39. Leo X Female!MissIndependent!Reader

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Requested by chu1luc

Three weeks when the turtles greeted (Y/N) in a school project with April, Leo had a tiny crush on the serious (Y/N) 11 days in during a Jupiter Jim convention.

She wasn't into the series as her entire family constantly quotes movies and other media that she just accepted it after meeting the guys who were also fans. She even outwitted Donnie in a fan version trivia game knowing details not covered in the behind the scenes commentary.

Leo felt discouraged as she connected with Donnie almost close to similar personalities (minus the snarky remarks) but that didn't stop him attempting to impress her in his own way.

Attempt 1: One Liner Laughs

He said at least nine of his jokes and thankful one separate for each day so his brothers or April won't be suspicious about his behavior. (Y/N) tilts her head not getting the punchline at each one causing him to wave his hand telling her to forget about it as she shrugs going else where. He almost fainted at her head tilt imaging her as a (cat/dog/other fave pet) now with a red face.

Attempt 2: Awe the Gal with Wicked Skate Tricks

When (Y/N) witnessed Leo achieved three new skate tricks, her eyes enhanced astonished at him. He should have stick with just those three but overconfidence got the better of him trying a fourth one seeing if he could make her smile. He was unconscious for 18 minutes but woke up to see her rearranging the first aid kit by his side.

Attempt 3 (almost final): Brainstorm Poetry (I guess...)

The poor turtle felt sick typing poetry on his phone to sound sophisticated like Donnie. He eventually closed the tab only half way through the first page about to vomit from the cheesy and small text lines. He blinked realizing having a book that got discarded from the Mystic Library and scrambled to his room getting it under his bed.

However, he put it back sitting down dissatisfied only reading six life lessons and no poetry like words in the text.

He wasn't sure if (Y/N) was into people who had goofy charisma like him as he let out a sigh. Gloom arose on his face for a few seconds until his phone rang.

"Yo..." Leo said nearly miserable.

"Hey Leo."

"Did I call you at a bad time?" (Y/N) asked her voice filled with trouble by his tone.

("One more time!")

("I can roll my way to her heart this time!")

"Nah! Any time is okay with you (Y/N)!"

"Whatcha need?" Leo cheered with new morale.

"I don't know if I'm saying this phrase correctly but..."

"Can you be the hype man at my place?"

"Another new generation of Jupiter Jim fans.."

"And I don't want my younger cousins being stuck with the boring auntie or whatever relative name it's supposed to be." (Y/N) said.

Leo hated when she talks like as he frowns.

He could listen to her speech mode more at ease than Donnie's. Heck he's even found the positive side of words that negatively describe her.

("The way to forget is to remember...")

His previous attempts weren't the best but her noticing him in those moments, it counted as progress as he now half smiles.

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