Montgomery de la Cruz x Reader

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You were known as the 'Sweetheart of Liberty High.' Kind, generous, and always smiling. That's why everyone was surprised with the name at the top of you Dollar Valentine list.

Montgomery de la Cruz, however, was the exact opposite. Brash, rude, and always getting into a fight. That's why everyone was surprised by the name at the top of his Dollar Valentine list.

"Dude who the fuck made these lists?" Bryce snorted as he ripped the paper from Monty's hands.

"Y/N Y/L/N, the 'Sweetheart of Liberty High?'" Bryce continued mockingly.

"Hey, knock it off, man." Monty snatched the paper back.

Bryce looked at him in shock and started laughing again.

"Don't tell me your actually gonna try for her." Bryce said with disbelief.

Monty grabbed his stuff and made to leave. "Fuck off."

His friends' laughter could be heard through the closed doors as he left.

~~~

"Montgomery de la Cruz?" Clay looks at you with disbelief. "Does the person who made the lists know you at all?"

You bite your lip, uncertainly staring at the name.

"Keep in mind that this is the guy who beats people up on a regular basis." Alex added.

"No I know," you assured them. "He's bad news, I get it."

The bell rang then, and your friends left with promises to meet you after school.

You shut your locker and began the trek to your next class.

With only your thoughts for company, your mind drifted to the boy whose name occupied the top spot on your Dollar Valentine.

Montgomery de la Cruz was a bad influence. Realistically, you knew that you would probably be better off if you stayed far from him. But despite every sensible bone in your body urging you to stay away from the baseball player, you always found yourself stealing glances at him in your shared classes.

You were brought out of your trance when a hand grabbed your arm and pulled you near the lockers.

You looked up into Monty's face. It took you a second to fully realize what was happening, and when you did your palms began to sweat.

"Hi, Montgomery." You said, trying to mask your nervousness.

A half grin found its way onto his face when you used his full name.

"Hey, Y/N. Look, I got your name on my Dollar Valentine, and I was wondering if you maybe wanted to hang out or something?"

You noted the way his eyes looked anywhere but yours, and a half grin of your own appeared.

"What, like a date?" You said, grinning shyly.

"I mean, yeah." He met your eyes and smiled in the way that entranced you during class.

"Just let me know when." You replied, readjusting your bag on your shoulder. "You have my number."

You turned to leave, a smile on your face despite knowing how disappointed your friends would be.

Who knows, maybe you would be good for him.

~~~

<Season 2>

~~~

You took the headphones out of your ears and stared at your phone in shock.

You'd finally finished the tapes that Hannah Baker had left behind, and although the names on them were shocking, you were also shocked by the fact that your boyfriend's name didn't occupy that list.

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