How to Hack a Heartbreak Read online

  Swipe right for love. Swipe left for disaster.

  By day, Mel Strickland is an underemployed help-desk tech at a start-up incubator, Hatch, where she helps entitled brogrammers—“Hatchlings”—who can’t even fix their own laptops but are apparently the next wave of start-up geniuses. And by night, she goes on bad dates with misbehaving dudes she’s matched with on the ubiquitous dating app Fluttr.

  But after one dick pic too many, Mel has had it. Using her brilliant coding skills, she designs an app of her own, one that allows users to log harassers and abusers in online dating space. It’s called JerkAlert, and it goes viral overnight.

  Mel is suddenly in way over her head. Worse still, her almost-boyfriend, the dreamy Alex Hernandez—the only non-douchey guy at Hatch—has no idea she’s the brains behind the app. Soon, Mel is faced with a terrible choice: one that could destroy her career, love life and friendships, or change her life forever.

  Praise for the novels of Kristin Rockaway

  “Smart, fun, fast-paced. Rockaway seamlessly blends the trials of modern dating with the challenges of being a woman in a male-dominated workplace.”

  —Helen Hoang, author of The Kiss Quotient

  “For everyone who has been wronged in the world of online dating! Revenge is a dish best served digitally in Kristin Rockaway’s book capturing what it’s like to pursue ambition and love in New York City. Snappy pacing, a delightful group of best friends, women innovating in tech and a workplace love interest made this a book I really enjoyed.”

  —Sally Thorne, USA TODAY bestselling author of 99 Percent Mine

  “Rockaway has masterfully painted the current dating landscape so many are navigating these days.”

  —Renée Carlino, USA TODAY bestselling author of Blind Kiss

  “Will have readers laughing and celebrating... Perfect for fans of Doree Shafrir’s Startup and Hannah Orenstein’s Playing with Matches.”

  —Booklist

  “A fun, sexy debut perfect for readers who love exotic settings and a great love story.”

  —Karma Brown, bestselling author, on The Wild Woman’s Guide to Traveling the World

  “Brilliantly navigates one woman’s quest to let go of what is practical to pursue her passion and surrender to her inner dreamer.”

  —Kerry Lonsdale, bestselling author, on The Wild Woman’s Guide to Traveling the World

  “Can a novel be smart and loads of fun? Kristin Rockaway’s debut is proof that it’s possible.”

  —Camille Pagán, bestselling author, on The Wild Woman’s Guide to Traveling the World

  Also by Kristin Rockaway

  The Wild Woman’s Guide to Traveling the World

  How to Hack a Heartbreak

  Kristin Rockaway

  For Emilio.

  I’m grateful the internet brought us together.

  Contents

  Chapter 1

  Chapter 2

  Chapter 3

  Chapter 4

  Chapter 5

  Chapter 6

  Chapter 7

  Chapter 8

  Chapter 9

  Chapter 10

  Chapter 11

  Chapter 12

  Chapter 13

  Chapter 14

  Chapter 15

  Chapter 16

  Chapter 17

  Chapter 18

  Chapter 19

  Chapter 20

  Chapter 21

  Chapter 22

  Chapter 23

  Chapter 24

  Chapter 25

  Chapter 26

  Chapter 27

  Chapter 28

  Chapter 29

  Chapter 30

  Chapter 31

  Epilogue

  Acknowledgments

  1

  Never trust anything you read on the internet.

  It’s sound advice. I’d read it somewhere, possibly on the internet, but I’d never really taken it seriously until the night Brandon, 26, from Brooklyn stood me up.

  According to his bio, Brandon was a “thrill seeker who lived for the moment and loved with abandon,” which should’ve been my first clue that he was full of shit.

  As I sat alone at the bar, staring at the bottom of my empty cocktail glass, I cursed myself for agreeing to this date in the first place. Normally, I’d never waste a Friday night meeting some random guy I matched with on the internet. First dates were reserved for Tuesday or Wednesday nights only, when there was almost always nothing better going on. But when Brandon’s beautiful bearded face slid across my screen asking me to join him for a drink at a bar in the Financial District, I thought there’d be no harm in making an exception to my rule.

  That was a rookie mistake.

  I tapped my phone and stared at the screen. It was 6:18. The last message I’d received from Brandon was at 4:37: meet u @ the barley house @ 6.

  Maybe he was just running late. I messaged him back: Are we still on for tonight? then waited in vain for a response.

  “Another vodka soda?” The bartender whisked my glass away and wiped down the lacquered wood countertop. I had a choice: I could escape now with my dignity and go find Whitney, who was likely tearing it up somewhere on the Lower East Side. Or I could give Brandon from Brooklyn the benefit of the doubt, and nurse another drink while I waited for him to arrive. I swiped through his profile photos and felt giddy at the sight of his pouty lips and deep-set eyes.

  “Sure, I’ll have another.” Yeah, he was probably just running late. After all, this was New York. There were a million obstacles that could be preventing him from getting here on time: train malfunctions, traffic snarls, police investigations shutting down major thoroughfares. I needed to stop being so cynical.

  Still, Whitney’s words echoed in my head: Don’t put all your eggs in one basket. So I fired up the Fluttr app and checked to see if there were any potential love interests in the immediate vicinity.

  Fluttr was the dating app of choice these days. There wasn’t anything particularly special about it—it worked just like every other dating app I’d ever used: post a couple of not-terrible photos. Enter your name, age, and location. Then swipe through a seemingly infinite pool of available men. A left swipe meant no, a right swipe meant yes, and if you swiped right on a guy who swiped right on you, you could message each other through the app. Simple, straightforward, and not at all original, but for some reason, it was hugely popular. There were more people signed up for Fluttr than any other dating app in the city.

  So far, I hadn’t had much luck with it. Most of my matches led to disappointing first dates, endless go-nowhere in-app messaging, or the occasional unsolicited dick pic. But with so many guys to choose from, I was sure Mr. Right was only one swipe away.

  “Here you go.” The bartender set my drink down on a fresh cocktail napkin. The first sip made my head swim. Time to get to swiping.

  Bachelor number one was shirtless. Swipe left.

  Bachelor number two was slamming a beer bong. Swipe left.

  Bachelor number three was sandwiched between two bikini-clad women. Swipe left.

  Finally, hope appeared in the form of Joe, 25, from Murray Hill. Hazel eyes, thick black hair, and the perfect amount of five o’clock shadow. No booze or half-naked babes to be seen. And he was wearing a sweater. Swipe right.

  Digital confetti rained down from the top of my screen. Fluttr proclaimed: It’s a match!

  “Melanie?”

  Aha! My patience and faith were rewarded. I quickly switched off my phone and swiv
eled toward the sound of his voice. But the guy addressing me wasn’t Brandon from Brooklyn. It was Alex Hernandez, the new guy at my office, and a fine specimen of manhood.

  “Hi.” The word tripped over my vocal chords. I was surprised he even remembered my name. A few weeks earlier, we’d received the briefest of introductions during his orientation tour of the building, but we hadn’t spoken since.

  He’d left a big impression, though. In an office full of bedraggled computer nerds, Alex’s sense of style was an anomaly: hair perfectly mussed, jeans perfectly cuffed, button-down shirt perfectly fitted to his lean, solid torso. I’d wanted to see him again, but there was never a good excuse for me to swing by his cubicle, no good reason for us to strike up an idle chat. If I’d known he hung out at The Barley House, though, I probably would’ve started coming here sooner.

  “Mind if I sit here?” he asked.

  “Of course not.”

  He slung his laptop bag along the back of the barstool and slid into the seat. I fussed with my earring, struggling to act casual. It was difficult, given the fact that Alex Hernandez was mere inches away from me. He smelled like leather and cloves. I bet his skin was warm to the touch.

  “How’s the help desk been treating you?”

  Alex was, of course, referring to my role at Hatch. If any employee had a problem with their personal computer—a broken mouse, an outdated version of Word, a virus they’d accidentally downloaded from an infected website—I was the gal to solve it.

  “The usual,” I said. “Fine. Busy. Nothing exciting.”

  “Cool. So, what are you doing here all alone?”

  “I’m not alone.” Of course, I was obviously alone, but I didn’t want Alex thinking I was some loser who hung out in bars by myself on Friday nights. Then I remembered why I was really there: to meet a guy from Fluttr, who was most likely in the process of standing me up. “I’m meeting someone. Maybe.”

  “Maybe?”

  Here was another rookie mistake: arranging an internet date within walking distance of my office building. I worked on Water Street, right at South Street Seaport, so most of my coworkers grabbed their happy hour drinks at bars along those cobblestone streets surrounding Pier 17. The Barley House was farther west, closer to the Stock Exchange, tucked away in a hidden corner of Maiden Lane, so I figured it was a safe zone. I thought I’d disappear into a sea of off-duty traders celebrating the end of their workweek. I didn’t realize the place would be half-empty, or that my secret office crush would roll in and sit down next to me.

  Rather than risk embarrassing myself with a truthful answer to Alex’s question, I deflected. “Is this bar some hush-hush Hatch hangout I’ve never heard about?”

  “Nah, no one ever comes here except for me. I live down the block. I’m here all the time. And after the day I’ve had, I need a stiff drink.” He flagged down the bartender and ordered a Maker’s Mark on the rocks, then turned to me and asked, “Do you need another one?”

  “No, thanks.” This second vodka soda was already going straight to my head. I doubted I’d be able to finish it. “Why was your day so bad?”

  He let out an exasperated groan. “A deployment went totally bonkers. I had to code a last-minute bug fix, but then that introduced another bug.” The bartender delivered his whiskey and Alex paused to take an urgent gulp. “I finally got it all sorted out, but by then everyone was pissed.”

  “That sucks.”

  “No kidding.” He ran a hand through his thick, dark curls. “And it didn’t help that Greg dumped a giant cup of coffee all over his brand-new laptop.”

  “Yeah. That thing was toast.”

  The coffee incident had taken up most of my morning, actually. Greg had strolled into my cubicle, slack-jawed, holding his four-thousand-dollar laptop by the corner of its cracked screen. “Uh... I spilled,” he said, as if it wasn’t obvious from the liquid oozing out from under the keys and dripping onto the carpet.

  “What’s up with the broken screen?” I asked, gently taking the computer from his hands and placing it on my desk.

  “Uh... I dropped it.”

  For a man who was supposed to be the brains behind a burgeoning business, Greg didn’t seem particularly bright. Or motivated, for that matter.

  “Give me a few hours,” I’d said. “I can try to salvage the hard drive and set you up with a new machine.”

  “Uh-huh.” He was already engrossed in his phone, scrolling through something that looked like a Reddit thread. “Just text me when it’s done. I’ll be...out.” And he tripped over my cubicle wall as he walked away.

  The whole thing was laughable, honestly. That a man like Greg could secure hundreds of thousands of investor dollars without knowing much of anything or doing any work. But when I saw the anguish on Alex’s face, I swallowed my snicker. Of course it wasn’t funny to him.

  See, even though Alex and I worked in the same office, we had wildly different jobs. I worked for Hatch, a start-up incubator that provided seed funding and temporary office space for app developers with big ideas, also known as Hatchlings. I supported the Hatchlings in their day-to-day activities, and as a full-time employee, I enjoyed a regular salary, two weeks of paid vacation, and a phenomenal dental plan.

  Alex, on the other hand, was one of those app developers with the big ideas and Greg was his partner. They were a few weeks into their three-month incubation period, which meant they had only a short amount of time left to perfect their app. At the end of their stint, they’d show off their final project to big-time investors from venture capital firms all over the country. If their demo was a failure, that’d be the end of it. They’d be shooed out of Hatch and would have to start over somewhere else, doing something new. But I’d still be there, collecting my paycheck, replacing busted laptops for a whole new cohort of wannabe start-up founders.

  “How are things going with your project?” I asked. “What’s the name of your app again? Sorry, I should probably know this.”

  He waved away my apology. “There are like two dozen start-ups at Hatch right now. I don’t blame you for not keeping track. We’re Fizz.”

  “Fizz. And...what does it do?”

  “It’s a ride-sharing app.”

  “That’s cool.” Even if not totally original.

  “It’s all right.” He shrugged and took a long sip of bourbon. “To be honest, it’s not going so well.”

  “Oh. I’m sorry.”

  “It’s okay. Even if we fail, being at Hatch is still a foot in the door. A way to make contacts in the start-up community. I’m only twenty-six—there’ll be plenty of other opportunities.” He frowned slightly, like he was having a hard time convincing himself that failure was an option. “I mean, that’s probably why you’re working the help desk, right? As a stepping-stone.”

  “Right.” Except not really. I was working at Hatch because they were the first company to offer me a job after graduation, and I didn’t want to look a paycheck horse in the mouth. Not when I was drowning in student loans. Plus, rent in New York City wasn’t exactly affordable. I wasn’t worried about planning my career path; I was worried about how to pay my bills.

  Of course, I’d started at Hatch four years ago. Now, I was the same age as Alex, in the same position as when I first left college, with no goals or dreams beyond my current dead-end job.

  Sometimes I thought it’d be nice to be the person with the vision, as opposed to the person who fixed the broken laptops of the visionaries. But it’s not like I had any brilliant ideas worth pursuing. So working the help desk was where I had to be.

  “So,” he said, “where’s this someone you’re maybe meeting?”

  I glanced at my phone, tapping the screen as if I expected to see something there. “I’m not sure.”

  “Well, I’m glad I ran into you.”

  My mouth curled into an involuntary smile. “Really?”


  “Yeah.” He returned the grin. “You know, we only spoke that once and it was so quick. I kept meaning to stop by your desk and say hi, but I could never find a good excuse. Maybe we can grab lunch next week? If you’re free.”

  “Of course.” I had to fight to keep myself from squealing. Alex Hernandez was flirting with me. I mean, that’s what was happening, right? After a vodka soda and a half, it was hard to tell. The booze might’ve been playing tricks on my ego. I could be blowing our banter out of proportion.

  Still, he didn’t break my gaze, even as he brought the bourbon to his lips and took a long-drawn-out drink. He swallowed, licked his lips. My eyes dropped to the movement of his tongue. He was flirting with me, no doubt about it.

  Perhaps getting stood up was a blessing in disguise. In fact, I was glad Brandon from Brooklyn never showed his face. Because Alex was here, in the flesh. That was way better than a virtual Fluttr match.

  Just as I started fantasizing about how the rest of our evening would unfold—a candlelit dinner, a romantic stroll by the waterfront, a sexually charged taxi ride back to his place—a nasal voice called his name from across the bar. Instantly, he straightened. I turned and spotted a leggy brunette stalking toward us. Or, rather, toward Alex.

  “Hi!” She planted a kiss in the corner of his mouth, leaving behind a smear of berry lipstick.

  “Hi.” Alex looked sheepish. Of course he did. He was flirting with his coworker behind his girlfriend’s back. Asshole.

  He wiped the lipstick away with his fingertips. “Jenny, this is Melanie. We work together. Melanie, this is Jenny.”

  She smiled politely and shook my hand. “Hello.”

  “Hi.”

  Jenny slipped onto the stool on the other side of Alex, who was downing the rest of his Maker’s Mark with closed eyes. She looked past him, at me, a polite yet cold smile on her berry-painted lips. This was probably my cue to leave.

  I tapped my phone. It was 6:42. Safe to say Brandon from Brooklyn was officially a no-show. Asshole.