The Lost Bet

Sometimes people bring the worst upon themselves. In high school, my close group of friends would seemingly hang out every weekend. On this day, however, one of the girls made a terrible decision. Her name was Kathy. She was probably the most tomboyish out of the group of girls we hung out with. Let me clarify that a little – she had the most boyish personality out of the girls. For example, she loved video games, cars, and sports (namely hockey). However, she was still one of the girls in that she dressed fashionably well and worked part-time at one of the popular clothing chains.

We were hanging out at one of the guys’ houses and he dusted off his old Super Nintendo. Kathy immediately grabbed the copy of Super Mario Kart and challenged anyone to play. To her credit, Kathy was incredibly good. We played battle mode mostly, and she was virtually unbeatable.

Kathy started a personal rivalry with one of the guys who was able to stop her reign of terror – we’ll call him Steve. We played with rules that the loser of each round would have to rotate out so the next time Kathy and Steve got to play, the stakes were raised.

First time around, the loser would have to pay for the next time we went out for dinner. Then, it became the loser would have to do the other’s homework. It got to the point that Steve proposed the loser go streaking at school. Kathy obviously turned that down.

Kathy, however, countered Steve’s proposal with an interesting one.

“If I win, I get to shave your head,” Kathy said proudly.

“How short?” Steve asked, as he stroked his hair.

“The shortest the clippers can go,” Kathy smirked, confident in her abilities. At this point, Steve had only been able to dethrone her once.

“Do I get to shave your head if I win?” Steve asked.

“What? No!”

“Are you going streaking if I win?” Steve asked.

“Of course not!” Kathy said.

“Then what do I get?”

“Um,” Kathy thought for a second, “I’ll buy you dinner.”

“That’s not even close,” Steve laughed, “I could have no hair and all I get is a dinner?”

They started their negotiations. Steve constantly brought up streaking, so I guess in a way, it planted the seeds for Kathy to change her mind. At first, Kathy proposed not wearing her jacket to school (it was the fall, so it was somewhat chilly). Steve obviously did not accept. Kathy then offered up that she would wear a short skirt, rain or shine, still a no go.

After a little more back and forth, the two settled on Kathy’s shoe – not both, just one, because Kathy wouldn’t let him have both. The bet was set, if Kathy won, she got to shave Steve’s head. If Steve won, Kathy would have to give up one of her shoes for the day. Steve could choose any day of the week at school.

The terms of the duel were set. Kathy and Steve set off on the most intense game of Mario Kart (battle mode) that I had seen.

Kathy took the early lead with a couple of red shells. Steve was down to his final balloon early. He was not pleased. He began pleading with Kathy to let him have a chance.

Then, as if fate had intervened, an errant green shell struck Kathy’s kart. She was down to two balloons. Immediately after recovering, Steve found a star and was able to trap Kathy’s kart in the corner for another hit. The thing it, being trapped in a corner means she couldn’t get out and Steve took out the final balloon.

Kathy dropped her controller, now realizing what had happened. She lost the bet (which affectionately became known as “The Shoe Bet” within our circle).

To Steve’s credit, he didn’t cash in the bet right away, even though Kathy had offered her shoe up.

“Nah,” Steve smiled, “the day’s almost over.”

The next few days at school were hell for Kathy. The guys, mostly Steve, teased her day in and day out about when they’d strike and take her shoe from her. Monday, she wore a pair of Converse sneakers, the guys teased her by untying her shoes during lunch, but that was all. This went on for the next few days. Kathy would sometimes purposely switch seats in class or hide from us during lunch because she didn’t want to lose her shoe.

Finally, on Thursday, Kathy came dressed in skinny black pants tucked into black knee high boots, and a nice black top. She looked great. The guys were all waiting for her at her locker and Kathy knew what would happen next.

“Today’s the day Kathy,” Steve said as he motioned for her to pay up.

“What? No,” Kathy said, “not today!”

Kathy quickly packed her things into her locker and ran off to her next class. I was lucky that I had a few classes with Kathy, but she purposely sat far away from me, thinking I would be a part of her problem.

Kathy managed to dodge most of the guys until the period before lunch. She had to go back to her locker to pick up her textbooks.

Unfortunately for Kathy, the guys all knew it.

As she approached her locker, the guys gently pinned her down. A couple held her hands down.

“No, guys!” Kathy yelled, partially laughing while it happened.

Steve grabbed Kathy’s left foot. She was at his mercy now. He slowly unzipped her knee high boot. He had a little bit of trouble as Kathy tried to move her leg around. But she was only delaying the inevitable. Soon, Steve had the boot unzipped and was holding it in his hand. Kathy looked at her bootless foot, covered by her white sock.


The guys let Kathy up as Steve walked away with his new trophy.

“You guys suck,” Kathy said as she hobbled to her locker in one boot and one sock. She then proceeded to the next class.

This time, with nothing to lose, Kathy sat next to me and I kept teasing her about losing her shoe.

“My sock is getting so dirty,” Kathy said, “look!”

Kathy lifted her left foot to show the bottom of her sock. Her foot was clearly outlined on the bottom, but it wasn’t too bad yet.


“When are you getting it back?” I asked her.

“Knowing them? Probably never,” Kathy sighed.

I almost felt bad for Kathy as she had to do a presentation in front of the class. She contemplated taking off her other boot and just doing it in her socks, but it was the safe call to just do it one boot. I probably would have stolen her other boot if she did.

Kathy walked lopsided to the front of the class and did her presentation in one boot and one white sock. The teacher didn’t say anything, but I’m sure it was a burning question in his mind.

Kathy spent the lunch hour complaining about her sock. She was a good sport though as she laughed about it and would stick her dirty socked foot in our faces as emphasis.

After the last class of the day, Kathy hobbled back to her locker hoping to find the guys with her boot, but they were nowhere to be found. Kathy texted Steve only to get the reminder that he got to keep the boot for a full day.

one boot

I waited with Kathy to see if the guys would show up.

“My sock is so disgusting,” Kathy said as she lifted her foot up. Her sock was a dark dirty grey where her toes and ball of her foot was. There were specks of dust, dirt and even some hairs hanging off her foot. She tried to pat her sock off to clean it a bit.

“Ready to go?” I heard a voice from around the corner.

It was the girls.

“I don’t have my boot yet,” Kathy sighed.

“Well, we can’t wait all day.”

I asked Kathy where they were going.

Kathy said they had planned a shopping trip together after school and this was the worst possible time for her to have her shoe taken away. If it was any other day, she would have been fine, but today, she had to go shopping with the girls and they were going to go to one of the girls’ boyfriend’s place after.

Kathy reluctantly walked with the girls, limping to try to keep her already dirty sock somewhat respectable. I could only imagine how dirty her sock could have been after walking through the mall and then to someone’s house.

Filthy sock

The next day, Kathy, showed up to school, still in one boot, but a clean pair of white socks. Well cleaner, as she had already walked a bit in her one-shoed predicament.

Kathy waited at her locker and Steve finally showed up to return her boot.

“My mom was so pissed,” Kathy said to me in our next class together.


“She saw my socks in the laundry.”

“Did you tell her what happened?”

“No,” Kathy said, “I just said they probably got dirty because I was trying on clothes or something.”

“She didn’t notice that you came to school in one boot?”

“No,” Kathy replied, “I drove today.”

The best part of this was that Kathy became a constant target of shoe stealing in our group. She always took it so well. And she wasn’t scared to wager up another shoe bet every now and then.


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