[Patreon Exclusive] Roommate Dares: Chapter 1 (Patreon)

Aaron’s roommate, Jake, has a gambling addiction. He’s always betting on everything, and from time to time, Aaron can’t help but get in on the action. But soon enough, Jake runs out of money, so he starts getting more creative with his wagers.

One afternoon, Jake and Aaron find themselves betting on a hockey game with the biggest stakes yet: the loser has to be the winner’s slave for a day, and do whatever the winner wants within the confines of the house.

Chapter 1

My roommate, Jake, always wanted to bet on everything. We couldn’t play a game (cards, board games, or sports) without him putting stakes on it. We couldn’t even watch a game on the television without him making it into some kind of wager. He had a serious gambling addiction, which was getting worse and worse the longer I lived with him. And his gambling addiction was starting to rub off on me.

It was hard to decline his wagers from time to time. We were playing basketball once, and I had to make an easy, straight shot from the line. He called out, “I bet you one-hundred bucks you miss the shot.” I’d made the same shot a dozen times that day—it should have been an easy hundred bucks. I took the bet, and then I missed the shot. Losing one-hundred bucks burned, but I knew I would get a chance to win it back, as soon as there was another opportunity to bet; and I did win it back later that day, when he bet me another hundred bucks that the Penguins would lose to the Panthers. The Penguins won. Crosby scored a hat-trick in the third period.

After a year living with Jake, I was starting to get a good idea of how his mind worked. He didn’t just bet on anything, he would almost exclusively bet on the underdog, the least-likely victor. Like when he bet on the Panthers, the worst team in the hockey league, going up against the best; or when he bet on my missed throw, from my most comfortable spot—a shot I’d made a dozen times before with no effort. He must have liked the adrenaline of beating the odds. Regular odds weren’t exciting enough for him.

As a mathematics major, I decided to use this against him, choosing hockey (a game that he loved) as my vehicle. I wasn’t much of a hockey guy, but I did plenty of research, finding out who the best teams were, which players were injured, which teams were on hot-streaks, and which teams had injured rosters and were playing like crap. And once I was comfortable with my hockey-knowledge, I started being the one to make the bets. I knew I would lose a few, but on average, I would win more often than not.

And I was right. He won the first game, I won the next two, he won the next, and then I won the next three. There was the occasional upset—Jake would put a huge sum of money randomly on a team and then he would win, setting me back a few games, but I would eventually catch up. After a few months, I had him drained. I overheard him on the phone with his parents, asking for rent money. He’d lost everything gambling with me. I felt bad. I considered giving it all back to him, but at the same time, it seemed like a valuable lesson that he needed to learn. I thought that maybe he would stop gambling, finally…

I was wrong. His little addiction only got worse. Instead of betting money, he started betting his possessions. “I bet you my guitar that the Senators win this game,” he would say. Sometimes I wouldn’t take him up on his bets, knowing I was just enabling his dangerous behaviour, but sometimes when I didn’t take him up, he would phone up his friends and try to get them interested in his wagers. Sometimes he would even go to the bar, just down the street, and bet with total strangers. Occasionally he would come home with a big smile and a handful of cash, other times he would come home with red eyes, devastated.

After a year of living with him, he’d lost pretty much everything. “I think you need help,” I said to him, and after some teary-eyed resistance, he conceded. He scheduled an appointment with a therapist. “I go in two weeks—that’s the soonest he can see me,” Jake said.

It was a week before his appointment that he came to me, his hands trembling slightly as if he was going through some serious withdrawal. “What’s up?” I said.

“One more bet—before I go and get help—just give me one more,” he said.

I was reluctant but he kept on pressing. I ended up caving. I’d bet hundreds of times with him, what was once more? We went to the living room and he turned on the television. It was the Toronto Maple Leafs against the Minnesota Wild. “Two-hundred dollars,” he said, “on the Wild.”

I shook my head. “No way. Besides, do you even have two-hundred dollars?”

“I can get it,” he said.

“No, Jake. Why don’t we just make this a friendly bet?”

“What do you mean?” he said.

“If I win, you have to cook me dinner. If you win, I’ll cook you dinner. Something like that,” I said. I watched him bite his lip and take a deep breath. It wasn’t enough for him. It wasn’t enough excitement.

“How’s about our bikes?” he said.

I laughed. “I don’t need a second bike.”

“You can sell it.”

“Jake, no. Friendly bet, or nothing.”

The referee skated to the centre of the ice and prepared to drop the puck. The game was about to start and Jake had no stakes to fuel his adrenaline.

“Okay fine, how’s about this: slave for a day.”

“What does that mean?”

“It means, if I win, you have to do everything I tell you to do tomorrow. I you win, I have to do everything you tell me to do.” My eyes drifted over to the hockey game, which was now underway. The Leafs won the faceoff, getting control of the puck. One of the Wild players went to rush the puck, but the Leaf in possession made a quick move, easily dodging the aggressor. The Leafs were on a ten game winning streak and the Wild were on a four game losing streak. It should have been an easy win. Besides, I needed my car washed, my bed sheets cleaned, and it had been a long time since the garage had been cleaned out.

“Define ‘everything’,” I said. “Like, if you tell me to give you all of my money, I’m not doing it.”

“Okay, fine. It can’t cost anything, and it stays within the walls of the house.”

I looked back to the hockey game. The Wild were falling over themselves, and they looked tired. The announcer mentioned that it was their second game in as many days, on the road. How could the Leafs lose? “Okay, deal,” I said.

We both took a seat on the couch and watched the game closely. The game turned out to be much closer than I’d expected. Just ten minutes in, two of the Leafs’ best players were checked and sent off the ice, injured. Suddenly, it became a scrappy mess of a game, goal after goal on both sides of the ice.

And even though there was no money or material possessions involved, it was the most nerve-racking bet we’d ever made. I had no idea what he was going to make me do if he won, and he had no idea what I was going to make him do if I won. I looked over at him at one point. The back of his neck was damp and his face was a shade of red, as if he had been holding his breath since the game started.

The game went to a shootout, and the Leafs lost. Jake jumped up to his feet with his arms in the air. “Yes!” he called out loudly. He’d won his last-ever bet. He turned to me with a big grin on his face. “I’ll see you tomorrow, bright and early.”