There's always a chance for him to enter Yuna's room at night, day events dont matter.
He won't enter if:
- you had an event during the day where you gave him movie ticket
- you activated cheat code
So it's possible 😮 (kan also do what player exactly do) like kan enter yuna room and the player isn't there because (it's skipped night or night jog) because >I'm curious< if dev added this scenario like yuna enter your room and demand her clothes mess up(or it's just mechanic failure). it's happen just one time although I know how clothes mechanic work so it's impossible to miss up in a long run (5k+ stamina 10k+ life of the battery so impossible for me to miss up dressing yuna(except puzzle failure) no cheat promise