Childhood Bets Were Fun—Until My Final Win Brought Me to Tears

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

As kids, Jake and I used to wager on who could run faster, climb higher, or take the largest chance. However, there was no celebration when I won our last wager years later; instead, I experienced the heartbreak I never anticipated.

Since before we were able to walk, Jake and I had been great buddies. We met at daycare when two diapered toddlers got into a fight over a toy truck, according to the narrative our moms liked to tell. Even back then, they found it amusing that we were constantly in competition.

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Our homes were only a few doors away, and we grew up next to each other. Our parents knew just where to look if one of us wasn’t home. Together, we accomplished everything. But what truly made us who we are? The wagers.

Jake would say, “I bet you can’t reach the end of the block before I do.”

“Bet you I can,” I would retort, already in motion.

We wager on everything. Who had the longest breath-holding capacity? Who could consume more pizza? On an exam, who would receive the highest score? The bets never really mattered, even if we occasionally won and occasionally lost. It was important to push each other to be better, faster, and braver and to prove something to one another.

Nobody had the same understanding of our friendship as we did. It was about trust, not simply about competition. I knew Jake would do something wild if he challenged me to. He would leap if I did. That was the way it was.

Then, one evening, things became serious.

Lying on my house’s roof and gazing up at the stars, we were sixteen. It was one of those evenings when you could discuss anything you wanted.

“Paul,” Jake remarked in a softer-than-normal voice, “we ought to place the biggest wager.”

I glanced in his direction. “Yes? What sort of wager?

“Who lives longer.”

I gave a little chuckle. “That wager is foolish. How could we even determine the winner?

Jake grinned. Simple. A drink is due to the first person to go.

I shook my head and laughed. “All right. However, you had better not lose.

Jake smiled. “I never lose.”

We believed that we would always be pals. Then, however, everything was different.

I had no intention of falling in love with Laura. It simply occurred.

She was intelligent, humorous, and compassionate, which set her apart from the other girls at school. She gave me a new sense of identity and made me feel important. Although we had been friends for some time, I eventually came to the realization that I wanted more.

Jake was the issue. I had no idea how he would react. Previously, we never allowed anything to separate us, but this seemed… different.

For weeks, I kept it to myself, attempting to ignore the way my heart raced whenever Laura laughed or the ways I looked for reasons to spend time with her. Jake, however, saw me looking at her in the hallway one day.

He smirked and asked, “You like her, don’t you?”

I paused. “Yes. Yes, I do.

His smile got bigger. “Let’s then add some interest. The first one to remove her wins.

I blinked. “What?”

“A bet,” he stated. “Me and you. The first one to ask her out wins her.

I didn’t experience the excitement of competitiveness for the first time in my life. I had no desire to win. All I wanted was her.

The words “she’s not a game, Jake,” I murmured quietly. “She’s a person.”

He gave an eye roll. “Paul, hurry up. We’ve placed wagers on everything. “What’s the difference?”

“The difference is that this actually matters.”

He chuckled. “You’re acting like you’re in love with her or something.”

I balled my fists up. “Maybe I am.”

His grin vanished. “Oh.”

I turned to go, shaking my head. “I’m done with this, Jake.”

Laura wasn’t standing at the lockers when I looked. I was unaware that she had listened to the entire thing.

“Paul,” she yelled as she caught up with me.

With my heart racing, I came to a standstill. “Laura.”

She grinned. “You really meant that?”

I took a deep breath. “Yeah.”

Lacing her fingers with mine, she reached for my hand. “Then let’s make it official.”

Jake was enraged.

He pretended not to care at first. He joked that I had “cheated” and broken our agreement. Then, however, the rumors began. I stabbed him in the back, he told others. That I had always envied him. I had betrayed him for a female.

It was more painful than I had anticipated.

I attempted to solve it and speak with him. It’s not about you and me, Jake. It concerns her.

He yelled, “She was supposed to be a bet,” “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.”

He refused to listen, though.

Jake had left by the time graduation arrived. Without saying a word, he packed up and departed town.

My best friend, whom I had trusted above all others, vanished into thin air in an instant.

Life went on. A year after graduating, Laura and I were married. We remained in the city, purchased a home close to our childhood home, and established a life together. A good life.

A few years later, we had our daughter, Emily. She shared my tenacity and Laura’s gaze. It felt perfect every time she laughed.

I felt content. Yes, I was. However, there were occasions when I would sit outside and let my thoughts to stray to the past after Laura and Emily had gone to bed.

To Jake.

I was curious about his whereabouts and activities. If he ever considered me. If he ever felt bad about how things turned out.

I made an effort to ignore those ideas, but they persisted. It wasn’t like splitting up or drifting apart when you lost your best buddy. It was similar to losing a piece of who you were that you could never regain.

I was going through the mail one afternoon, sifting through bills, rubbish, and the rest, when a little envelope slid out. On the front was my name in handwriting I hadn’t seen in a long time.

The handwriting of Jake.

I ripped it open with trembling hands.

Paul

I’ve returned to the city. Too much time has passed. Tomorrow at seven o’clock, meet me at O’Malley’s. Let’s have a conversation.

— Jake

That was it. No apology, no explanation. Only a request. I half expected the words to change as I read it three times.

Laura saw the expression on my face. “What is it?”

I gave the letter to her. After reading it, she looked me in the eye. “Are you going?”

After hesitating, I nodded. “Yeah.”

I was at a loss for words. I wasn’t sure whether he or I was still upset. All I knew was that I was finally able to see my dearest friend again after a ten-year absence.

I got to O’Malley’s 10 minutes early the following night.

Since we were children, not much had changed there. I expected to see Jake at a corner table, smiling as if nothing had occurred, so I looked around the room.

However, he was absent.

I looked at my watch. He might have been late. Time was never his strong suit.

A waiter came up to me after a few minutes. She was a young woman, perhaps in her twenties, with a gentle smile and weary eyes.

“You Paul?” she questioned.

I gave a nod. “Yeah.”

She pointed to a tiny booth at the rear. “Follow me.”

Perplexed, I followed her instructions. She took a folded piece of paper out of her apron and placed it on the table as soon as I sat down. She set a pint of beer beside it after that.

She said, “He asked me to give this to you,”

I felt sick to my stomach. “Where is he?”

She paused. “Just read it.” Then she turned to leave.

I unfurled the letter, my fingers numb, and peered at it. My chest constricted as soon as I noticed the penmanship.

Paul

You have, in fact, come home if you are reading this. I wanted to be buried in my hometown as my final desire.

I took a deep breath, but I made myself read on.

Shortly after graduating, I became ill. skin cancer. For a period, it went into remission, but it returned. Even worse this time. According to the doctors, I had no other options.

I didn’t write to belittle you. I wrote because I didn’t want to die without making up for my mistakes. Paul, I was a complete idiot. I let my pride to destroy our friendship, which was the best thing I’ve ever had. I threw it away for a foolish wager, and you were my brother. I don’t think you’ll pardon me. I just want you to know how much I’ve missed you.

With a sharp gulp, my eyesight became blurry.

Regarding that final wager… You seem to have won, my friend. I’ll pay for the beer.

— Jake

I gripped the letter fiercely, causing the paper to crumple under my fingers. Jake had left. I had come here hoping for a second opportunity, but all I received was an unwelcome farewell.

The pint of beer in front of me caught my attention. It appeared to be a typical drink, but I understood what it meant.

Jake had fulfilled his promise.

I raised the glass with unsteady hands. “You idiot,” I said in a whisper. I took a sip after that. It had a bitter flavor. Or perhaps it was simply the pain.

I was in front of Jake’s cemetery a week later. I was accompanied by Laura and Emily, but they allowed me room. I was the only one who could do this.

With a trembling breath, I bent down and ran my fingertips over the name etched on the stone.

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

I shook my head and wiped my eyes. I used to wonder if you ever gave me any thought. If you ever felt bad about what transpired. As it happens, you did. I also regret not knowing sooner.

I took a pint of beer out of the bag I had packed. I put it down in front of the headstone and popped the cap.

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

There was silence between us. I could hear Emily laughing in the distance as the wind rustled the trees.

I grinned. “Jake, I forgive you. I’ve long since forgiven you.”

Wiping my hands on my jeans, I got to my feet.

Laura grasped my hand and gave it a light squeeze. “You okay?”

I gave a nod. “Yeah.”

I took one final look behind me as we left. The ache persisted. Most likely, it would always be. However, I didn’t feel as though I had lost my best friend for the first time in years. It was as though I had finally bid farewell.

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