I did not expect something like this in a 4 day game jam! The song started soon getting on my nerves, but the art was great! Just be sure that the horizon line of the background roughly aligns with eyes of the characters or it wont work (like the background for the initial dialogue with mom, where it seems like you are looking down to floor, but the character is drawn like you are looking in front of you)
One thing I was thinking about. Wouldn't it be better to reset at the end of the day? Like you are trapped in a time loop like in Groundhogs day which resets in the evening back to the morning. And when you get everything right you will escape the time loop. It would allow player to gather clues throughout the day so he can better answer the questions. Resetting for each character is just guess work and a little bit tedious. It also promotes rushing through dialogues.