Jacob stared at the worn leather cover of Tiffany’s diary, his stomach twisting with guilt. What had seemed like a brilliant plan now felt invasive and wrong. He ran his fingers over the embossed flowers, picturing Tiffany’s delicate hands tracing the same pattern.

“I’m such an idiot,” he muttered, flopping back onto his bed.

But it’s not like he can just give that back to her. That wouldn’t be smart. If he returned the diary, he’d lose his only leverage. His one shot at getting Tiffany to notice him.

She’d never go to prom with him otherwise, he reasoned, pacing the length of his small bedroom. Little Miss Perfect would rather go alone than be seen with the school’s resident bad boy.

Jacob paused, staring at his reflection in the mirror. His leather jacket and ripped jeans screamed trouble. But underneath was just a guy desperate for a chance.

“I don’t have a choice,” he said to his reflection. “It’s blackmail or nothing.”

The word left a sour taste in his mouth. But as he pictured Tiffany in a shimmering prom dress, her light brown hair cascading down her back, his resolve strengthened.

Too late to feel guilty now, he told himself. One perfect night with her. Then he will give it back.

Jacob put Tiffany’s diary in his dresser drawer. He carefully tucked it beneath a stack of t-shirts. The upcoming prom loomed in his mind, an event he’d always dismissed as stupid and pointless. But now, knowing Tiffany would be there with him, everything had changed.

“Can’t believe I’m actually looking forward to this ridiculous dance,” he muttered, closing the drawer with a soft thud.

Grabbing his phone, Jacob decided to push those thoughts aside. He opened his messages, a mischievous grin spreading across his face as he typed out a text to Tiffany.

“Hey Princess, pick out your glass slippers yet? Better hurry, this bad boy Cinderella story has a strict midnight curfew.”

His thumb hovered over the send button for a moment. “Too much?” he wondered aloud. Shaking his head, he pressed send before he could second-guess himself. “No turning back now,” Jacob murmured, his stomach doing somersaults as he waited for her response.

Tiffany’s phone buzzed, interrupting her homework session. She glanced at the screen, her eyes narrowed as she saw the unknown number.

“Unbelievable,” she muttered, rolling her eyes when she realized it was Jacob who was texting her. But despite her irritation, a small smile tugged at the corners of her mouth. She tapped her pen against her textbook, debating whether to respond.

After a moment’s hesitation, she picked up her phone. “Why not?” she thought, her fingers hovering over the keyboard.

Tiffany’s mind raced, searching for the perfect comeback. She wanted to put Jacob in his place. It was infuriating how easily he got under her skin.

Finally, she typed out her response, her lips curving into a smirk:

“I didn’t realize you needed glass slippers. Don’t worry, I’m sure we can find some in your size.”

She hit send, her heart racing slightly as she imagined Jacob’s reaction. Part of her couldn’t believe she was actually engaging in this flirtatious exchange with him, of all people.

Jacob’s phone buzzed, and a grin spread across his face as he read Tiffany’s message. Leaning back in his chair, he crafted his response:

“Please. I’m more of a combat boots kind of guy. But if you’re offering to be my Cinderella, I might just have to sweep you off your feet.”

Seconds later, his phone lit up again:

“Sweep me off my feet? That’s cute. I’d rather wait for a REAL prince charming, thank you very much.”

Jacob laughed out loud.

“Challenge accepted, princess,” he typed back. “I’ve got moves you’ve never seen. How about I show you at prom?”

As he waited for her response, Jacob couldn’t wipe the smile off his face. This was turning out to be way more fun than he’d anticipated.

“I can’t believe you are forcing me to go to prom with you,” Tiffany wrote.

“Not your style, huh? What would you rather be doing on prom night?” he typed.

“Oh, I don’t know…read?” she replied.

Jacob chuckled as he read Tiffany’s reply. Of course, Little Miss Perfect would rather spend prom night with her nose in a book.

“Read? While the rest of the school’s stuck in stuffy tuxedos and dresses? That’s tragic,” he texted back.

Tiffany smirked at his message, rolling her eyes. She wasn’t surprised Jacob found the idea of reading boring. “Some people appreciate more than just dancing and loud music,” she typed quickly, biting her lip as she thought about their conversation.

She’d never had much patience for Jacob and his reckless ways, but now…this banter was kind of fun. Against her better judgment, she found herself enjoying the back-and-forth.

“Guess I’ll just have to make prom worth your while then,” he replied, leaning back with a satisfied smirk. “Bet I could surprise you.”

Tiffany hesitated for a moment. “I don’t know if I want surprises from you.”

“Why not? Okay, if you don’t want to go to the prom with me, we could go somewhere else. Like the library.”

Tiffany snorted at the text. Now, he was just trying to make fun of her.

“Sure, Jacob. We could spend the night reading,” she typed back. She hesitated before typing the next line. “But wait…do you know how to read?”

Jacob laughed when he read Tiffany’s message, the sharp wit behind it making his grin even wider. He could practically hear her sarcastic tone.

“Funny, princess. I actually can read—who do you think wrote the instructions on how to break the rules?” he shot back, leaning back on his bed, satisfied with his comeback.

Tiffany bit her lip, suppressing a smile. He was quick, she had to give him that. But that didn’t mean she was going to let him win this. She typed her reply:

“Good to know. I’d hate to think you’re still stuck on picture books.”

Jacob chuckled, shaking his head at her response. “Cute. But if you’re implying I’m not smart enough for real books, I might have to prove you wrong.”

Tiffany paused, wondering what he meant by that. As much as she wanted to brush off his teasing, something about Jacob intrigued her.

“Prove me wrong how?” she texted, curious to see what he’d say next.

A minute passed before her phone buzzed again:

“Maybe I’ll pick a book for us to read together. But I get to choose… something that’ll make your nerdy little heart skip a beat.”

Tiffany rolled her eyes but found herself smiling again. She couldn’t believe she was even entertaining this conversation. This was Jacob—troublemaker, a notorious flirt, and probably the last person she’d ever considered talking to about books. Yet here they were, bantering like they’d done it a hundred times.

“Fine,” she typed. “But if your book choice is trash, I’ll revoke your prom date privileges.”

Jacob laughed, running a hand through his hair. “You can’t. I still have your diary held hostage.”

Tiffany didn’t reply for several minutes, and Jacob started to panic. Shit…did he push it too far? She was probably angry now. Leave it to him for ruining a perfect moment.

He nearly jumped as his phone buzzed.

“Did you read it?” she wrote.

Jacob stared at the screen, his heart pounding. He didn’t read it. But would she believe him if he told her?

Taking a deep breath, he typed slowly, deliberately:

“Not a word.”

He hit send, watching the message go through, feeling nervous.

Seconds felt like hours as he waited for her reply. He paced around his room, wondering if she’d believe him. Technically, he wasn’t lying—he hadn’t opened the diary. But that didn’t change the fact that he still had it, that he’d been using it as leverage.

Finally, Tiffany’s response came through, simple and direct:

“Good.”

Jacob exhaled, feeling a small weight lift off his chest. She seemed to believe him.