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

Jake and I spent our childhood locked in endless competition—who could run the fastest, climb the highest, take the biggest risk. But when I won our final bet, there was no thrill of victory. Just an ache I never saw coming.

We were inseparable from the start, growing up just a few doors apart. If Jake wasn’t home, he was at my place, and vice versa. But what really defined us? The bets.

“Bet you can’t beat me to the end of the block,” Jake would say, already sprinting.

“Bet you I can,” I’d shoot back.

We bet on everything—until one night, lying on my roof at sixteen, Jake proposed the ultimate one.

“Whoever lives longer wins.”

I laughed it off. “How would we even know?”

“Whoever goes first owes the other a beer,” he said.

For years, I believed he would never lose. Then Laura came along.

I didn’t plan to fall for her, but Jake noticed before I could admit it to myself. “You like her,” he smirked. “First one to ask her out wins.”

For the first time, I refused to play. “She’s not a game, Jake.”

But she made her choice—me. And that broke everything.

Jake called it betrayal, told people I had stabbed him in the back. By graduation, he was gone. No goodbye, no second chances.

Life moved on. Laura and I built a home, started a family. But sometimes, late at night, I still wondered where he was.

Then a letter arrived.

“I’m back in town. Meet me at O’Malley’s tomorrow at seven. Let’s talk.”

I went. But he wasn’t there.

A waitress handed me a note.

“Paul, if you’re reading this, I didn’t make it. Cancer came back worse. I didn’t want you to see me like that. But I couldn’t leave without fixing what I broke.”

“I was a damn fool. You were my brother, and I threw it away over a stupid bet. I don’t expect forgiveness, but I never stopped missing you.”

“And that last bet… well, looks like you won. The beer’s on me.”

Tears blurred my vision. I raised the pint left in front of me. “You idiot.”

A week later, I stood at his grave, setting down a beer. “You still owe me a rematch.”

As I walked away, Laura squeezed my hand. “You okay?”

I nodded. “Yeah.”

And for the first time in years, I didn’t feel like I lost my best friend.

I felt like I had finally said goodbye.

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