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The Midnight Bet

By HeartofInk All Rights Reserved ©

Romance / Action

The Midnight Bet

There were two things Brian Hayes learnt very quickly in his early high school years.

One: Never take advice from his new best mate.

Two: Never agree to dares set up by his new best mate.

Sadly for Brian, he was never very good at remembering rules or following them.

It’d been four months since his family had shifted to a new town and three months, twenty-nine days since he’d joined his new school. In those four months, Brian had managed to get chummy with one of the most dangerous people in town, fail miserably at football, and also fall in love with a random brunette.

First came the best mate.

Caleb Ray was not only ridiculous, but also terribly hilarious. He just happened to find himself sitting next to the new gangly kid in school three classes in a row, and then turned around in the third and said, “Hey, new kid. What do they call you?”

Brian had been heavily offended. “My name’s Brian Hayes,” he’d said stiffly.

Caleb grinned. “Caleb Ray.”


“Our names rhyme! We should totally start hanging out.”

Cue a skeptical look on Brian’s behalf. “No, they don’t rhyme.”

Caleb had mulled it over. “You’re right, they don’t. So, I’ll save you a seat at lunch then.”

After Brian got over the nagging doubts that Caleb might be an idiot, an undercover spy, or possibly gay, the two boys found themselves sitting in the corner of the cafeteria comparing jacket stains. Needless to say, a few lines of poetry, a stolen cigarette, Green Day songs and a punch later, they were friends by the end of the day. (Brian had very responsibly declined the cigarette.)

It hadn’t taken long for the two of them to discover common interests, each other’s stupidity and portions of their deep dark pasts. By the time those three months and twenty-first day rolled around, they were fast friends.

Sure, Brian had problems in his life. He couldn’t get his brown, mousy hair to lie flat—they stuck up in different directions in all their glory—and still couldn’t understand how to pass the ball to his teammates and not the other team’s.

Being a sixteen year old dude, the main problem he was focusing on though was girl trouble. (At least that’s how his mom always put it as.)

He hadn’t seen Katherine until his second day at school. She walked in late in first period English class with her perfect, long caramel-coloured hair and her olive-green eyes and Brian dropped his copy of Shakespeare and his carefully sharpened pencil on the floor.

But that wasn’t even the start. The start was when their English teacher turned on her, with a “Why are you late, Ms. Ross?”

Katherine had flushed a deep scarlet. “I’m sorry; I was out all morning selling the cookies for our charity-fund, and I got late for the bus.”

The teacher had the Oh-dear-God-look-how-nice-this-girl-is look on his face as he softened into a marshmellow and gestured towards an empty place. “It’s alright. Don’t be late again,” he added, trying to be stern after his momentary lapse into niceness (like who does that?).

“Oh I won’t!”

Well, that was that. Five days later Brian plucked up the courage to go talk to her, and realized she was one those people who talked to everyone. In his mind, he saw her and her charity-club friends as the royalty who were just nice enough to be kind to the commoners like him. She was the cookie-seller, the girl who helped out with homework, the girl who read Shakespeare and Jane Austen, the girl who took old people across the street, the girl who rejected guys with a hug and a kiss on the cheek.

By the end of the week, Brian turned to Caleb and said, “I’m in love with Katherine Ross.”

And Caleb whistled. “Dude, take it easy. You’ve been here what, a week?”

But he’d already lost Brian. His friend was lovesick and staring off into the distance. “I need to go tell her.”

Caleb shrugged. “I’ll buy you a Twilight T-shirt while you go serenade her. That help?”

Unfortunately, his friend didn’t seem to have the will to even produce a mild glare at the suggestion of a Twilight T-shirt, which kind of disappointed Caleb. Making fun was his job, and he needed a bonus by the time this month ended.

At any rate, after Brian’s strong resolution in April to confess his mushiness to Katherine (“There’s no turning back now! I’m going to do it!”), he was still talking about the weather and the cafeteria food with her in mid June.

He had a million worries, of course. He’d go back home and stare at the mirror, wondering whether Katherine preferred boys who were thin and gangly, had dull grey eyes hid behind big glasses, and had hair like a crow’s holiday resort.

Not to mention the unlucky state of his wardrobe; it looked like a rainbow had barfed up in there, because his mother and sister had got him button-down T-shirts of almost every shade of colour in existence and a few had macho polka-dots on them. (“Oh, but honey, they were on sale! And you know how lemon yellows suit you!”)

Caleb, of course, had done his job as a true friend and helped raise Brian’s self esteem. On a rainy Tuesday morning when Caleb was over at Brian’s place playing Halo and gorging on pizza, Brian got romantic looking at raindrops on the window pane and said, “Well, maybe Katherine will like me anyway. Girls dig nerds, right?”

His friend spared him a glance from the sofa. You had to admire his patience for putting up with these random Katherine attacks of Brian. “Oh, no,” He assured. “Only hot nerds. You’re not hot, mate.”

Brian stared at him. Then: “Well, maybe if I get those stereotypical black nerd-glasses…”

His well-wisher looked at him, pausing the game.  “What’s the last book you read?”

“Uh…A Lonely Planet magazine last month, I think.”

Caleb grinned, turning his eyes back to the TV screen. “You’re not a nerd, mate. You’re unclassified.”

Fast forward to start of July, roll in fluffy clouds and bright sunshine and all things that make Brian Hayes’s sigh after Katherine Rosses.

Then came the turning point.

Now Caleb was the guy in the absurdly coloured pants, free breathmints, and a plasticky camera that clicked everything from the album picture to the student bodies for the school magazine. In other words, he was the ladies’ man. His grades waved through As and Bs and some things in and around those alphabets, but he was popular and that was what made Brian sit up and cave in.

It was time to take advice from Caleb. (The last few times he’d done that, it had ended once with him in a Dumpster and another time in a situation so mortifying it cannot be put into words, but he figured what the hell.)

Also, important things were coming up in Brian’s life; there was going to be a school dance next week, and he needed to figure out a way to trick—er, convince—Katherine into going with him.

On a sad note, Caleb asked him to be creative, listen to some Adele and get ideas to ask Katherine out himself. Brian found it futile to try and explain to his friend that he’d been trying exactly that—minus the Adele—for the last few months but words kind of stuck on the tip of his tongue whenever he attempted to talk to Katherine about it.

Ultimately, destiny did it for him.

There was a match the coming Sunday and Caleb was supposed to come over to Brian’s house with two other guys to watch it. That night, was a fated one. Probably the night Brian would carry with him to his grave, but it was a fated one all the same.

At eleven, when the match ended, the other two guys went back home. One had an angry mom on the phone and the other had an angry girlfriend.

At any rate, Caleb’s parents were at a wedding at a coast, and he was free to stay over if he wanted to. His house was two blocks away anyway. Brian’s dad was in another continent doing the big man stuff in his big man business, and his mother and sister were asleep on the second floor.

The two were lying on two different sofas, lazily pushing candied popcorn into their mouths and yawning at the commercials on television, when Caleb sat up.

For all those who are ignorant, when Caleb sits up, something is about to go haywire because that’s when he gets an idea. His ideas, though he described it as a ‘Ray of light. Geddit? Caleb Ray? Ray of light? No?’, were mostly hazardous and should be kept out of the reach of all human beings who wish to live on without wanting to leave their countries.

“Truth or dare?” He shot at Brian, who stared at him.

“Neither,” he answered, with all the excitement of a dead butterfly.

“Don’t be a prat. I’m trying to help you in mysterious ways. Now, truth or dare?”

“Help me?”

“Would you answer me?”

“Truth.” Brian shrugged. He was mostly used to Caleb’s sudden bursts of idiocy, but just in case it was serious this time around, he played it safe.  

Caleb grinned and leapt off the sofa. “Nah, that’s the wrong choice. Dare it is then!”


“I dare you,” Caleb said slowly and in a way that would’ve made every melodramatic scene in Hollywood proud. “To go serenade Katherine to the dance. Now.”

Brian sat up too, and by now he was positively regretting his friendship with this wacked up guy in front of him. “You want me to go sing at her doorstep? Really? What was the century last time you checked, Caleb?”

Caleb clapped his hands down on his friend’s shoulders. “Below her window,” he amended. “Tonight’s the night, mi amigo. I feel it in my blood.”

Brian was seriously considering pressing 911. “Okay, first off, I didn’t agree to this dare. Second of all, I’m not going to serenade the girl! Thirdly, it’s almost midnight. Four—”

“Fine, I’ll relent and be nice,” Caleb grumbled. “Go just ask her out normally instead, but do it now. Like they do it in movies.”

“This is crazy. You’re crazy.”

He felt Caleb’s fist come in contact with his face, and it wasn’t exactly a gentle caress. “Grab your shoes. We’re going out.”



“I said no. I’m not doing it.”

“I can’t believe I’m doing this.” Brian had a very manly expression on his face; trembling bottom lip, nervous eyes and furrowed eyebrows. The two boys were standing on the Ross’s lawn. The streets were deserted and dark, and there was single street lamp flickering without much enthusiasm at one corner.

Brian gulped as he looked up at Katherine’s house. He’d been here before, when he’d walked her back home one day, but that was it.

Caleb was calmly taking out a cigarette from his pocket. “ Dare’s a dare, mate. Also, someone’s gotta make you do it, or you’ll never get around to it. Dude, you’re scared of asking for a second scoop of blackberry ice cream!”

Brian looked hurt. “They look at me weird if I do,” he protested weakly. His hair was sticking up more in his anxiety.

His best friend sighed and pulled him by the sleeve into the girl territory (Brian had been hovering feebly in and around the lawn and the pavement).

Yes. An epic moment. Two boys, one about to soil his pants and the other about to start off underage smoking, standing on a fated patch of grass.

In his heart of hearts Brian knew that as crazy was Caleb was, he did have a point. Someone had to push him into the deep side of the pool, and if it was Caleb with a bat shooting him carelessly into the ocean, who cared? And he knew he’d never really ask Katherine out himself, so yeah, why not at midnight by shouting out words he hadn’t rehearsed even once?

“You done thinking yet?” Caleb snapped him out of his reverie. “Go do your thing.”

Brian glared at him with force enough to shame a Basilisk, flicked the cigarette out of Caleb’s fingers and elbowed him to the side. “If I die tonight,” he said. “Bury me in my Captain America suit, okay?”

“I swear,” Caleb said solemnly. When Brian wasn’t looking, he picked up the cigarette. “Shield and all, mi amigo.”

“Here goes nothing.” Brian opened his mouth, about to launch into Shakespeare-worthy lines, before he realized he didn’t even know which window was Katherine’s. How would he know who was yelling out his love for? The last thing he needed was Katherine’s father popping his head out of the window as he confessed his everlasting love.

 He froze in place, looking very much like he’d swallowed stick jaw in reverse mode.

Caleb had conveniently disappeared into the shadows, and wasn’t going to be much help.

There was an awkward moment where Brian saw his life flash before his eyes, before he took a deep breath and jumped into the waters. “Katherine!” He shouted up at the windows. “Katherine Ross!”

“Keep going.” Caleb’s voice drifted out of the darkness.

“Katherine, I have something I need to tell you!”

“Keep going, you’re doing goo—”

“Would you shut up and let me speak, you moron?” Brian shot back in the direction of Caleb. Then, with his pride in one hand and his self-esteem in his arms, he yelled up again. “Katherine, here goes! I hope you’re listening!”

There was a brief pause in which Brian felt most of his internal organs turn against him like nope. “Katherine,” he said, and her name felt great to shout. “Ever since you walked in late to English class and interrupted Merchant of Venice and started talking about cookies and charity shit—I mean fund—I’ve been in love with you!”

A light was switched on in the Ross’s house, and Brian was almost hopeful—maybe it’d work out all fine like in the movies and it’d be Katherine who rushed to a nonexistent balcony and accepted his undying love.

“Your hair is like honey, only like honey when it’s held in sunlight, you know?” My God. Sixteen and all that it took to intoxicate him into silliness was candied popcorn and Mountain Dew. He was a basket case. “Your smile! It’s like sun breaking through the clouds!—Caleb, help me!”

“Like rain after a drought,” Caleb supplied, but Brian wasn’t taking that. Even cheesiness had its boundaries and this was all over foreign territory.

 Brian cleared his throat and continued, “And your eyes! Katherine, your eyes are like olives but like olives in—”

He broke off. Something was wrong. Not only were all the lights in the top floor of the house being switched on at a rapid pace, but the whole neighbourhood was rumbling awake. People were slamming open door and peering out of windows. In fact, Brian hadn’t seen Bolt run as fast as the whole street was suddenly lit up. Somewhere very close to him, a dog started barking, and not in a very nice way.


The window Brian had been staring at opened quickly, and he caught sight of a shocked Katherine Ross, with all her honey-in-sunlight hair tied up in a topknot. Her face was flushed and she was gawking at Brian like he’d come running out to her lawn in nothing but a pair of Speedos (though the situation was embarrassing enough to rival that imagination).

All he could think of though was Damn, she’s hot.

Caleb peered out from the side of the house. His cigarette was stuck to his ear in nervousness.

The front door slammed open and a tall man with a look on his face that wasn’t necessarily a happy expression stormed out.

Brian stared at Mr. Ross. Mr. Ross stared at Brian. Caleb chewed his fingernails, his cigarette dangling down his ear.

 “Just WHAT DO YOU THINK YOU’RE DOING?!” Katherine’s dad roared, and Brian felt all his confidence pool onto the floor in a distressed mess. “Do you know what time it is?!”

“Um,” said Brian intelligently. Candied popcorn didn’t sound so good right about now. “I think I’ll just er…go now.”

People had started to retreat back into their houses and it was going dark again, but Katherine’s family seemed wide awake. It was pretty clear that Brian had a loud voice and rather striking words.

“Oh no you won’t. What’s your name, kid? And how dare you come here and say all this about my daughter?”

“Yeah…about that…” Damn you Caleb. Looks like he got his bonus of the month.

“What’s your name boy?”



What happened next was described later on my Brian as entirely and utterly Caleb’s fault, and by Caleb as a heroic rescue which went a tad awry.

Whatever the case, before Brian was castrated on spot by Katherine’s not-so-thrilled dad, Caleb rushed out from the darkness yelling, “Come on, Brian! This way!”

Another boy materializing on his lawn and out of the shadows was enough to give Mr. Ross a probably cardiac arrest, because he uttered a very unmanly squeak and a staggered back a few steps. In the time that it took him to realize it was two guys in on the drill, Caleb was already flicking cigarettes at Brian and leading the way. “Hurry up!”

Brian didn’t have the courage to look up at Katherine even once as he sprinted across the Ross’s lawn; he just knew she was watching the whole thing and would probably come to school the next day dishing out blueberry gums for everyone that said Hate Brian Hayes on them.

Unfortunately for Brian, things started to rush even more downhill as the night progressed. Caleb had taken advantage of the empty street and was rushing along it, but Brian who was always the you-should-walk-carefully-on-pavements guy was running past other people’s houses when he felt a massive tug on his leg.

He screeched to a halt, and frantically tried to free himself from whatever his jeans had snagged on, but when he turned around, he froze. The dog that had barking away to glory a little while ago was obviously not very thrilled at being disturbed at this time, because it had broken free of its chain and was growling ferociously, clamping onto Brian’s jeans with determination.

Note to self, Brian thought. Never try to ask a girl out at 1 AM when there’s a Rottweiler in the vicinity.

“Caleb!” He called helplessly, but the angry dog clamped down harder. Apparently, he didn’t like his prisoners to call for help. “Why couldn’t you just take the other way?!”

“What?” Caleb was trying and failing at suppressing his laughs on the other side of the road. “Your house’s this way!”

“Ah, shut up!”

The dog’s owners seemed to be asleep, or unbothered. Nevertheless, Brian was starting to freak out because dogs had never been his area of specialty ever since his sister made a puppy do the unspeakable on him.

“Just run!” Caleb adviced. He’d noticed Mr. Ross recover near the house and start to step out onto the sidewalk.

Against his better judgement, Brian tried to run. Then he tried to run very fast.

As he gasped forward, he first heard the Rottweiler growl very loud, and then heard the distinct ripping of pants.

His jeans ripped apart at the thigh, and in his desperate attempt to get away, he pretty much wriggled out of them and raced towards the other end, heedless of the fact that Katherine’s dad was still alive and kicking right there.

The Rottweiler and Mr. Ross seemed to have something in common. Neither of them really wanted to miss out on an opportunity to embarrass Brian Hayes to death.

They rushed in unity after Brian (Caleb wished he got his camera), who was running faster than he’d ever on the field in his blue Spongebob boxers. Mr. Ross was yelling after him unintelligibly, and the dog apparently had unfinished business with his bum.

Long story short, the view that Katherine got that day was her father and her neighbor’s angry dog chasing after a boy in Spongebob boxers, skinny chicken legs and glasses which kept falling down his sweaty nose.

On the other end of the street, Caleb was on the ground, crying helplessly with laughter.

“Cornflakes, honey?”

“Death.” Brian had his face flattened against the kitchen table. “Just give me death.”

“Aw, cheer up mate.” Caleb Ray was sitting casually on a chair next to him with his feet up on the table. He reached out and patted Brian on the back. “Shit happens.”

“Caleb!” Brian’s mom stood up, holding the cornflakes box in her hand and frowning. “Mind your language! And NO feet on the dinner table!”

Caleb grinned up at her apologetically. “Sorry, Mrs. H.” Then he gesticulated in a very unnecessary wild manner towards his friend. “What do we do with this one, Mrs. H?”

Brian’s hair, for once, was lying flat now. That was mostly because he’d had his face against the kitchen table ever since he arrived home in his boxers, and his arms hung limply at his sides. Caleb had decided not to tease him about the tear-tracks on the wood.

He truly was the picture of a happy, sixteen year old guy.

“Well, we have some bacon,” Brian’s mom piped up, moving to the refrigerator. “How about some bacon, honey?”

“Just leave me here to die,” Brian groaned against the table. Caleb sighed dramatically.

“Oh come on Brian, it’ll be okay.”

After three hours, Brian slowly unplastered his face from the table and looked at Caleb, who tried not to dive under at the sight of his friend’s face. He looked like a drug-addict, a hobo and a junior professor all rolled into one geeky guy.

“It’s all your fault,” He mumbled without enthusiasm. “Now Katherine hates me.”

“No one hates you honey,” soothed Mrs. Hayes. “Now have some cornflakes. Go on.”

“I thought I was getting bacon!” Brian looked up at his mother, betrayed. “God! No one listens to me in this house!”

“Well, don’t get your panties in a twist now,” Caleb muttered under his breath, only loud enough for Brian to hear, who glared at him. Not for long though; it wasn’t the first time that Caleb had deprived him of his gender rights. (In Caleb’s defense, he only did it when Brian was bawling for things absolutely bawl-unworthy).

It was six in the morning but Brian’s mom always got up early, and despite Caleb’s slight mistakes the other night, he’d stayed up with Brian all night. His sister had rushed off jogging with her boyfriend an hour ago.

Despite Caleb’s slight mistakes the other night, he’d stayed up with Brian till morning. Brian hadn’t really done much since he came home except for changing into his PJs, flinging his glasses onto the bed, and moping all over and around the dinner table, but his friend supported him nevertheless.

They were interrupted by the doorbell. Mrs. Hayes looked up. “Brian, go get it will you?”

“I can’t.” Brian stared off moodily into the distance. “I’m dying, Mom. My crush saw me in my Spongebob undies and I’ve been stripped of my manliness.”

But Mrs. Hayes had picked up the newspaper, and forgetting about cornflakes, bacon and her son, she motioned impatiently towards the door. “Oh, don’t be silly. Go open the door; it’s probably the mailman. I had a parcel ordered in last—”

“FINE! I get it!” Brian shot a single murderous glare at Caleb who calmly choosing a toast for himself and got up. The bell rang again, and Brian dashed to the door.

He opened and stood staring for a very long time.

Katherine was wearing a white shirt and jeans, her hair tied up in neat ponytail. She had her bag slung across her shoulder, which probably meant, as Brian cleverly deduced, that she was heading to school.

They stared at each other for a moment, each remembering the rather eventful night last night, but Katherine was first to speak. “Hi, Brian.”

Brian coughed, panicked, and shut the door in her face.

“Brian?” He heard her voice grow small outside.

He had one of those proud moments where he stood in one place, completely lost, and not knowing what to do. (His usual behaviour in libraries.)

He caught Caleb throwing up his arms and staring at him with a what’s-wrong-with-you expression on his face from across the room.

“Go talk to her, you idiot!”

Brian sighed and then wrenched the door open again. Katherine was halfway down the path, but turned at the sound of the door opening.

Feeling like he was still standing around in his Spongebob boxers, Brian stepped out and shoved his hands defiantly in his pockets. “Hi, Katherine.”

The girl gave him a shy half-smile. “I uh…I cooled my dad down. So you know, if you want to come and shout under my window again,” she shrugged. “He probably won’t try and kill you.”

Brian was suddenly standing there in the sunlight and realizing that he hadn’t even washed his face since he came back. Judging from Caleb’s expression, he probably looked like he’d spent the night in a freezer. Fantastic; he was just great at impressing Katherine.

“Look, Katherine,” he said at last, looking down and gnawing away at his bottom lip. “I’m sorry for all that shi—I mean stuff—last night. It was a dare…er, it was stupid…just don’t hate me okay?” He finished lamely. “I’m really sorry. I’ll make it up to you, I swear.”

Katherine didn’t look like she hated him. When she grinned at him next, it didn’t feel like she hated him either. Brian felt his spirits rise a bit and flop around weakly.

“Yeah, I noticed Caleb Ray running away,” she said. “I figured it was a dare. But…” she shrugged again. “It was kind of sweet, Brian. No one’s ever done that before…I mean, you braved a Rottweiler and my dad to come and say all that…Of course I don’t hate you.”

In all truthfulness, Brian had had no freaking idea that those two abominations of nature were going to be there (at least not the dog), but if Katherine was looking at him a hero, he wasn’t going to ruin that any time soon.

“So, you like me?” She said without much embarrassment. “You could’ve just told me, but I guess you like to do things in style.”

“Uh…” Brian decided he had to get something clear before he jumped in again. “Well, yes, by now it’s kind of obvious that I do. How much of that did you hear, anyway?”

Katherine blushed. “All of it,” she mumbled out. “I wasn’t asleep, so, I heard it from the beginning. I even switched on my light.”

“Yeah,” Brian remembered. “What were you doing up so late?”

“I was listening to Mr. Mister,” said Katherine shamelessly.

In that moment, Brian knew that the universe had written down his marriage with Katherine already. His eyes shone. “I love Mr. Mister!”

“But,” Katherine said teasingly. “You never did tell me. What are my eyes like?”

“Oh, that,” Brian stood up straight. “Like olives, but only like olives in—”

They were interrupted by Brian’s mom calling him from inside; “Brian, did you put your boxers in the wash? And who’s out?”

The two of them stood there awkwardly, which was enough time for Brian to reflect that between Caleb and his mom, he wasn’t going to have many conversations with Katherine that didn’t involve his underwear.

“I guess I should go then,” Katherine said finally, but her green eyes were laughing. “I’m late already. Aren’t you coming?”


“Um, we’re late for school?” He’d got the school part, but he kind of forgot what the time was in his misery.

“WE’RE LATE FOR SCHOOL?!” Caleb echoed from the house. Brian rolled his eyes.

“We’re coming,” he said, starting to walk back towards the house. He was feeling miles better. In fact, he was starting to admire just how beautiful everything was starting to become. How could he never notice the beauty of that dead beetle by the window?

Katherine nodded, stepping back. “Catch you later,” she said. “Nice boxers by the way,” she added, grinning. “I forgot to tell you last night.”

Fifteen minutes later Caleb was chucked out of his seat by his best mate and squashed between two geeks reciting Frost to each other. But in between muttered curses, he was grinning at two people in a corner of the class.

Brian Hayes, sitting next to Katherine Ross. She was talking animatedly about a book, and he looked like he was listening intently, when really he was wondering what perfume she used.

That’d continue for a while, but for Brian right then, life was perfect.



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