by Lila Monroe
We head down the block to our usual brunch spot and grab a table in the window.
“… So I know you can’t get much more off-Broadway than that,” Jill says. “But maybe the director can pull it all together in time.”
“We’d love to come see the play,” Tessa jumps in. “Right, McKenna?”
“Of course.” I give Jill a thumbs-up. We always go to her plays, as terrible as those off-off-off-Broadway productions usually are. Jill is always as brilliant as the script and the directing allow. It really is ridiculous that Broadway hasn’t let her in yet.
“Enough about me!” Jill takes a sip of mimosa. “How’s pitching? When can I start shouting about that app from the rooftops?”
I cringe, and Tessa pats my arm. “I think that’s a bit of a sore subject.”
Jill’s face falls. “Oh, honey.”
“It’s not that I can’t take some criticism. It’s just—” I run my hands back through my hair, frowning at the menu. “Maybe, if I was sure the problem was I didn’t have a solid enough product or pitch, it wouldn’t be so frustrating. That would be something I could fix. But half of these guys take the meeting as an opening to hit on me. And the other half stop listening before I get one sentence in and make a bunch of comments that show they can’t imagine I have any clue how to even start up a computer because I’m a woman.”
Jill winces. “That really sucks, Mac.”
I nod. “The worst part is, some of them, without even listening to me, go off on a tangent about Shelby Summers. Shelby.” I wince at the name. “They think if I want to get this app made, I should have a ‘platform’ like she does. You know, a bestselling self-help book that tells women the only way to land a man is to pander to chauvinistic bullshit all day?”
It probably wouldn’t sting so much if I didn’t know Shelby personally. We went to college together, did our theses about the psychology of relationships under the same supervisor. I watched firsthand as my knuckling down on the work got overlooked every time she fluttered her eyelashes at one of the male profs.
That’s the Shelby approach to dating in a nutshell. Play hard to get, flirt and back off to make him chase, cater to every physical whim he has. Hell, dye your hair blonde if that’s what he goes for, who cares if it’s 2018, not 1950? And then she has the balls to say it’s all “empowerment” because the women are getting what they want in the end. How can anyone really want a guy who thinks he pretty much owns you? It’s like The Rules 2.0—and a runaway bestseller, of course.
Those fake relationships always end badly anyway. It’s hard to maintain a pretense your whole life. Either your feminine facade will crack and you’ll have to find out your partner isn’t into the real you, or you’ll end up miserable suppressing who you really are. What’s the point of being with someone if it’s not you who’s with them? That’s part of the whole Perfect Match algorithm: making sure people are matched up for who they are, not who they’re pretending to be.
I don’t say all that, because Tessa and Jill have listened to me rant about Shelby too many times already.
“I don’t see how the app isn’t your platform,” Tessa says. “You can back up everything you claim it does. Why doesn’t that count?”
I shrug. “They want me to be some big TV personality, I guess. Going on talk shows, writing books all about getting a man, like she does. But somehow I don’t think they expect the same thing from every guy who comes to them looking for funding. But you know what, I’m just going to keep at it. I’m not quitting now.”
“Atta girl.” Tessa clinks her glass to mine in a toast, and I quickly change the subject before I sink back into failure and gloom. I almost manage to forget about work stress as we get chatting about Jill’s Tom Cruise sighting earlier in the week—“The camera adds two feet”—and Tessa’s trip with her boyfriend Doug to visit his new niece.
“It was so sweet seeing him holding her,” she gushes. “I really think he might be getting into that settling-down mindset now.”
Jill and I exchange a glance. When Tessa isn’t around, we refer to Doug as “Drippy Doug.” He’s so not worthy of Tessa’s smarts or her kindness. Bland as white bread, with a stick up his ass, too. I’ve tried to be friendly every time I’ve bumped into them in the hall, but he always seems to think his phone is worthy of more attention than his girlfriend or her friends. I know how he sounds when he’s climaxing—thank you, thin apartment walls!—but I’m pretty sure he still doesn’t know my name.
Sometimes, I wish life worked like one of the rom coms I secretly love. A little cheesy, sure, but sweet and heartfelt too. And everyone gets what they deserve. Tessa would be played by a ‘90s-era Julia Roberts, and Drippy Doug would be kicked to the curb in the first act, while she gets swept off her feet by someone who really deserves her.
I like to think Perfect Match will get real life a little closer to that ideal. I’m dying to see who Tessa could match with—almost anyone would be better than Doug. But friendship needs respect and boundaries. Until she comes to her senses, we have to keep our mouths shut.
As we dig into brunch, the couple at the table next to us gets up. The wife leaves the Saturday paper behind. It must be the business section on top, because Tessa glances over and makes an exclamation. She grabs the paper.
“It’s Mr. Sexy Ass!”
Jack Callahan’s handsome face smirks at me from the article’s photo, his blue eyes as striking as ever.
“Who’s he flashing this week?” Jill giggles, but I sigh.
“I really thought I had him for a minute there. But no dice. He dismissed the whole idea. All the risks he’s willing to take, and the idea of measuring compatibility is just too much for him?” I shake my head.
“Maybe you should try again,” Tessa says. “Now that he’s had some time for the pitch to sink in.”
“Yeah,” Jill agrees. “Show that guy he can’t just ignore you.”
“I’ve tried,” I say. A few days ago I had a similar idea, but when I called into his office, whoever picked up told me he was booked solid for the next few months now. Of course, I have no idea whether that’s true or he told them he never wanted to see McKenna Delaney again. “I can’t even get an appointment with him now. Not after that locker-room stunt I pulled.”
“So catch him somewhere else. Somewhere better for talking than the climbing gym—with more clothes on.” Jill winks at me. “Those playboy types are always out on the town. You should find out where he goes for drinks. Do a little schmoozing.”
Find out where he goes for drinks. An idea blinks on in my head like a cartoon light bulb. Wait a sec. I can do even better than finding out. A smile slides across my face.
“You,” I tell Jill, “are absolutely brilliant.”
“So can you do it?” I ask eagerly.
“Well, sure. Piece of cake.” Warren looks from me to his laptop and back again. His curly brown hair is gelled back, and he’s wearing contacts instead of his usual glasses, which makes me suspect my urgent weekend call interrupted one of his Skype dates with his “girlfriend” in Berlin. My bad. But he did rush straight over to the office, so they couldn’t have been doing anything too, er, intimate. However exactly that works when you only interact via computer screen.
“Just to be clear,” he continues. “You’re asking me to hack into one of the biggest dating apps in the world so we can set you up on a date with Jack Callahan?”
“Yes.”
“Oh my God.” Riley beams on my other side, dressed in skin-tight yoga gear. “This is so awesome. And so completely unfair that I can’t Snapchat the whole thing.”
Warren shoots her a look, and she holds up her hands. “I really won’t! I promise. No one will be facing criminal charges just for the followers. But we would get so much attention. I’m just saying.”
“And you’re okay with us using your photos?” I say to her. “He’d never swipe right for me, not after our last encounter.”
“Sure, sure.” She grins. “Al
l in the name of getting that funding—and my raise. I’ll find my best pics.”
She starts skimming through her phone, and Warren leans closer to his laptop. “Just give me a few minutes,” he says.
I fully believe he can hack into one of the biggest dating apps in the world in just a few minutes. Warren and I met after he hacked a major tech company I was consulting for—just for the LOLZ. He left all the data untouched while sticking animated kitten gifs all over the website. Skill plus restraint plus a sense of humor—not an easy combo to find. So, I talked the tech company out of charging him, then promptly hired him. As long as I keep the kitchenette full of caffeine drinks and Red Vines candy, and don’t make him work before noon, he’s happy.
“Okay, we’re in,” Warren says, literally three minutes later. I let out a little cheer. “Send those photos over, Riley.”
“Here they come.”
She sends over a variety of cute blonde bikini pics: perfect playboy bait. A slightly maniacal light comes into Warren’s eyes as he constructs my fake profile, but it’s kind of endearing. At least, I’d like to think so. And I’m not at all trying to justify asking my employees to hack a website to con a guy into meeting me for drinks.
Then I have an even more devious thought.
“Wait!” I tell him. “If you can hack the system to put me in front of him … can you do it to show him other options, too?”
Riley looks confused. “What are you thinking?”
“Well … I want to convince him to give Perfect Match a shot, so why not show him the … limitations of his existing programs?
Warren laughs. “I see what you mean. Let’s see …” He clicks through the profiles on screen, his grin getting wider. “Callahan is going to have a great time with these lovely ladies …”
“Perfect.” I grin. “Give him a few not-so-dream dates, and he’ll be putty in my hands.”
I hope.
“All set,” Warren says. “You sure about this, boss?”
“I’m sure.” I feel a flutter of nerves. This is absolutely my last shot to get Maverick Capital on board, and I can’t screw it up. “Jack Callahan won’t know what hit him.”
4
Jack
“… So that’s when I became a tattoo artist. There’s something about like, drawing blood that really gets me off. Do you have any ink?”
The woman across from me has a terrifying glint in her eye, like she’s about to pull a tattoo gun from her purse and pin me down on the bar right there.
“Actually, no,” I reply carefully. She was hot on her RightNow profile, but she didn’t say anything about a blood fetish. “I don’t.”
The glint gets brighter. “Virgin skin!” she exclaims. “You gotta come by the shop. I see you with like, dragon wings. It would only take twenty hours, but the pain is the fun part, right?”
I clear my throat and pretend to check my phone. There’s hot, and then there’s a felony waiting to happen. “This has been lovely, Mona—”
“Moira.”
“—but I have to get going. Thanks for the drink.”
I text my driver to meet me in front of the bar, and make a polite retreat-slash-escape.
“Back to your apartment?” Henri asks from the front seat.
“Hold that thought,” I say. It’s still early, which means there’s more than enough time to find different company for the night. Not that I’ve had the best record. For the past week, every woman I’ve met has turned out to be … well, utterly insane would be the polite way of putting it. Sure, their profiles were all attractive, but the minute I got them alone, they flipped a switch. First, there was the amateur masseuse, who almost broke my back. Then there was the blonde cutie who invited me back to her place, only to reveal a bedroom piled high with creepy glass-eyed dolls. Last night, I barely escaped from a woman who’s four ex-husbands had all died under suspicious circumstances—But luckily, they’d all updated their wills to leave me their assets—and finally, we have tonight’s charming entertainment: the serial killer Kat von D.
I open the app, determined to be more selective this time. But luckily, the first face that pops up is a 10: blonde, cute, perky, and twenty-two. She even lists her hobbies as baking and amateur gymnastics.
Just my type.
I swipe right and shoot her a quick message, and she immediately replies.
Just finishing dinner with friends in Soho. Fancy a nightcap?
I type back. Zero Black, see you there.
I direct Henri to the restaurant and use the ride to scan through work emails and messages. It may be Friday night, but I didn’t get where I am today without taking care of business. I find a couple of issues with the acquisition contract for one of my new companies, and tell my assistant to set a meeting with legal first thing Monday morning. By the time we pull up, I’ve saved two million dollars in royalty fees, short-sold some stock in an overvalued company, and confirmed a restructuring that will revitalize a manufacturing plant in Idaho.
And they say taking the subway is economical.
I walk into the restaurant feeling ready to celebrate. Hopefully, with the gymnast blonde, back at my place: clothing optional. I check the app again for her photo, then scan the packed room, looking for her.
I feel a tap on my shoulder. I turn, ready to flash her my best seductive smile, then stop.
“Looking for someone?”
It’s not the blonde. Not even close. It’s the smart-ass brunette who stalked me to my gym two weeks ago.
“McKenna Delaney,” she introduces herself again.
“I recall. Look, following me once was charming and persistent,” I say, controlling my annoyance. “Twice is bordering on harassment.”
“I’m not following you,” she says. “I’m your date.”
“No, I’m meeting Andrea. Yea high, perky, loves puppies and …” I trail off. McKenna is still smiling at me, looking smug. “She’s not coming, is she?”
“Afraid not. Why the long face?” she asks. “You could just use your app to find someone else. Or has it not been delivering lately?”
“How do you know—?” I stop, finally putting it together. Her smug grin, the fake profile … the parade of terrible dates I’ve been on this week.
“You set this up,” I say accusingly.
“And?” She shrugs. “You know that saying, ‘All’s fair in love and war’? I think they should probably add business to the list.”
I open my mouth and then close it again. Dammit, but I’m impressed. She would have had to hack into the other app, select women she knew were all wrong for me, and design the fake profile, too.
“How did you know I’d swipe right on your fake profile?” I ask.
She snorts. “Puppies? Baking? Gymnastics? There isn’t a straight guy in Manhattan who wouldn’t swipe for that.”
I narrow my eyes. “Are you saying I’m predictable?”
“No, I’m saying everyone is,” McKenna declares. “At least when it comes to dating. Which is how Perfect Match is going to take over the world. Come on, let’s sit down, have a drink, and talk about this properly. What have you got to lose?”
Not a night of hot, flexible sex—at least, not anymore.
“Fine,” I sigh. “But it’s too loud to think here. Come on.”
I usher her to the member’s-only room in the back—and take a moment to check out the woman who bested me. This time, at least. Last time we met, she was wearing some sensible suit, but tonight, she’s in a sexy pencil skirt that hugs her curves just right. With those square, black-rimmed glasses balanced on her nose, she looks like a stern, sexy librarian.
I always had a thing for librarians.
In the back, I nod to the doorman guarding an unmarked door. He opens it for us, and I lead McKenna into the private club. You need to play in the big leagues to drink back here: Fortune 500 CEOs, hot start-up entrepreneurs, and the biggest financiers around. Most of the faces are familiar, and I take my time greeting them all, from the
CEO of New York’s biggest financial brokerage, to an international retail baron.
My favorite waiter appears the second we’ve sat down at a booth in the corner. “What can I get for you tonight, Mr. Callahan?”
I skim the wine menu. “Anything special I can get uncorked, Ricky?”
He nods. “There’s a 1985 Cabernet Sauvignon we just got in that I think would suit your tastes.”
“Perfect. I trust your judgment. Bring it over.”
I finally look to McKenna, expecting her to be impressed by the show, but she’s just watching me with a faint smirk on her face. “Are you done?” she asks. “Or do you want to take out your wallet and flash me a stack of hundreds, just so I get the message?”
I narrow my eyes. “For someone who wants a favor, you’re going about it in a funny way.”
Her smile drops. “Shit, you’re right. I’m sorry.”
“No, you’re not, but that’s OK.” The sommelier returns, and I take a sip, tasting the wine before giving a nod of approval. When he’s poured us both a glass and retreated, I settle back and wait for the hard sell.
“So what’s your approach tonight?” I say. “I already told you I don’t believe you can reduce romance to a formula.”
“And that’s totally fine,” McKenna says. Now that I can pay a little more attention, I can see her shifting into business mode. Her back draws a little straighter, her eyes flash with determination. “You don’t have to believe Perfect Match is going to work. You just need to believe that we can convince everyone else it’s going to work.”
I take another sip of wine, getting comfortable. “Go on.”
“You know the value of Tinder, Bumble, all the big dating apps. Anyone who invested in those made a huge return. Finding love is a basic human drive. You give people something that sounds even a little different from what’s already out there, and they’ll jump all over it.”