Imagine Will being dared by his friends to ask you out for $20. You were the schools nerd and got bullied daily for it. Will never in a million years would have guessed he’d fall in love with you but he did and you find out how this all started at prom. (10 Things I Hate About You theme.)
Used to the whispers when you answered too many questions in class. Used to the boys snickering when you carried around novels thicker than their textbooks. Used to eating lunch in the library because it was easier than pretending empty seats didn't exist.
And somehow, despite all that, you'd still fallen for Will Smith.
At first, he was just another hockey player. Another popular guy who walked through the halls with his friends like they owned the place.
Then he'd started sitting beside you in chemistry.
Then borrowing your notes.
Then texting you random questions at midnight.
Then showing up at your locker.
Then smiling at you like you were the only person in the room.
And somewhere between study dates and late-night drives and stolen kisses behind the rink, you'd made the mistake of believing him.
Believing he actually saw you.
Believing you were more than some joke.
Prom night shattered that illusion.
The gym glittered with cheap decorations and fairy lights. Music echoed through the room while couples danced beneath the streamers.
You'd spent two hours getting ready.
Two hours trying to convince yourself you belonged there.
Will hadn't stopped staring at you all night.
"You look beautiful."
You rolled your eyes.
"You've said that six times."
"And I'll say it seven."
His hand found yours.
The familiar warmth should've comforted you.
Instead, something felt off.
Maybe it was the way his friends kept glancing over.
Maybe it was the way Ryan and Gabe kept looking guilty.
Maybe it was the knot in your stomach that refused to disappear.
You excused yourself to get a drink.
That was when you heard them.
A group of hockey players standing around one of the tables.
Laughing.
Talking.
Not realizing you were right behind them.
"Dude, best twenty bucks I've ever spent."
Your stomach dropped.
You knew that voice.
Ryan.
"What was it, anyway?" another guy asked.
"You don't know?" Connor laughed. "Beginning of the year. We dared Will to ask her out."
Silence.
"No way."
"Swear to God."
Your pulse thundered in your ears.
"No, seriously. Twenty bucks. We thought she'd say no."
Someone laughed.
Someone else muttered something about how insane it was.
And then came the sentence that made the entire room tilt.
"Crazy thing is he actually fell for her."
You couldn't hear anything after that.
The music blurred.
The lights blurred.
Your vision blurred.
All you could think was:
Twenty dollars.
Your relationship had started because someone thought you were worth twenty dollars.
You turned and walked away.
"Hey!"
Will's voice echoed behind you.
You ignored it.
"Y/N!"
His footsteps followed.
You pushed through the gym doors and into the empty hallway.
"Stop."
You spun around.
"What?"
Will froze.
Because he'd never seen you look at him like this.
Like he was a stranger.
"What happened?"
You laughed.
The sound was horrible.
Broken.
"How much was I worth?"
His face went white.
Immediately.
And that told you everything.
Everything.
"No."
"How much, Will?"
He didn't answer.
You nodded.
"Right."
"Y/N—"
"How much?"
His jaw clenched.
"...Twenty."
The number hit harder than you expected.
Because hearing it made it real.
You swallowed.
"Twenty dollars."
"It wasn't—"
"Twenty dollars."
"It was a stupid dare."
You stared at him.
The boy you'd loved for almost a year.
The boy who knew your favorite books.
The boy who kissed your forehead when you were stressed.
The boy who knew exactly how much you'd been hurt by people.
And he'd started all of this as a joke.
"You asked me out because your friends paid you."
"No."
"That's literally what happened."
"At first."
The words slipped out before he could stop them.
At first.
You laughed again.
A tear rolled down your cheek.
"Oh my God."
His face crumpled.
"No, no, that's not what I meant."
"Then what did you mean?"
"That was before I knew you."
His voice cracked.
"I didn't know you."
You looked away.
Because if you looked at him any longer, you'd cry.
"I was an idiot."
"Yeah."
"I know."
Silence.
Will took a shaky breath.
"After the first week I forgot about the dare."
You said nothing.
"After the second week I couldn't stop thinking about you."
Still nothing.
"After a month I was completely screwed."
His voice was quiet now.
Raw.
"Do you know how many times I tried to tell you?"
That made you look up.
His eyes were red.
"I wanted to tell you."
"Then why didn't you?"
Because that was the question.
Will looked miserable.
"Because I was terrified."
You scoffed.
"Of what?"
"Of losing you."
His answer came instantly.
"You would've hated me."
A bitter laugh escaped you.
"Well congratulations."
The words hit him like a slap.
You could see it.
The hurt.
The panic.
The realization.
Because for the first time since you'd met him, Will looked like he might actually cry.
"I love you."
The hallway went silent.
You froze.
His voice shook.
"I love you."
Another step.
"I know I don't deserve you."
Another.
"I know I screwed this up."
Another.
"But every single thing after that stupid dare was real."
Your heart broke a little.
You believed him.
That was what made it hurt so much.
You believed him.
And you still loved him.
Which was honestly the most infuriating part of all.
Will stopped a few feet away.
Close enough to reach you.
Not close enough to touch.
"You don't have to forgive me tonight."
You stared at the floor.
"You don't have to forgive me at all."
The crack in his voice nearly undid you.
"But don't think for one second that you were ever worth twenty dollars."
Slowly, you looked up.
His eyes met yours.
"You were the best thing that ever happened to me."
The tears you'd been fighting finally escaped.
And for the first time all night, neither of you knew what happened next.
Only that whatever came after this would have to be built on the truth.
