Anime Crossover: I'm at Shuchiin Academy, So How Did I Become a Casanova?

I wake up to find that I've transmigrated into Love Is War as the gloomy shut-in Yu Ishigami!

Bound to a System from the start, my missions are actually to go on dates with the heroines, Kaguya, Miko, Rinko, and the others?!

Looking at my handsome but antisocial self in the mirror, I grin.

"The original Yu, you wasted that face and rich-kid background!"

But then I remember his stalker past and gloomy hairstyle.

"Damn! This is a nightmare-difficulty start!"

Luckily, the System delivers. My skill proficiencies skyrocket, unlocking reading, acting, physical fitness, and more!

As the gloomy boy transforms into the campus heartthrob, Miko Iino blushes as she hands him a love letter, Rinko Kobayakawa secretly slips him a lunchbox, and even Kaguya can't help wavering...

"Wait, this doesn't seem right. I just wanted to complete the missions!"

This novel and its characters are entirely fictional. Any resemblance is purely coincidental. Please do not imitate.