Then as an explanation to me, “Katie freelances for Esquire.”

  “And you two are . . . ?” she presses. “Together?”

  “Here on a date.” He grabs my hand.

  “Oh! I didn’t realize. You’re so . . .” She takes in my denim shorts and shabby sandals with the straps wearing thin. “Cute. Well, have fun, you two.” She slides down the row of seats and excuses herself to the table of wine.

  Neither one of us knows what to say.

  “That was awkward,” I announce.

  “I didn’t know how to introduce you,” he admits. “It’s too soon for ‘girlfriend.’ ”

  “Definitely too soon for ‘girlfriend,’ ” I agree.

  Then again, in my head, I’ve already started thinking of him as my next boyfriend. My birthday is in November, three months away; I kind of hoped he would be around for it. It’s probably unhealthy to jump into a relationship with Adam so quickly. But being around him feels easy and right. I’m happy when I’m with him, and I haven’t been happy all that often this summer. I don’t want to end up like Mindy and Gretchen, alone at forty with no kids and a five-page checklist.

  A bookstore employee taps the microphone at the front of the room. “Hey, guys. Guys? I think we’re going to get started.”

  She introduces Lily with a string of compliments that goes on for approximately a minute and a half, and then asks her to read a chapter of her book out loud. Lily has a mesmerizing speaking voice, steady and confident, even—especially—when delivering the dirty jokes that litter every page. She flips her glossy mane of hair over the top of her head as she reads. I can’t tell if I want to be able to write like her, or if I just want to be her. Lily closes the book and bows her head as the audience claps.

  Lily and the event moderator talk about the book, then open up the conversation for questions from the audience.

  “Come introduce me to Lily?” Adam asks when it’s over.

  She’s holding court behind a mountain of books at the front of the room, signing each one with a red Sharpie. I tentatively approach her, and when I’m a few feet away, she spots me through the small crowd of fans. When she finishes scrawling her signature into a copy, she gives me a big wave and gestures for me to come closer.

  It strikes me all of a sudden that Lily should be dating someone like Adam. I could see them together so easily—they’re more age-appropriate for each other, and in the same industry, and they know all the same people. I feel young and small, ridiculous for thinking this thing with Adam could possibly work. My job is to boil down compatibility from an art into a science; I should know when a couple makes sense. But so far, I haven’t pulled that off for any of my clients, and I’m certainly not getting it right for myself.

  “Hel-lo, Dolly!” She looks Adam up and down. “So this is my betrothed?”

  “Ha. I’m still on the hunt,” I say.

  “I’m just a fan,” Adam says, reaching out for a handshake. “Big fan. Adam Rubin. From Esquire.”

  “I loved hearing you read,” I say. “I wish I could write like you do.”

  “Dude, do you write? I didn’t know that.”

  “I mean, I used to.”

  “You could totally write about matchmaking. People would eat that shit up.”

  She has a point. I can tell Adam is just dying to talk to her, so I let him steer the conversation toward Lily’s book. His thumb rubs the inside of my palm as he talks to her—a gesture she doesn’t miss. A line is forming behind us, so he grabs a copy of Lily’s book and asks her to sign it for him. She obliges.

  When Adam and I are outside the bookstore, he cups my chin and kisses me deeply.

  “Thanks for bringing me,” he says. “You’re the coolest.”

  It’s a bizarre sensation, realizing the way you see yourself isn’t the way others do. I’m just a kid faking her way through her first job and scrambling to start paying off her student loans. But to Adam, I’m a girl with a sexy career, connections to one of New York’s most notorious writers, and the kind of unhinged confidence that led me to track him down in a bar on a sweaty Monday night.

  If he sees me that way, it just might be true.

  I can’t stop thinking about what Lily said. I should write about matchmaking. I lie awake, my brain buzzing, for an hour after Adam falls asleep. My mind churns over exactly what I could write, where I’d pitch my stories, and how maybe—just maybe—this would get my writing career back on track. I didn’t like the way that woman Katie’s eyes glazed over when she realized I wasn’t paying my bills with my writing.

  The next morning, as I watch Adam pull on jeans and muss product through his hair, I pitch him my plan.

  “You know that I write, don’t you?” I ask, trying to sound casual.

  “Mhm.” He’s focused on the hair product.

  “I was thinking maybe I’d like to start my own column,” I continue, “give guys dating advice based on what I’ve learned as a matchmaker.”

  “Huh!” He turns around, wiping his hands on his jeans. “That could be great.”

  “Do you think that Esquire.com might be interested in a column like that?”

  He looks at me seriously. “You have clips?”

  He means writing samples.

  “Four years’ worth.”

  “Yeah, I could connect you with my editor.”

  “You’d do that for me?”

  “Of course.”

  I squeal and throw my arms around his neck in a hug. “Thank you, thank you, thank you.”

  He gently puts his hands on my waist. “I didn’t say I could make it happen. My editor will have to say yes.”

  “I know,” I say, rolling my eyes. I sink back onto the bed, feeling triumphant. “He will. I know he will.”

  “You’re cocky,” Adam says, lifting one eyebrow.

  “Yeah, I am. Half my job is knowing how to make men do whatever I want.”

  “Oh, come on.”

  “I wanted you to go out with Mindy, so you went out with Mindy. And I wanted you to go out with me, and you did.” I cross my arms. “So there.”

  Adam pauses in the doorway, where he had begun putting on his shoes. Instead, he places both shoes back on the floor and dives onto the bed to kiss me.

  “What do you want me to do now?” he growls in my ear.

  Later, after I’ve showered at Adam’s place, run home to feed Orlando, and installed myself at a David’s Bagels to work for the day, I email Penelope to see if I’m even allowed to write about matchmaking. I explain that I was hoping to pitch a column to Esquire.com—not as a full-time job, but just as a freelance gig on the side.

  “Esquire?” she writes back. “Please. We need all the press we can get.”

  So, slurping up iced coffee as I go, I draft a sample column. I want to send Adam’s editor, Diego Vidal, a sample of what I can do. The words spill out easily; I write about Mark, the investment banker I had met for coffee at Starbucks who only wanted to date thin, busty blondes, giving him a pseudonym. I start by appealing to the average Esquire.com reader who probably would love to date a
whole cheerleading team’s worth of thin, busty blondes, but then segue into why Mark’s approach to dating isn’t doing him any favors. He comes across as desperate and gross. The kind of girls he wants just don’t want him. He’s probably not even getting laid that much. I wrap up by offering readers three suggestions. First, dating is a full-time job (I explain that it’s literally my full-time job), and so you’ll get the best results if you actively put yourself out there on multiple dating apps and in real life. Second, pursue partners who are equally as attractive and successful as you are. And last but not least, if you’re still struggling, hire Bliss.

  I make Caroline read it over twice, and she signs off on it after just a few minor edits. I send it to Adam, preparing myself for him to hate it. But miraculously, he doesn’t hate it at all.

  “Goddamn, you’re good,” he writes back. “Here’s Diego’s contact info.”

  Three email drafts later, I attach my sample column and hit send. I’ve spent so much time watching the men I date pursue their dream careers. It’s time I go after my own.

  — Chapter 18 —

  Anyone can date. It’s not hard. You go out with someone, you go home with someone, whatever. But turning a series of dates into a real relationship requires a series of small victories—meeting each other’s friends; taking and posting pictures of each other; agreeing not to see other people. Left to their own devices, guys won’t ever initiate any of these steps. Girls have to carefully strategize how to move the fledgling relationship forward without freaking out the guy. So on Saturday afternoon, when Adam texts to ask if I’m free to join him at a concert tonight, I take a calculated risk.

  Caroline and I are stretched out on a beach towel in Washington Square Park to sunbathe in bikini tops and cutoffs. She flips through Cosmo as I draft a second column for Esquire.com, just in case Diego likes the first.

  “Hey,” I say, poking her arm with my iced coffee cup. “Are you doing anything tonight?”