My Friend and I Loved to Make Bets with Each Other as Children — My Last Win Made Me Cry

Jake and I had been best friends since before we could walk. Our moms liked to tell the story of how we met—two toddlers in diapers, fighting over a toy truck at daycare. They thought it was funny how we were always 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 slices of pizza? Who would get the best grade on a test? Sometimes we won, sometimes we lost, but the bets never really mattered. What mattered was proving something to each other, pushing each other to be better, to be faster, to be braver.

No one understood our friendship the way we did. It wasn’t just about competition—it was about trust. If Jake dared me to do something crazy, 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 16, 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 my head to look at him. “Yeah? What kind of bet?”

“Who lives longer.”

I let out a short laugh. “That’s a dumb bet. 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 our friendship would last 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 different, like I actually mattered. We’d been friends for a while, but somewhere along the way, I realized I wanted more.

The problem was Jake. I wasn’t sure how he’d take it. We never let anything come between us before, but this felt… different.

I kept it to myself for weeks, trying to ignore the way my heart sped up whenever Laura laughed or the way I found excuses to be near her. But one day, Jake caught me staring at her in the hallway.

“You like her, don’t you?” he said, 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. “You and me. 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, my voice low. “She’s a person.”

He rolled his eyes. “Come on, Paul. We’ve 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 turned to leave. “I’m done with this, Jake.”

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 acted like he didn’t care. He made jokes about how I’d “cheated” and broken our deal. But then the rumors started. He told people I’d stabbed him in the back. That I’d always been jealous of him. That I had turned on him for a girl.

It hurt more than I thought it would.

I tried to talk to him, tried to fix it. “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 into a fight, not me.”

But he wouldn’t listen.

By the time graduation rolled around, Jake was gone. He packed up and left town without a word.

And just like that, my best friend—the person I had trusted more than anyone—became nothing more than a memory.

Life moved on. Laura and I got married a year after graduation. We stayed in town, bought a house not far from where we grew up, and built a life together. A good life.

Our daughter, Emily, was born a few years later. She had Laura’s eyes and my stubbornness. Every time she laughed, the world felt right.

I was happy. I really was. But some nights, after Laura and Emily had gone to bed, I’d sit outside and let my mind drift back to the past.

To Jake.

I wondered where he ended up and what he was doing. If he ever thought about me. If he ever regretted the way things ended.

I tried to push those thoughts away, but they never really left. Losing a best friend wasn’t like breaking up or drifting apart. It was like losing a part of yourself, a part you never got back.

One afternoon, I was sorting through the mail—bills, junk, the usual—when a small envelope slipped out. My name was on the front, written in handwriting I hadn’t seen in years.

Jake’s handwriting.

My hands shook as I tore it open.

Paul,

I’m back in town. It’s been too long. Meet me at O’Malley’s tomorrow at seven. Let’s talk.

—Jake

That was it. No explanation, no apology. Just an invitation. I read it three times, half expecting the words to change.

Laura noticed the look on my face. “What is it?”

I handed her the letter. She read it, then met my eyes. “Are you going?”

I hesitated, then nodded. “Yeah.”

I didn’t know what I would say. I didn’t know if I was still angry, or if he was, either. All I knew was that after 10 years, I finally had a chance to see my best friend again.

The next evening, I arrived at O’Malley’s ten minutes early.

The place hadn’t changed much since we were kids. I scanned the room, expecting to see Jake at a corner table, grinning like nothing had ever happened.

But he wasn’t there.

I checked my watch. Maybe he was late. He was never great with time.

After a few minutes, a waitress approached me. She was young, maybe in her twenties, with tired eyes and a kind smile.

“You Paul?” she asked.

I nodded. “Yeah.”

She gestured toward a small booth in the back. “Follow me.”

Confused, I did as she said. When I sat down, she pulled a folded piece of paper from her apron and set it on the table. Then, she placed a pint of beer next to it.

“He asked me to give this to you,” she said softly.

My stomach dropped. “Where is he?”

She hesitated. “Just read it.” Then she walked away.

I stared at the letter, my fingers numb as I unfolded it. The second I saw the handwriting, my chest tightened.

Paul,

If you’re reading this, have indeed returned home. My last wish was to be buried in my hometown.

I sucked in a breath, but I forced myself to keep reading.

I got sick right after graduation. Skin cancer. I went into remission for a while, but it came back. Worse this time. The doctors said I was out of options.

I didn’t write to make you feel bad. I wrote because I didn’t want to leave this world without fixing what I broke. I was a damn fool, Paul. I let my pride ruin the best thing I ever had—our friendship. 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.

I swallowed hard, my vision blurring.

And as for that last bet… well, looks like you won, my friend. The beer’s on me.

—Jake

I clutched the letter, my fingers gripping the paper so tightly it crumpled. Jake was gone. I’d come here expecting a second chance, but all I got was a goodbye I never wanted.

I stared at the pint of beer in front of me. It looked normal—just an ordinary drink—but I knew what it meant.

Jake had kept his word.

With shaky hands, I lifted the glass. “You idiot,” I whispered. Then I took a sip. It tasted bitter. Or maybe that was just the grief.

A week later, I stood in front of Jake’s grave. Laura and Emily were with me, but they gave me space. This was something I had to do alone.

I knelt down, brushing my fingers over the name carved into the stone, and let out a shaky breath.

“Hey, Jake.” My voice cracked. “Guess you really went through with it, huh?”

I wiped my eyes and shook my head. “You know, I used to wonder if you ever thought about me. If you ever regretted what happened. Turns out, you did. And I hate that I didn’t know sooner.”

I reached into the bag I brought and pulled out a pint of beer. Popping the cap, I set it down in front of the headstone.

“You still owe me a rematch,” I muttered. “But I guess this’ll have to do.”

Silence stretched between us. The wind rustled the trees, and somewhere in the distance, I heard Emily laughing.

I smiled. “I forgive you, Jake. I forgave you a long time ago.”

I stood up, wiping my hands on my jeans.

Laura took my hand, squeezing it gently. “You okay?”

I nodded. “Yeah.”

As we walked away, I glanced back one last time. The pain was still there. It probably always would be. But for the first time in years, I didn’t feel like I’d lost my best friend. I felt like I’d finally said goodbye.