Oretachi ni Tsubasa wa Nai: Under the Innocent Sky.
俺たちに翼はない -under the innocent sky.
Synopsis
Haneda Takashi has a secret he cannot speak of. To leave his dull school-life, he was supposed to have escaped to another world. However, he is reeled in by certain ties on his heart. One of these is Kobato, his awkward younger sister. The other is Watarai Asuka, his negligent girlfriend. Chitose Shuusuke is a poor freeloader. He passes his days working at various part-time jobs. One day, he has a disastrous first encounter with Tamaizumi Hiyoko. The next time they meet, Shuusuke discovers that they are fellow employees at his part-time job. Narita Hayato sees himself as a "hard-boiled" person. Back-breaking jobs are nothing to him. Hayato shuns normal human contact, but, during the nights, he would get together with delinquents and other denizens of the night. One such night, he meets the cheerful and oblivious Otori Naru. The relationships with these girls will greatly affect these 3 young men. But what, exactly, is the relationship these young men have with each other? (Source: AnimeNFO)
Characters

Watarai Asuka
Main

Tamaizumi Hiyoko
Main

Ootori Naru
Main

Haneda Kobato
Main

Haneda Takashi
Main

Mochizuki Kinako
Supporting

Yamashina Miyako
Supporting

Chitose Shuusuke
Main

Narita Hayato
Main

Ootori Kakeru
Supporting

DJ Condor
Supporting

Itami Karura
Supporting

Yoneda Yuu
Supporting

Alice
Supporting

Hino Eriko
Supporting

Takauchi Masako
Supporting

Kasuga Harue
Supporting

Kohda Ai
Supporting

Haneda Youji
Main

Morisato Kazuma
Supporting
If You Liked Oretachi ni Tsubasa wa Nai: Under the Innocent Sky.
AI picks
Happy☆Lesson (TV)Both feature male protagonists gaining a household of female companions who disrupt their isolated existence through unexpected living situations and emotional connection.
Hoshizora e Kakaru HashiShares the tone of comedic school harem dynamics balanced with underlying character vulnerability and familial bonds that ground the romantic premise.
To Heart 2Centers on a male protagonist reconnecting with a significant female character while navigating a gradually expanding circle of relationships in a school setting.