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: Student council
04/12: Math class
04/15: Treasurer
04/21: Ryouta
05/06: Math class
05/21: 3-legged race
06/22: Cafeteria / Leave it to me!
06/26: Math class
07/07: Conquer the world by force / No thank you
07/11: Math class
07/13: Go yell at the doctor
07/20: Nevermind
07/24: Get a job
07/25: Give the job to Ryouta
08/06: Ryouta
08/30: Return to my glorious abode
09/03: Math class
09/13: Would love to!
10/07: Side with Shuu
10/19: I'll ask for you when I go there
02/02: Calm corn