I got stuck with Jessie on Carnival as well [Mac].
Though I had run through each 4 scenarios for each character, when the next weekend arrives: Only Jessie is still available > Only the Chocolate scenario is available > I run through the scenario again > All scenarios are now disabled > BUT, you need 2 scenarios to complete the date. This is where I get stuck.
Need to be able to re-open a 2nd scenario to clear the date (or a master reset to reopen all of them and try again...can we do that anyway? lol).
NOTE: I can use the Mouse Wheel to scroll back and exit the date, but that doesn't do much to Complete the date.