—Sasha
A few minutes later, he writes back.
What is this client of yours like? Can I see a picture?
I immediately hit reply.
Thanks so much for your quick response! Bliss clients remain anonymous—it’s just one of the perks of a paid membership. But I’d be happy to tell you more over coffee. Do you have time to meet this week?
I feel like I sound too desperate, but apparently that doesn’t faze him. He responds a minute later, making me think I can actually pull off pretending to know what I’m doing.
9 am tomorrow. Starbucks, West between Albany and Liberty. See you there, Sasha—it’ll be my pleasure.
The dude’s kind of abrupt. But that’s fine. I know that Starbucks; it’s right by Jonathan’s office. I text Mindy that I’ve already begun the hunt, and she texts back a string of clapping emojis. I schedule Mark’s coffee into the calendar on my phone. I don’t know if he’s necessarily The One, but even if he turns out to be perfect, Mindy purchased the $700/month package that guarantees her two dates a month. I’ll need to find her a second guy soon.
I close my laptop and relax at the table while I finish my coffee. I spent four years at Think Coffee, working toward a future as a writer. I figured I’d meet sources for interviews one day, or curl up in the cozy armchair in the back corner to knock out a thousand words, or even hold readings of my work here someday. I’m not ready to rule out that future just yet, but it’s time to put it on hold.
When I walk into our apartment on First Avenue and Eighteenth Street, Caroline is flopped horizontally across the couch watching TV and petting our cat, Orlando (named for our shared childhood crush, Orlando Bloom). Broad City is on. We’ve both seen the whole series four times. Our friendship is as solid as Abbi and Ilana’s, except we would never have sex with our boyfriends while Skyping each other like they do, because hello, boundaries. Although last weekend, I did spend twenty minutes hunched over her bare butt with a pair of sterilized tweezers to help her remove a splinter she got sitting on a park bench in a short dress. I am a spectacular friend.
“Hi! I thought you were starting work today?” Caroline asks.
“I did! I met my first client and started finding guys for her. Scoot.” I motion for her to move her legs and I curl up on one side of the couch.
“I can’t believe you’re really going to be a matchmaker,” she says, reaching for the Apple TV remote to pause Broad City. “That’s so fucking cool.”
“I’m a real person now, just like you. Thank god.”
“Welcome to the ranks of serious adults with serious jobs. Thank you for noticing how dedicated I am to my career,” she deadpans.
Caroline works a couple of shifts a week at an East Village shop called Flower Power that sells herbs and is a part-time receptionist at a barre studio, which she mostly hates, but she gets free classes and a lot of time to work on the pilot for her TV show. I mean, theoretically. There has not been much writing going on. Instead, we stay up until one or two in the morning every night, drinking cheap pinot grigio, taking photos of Orlando, and making fun of her Tinder dates. Caroline can eat a whole box of Girl Scout Thin Mints in one sitting, never messes up her winged eyeliner, and has a crippling addiction to Candy Crush. She plays it constantly and texts me updates whenever she beats her previous personal record. We met while smoking pot in a dorm bathroom freshman year and are way deep in love.
“You know what? This calls for wine. We should celebrate your first day,” Caroline says.
“But we’re having dinner to celebrate with Jonathan and Mary-Kate and Toby in two hours.”
“So?”
She’s already up and rummaging in a drawer for our corkscrew. There’s a cheap bottle of wine chilling in our fridge. It was six dollars on the sale rack at the liquor store across the street, but I’ve made a point of becoming friendly with the owner, so he gave it to me for five. Caroline finds the corkscrew, opens the bottle, and pours the wine into two glass ice cream goblets since neither of us has run the dishwasher lately. She hands me a goblet and I tell her all about my day.
“So, I need your help with Tinder,” I announce.
Caroline is single. You know how everyone on Sex and the City and Friends and Seinfeld dated someone new every week? She does that, too, because none of them ever stick. She’ll go out with almost anyone who asks because she thinks dating is a numbers game: the more dudes she dates, the more likely she is to find a relationship. But in practice, that doesn’t work out. It just means she goes out with a lot of losers with commitment issues. In the four years I’ve known her, she’s never had a boyfriend—just dozens of failed dates and a self-diagnosed case of carpal tunnel syndrome from swiping through apps.
“What do you mean, you need help?”
“Well, I found one guy in the database. But I need another.”
“Are you telling me you’re getting paid to swipe through dudes?”
“Technically, yes.”
Her jaw drops. “I could be a gazillionaire by now! How is that fair?”
“Caroline, you are a gazillionaire. Let the little people have a slice of the pie, too.”
She starts to stammer out a response, but stops. Her parents are both lawyers who put $2,000 into her checking account every month to cover her “living expenses.” (Living expenses, according to Caroline, include things like toilet paper, coffee, and the fur sandals Rihanna once wore on a yacht.) She curls her long blond braid around her fingers and mumbles, “Fine, give me your phone.”
Caroline thinks for a moment, types something out, then hands my phone back to me. She shows me the pithy tagline she’s written under my photos: “I don’t want no scrubs.” A TLC reference.
“Seriously?”
“Trust me.”
We adjust my settings to find men in Mindy’s age range, and then I watch Caroline swipe left on one, two, three, six, twelve guys in a row. She barely registers each guy’s face before she makes her decision. She’s good at this. Too good, almost, after years on the app.
“Okay, your turn. Swipe right on the guys you like, left on the guys you don’t.”
I swipe right on the guy in the beanie, left on the guy in the snapback, hard left on the guy whose only photo is a faceless, shirtless selfie in a scummy bathroom mirror. I haven’t even finished my first goblet of wine and I’m already drunk on power thanks to Tinder. I keep swiping until I stumble across a gleaming specimen: Adam, thirty-three. That makes him too old for me, but it’s fine, since he’s not actually for me.
Adam has a mess of short, dark curls and a five o’clock shadow. In his photo, he’s looking up over the top of an actual printed newspaper, eyebrow cocked, like someone caught him off guard. I tap open the rest of his profile. “I’m an editor at Esquire by day and I’m working on a novel by night,” he wrote. “Intelligence is sexy, chivalry isn’t dead. Hope you like the southern twang. 6'3".” That’s it. I scroll through the rest of his pictures—one of him hiking in the woods, a photo with his tiny, elderly grandmother, and another with his arm draped around a girl in a clingy white sundress that makes me jealous in a way I can’t explain. I’m smitten. The combination of his hair, his eyes, and the fact that his name is Adam makes me think he’s Jewish. I swipe right.
“It’s a match!” Tinder announces, our two faces flooding the screen. I get why single people are addicted to this. It’s easier to order a boyfriend than it is to Seamless a pizza.
Caroline peers over the screen. “Congrats! He’s cute,” she says. “Maybe more your type than mine, but cute.”
Given her track record, that’s a good thing. I refill our goblets with more wine and we swipe on Tinder for a while, making fun of the worst profiles. It’s like a sad version of Whac-A-Mole—just when you think you’ve found the most depressing or poorly written profile, another one pops up.
“You should message Adam,” Caroline finally declares. “He’s your best bet.”
“I don’t know. The database is one thing . . .
I don’t know how to talk to people on these apps.”
“That’s dumb. You should talk to him.”
I struggle to come up with a response. “Girls never send the first message, though, do they?”
Caroline grabs the phone, rereads his line, “Intelligence is sexy, chivalry isn’t dead,” and types out a response. She hits send with a flourish.
“There!”
“Wait!” I yelp, grabbing the phone. “What did you say to him?”
You say chivalry isn’t dead? I don’t believe you. I’m Sasha—nice to meet you.
Ughhhhh.
“Caroline, now he thinks I’m hitting on him. That’s not how you’re supposed to message potential matches.”
She blanches. “I’m sorry, did I fuck that up?”
I’m not sure.
I reread her message. It’s not bad. If I’m going to be a matchmaker, I can’t sit around all day waiting for men to talk to me—I should be putting myself (really, my clients) out there, even if the prospect of that makes my skin crawl. If (when?) Adam writes back, I’ll let him know the deal with Bliss. But for now, there’s nothing I can do.
Two Broad City episodes, two goblets of wine, and a handful of obscene Tinder messages from horny guys later, it’s time to celebrate my entrance into the world of employed people with a dinner at Hotel Tortuga, my very favorite restaurant in the world. The guest list is small: Caroline, Jonathan, his sister (and my friend) Mary-Kate, and her fiancé, Toby. Tortuga is not a hotel at all, but rather a hole-in-the-wall Mexican place near Union Square that’s almost solely to blame for the thirteen pounds I gained freshman year. The restaurant is simultaneously bright and a little dingy, with snug booths, a tropical seascape painted on one wall, the others papered with crayon drawings, and sticky red residue on the tables from spilled frozen sangria. When Caroline and I breeze in, we spot Mary-Kate hunched over her phone in the corner of the back booth. Our usual spot. Toby has one arm slung around her shoulders.
“Hey!” I lean down to give them both hugs. Caroline and I slide into the booth across from them. Mary-Kate doesn’t look up from frowning at her screen. “What’s wrong? You look upset.”
“No, I’m fine. My work wife and I are making fun of our intern. We had to hire her because she’s the editor in chief’s niece, but her outfits are truly tragic. Think 2008 Kim Kardashian.”
I can’t fathom anyone wearing that much leopard print these days. “That’s terrible.”
Mary-Kate is the social media editor for Glamour.com, which means she knows how to make a meme go viral, but has not sustained a full conversation without checking Twitter since she was hired three years ago. She has a trendy long bob tousled just so, crisp red lipstick, and pristine cuticles. Today, she’s wearing a royal blue dress that brings out her eyes. Most New Yorkers wear only black, myself included, but Mary-Kate’s philosophy is that all black is for lazy people. She has no problem telling me this. We’ve been close ever since we first met, when she visited Jonathan in Paris during our semester abroad. Mary-Kate and Toby are getting married this summer. I’m a bridesmaid.
Toby flags down the waitress. “Could we have another bowl of crisps, please? Thanks, love.”
“Crisps, please?” Caroline mimics his accent. He’s British. Some people have all the luck.
“Chips,” Mary-Kate tells the waitress.
I’ve always liked Toby. I’ve always felt a kind of kinship with him because we both have more or less the same goal: to marry into the Colton family. So far, he’s doing a better job than I am; he popped the question last year. Toby’s also far cooler than I am. He’s the founder of Rolodix, an app that allows serial daters to input biographical information and photos for each of their suitors, lovers, and Tinder matches, Rolodex-style, to share with their friends. (Even I used it when I couldn’t remember if Evan was the chef who made Caroline a pork roast or the trust fund baby/aspiring director. Turns out he was neither—he was the scruffy guy who invited her to his improv comedy show, which, spoiler alert, was not funny at all.) Not only is Toby making a pile of money off of it, but GQ called him “the hottest brogrammer this side of Silicon Valley” and the Wall Street Journal referred to Rolodix as “clever” and “ideally suited to today’s swipe-heavy dating culture.” I can quote these directly from memory because Mary-Kate does it constantly. Because life is unfair, Toby is also kind of a hunk: six foot one and half black with a razor-sharp jaw. If he weren’t so hideously nice, most people would probably hate him out of jealousy.
Our phones all light up at the same time with a text from Jonathan: “Running 15 minutes late, be there soon.”
“Duh,” Mary-Kate says, rolling her eyes.
She brushes her hair to the side with her left hand, which she does a lot these days—ever since she got engaged. I know people have tics. Fine. But I never saw her fiddle with her hair so often until there was a two-carat, round-cut Anna Sheffield diamond with a pavé band attached to her hand.
“Soooo, tell us about your first day on the job!” Mary-Kate says, ladling us each a glass of frozen margarita from a pitcher. Tortuga’s margs are famously lethal.
“Yeah, how’d it go?” Toby echoes.
“Wait for Jonathan,” I say. “I want him to get here first.”
Jonathan arrives eventually, dropping his Goldman Sachs duffel bag on the floor. I get up to kiss him, breathing in whatever makes him him. He smells like sea-salt cologne and office supplies.
“Sorry I’m running late. Mitch needed me to revise the presentation for a deal today. He said it only needed a few tweaks, but you know that means—”
“A lot of tweaks,” I finish.
It comes down to this: Jonathan is normal. Better than normal—privileged. He grew up eating pancakes from scratch for breakfast, skiing on the weekends, and wearing Abercrombie & Fitch without caring what was on the price tag. He played lacrosse in high school and went to Columbia because his father did. He was always popular, so he was free to indulge his nerdiest hobbies without fear of judgment: collecting 1970s comic books in high school, joining the trivia team in college. He never had to study sitcoms to understand how regular families communicate or watch the cool girls, hawk-eyed, across the elementary school cafeteria to know what foods were okay to eat for lunch. (Apparently, borscht wasn’t cool. My bad.) I crave his easy normalcy the way that addicts crave heroin. And right here is six feet of an exemplary all-American man, ready for me to observe his habits and learn which movies are supposed to induce nostalgia in me and how to use “summer” as a verb.
Jonathan slides into the booth next to me. “How was your first day?” he asks, squeezing my thigh.
I swallow a slurp of margarita. “It’s insane. I can’t believe I’m getting paid to do this. I just hung out with my first client, Mindy, who’s actually really awesome, and then I looked for guys she could date.”
Here’s the part I can’t say in front of Caroline: the job reminds me how lucky I am to be happily settled into a serious relationship.
Mary-Kate squeals and begins to bombard me with questions: How does matchmaking work? Do I have any other clients? Can I find her single bridesmaid a date to her wedding?
“No, set me up first!” Caroline says.
“You don’t even need any help,” I say.
Caroline contorts her face into a look of mock confusion. “But you’re here with your boyfriend, and Mary-Kate’s here with Toby, and—” She hoists herself up onto her knees and swivels to peer around the restaurant. “Hold on a sec, I don’t see my boyfriend anywhere. Do you see him?”
“Fine, Caroline first!”
I fill Jonathan, Mary-Kate, and Toby in on meeting Mindy and Bliss’s database, and how I’ve already scheduled coffee with Mark for tomorrow.
“And I got her set up on Tinder,” Caroline says. Then she leans across me to talk to Jonathan. “Sorry, dude.”
“Hey, as long as they know she’s taken, I don’t have a problem with it.” Jonathan shrugs.
&nb
sp; “Are you sure?” I ask.
I feel weird putting him in this position. I don’t know anyone whose job requires them to download dating apps. Jonathan and I talked about it after my training session, and he said it wasn’t a big deal, but I still worry it bothers him.
He stretches his arm around me. “Of course. I know you’re my girl.”
The words “my girl” still turn my insides warm and mushy. I love him.
“Sasha, I’m really happy for you. I am,” Mary-Kate begins, which I know must be followed by a massive “but.” “But don’t you need experience for something like matchmaking? Why would anyone who wants to get married hire an unmarried twenty-two-year-old matchmaker?”
“They hire young matchmakers on purpose. My boss said she was looking for someone who had actually had sex in the past decade.”
Jonathan bites off half the chip he’s holding with a loud, smug snap.
Mary-Kate makes a sour face. “Ew.”
“But she’s right, though, babe,” Jonathan says. “I mean, before me, you had hardly dated anyone.”
“That’s not true. I dated people.”
“Sure, just no one tolerable,” Caroline points out.
“Look, our food’s here,” Toby says, pushing the margaritas out of the way so the waitress can set down the platters of burritos and quesadillas.
It’s too late to worry about my qualifications for matchmaking. I’ll do whatever it takes—I have to.
— Chapter 4 —
We splinter off after dinner. Mary-Kate and Toby head home to binge-watch Netflix, or whatever it is engaged couples do on Friday nights. Caroline and I swing by our apartment to change. There’s a birthday party tonight for a girl we knew in college, but that’s not why we’re going out. We’re going because it’s a rooftop party on the Lower East Side, which means we’re guaranteed breathtaking views of the city, cool-girl fashion eye candy, and the heady feeling of a New York summer night done right. Jonathan darted out after dinner to finish up “just one or two small things” at the office, but promised he’d meet us at the party later if he can.
Playing with Matches Page 3