Character Relationship Map: Pretty Problems

Characters

• Lindsay Simpson (played by Britt Rentschler) — protagonist

  Lindsay Simpson is a clothing-store worker whose awkward attempt at intimacy with Jack Brown opens the story. During the retreat, she is nicknamed “Lazy Lindz” and helps imagine a sustainable clothing...

• Jack Brown (played by Michael Tennant) — supporting

  Jack Brown is Lindsay Simpson’s partner, struggling with probation, mandatory drug tests, unstable work prospects, and insecurity about not earning enough money. At the retreat he fears exposure to co...

• Cat Flax (played by J.J. Nolan) — supporting
• Kerry (played by Alex Klein) — supporting

  Kerry is a retreat guest whose open cocaine use alarms Jack Brown because he is on probation and must pass regular drug tests. The presence of marijuana and later the group’s excessive mushroom intake...

• Matt Flax (played by Graham Outerbridge) — supporting

  Matt Flax is identified as Cat Flax’s partner and has a candid conversation with Jack Brown during the retreat. Jack admits that he worries Lindsay Simpson may leave him because of his limited income,...

• Becca (played by Katarina Hughes) — supporting

  Becca is a member of the retreat group whose education and talents become targets of teasing. Her treatment by the others contributes to the weekend’s exposure of rivalry, insecurity, and self-indulge...

Canonical Relationships

Family, romantic, and professional connections based on plot evidence.

• Lindsay Simpson → Jack Brown (Romantic Partners) — They are romantically involved but experience uncertainty and awkwardness.

  Lindsay and Jack make an awkward attempt at intimacy and discuss trying again.

Story Dynamics

Alliances, conflicts, and narrative interactions that evolve throughout the story.

• Cat Flax → Matt Flax (Social Retreat Associates) — They belong to the same retreat social circle, although no more specific interaction is established.

  Cat Flax and Matt Flax are both identified as members of the weekend gathering organized by the friends.

• Jack Brown → Cat Flax (Social Acquaintances) — Jack is socially connected to Cat's circle during the gathering.

  Jack discusses his fear that Lindsay may leave him in a conversation involving Cat Flax's partner during the retreat.

• Lindsay Simpson → Kerry (Social Retreat Companions) — They are connected through the shared retreat and its risky social atmosphere.

  Lindsay and Kerry participate in the same resort gathering, where Kerry's cocaine use becomes known to the group.

• Jack Brown → Becca (Social Retreat Companions) — They share the retreat's increasingly chaotic social environment.

  Jack and Becca are both present during the retreat's drinking, karaoke, murder-mystery, and improvised group activities.

• Lindsay Simpson → Becca (Social Retreat Companions) — They are members of the same socially competitive retreat group.

  Lindsay and Becca attend the same weekend retreat, where Becca's education and talents become a subject of group teasing.

• Jack Brown → Kerry (Conflict Source Of Anxiety) — Kerry's visible drug use increases Jack's fear of violating probation.

  Jack becomes nervous when he learns that Kerry openly uses cocaine because drug use could threaten his probation.

Story Analysis

A strained couple enters an indulgent digital-detox retreat where social performance, insecurity, and accidental intoxication expose the group's instability.

Plot Progression

1. Unsteady Intimacy — Lindsay and Jack struggle with intimacy while their relationship remains uncertain. Jack's probation and drug testing establish a vulnerability that later threatens his ability to relax.
2. The Detox Retreat — The couple joins a carefully planned digital-detox weekend with a socially confident group. Activities, nicknames, and the isolated setting create pressure for Jack to fit in.
3. Pleasure Turns Competitive — Heavy drinking and a murder-mystery game transform the retreat into a display of rivalry and insecurity. Becca is teased while the group reveals its self-indulgent side.
4. Fears Beneath the Party — Jack confesses his fear that financial insecurity could cost him Lindsay. Meanwhile, the group's clothing-line ideas offer creative energy but also become increasingly irrational.
5. The Accidental High — The guests discover that they consumed far more mushrooms than intended. Their admission of serious intoxication ends the available story with the consequences still unresolved.