Any manga or anime like this?
School Rumble has this to an extent
>>39636
The author is fumitan, he is drawing "Tomo-chan wa onna no ko!" but it's not really what you want.
Satou and Todoroki from Working!! come to mind, but they aren't the main characters, and their development takes a long time.
>>39832
Otako from Oshiete! Gyaruko-chan
Camera from Denkigai no Honya-san
Nozoki ana
School days
Molester man
At least the story, not exactly the characters
>>40323
Isn't School Days the reverse?