Jake and I spent our childhood making bets—who could run faster, climb higher, or take the biggest risk. It was our thing. But years later, when I won our final bet, there was no celebration—just a heartbreak I never saw coming.
Jake and I had been best friends for as long as I could remember. Our moms loved telling the story of how we met—two toddlers fighting over a toy truck at daycare. They thought it was funny how we had always been competing, even back then.
We grew up side by side, our houses just a few doors apart. If one of us wasn’t home, our parents knew exactly where to find us. We did everything together. But the thing that really defined us? The bets.
“Bet you can’t make it to the end of the block before I do,” Jake would say.
“Bet you I can,” I’d shoot back, already running.
We bet on everything. Who could hold their breath the longest? Who could eat more pizza? Who would get the best grade on a test? Winning never really mattered. What mattered was proving something to each other, pushing each other to be better, braver.
No one understood our friendship the way we did. If Jake dared me to do something, I knew he’d do it too. If I jumped, he jumped. That was just how it worked.
Then, one night, things got deep.
We were sixteen, lying on the roof of my house, staring at the stars. It was one of those nights where you felt like you could talk about anything.
“Paul,” Jake said, his voice softer than usual, “we should make the ultimate bet.”
I turned to him. “Yeah? What kind of bet?”
“Who lives longer.”
I let out a short laugh. “That’s dumb. How would we even know who won?”
Jake smirked. “Easy. Whoever goes first owes the other a beer.”
I chuckled, shaking my head. “Fine. But you better not lose.”
Jake grinned. “I never lose.”
We thought we’d be best friends forever. But then, everything changed.
Falling for Laura wasn’t something I planned. It just happened.
She wasn’t like the other girls at school. She was smart, funny, and kind. She made me feel like I actually mattered. I had liked her for a while, but I didn’t know how Jake would take it. We had never let anything come between us before, but this felt different.
One day, Jake caught me staring at her in the hallway.
“You like her, don’t you?” he asked, smirking.
I hesitated. “Yeah. I do.”
His grin widened. “Then let’s make it interesting. First one to take her out wins.”
I blinked. “What?”
“A bet,” he said. “Whoever asks her out first, gets her.”
For the first time in my life, I didn’t feel the rush of competition. I didn’t want to win. I just wanted her.
“She’s not a game, Jake,” I said. “She’s a person.”
He rolled his eyes. “Come on, Paul. We bet on everything. What’s the difference?”
“The difference is that this actually matters.”
He laughed. “You’re acting like you’re in love with her or something.”
I clenched my fists. “Maybe I am.”
His smile disappeared. “Oh.”
I shook my head and walked away. I didn’t see Laura standing by the lockers. I didn’t know she had heard the whole thing.
“Paul,” she called out, catching up to me.
I stopped, my heart pounding. “Laura.”
She smiled. “You really meant that?”
I swallowed hard. “Yeah.”
She reached for my hand, lacing her fingers with mine. “Then let’s make it official.”
Jake was furious. At first, he made jokes about how I had “cheated” and broken our deal. But then the rumors started. He told people I had stabbed him in the back. That I had always been jealous of him. That I had picked Laura over him.
I tried to talk to him. “Jake, this isn’t about you and me. It’s about her.”
“She was supposed to be a bet,” he snapped. “Not the reason you picked someone else over me.”
“I never picked anyone over you,” I said. “You made this a fight, not me.”
But he wouldn’t listen.
By graduation, Jake was gone. He left town without a word.
Years passed. Laura and I got married, had a daughter, Emily. Life was good, but sometimes, I wondered about Jake. If he ever thought about me. If he regretted what happened.
Then one day, I got a letter.
Paul,
I’m back in town. It’s been too long. Meet me at O’Malley’s tomorrow at seven. Let’s talk.
—Jake
I didn’t know what to expect. But the next night, I showed up.
Jake wasn’t there.
Instead, a waitress handed me an envelope and a pint of beer. “He asked me to give this to you,” she said softly.
I unfolded the letter, my chest tightening.
Paul,
If you’re reading this, I’m already gone. Cancer. I didn’t want to leave without fixing what I broke. I was a damn fool, Paul. You were my brother, and I threw it away over a stupid bet. I don’t expect you to forgive me. I just hope you know I never stopped missing you.
As for our last bet… well, looks like you won. The beer’s on me.
—Jake
My hands shook. I stared at the pint of beer in front of me. Jake had kept his word.
A week later, I stood in front of his grave. I set a pint of beer down next to it.
“You still owe me a rematch,” I muttered. “But I guess this will have to do.”
I smiled, wiping my eyes. “I forgive you, Jake. I forgave you a long time ago.”
As I walked away, I glanced back one last time. The pain was still there, but for the first time, I felt like I had finally said goodbye.
