Thanks so much for the save! I figured out the issue.
When you breakup with someone it's supposed to change their relationship state, but not adjust the number of stars you've earned with that person. Anthony was the only one that accidentally had the stars reset down to 6. This causes the game to try to replay the old events, which it refuses to do since you've already seen them.
I've added a save migration fix to version 1.4.5 of the game that will fix the save for anyone who has run into this problem.
In the meantime you could also adjust your friendship and star count for anthony by changing these lines:
"friendship": 140,
"numberOfStars": 6,
to:
"friendship": 200,
"numberOfStars": 9,
Under Anthony's section of the json Player.txt file
But willing to wait for 1.4.5 that would be a lot easier. I have a few other issues to look at after yours. Thanks!
-Andy