Christ this game is clunky as all fuck.
I'm fine with the grind, and the event viewer is nice, but after getting stuck on "16:00 at the pool" which I'd done, seemingly 80,000 times, it seems that if you do other events, or affect moods in any way, your "Progress" towards the 4 photoshoots, which all have identical dialogue, goes away.
I'd suggest making the entry in the event viewer 4fold "16:00 at the pool 1/4, 2/4 ETC", or "16:00 at the pool, 16:00 at the Pool again, 16:00 at the pool a third time, 16:00 at the pool one last time" as the dialogue not changing, and the poses looking similar gives little indication that progress is being made.
Long and short, the game needs polish, and lots of it to remove frustration and sticking points.