I'm probably too late and you figured it already out.Really weird.
I can't find anything about it.
On day 58 you can have the first video with Pink, or (if you are not in the dom path) invite Yvette to your home. As Main Events.
If neither of these two events is triggered you have the usual choice between the various events available.
I couldn't find anything that sends to day 54 (not even 52 53 55 56).
In Dom path you talk with Yvette and Randy, she hiumiliate you. Then you go away (if you are in a relation with Ashley you have a little chat with her).
Leaving the gym you see Jennifer and Boris.
You go to the Mall
You meet Yoshi
(if Yvette told you she need to talk with you (only if you're not in girlfriend path but you're trying to) you call her on the phone
Then you go home and you can get Pinky event, or Yvette come to your place to see a movie (not in dom path) or you get a menu with all the different events you can get.
I don't see any error about it.
I tried to replay it and could the problem be ashleychat? It sends you straight back to jump day5306b if you didn't have any chat with Ashley before. And the birthday is on Day 53.