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

admin March 6, 2025

Jake and I spent our childhood locked in an endless, exhilarating competition—who could run the fastest, climb the highest, take the biggest risks. From the moment we met as toddlers, squabbling over the same toy truck in daycare, we were inseparable. Growing up just a few doors apart, we weren’t just best friends—we were like brothers. Everything in our world revolved around dares and challenges. Who could hold their breath the longest? Who would ace the next test? Who could sneak the farthest into the woods before chickening out?

It was never really about winning; it was about the thrill of pushing each other further, of knowing that no matter the outcome, we’d always have another challenge waiting. That was our unspoken bond—until one night, when we were sixteen, Jake came up with the ultimate bet.

We were lying on my roof, staring at the stars, when he turned to me with a smirk. “Alright, last bet—who lives longer?”

I laughed, shaking my head. “That’s a stupid one.”

But he was serious. “Whoever goes first owes the other a beer.”

I rolled my eyes, but we shook on it anyway, sealing our pact with a laugh. At the time, it was just another silly challenge, one we assumed we’d joke about decades down the road. We never imagined how real it would become.

A few months later, everything changed. Laura entered our lives. She was sharp, funny, and kind, with a laugh that could light up a room. I never intended to compete for her, but Jake saw it differently. He was convinced I had betrayed him. He started pulling away, spreading rumors that I had stolen something from him that he could never get back. I tried to talk to him, to tell him that nothing had happened, that I would never hurt him like that—but he didn’t want to hear it.

By the time we graduated, he was gone. No goodbye, no explanation—just silence.

Years passed. Life moved forward, but a part of me still held onto that last conversation, the one we never had. Then, out of nowhere, a letter arrived. Jake had written it, but the words weren’t meant for a long-lost friend. They were his goodbye.

He had been fighting cancer. He never told me, never wanted me to see him that way. In his final words, he admitted that I had won the bet. But reading that letter, all I felt was an ache I couldn’t explain.

Winning had never mattered. I would have given anything to lose that bet.

So, I bought that beer—the one he said he owed me—and sat under the same sky we used to stare at, whispering the goodbye I never got to say.

And I forgave him. But the truth is, I had forgiven him long before he was gone.

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