I have tried in many combinations but for me it does not work.
I will try to describe in more details the issue: so i go on Sunday on the public event, then Monday I go to Biff and the photo-session with hearts dress starts, I make the first part just fine.
Then, no matter what I do, whenever I go back to Biff, the dialogue before the public event starts, and everything has to be restarted (only next day I am not able to change the dress needed for the public event as this option does not exist anymore with the photographer)...
Also I have noticed that the 5000 due each Friday does not reset, so even if I don't get the 5000 there is no change in the messages...