Name and display human portraits don't matter, you can choose whatever you want.
You can press
to make things faster. It will stop when you have to choose or when the game loads the next part of the story.
My choices to get this trophy were :
*** Spoiler - click to reveal ***
04/11: Track team
04/12: Gym class
04/15: Sprint
04/21: Ryouta
05/06: Gym class
05/21: Marathon
06/22: Infirmary / Skip class
06/26: Gym class
07/07: Conquer the world by force / No thank you
07/11: Gym class
07/20: Join him
07/24: Get a job
07/25: Do the job I was hired for
08/06: Ryouta
08/24: Azami's scooter