My Friend and I Loved to Make Bets with Each Other as Children — My Last Win Made Me Cry
Growing up, my best friend and I had a tradition that we both loved: making bets. We were inseparable, two kids with a shared love of competition, adventure, and a good laugh. Whether it was something as trivial as who could run faster or as significant as who could eat the most ice cream without feeling sick, the stakes were always high, and the rewards—or consequences—were never quite what we expected. But in all our years of betting, I never imagined that my last win would bring me to tears.
It started when we were about 10 years old. We would walk home from school together, dreaming up ridiculous bets to entertain ourselves during our walk. One day, on a particularly sunny afternoon, we found ourselves at the park, sitting on the swings. I bet her that I could swing higher than she could, and she, of course, eagerly accepted. We always did this—one of us would dare the other, and we’d find a way to compete, no matter how small the challenge.
As the years went on, our bets grew more elaborate. They evolved from simple playground competitions to dares that involved actual stakes. If I won a bet, she would have to help me with my chores for a week; if she won, I had to do the same for her. The bets weren’t just about the challenges—they were about proving ourselves to one another, solidifying the bond that had formed between us over time.
But as we grew older, the bets slowly started to fade. Our lives changed; we became busier with school, extracurricular activities, and family commitments. The playful, carefree days of childhood eventually gave way to teenage responsibilities. Still, we would sometimes laugh about our old bets when we saw each other, reminiscing about the simpler times.
It wasn’t until the summer before our senior year of high school that we found ourselves face-to-face with one last bet. We were sitting in my backyard, staring at the setting sun, when I jokingly said, “I bet you I can beat you at basketball, even though I haven’t played in years.” She laughed and accepted. But this bet felt different—it wasn’t about winning or losing anymore. It was about something deeper, something unspoken between us.
The game was intense. We were both competitive, laughing, shouting, and even trash-talking a little like we did when we were kids. But as the final whistle blew, I had won. It was a small victory in the grand scheme of life, yet it hit me in a way I didn’t expect. The tears came unexpectedly as I realized that this was likely the last time we would ever make a bet like this again. We were both about to head off to different colleges, our lives heading in different directions. The thought of not having her by my side for those small, silly moments left me feeling overwhelmingly emotional.
She looked at me, confused at first, but then she understood. We had spent our entire childhoods challenging each other, learning from each other, and growing together. This bet, simple as it was, was a symbol of everything we had shared. As I wiped away the tears, she gave me a hug, and we both silently acknowledged that while the bets were over, our friendship would last forever. That last win wasn’t just about basketball—it was a bittersweet reminder of the times we had and how much they meant.
