I think games with large casts of characters can sometimes be hard to manage and some characters end up feeling like they have been forgotten, but so far with this game the dev has done a great job so I don't see any problem.
If it gets to the point where I don't know the name of the person on screen without looking to the dialogue box, then I say there's too many characters ...
Girl: Hi, MC!
MC: Oh, hello ... you!
Girl: Did you remember our date tonight?
MC: Um ... yeah ... sure.
Girl: You don't look so sure! Remember ... I'm Ruby's friend from the dog park? You pet my puppy and agreed to spend time with me because I looked sad.
MC: ((Who the fuck is Ruby?)) I have basketball practice, a press conference, and four other dates tonight ... but I live outside spacetime so why not?
Girl: Great, see you at 8!
MC: Jaime, add this shit to my calendar.
Jamie: YAY MY BF IS GOING TO FUCK ANOTHER GIRL I'M SUCH A CUCK QUEEN LOL
((End Scene, curtains fall, another successful update))