For some reason, starting a new day sets your relationship level with Jessica and Midna to 15. I don't know why this is in there, and Jessica seems to be somewhat broken, which might be related - I can't advance her friendship level past "Acquaintance".
Edit: Not being able to advance with Jessica seems to be unrelated. The check for whether you can 'have fun' with her if you're specifically Shy and Female is broken (uses "gte" where there should be "or"). No other combination is bugged this way, but anyone who habitually plays a female character will probably run into this if their first time befriending Jessica is while trying to get her corresponding Focus unlocked, which requires Shy.