Kaito is an awfully timid young man trying to become a mangaka. He has talent but he's been too scared to show his work to any editors. Then one day he bumps into a woman on the streets and runs off. Due to his anxious attempt to get away the woman ends up going home with a copy of his work. She turns out to be the chief editor of an up and coming manga company. Kaito gets a call and she tells him she likes his work and might want to hire him. When they meet in person the woman finds herself interested in more than just his work. Then, he catches the eye of a co-worker and/or assistant to the chief editor his age. Suddenly, this timid young man finds himself in the middle of a love triangle.

I'm looking for someone willing to play both the chief editor and assistant if that's okay.

At this highly prestigious high school, only the immensely wealthy families could afford, she was the queen. One of the richest students there, she was beautiful, popular, and talented. There was no one who didn't adore her...until he showed up. Normally, he wouldn't be able to afford to stand in front of the gates but he had got in on a scholarship. He didn't seem to pay her any attention. How could he ignore someone as flawless as she? If anyone should be treating her like royalty it was this commoner. Then, one day his scholarship was reduced. He couldn't possibly pay the difference. There was her chance to make him treat her with the respect she deserved. And so she offered to help pay his tuition as long as he became her personal servant.

I'd actually like to work this one out a bit more with my partner. The set up can be changed for how the arrangement comes about and the rich girl doesn't have to be as conceded/bitchy as I've described here. Gist is low-income student gets into rich private school but becomes unable to pay his tuition and must become a servant to keep attending.

As a child he was always sick but he loved spending time at the local guild. While most people seemed to pity him or treat as if he was too fragile to experience life, the guild didn't. They never held back around him and he even got caught up in the occasional brawl. And despite his weak body he loved all it. Hearing about their adventures and getting a few scrapes and bruises. Unfortunately, the fun times had to come to an end. While his condition wasn't getting worse, he wasn't getting better either. So, his family decided to move to a more rural area where the environment could help his health while being treated by better doctors. He didn't want to leave. He loved it here. "DON'T FORGET ME! I PROMISE I'M GONNA COME BACK A STRONG WIZARD AND JOIN THE GUILD! I WILL! BECAUSE THIS IS MY HOME TOO!" With tears in his eyes he made his vow. Now, he's come to make good on his promise.

For this I want to go with a Mentor x Student pairing. When the young man returns he's become a strong wizard but he's never taken missions and still has things to learn. So, the master makes one of the older members his mentor. She could have been there when he was around or someone who showed up after he left.

They're two of the most promising students at the DWMA. Top of their classes and having completed more missions than anyone else by a large margin. All the more impressive when they're both solo operators. One, a meister; the other, a weapon. However, while their performance has been consistently excellent, neither seems to be getting any stronger. Concerned with their stagnation, Lord Death has decided to pair them together in hopes that they'll further grow. One problem. They hate each other. If they can't come together and achieve Soul Resonance by the end of the semester, they'll be expelled. Will this forced partnership end in expulsion or will they form a powerful combination and become something more they alone?

A young man is in need of a job and sees a flyer hiring for a maid. Confident he can perform the job just as well as an actual maid, he decided to go to the address on the flyer. To his surprise the employer turns out to be a dragon woman from another world. She is in need of someone to not only keep her home clean but also teach her about and how to navigate the human world.

So yeah, this would a kind of reversal of the situation in Miss Kobayashi's Dragon Maid.