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It's a time crunch
And it seems there is by everyone's theories too many events and not enough time for it all fall in one evening. Assume the following:
David/Anna arrive at the restaurant it's 5:30... and at best leave at 6:15
David/Anna/ Chris meet up let's say it takes 30minutes to arrive at the club that is 6:45
So that leaves what 2 hours to have the club event happen that's about 8:45
Anna heads to the poker game and say it's 30min drive home by whatever means That is 9:15
Takes time for Anna to change and that takes 15-30min so 9:30/9:45
Let's say just for agreement's sake they call it quits at 12:00
All that is a working timeline if you are writing a train schedule... but that assumes a lot. What happens at the club? Is Anna going to be in the mood to go play poker or will something happen where the game is out of the question? The problem with the club event is Chris since he has to cock-block David... seduce Anna... and spread more poison into Anna and David's marriage. Mr. Palmer has to come up with a plausible story to get Anna away from Chris and David to make it to the poker game in time...
Or maybe...
Dinner with David happens and they meet up with Chris and
something happens that causes Anna to want to blowoff the poker game and hangout with Chris... and David and the scene plays out. In this case the player is given a "trigger" like Anna gets made at David or Chris makes too bold a move and Anna reject him
Alternatively, depending how the trigger is tripped if she rejects Chris, Anna goes to the poker game and that scene plays out