I know a lot of bugs with free time have been reported but I didn't see this one mentioned.
After viewing any given free time scene, triggering it again on a different playthrough (whether by loading an old save* or starting a new game) will give you a single line "You spent time with [name]." If there is a second associated scene (Sabrina, May) it will trigger that instead.
This seems to occur regardless of that playthrough's roomate or other variables that would affect the scene, though I've only experimented from April 10.
Closing and reopening the application seems to clear this issue, so it doesn't seem like a global save issue, but data not being scoped correctly.
* Even if the save was _before_ free time started, despite that being mentioned as a workaround to other free-time bugs reported.
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