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If the struggle button says pretend struggle, then you need to press the cramped button instead until your mood lowers enough to return it to a regular 'struggle'. From there, just spam it over and over again and you'll get out, which shouldn't take too long. Took me a bit to realize this and I spent a few in-game weeks stuck inside trying escape and ask to be let out to no avail. Thought that maybe the chat she had with Fitria when I was depressed would make her let me out but she doesn't seem to give a shit.

Found her at the door Sunday afternoon, so I'd guess that weekend is correct.  She wasn't there in the morning so make sure it's the right time. Thanks for the help!

Ok I'm probably just blind/dumb but I need to strategise with Jessica and she doesn't seem to exist anywhere?