The Bet

Chapter 1: The Pact

The text message arrived at 7:43 AM on a Tuesday, which Doug Henderson later considered the universe's way of telling him to stay in bed.

"20-YEAR REUNION! WESTBROOK HIGH CLASS OF 2004! SAVE THE DATE: OCTOBER 12TH!"

Doug stared at his phone while standing in line at a coffee shop that charged seven dollars for what was essentially hot brown water with foam art. He was forty-two years old, recently divorced, and currently living in what his real estate agent had optimistically called a "cozy studio apartment" but what Doug called "a closet with plumbing."

His phone buzzed again. Then again. A group chat was forming, one he'd been added to without his consent, which seemed to be the defining characteristic of his life lately.

STEVE: Holy crap did you guys see this

KEVIN: I'm not going

STEVE: Come on man

KEVIN: Absolutely not. No way. Never.

Doug typed his response with his thumb while the barista called out names that all sounded like they belonged to people more successful than him.

DOUG: I'm with Kevin. What's the point?

The point, as Doug remembered it, was that high school had been four years of concentrated misery. He'd been the kind of kid who ate lunch in the library, not because he loved books, but because the library was the only place where no one actively tried to make him feel like garbage. Steve had been the awkward theater kid who somehow managed to be too weird even for the theater kids. And Kevin had been the overweight computer nerd before being a computer nerd was cool and profitable.

The three of them had bonded over their shared status as social outcasts, forming a friendship that had survived two decades of adult life, three divorces between them, and one unfortunate incident involving Steve, a karaoke machine, and a restraining order from a woman named Brenda.

Steve's next message appeared.

STEVE: Remember Jessica Palmer?

Doug's thumb froze over his screen. Of course he remembered Jessica Palmer. Jessica Palmer had been the reason he'd failed sophomore chemistry. Not because she'd distracted him—she hadn't known he existed—but because he'd spent every class period staring at the back of her head instead of paying attention to anything the teacher said.

Jessica Palmer had been perfect. Blonde hair, green eyes, a laugh that sounded like wind chimes if wind chimes could make a teenage boy forget his own name. She'd dated the quarterback, obviously, because that's what perfect girls did in 2004.

DOUG: What about her?

STEVE: She's going. I saw the RSVP list on Facebook.

KEVIN: How do you have access to the RSVP list?

STEVE: I may have created a fake account and friended the reunion organizer

KEVIN: That's creepy Steve

STEVE: That's RESOURCEFUL Kevin

Doug found himself scrolling through his own Facebook, searching for Jessica Palmer. He found her immediately. Jessica Palmer-Morrison now, according to her profile. The profile picture showed her at what looked like a beach vacation, sunglasses pushed up on her head, smiling at the camera.

She looked exactly the same. Better, actually. Some people aged like fine wine, and Jessica had apparently aged like whatever was fancier than fine wine. Champagne, maybe. The really expensive kind that came in bottles you needed a special tool to open.

His phone buzzed.

STEVE: Also Vanessa Chen is going

KEVIN: Don't.

STEVE: And apparently she's single now

KEVIN: I said don't.

Vanessa Chen had been Kevin's Jessica Palmer—the girl he'd worshipped from afar throughout all four years of high school. She'd been the smart, pretty girl who'd tutored him in math and never once seemed to notice that he turned into a stammering mess every time she leaned over to check his work.

Doug watched the three dots appear and disappear as Kevin typed and deleted several responses.

KEVIN: Fine. I'm listening.

STEVE: Guys. We're not the same losers we were in high school. We're grown men now. Successful. Sophisticated.

DOUG: Steve you work at a car dealership

STEVE: I'm the ASSISTANT sales manager Doug. There's a difference.

KEVIN: I work from home in my underwear writing code for a company that makes software for dentist offices

STEVE: That's tech! Tech is sexy now!

DOUG: I just got divorced and I'm living in an apartment so small I can touch both walls at the same time

STEVE: Okay so we need some work

The conversation died for a few hours. Doug went to his job at the insurance company where he spent eight hours a day processing claims and wondering where his life had gone wrong. He ate a sad desk lunch. He processed more claims. He thought about Jessica Palmer and felt like a pathetic teenager all over again.

At 6:47 PM, Steve sent another message.

STEVE: Guys. I have an idea. Drinks tonight. My place. 8pm.

KEVIN: I don't like your ideas

STEVE: This one is good I promise

DOUG: Your last "good idea" ended with us banned from that karaoke bar

STEVE: This is different. This is about our dignity. Our legacy. Our chance to finally show everyone who we really are.

KEVIN: Who we really are is three middle-aged men with bad knees and worse credit

STEVE: Just come over. Please.

Doug stared at the message. He thought about his empty apartment. He thought about the frozen dinner waiting for him in his mini-fridge. He thought about Jessica Palmer's profile picture.

DOUG: Fine. But I'm not singing karaoke.

---

Steve's apartment was exactly what you'd expect from a forty-two-year-old assistant sales manager at a mid-tier car dealership: beige walls, a leather couch that was trying too hard, and a collection of motivational posters that seemed to be mocking him.

"BELIEVE AND ACHIEVE," declared one poster, featuring an eagle soaring over a mountain.

"THE ONLY LIMIT IS YOU," announced another, this one with a guy climbing a rock face.

Doug wondered if Steve actually believed this stuff or if the posters had come with the apartment.

Kevin was already there when Doug arrived, sitting on the trying-too-hard leather couch with a beer in his hand and a suspicious expression on his face. Kevin had lost some weight since high school—not a lot, but enough that he no longer looked like he might tip over in a strong wind. He'd also grown a beard, which he claimed made him look "distinguished" but which actually made him look like a computer programmer who'd given up on shaving.

"He hasn't told me the idea yet," Kevin said as Doug walked in. "He's being dramatic about it."

"I'm building suspense," Steve called from the kitchen. "It's a sales technique. You create anticipation, and then you deliver."

"What are you selling us, Steve?"

Steve emerged from the kitchen carrying three more beers and a bowl of chips that looked like they'd been sitting in his pantry since the Obama administration. He was still thin, still had that nervous energy that had made him exhausting in high school, but his hairline had retreated significantly. He compensated for this by styling what remained into an aggressive swoop that fooled no one.

"Gentlemen," Steve said, setting down the beers with ceremony. "I've been thinking."

"Dangerous," Kevin muttered.

"About the reunion. About our lives. About everything we've accomplished and everything we haven't." Steve paused for effect. "And I've realized something important."

"That we're all going to die alone and unmourned?" Doug offered.

"No. Well, maybe. But that's not the point." Steve took a dramatic sip of his beer. "The point is that we have an opportunity here. A once-in-a-lifetime chance to rewrite our high school legacy."

Kevin groaned. "Steve, we're in our forties. We don't have legacies. We have lower back pain and disappointing 401(k)s."

"That's exactly my point!" Steve was getting excited now, the way he always did when he was about to propose something terrible. "We've spent twenty years being... fine. Average. Unremarkable. And now we have one night—ONE NIGHT—to show everyone who we could have been."

Doug exchanged a look with Kevin. This was going somewhere bad.

"What exactly are you proposing?" Doug asked carefully.

Steve grinned. It was the grin of a man about to suggest something monumentally stupid.

"A bet," he said. "Between the three of us. We go to this reunion as the men we always wanted to be. Successful. Confident. Irresistible. And we each try to hook up with our high school crushes."

Silence.

"That's insane," Kevin said.

"That's impossible," Doug added.

"That's the POINT," Steve insisted. "We're not going as ourselves. We're going as better versions of ourselves. Upgraded versions. The versions that should have existed if the universe wasn't so unfair."

"Steve, you can't just... become a different person for a night."

"Why not? It's a reunion. Nobody's seen us in twenty years. Nobody knows what we've been doing. We could be anyone. We could have done anything." Steve leaned forward, his eyes gleaming with the dangerous light of a man who'd clearly been thinking about this for too long. "I've done the research. Jessica Palmer is divorced. Vanessa Chen is single. And my old crush—Amanda Holloway—she's going through a separation."

"How do you know all this?" Doug asked.

"Facebook. Instagram. A little light LinkedIn stalking." Steve waved his hand dismissively. "The point is, they're all available. And they're all going to be at this reunion, probably feeling nostalgic and vulnerable and ready to make questionable decisions with men who seem successful and interesting."

"And you think we can seem successful and interesting?" Kevin asked.

"I think we can seem like anything we want." Steve stood up, pacing now, fully committed to his pitch. "Think about it. Doug, you tell everyone you're a tech millionaire. You sold a startup. You're retired at forty-two, living the dream."

"I don't know anything about tech."

"You don't have to! You sold the company. You just have to seem rich and mysterious." Steve pointed at Kevin. "And you—you actually work in tech. You can help Doug with the details. Meanwhile, you tell everyone you invented something. Something cool. Something that makes people say 'wow.'"

"Like what?"

"I don't know, an app or something. Or... wait, what about an energy drink? Those are huge right now. You invented an energy drink."

"I don't know anything about energy drinks."

"Again—you don't have to! You invented it, you sold the formula, you moved on. You're a behind-the-scenes genius."

Kevin looked skeptical, but Doug could see him considering it. That was the problem with Steve's ideas—they always sounded just plausible enough to be tempting.

"And what about you?" Doug asked. "What's your fake identity?"

Steve's grin widened. "I'm going to tell everyone I dated a supermodel."

Silence again.

"That's it?" Kevin asked. "That's your whole thing?"

"It's not just any supermodel. It's Claudia Vega."

"Who?"

"She was in a Super Bowl commercial three years ago. She's gorgeous. She's famous. And she's completely unreachable, which means no one can verify it."

"Steve, that's the dumbest thing I've ever heard," Doug said.

"Is it? Is it really?" Steve pulled out his phone and showed them a picture of a stunning woman in a bikini, posing on what appeared to be a yacht. "Look at her. Look at me. Is it really so impossible that a woman like this could fall for a charming, sophisticated man like myself?"

"Yes," Doug and Kevin said in unison.

"You're wrong. And I'm going to prove it." Steve sat back down, his expression shifting to something more serious. "Look, guys. I know this sounds crazy. But think about what we're actually risking here. Our dignity? We don't have any. Our reputations? Nobody remembers us anyway. Our pride? We lost that when Doug got divorced and had to ask his mother for help moving his stuff."

"That was a low blow," Doug said.

"But accurate." Steve leaned forward again. "We have nothing to lose. And we have everything to gain. One night. One chance. One opportunity to finally be the men we always wanted to be."

The apartment was quiet except for the hum of Steve's refrigerator, which was working harder than it should have been.

Doug thought about Jessica Palmer. About the way she'd walked through the halls of Westbrook High like she was floating. About the one time she'd asked to borrow a pencil from him and he'd been so flustered he'd handed her a pen instead. About twenty years of wondering what if.

"This is insane," he said.

"Completely," Kevin agreed.

"So we're doing it?" Steve asked.

Doug looked at Kevin. Kevin looked at Doug. They both looked at Steve, who was practically vibrating with anticipation.

"We're going to regret this," Doug said.

"Probably," Steve agreed.

"I need another beer," Kevin said.

Steve jumped up to get more drinks, and just like that, the bet was on.

They spent the next three hours getting progressively drunker and hammering out the details of their respective fake identities. Doug would be a tech entrepreneur who'd sold his company for an undisclosed sum that he would heavily imply was in the hundreds of millions. Kevin would be the inventor of an energy drink called "ZapMax," which he'd created in his garage and sold to a major beverage company. Steve would be a former model scout who'd dated Claudia Vega for two years before they'd amicably parted ways due to her demanding travel schedule.

"We need props," Steve declared around midnight, when they were all thoroughly drunk. "Visual evidence of our success."

"Like what?" Doug asked.

"I'm going to rent a Lamborghini," Steve said. "One of the yellow ones. I'll tell people it's mine."

"That's expensive."

"It's an investment in our dignity." Steve was slurring slightly now. "Doug, you need a nice watch. One of those expensive ones that rich people wear."

"I can't afford a nice watch. I can barely afford my rent."

"You don't have to buy it. You rent it. Or borrow it. Or... okay, I don't know. We'll figure it out."

Kevin was looking at his phone. "Guys, there's actually an energy drink called ZapMax."

"What?" Steve grabbed the phone. "No way."

"It's real. It's got a website and everything. 'ZapMax: Maximum Energy, Maximum Life.'"

"That's perfect!" Steve exclaimed. "You didn't make up a fake drink—you invented a real one! That's even better!"

"Steve, I didn't invent it. Someone else did. Someone who might be at the reunion. Someone who might take issue with me claiming I invented their energy drink."

"What are the odds of that happening?"

"I don't know, but—"

"Exactly! You don't know! Which means it's probably fine!" Steve raised his beer. "To the bet, gentlemen. To reinvention. To finally getting what we deserve."

They clinked their bottles together, and Doug felt a surge of something that might have been excitement or might have been indigestion from the ancient chips.

Either way, there was no turning back now.