Flynn Rider spent five years in prison after he is caught attempting to steal the old crown of Corona's princess. He is now working as a bartender, while fulfilling his parole condition by visiting his therapist Dr. Jones every week. One night, he meets Rapunzel, a hoodie-clad eighteen year old with No Social Skills. The two quickly become friends, even though - or perhaps because - both of them have have plenty of issues.
- Ambiguous Disorder: The exact mental disorder that Rapunzel suffers from is unknown, and it's probably impossible to pinpoint her condition, given the unique circumstances that she endured.
- Dark Fic: The personalities and circumstances of the two main characters are interpreted seriously.
- Go Mad from the Isolation: Never going outside obviously did this Rapunzel's mental health no favors, and is probably a factor in why she needs therapy.
- Green-Eyed Monster: When Rapunzel comes to the bar with a boy after a misunderstanding between Flynn and her, Flynn is so overcome with jealousy that he completely messes up his apology and drives Rapunzel away.
- Imaginary Friend: Pascal the chameleon can only be seen by Rapunzel, although Flynn tries to play along.
- Inferiority Superiority Complex: Flynn might look like he's full of confidence, but inside he is insecure and feels that he's not good enough for Rapunzel. Tom, his therapist, speculates that this might be because he was abandoned by his parents when he was young.
- Manic Pixie Dream Girl: Rapunzel's quirkiness and enthusiasm is what helps Flynn open up. However, this is deconstructed when she is caught painting/vandalising and sentenced to ten hours of community work. Interestingly, she does not fit the "wild hair dye" stereotype - she can't stand the smell of bleach, because it reminds her of Gothel.
- Orphanage of Fear: St Benoit's, where Flynn was raised. When the story starts, it has just been closed down after the abuse going on was uncovered.
- Sesquipedalian Smith: The police gave Rapunzel a very mundane surname, although it's implied that "Rapunzel" is not the name her parents have given her, either. It's lampshaded by Flynn:Flynn: Rapunzel Smith? That's quite a contrast in names there.
- Sticky Fingers: Flynn. He mentions once stealing a fellow inmate's collection of gum wrappers, just because he could.
- Therapy Is for the Weak: Throughout the first part, Flynn refuses to open up to his therapists because this is his attitude, until Tom calls him on his bullshit.
- The Shrink: Dr. Jones seems to work well with and care about Rapunzel, but she clearly dislikes Flynn and they do not get along. Flynn's next therapist Tom fares better, and manages to finally get Flynn out of his " Therapy Is for the Weak" mindset.
- Where the Hell Is Springfield?: The Setting Update makes this more obvious. Corona seems suspiciously American in places - they mention GED at one point - but there is a vague European air to it as well.