The Dating Game

by Kiley Roache

  The Social Network gets a romantic twist in this fresh and engaging new read from the author of Frat Girl, Kiley Roache. Experience the whirlwind ups and downs of college life in this authentic and entertaining new novel!

  When a notoriously difficult class for future entrepreneurs leads to three freshmen developing the next “it” app for dating on college campuses, all hell breaks loose...

  Type A control freak Sara lives by her color-coordinated Post-it notes.

  Rich boy Braden wants out from under his billionaire father’s thumb.

  Scholarship student Roberto can’t afford for his grades to drop.

  When the three are forced to work together in one of the university’s most difficult classes, tension rises to the breaking point...until, shockingly, the silly dating app they create proves to be the most viable project in class. Late nights of app development, interest from investors and unexpected romance are woven into a true-to-life college drama that explores what it means to really connect online and IRL.

  Can three freshmen taking the university’s toughest class handle more success than most get in a lifetime?

  Praise for Kiley Roache’s debut novel, Frat Girl

  “Refreshingly honest and intelligently written, Frat Girl is filled with relevant topics and written by an author to watch!”

  —New York Times and USA TODAY bestselling author Julie Cross

  “A sweet, subversive deconstruction of frats and feminism, Kiley Roache’s debut will have readers sighing and snorting at Cassie’s adventure into fraternity life and finding her own truth.”

  —Christa Desir, award-winning author of Bleed Like Me and Other Broken Things

  Books by Kiley Roache

  Frat Girl

  The Dating Game

  KILEY ROACHE

  THE DATING GAME

  Kiley Roache graduated from the college that created Snapchat, Google, Twitter and Instagram, but she spent most of her time there writing words rather than code. She authored this book and her first novel, Frat Girl, while she was still an undergrad at Stanford. She is a journalist who has written for the Chicago Tribune’s teen publication, the San Francisco Chronicle, Huffington Post Teen, nytimes.com and The Wall Street Journal. She is originally from Chicago, but now lives in New York City, where she studies journalism at Columbia University and spends her free time searching for the best bagel in town. And yes, sometimes swiping through dating apps. Visit Kiley online at kileyroache.com and follow her on Instagram and Twitter, @kileyroache.

  For my sister.

  Contents

  Part One

  Chapter One

  Chapter Two

  Chapter Three

  Chapter Four

  Chapter Five

  Chapter Six

  Chapter Seven

  Chapter Eight

  Chapter Nine

  Part Two

  Chapter Ten

  Chapter Eleven

  Chapter Twelve

  Chapter Thirteen

  Chapter Fourteen

  Chapter Fifteen

  Chapter Sixteen

  Chapter Seventeen

  Chapter Eighteen

  Chapter Nineteen

  Chapter Twenty

  Chapter Twenty-One

  Part Three

  Chapter Twenty-Two

  Chapter Twenty-Three

  Chapter Twenty-Four

  Chapter Twenty-Five

  Chapter Twenty-Six

  Chapter Twenty-Seven

  Chapter Twenty-Eight

  Chapter Twenty-Nine

  Chapter Thirty

  Chapter Thirty-One

  Chapter Thirty-Two

  Chapter Thirty-Three

  Part Four

  Chapter Thirty-Four

  Chapter Thirty-Five

  Chapter Thirty-Six

  Chapter Thirty-Seven

  Chapter Thirty-Eight

  Chapter Thirty-Nine

  Chapter Forty

  Chapter Forty-One

  Epilogue

  Author’s Note

  Acknowledgments

  Part One

  Gamification

  Chapter One

  Roberto

  Is there a fun fact about me that might impress a billionaire? This is what I wonder as I sit in the first lecture for Professor Dustin Thomas’s class. Which is actually my first college class, ever. At the beginning of the hour, he asked the class to go around and say your name and a little bit about yourself.

  As the minutes click by and the chance to speak snakes through the room, getting closer to me, I have only a big, fat blank.

  I’m beginning to think I might be in over my head. That applying for this class might have been a mistake. That applying for this school might have been a mistake.

  The question has reached the guy sitting in front of me. He stands up, introduces himself as Joe. He takes a second to mention the place he was born before moving on to all the places he has interned.

  I can’t blame him. If I wasn’t a freshman whose job experience included mowing lawns, scooping ice cream and sorting the book drop at the library, I would probably do the same. When else are you gonna find yourself in the presence of Dustin Thomas?

  After all, he is not just a billionaire, but a billionaire-maker. A venture capitalist, Thomas was an early investor in companies like Instafriend. Yep, that Instafriend. He’s the guy who helped turn a group of kids working out of a dorm room into tycoons.

  Now he’s pretty much retired and tells all the tech blogs that he just wants to teach one class a year about the work ethic required for entrepreneurship, and research how the study of human behavior can be harnessed for marketing.

  We are all here pretending we care about those topics so that we can be in the same room as him. And maybe be around when he decides to come out of retirement.

  The next person stands up. “Hi, I’m Megan, and I went to a little school in Cambridge, Massachusetts, before coming here to Warren University to get my master’s.” She winks, and points to her Harvard crew sweatshirt, just in case she was so coy that we didn’t know what she meant.

  I’ve seen one-upmanship like this all throughout orientation, and it’s not that I don’t find it irritating; it’s just that I don’t have time to care. Of course, I want to grab some of these kids by the shoulders, tell them how ridiculous it is to debate whether Exeter is better than Andover when so many schools in the US—including the one I went to for K-8—are straining to afford books and basic supplies. But I can’t exactly do that.

  If I want to carve out a piece of that golden pie for myself, and even more important, for my family, I know I need to operate in this world under their rules. In my notebook, I jot down a few things I could share, like my magnet school acceptance and the community service recognition I got at high school gradation. I stare down at the paper. Neither seems like enough.

  “And, what was the last thing I was supposed to say—a fun fact?” Megan asks, tapping her chin. “Um, well last summer I received the award for best intern when I worked at Apple, so that was pretty fun!”

  A small laugh erupts two seats over, but it is quickly concealed by a fake cough.

  I look down my row. The guy who laughed reaches under his seat for a water bottle. Maybe to cover up more laughter, or maybe because he’s hungover. After all, he’s wearing sunglasses and a baseball cap inside the auditorium.

  He slips the bottle into the side pocket of a backpack bearing the large seal of what I assume was his high school. The logo incl
udes a gold shield and a founding date that means his school is older than the country. Fancy.

  He leans back and props his feet on the chair in front of him. This guy is either so rich that he doesn’t need this class, or straight up stupid.

  “Hi!” A cute blonde shoots up like her second-row chair is on fire. She straightens her shoulders. “My name is Sara Jones, and I’m a freshman studying computer science.”

  “Great,” the lounging dude mutters. “Hermione Granger is in this class.”

  I’m not sure if he’s talking to me, but I kind of hope he’s not.

  I am actually grateful for Sara, the only other freshman who has stood up so far. At this point, it seems that most of the students are upperclassmen, if not graduate students. I am trying my best to remember everything my high school guidance counselor told me about not letting anyone make me feel like I don’t deserve to be here because of my age or where I come from. It’s a bit easier to do so knowing I’m not the only freshman. In that small way, I am not alone.

  Sara collapses into her seat, as if that sentence exhausted her.

  Professor Thomas gestures for her to continue. But Sara just looks from side to side.

  “What?” she says, her voice even higher than before.

  “Your fun fact,” the dude next to me yells, still practically draped across the chairs. He looks like a heckler at a comedy show.

  “Oh.” She stands again and straightens her skirt with shaking hands. “I, uh...”

  My heart sinks to my stomach on this girl’s behalf. I know what it’s like to feel intimidated, like everyone around you is summing you up, just waiting to academically eat you alive. I’ve been in rooms where I am the only kid who looks like me, the only one who speaks two languages at home, the kid who’s “only” here because of a scholarship, who’s from that neighborhood your parents tell you to avoid when you drive back from the airport. People find this out about you, and it’s like they smell blood in the water.

  Of course, I have no idea what this girl’s story is, or why she looks like she might cry in the middle of this class right now. But I feel for that isolation.

  “Um...today I learned that twin sheets do not fit on a twin extra-long mattresses.” She forces a smile and sits down as a few people laugh, including, thankfully, Professor Thomas, who musters a chuckle.

  I decide I like this strategy, to say something that isn’t a thinly veiled résumé check. When it gets around to me I say, “Hi, my name is Roberto, but most people call me Robbie. I am a freshman and will either major in computer science or electrical engineering. I haven’t decided yet. And my fun fact is when the last Harry Potter book came out, I stayed up all night and read it in two days.”

  I sit back down. I guess that still was kind of a humble brag, depending on how you look at it. But it’s from elementary school so I think it’s okay.

  When the introductions are over, Professor Thomas moves his coffee cup before sitting on the desk at the front of the room, a causal gesture at odds with the fiercely competitive atmosphere in the auditorium.

  “People often ask me what makes an entrepreneur,” he begins. “What sets aside the man who has the type of success where he enters an industry, climbs to the mid or upper-mid level and retires fine, with the kind of mind that alters an industry completely, leaving a mark for decades after he’s gone? The kind of mind that takes an idea born in a garage and turns it into the kind of thing my colleagues and I trip over each other to invest in?”

  At the HP Garage reference, half the room scoots farther up in their seats. It’s Silicon Valley, after all.

  “The answer is failure.” He pauses dramatically. “Sure, all successful people experience setbacks. They are passed over for a promotion or don’t get a job. But some successful businessmen can make it through good careers without experiencing terrible failure. Catastrophic failure—down in the gutter, debt piling up, not sure if you can keep the lights on another week failure—that is where an entrepreneur lives. If you are innovating, you are coming up with an idea that either people have tried and failed to succeed with before you, or is so ridiculous that no human has even thought of it before. You will be laughed out of rooms. You will spend hours, if not months, building prototypes that fall apart.

  “You joined this class because you want to be entrepreneurs. But from what I could gather from the...illustrious introductions you all just gave, very few of you have ever failed. You’ve worked incredibly hard and jumped through the right hoops, checked the right boxes. But the thing about innovating is that you will work one-hundred-hour weeks, not for the six-figure checks you’d get if you went into established industry, but for doors to be slammed in your face. You don’t work hard and then succeed. You work hard and then you fail, you fail and then you fail again. And then, finally, just when you want to give up for the three-hundredth time, you succeed more than you could ever imagine.

  “I teach for this school and I make this class application-only because I don’t waste my time with students who aren’t worth it. I ensure that those who make it through my class leave having gained something, and I advocate passionately for my past students. But if they don’t have what it takes—the intelligence and technical skill, yes, but also the willingness to fail—they don’t get to have me as their teacher. You proved you had the first two in your application. Now let’s see the latter.” The professor stands up and steps away from his desk. “Over the next three weeks, you will form groups of three or four and come up with a product that you will pitch to me, as if I were a VC, the next time our class meets.”

  A murmur ripples through the room. The professor continues, unfazed. “There are no well-worn paths here. There are no test prep books or study guides for innovation. You must go forward, maybe for the first time in your life, with no clear direction set out for you. You can reach out to mentors, read books and do research, but in the middle of the night, when part of your project isn’t working, you have just you and your equally blind teammates to count on. With that in mind, I hope you choose wisely.” He walks behind the desk and picks up his briefcase.

  “I expect you to sink, but try to swim. This is, after all, worth a third of your grade for the class. Go ahead and get working. I’ll see you in a month.” With that, he walks out the door in the front of the classroom.

  The lazy dude sits up with a start at the sound of the closing door.

  The rest of the class is in stunned silence.

  A few rows up, Sara stands and looks around, a stricken expression on her face.

  People begin to murmur to those around them, and there’s an awkward laugh here, and a “Nice to meet you” there. Students start to stand and ask about being in the same group, for clearly there’s nothing else to do but to assume Professor Thomas was being serious.

  More and more students venture from their seats. They reach a critical mass and rapidly it seems like the whole room is power walking, introducing, teaming up and swarming together. They move like a school of fish rushing upstream, and I feel like a tiny minnow being tossed around.

  “Are you in the MBA program?” A man in a suit pushes through two young women tyring to reach another guy wearing a tie.

  “Who has a master’s?” a brunette woman yells into the crowd.

  My mouth feels like sandpaper. I slide my notebook into my backpack and reach for my water.

  Down the aisle, the lazy dude stands and turns to the row behind us.

  “Hi, Braden Hart.” He reaches out his hand to a bespectacled, white, hipster-looking guy, who has teamed up with an olive-skinned, preppy-dressed girl in the row behind us.

  “How many languages do you know?” the guy asks, skipping any introduction.

  “Three.” Braden crosses his arms with confidence.

  The hipster guy raises his eyebrows. “Which ones?”

  “French, Span—”

&nb
sp; “Coding languages, you idiot,” the girl snaps. The hipster guy just blinks at Braden.

  “Oh.” Braden steps backward. “I don’t really...uh...”

  The hipster guy scoffs. “Get out of my face.” He holds up a hand.

  I slide out of the row and walk up to a group of older-looking students. I could’ve tried for the group behind me—I do know three coding languages—but I don’t want to work with anyone that rude.

  A girl with a pink stripe in her hair smiles as I walk up.

  “Hi, I’m Roberto.” I clear my throat. “Robbie,” I add.

  “Hey, I’m Rebecca,” she says.

  “Chad.” The guy reaches for my hand, and as I shake it I can’t help but notice he’s wearing both twine bracelets and a Rolex.

  They ask me about my skills, and I nod along as I walk through my experience. They seem less interested when I mention my passion for social impact, but they don’t tell me to get lost or anything.

  “Do you have any experience at a start-up?” Rebecca asks.

  I start to answer, but my attention is pulled away. On the other side of the room, Sara is speed walking from group to group, her heels clicking. She barely makes it a few syllables through her high-pitched introduction before she is turned away. And turned away. And turned away again.

  I bring my attention back to the people in front of me.

  “I don’t, but I was in the prebusiness club at my high school,” I say.

  Rebecca nods. She leans over to whisper to Chad.

  Around us, groups lock together and push upstream toward the exit like mini tornados, probably trying to get from the classroom to the library without losing any members.

  “We’re really sorry, but my thesis coadvisees want to join and that would make us five,” Chad says. “You’re the only undergrad, so it’s only fair if you’re the one we cut.”

  “Sorry!” Rebecca shrugs sheepishly.

  I nod and say thanks anyway. Looking around the room, I count group members, looking for any that have an opening. But in a flurry of business cards and iPhones, the room has thinned. Just as quickly as it exploded with sound, the auditorium is quiet. Practically empty.