You have to make each of the three choices every day. If you don't make any mistakes, the story progresses on day 4.Then you start the loop over again to advance a little further in the story, and so on... When no further progression is possible, the game says: "This feature will be available in the next update."
To be on the safe side, I made the choices in order: spend time with Casey in the morning, work in the afternoon, eat something in the evening. It worked for me.
Note: Black screen during the pool scene, the game can't find the corresponding images. The dev will certainly have corrected the problem in the next update. I therefore recommend that you make a backup when this problem occurs, so that you can come back to it in the next version if you want to see the scene. No sex scenes yet, which is to be expected given that this is the very first version of the game.