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

We had been best friends since before we could walk. Our moms loved to tell the story—two toddlers in diapers, both stubbornly gripping the same toy truck at daycare, neither willing to let go. From that moment, we were inseparable.

We grew up in houses just a few doors apart. If Jake wasn’t home, his mom knew to check my place, and vice versa. We were brothers in every way except blood. But what really defined us? The bets.

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

“Bet you I can,” I’d shoot back, legs pumping.

We bet on everything—who could hold their breath the longest, who could eat the most slices of pizza, who could get the highest grade on a test. The wins and losses didn’t matter. What mattered was the challenge. The push. The proof that we were always striving to be better, to be bolder.

And most of all, that we had each other’s backs.

Then, one night, things changed.

We were sixteen, stretched out on the roof of my house, staring up at a sky that felt endless. The kind of night where silence wasn’t awkward—it was comfortable, safe.

“Paul,” Jake said, his voice quieter than usual. “We should make the ultimate bet.”

I turned my head to look at him. “Yeah? What kind of bet?”

He smirked. “Who lives longer.”

I let out a short laugh. “That’s dumb. How would we even know who won?”

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

I chuckled, shaking my head. “Fine. But you better not lose.”

His grin widened. “I never lose.”

For years, I believed that.

Then Laura came along.

I didn’t plan on falling for her. It just happened.

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