Darla, portrayed by Brittany Snow, finds herself struggling with her compulsive behavior as a sex addict. She attends a support group located at a local high school, where she crosses paths with Bailey, a character played by Sam Richardson, who is there for his cancer support meeting following a testicle removal surgery he had a year prior.
Despite claiming to be a researcher for her magazine column—focused on the topic of female orgasm—Darla indulges in flings with fellow support group attendees, often in empty classrooms after hours. Her reckless behavior catches up with her when her boss, Tanya, played by Jordana Brewster, fires her for having sex with an intern, using video evidence as proof. Tanya is frustrated, especially after a recent sexual harassment complaint involving Darla, and mentions how her writing has taken a downturn as well.
On the flip side, Bailey works diligently at a gym, maintaining the equipment. Unfortunately, his health piecing together isn’t getting any better—after a recent checkup, he receives disheartening news: his cancer has returned, and he faces another surgery to remove a lump from his other testicle. In a heartbreaking turn, his girlfriend, Elizabeth, portrayed by Anna Akana, breaks up with him, suggesting that they need to explore other relationships to understand what they truly want.
Facing professional pressure, Darla seeks out an intriguing story to keep her job, leading her to engage Bailey in conversation after he drunkenly stumbles into her support group. Here, they embark on an unusual journey where Darla shares with Bailey a peculiar map—a project devised by their group leader to annotate the locations each member has had sexual encounters, designed as a means of healing.
In a quirky twist, Bailey proposes that Darla visit each location marked on her map as a method of therapy. She agrees under the pretense of gathering material for her article. As they set off, everything starts to evolve; they end up visiting Dallas, where Bailey hopes to reconnect with Elizabeth. Unknown to him, Darla has coerced Tanya into letting her chronicle their journey through a daily blog, convincing her that Bailey is the real story, despite not informing him about it.
Their trip starts the next day as Darla brings a detailed map filled with X's to mark the places of her previous encounters. As they explore, a bond begins to form despite the awkward situation—Bailey finds out about Darla's past and her reluctance to sleep in the same bed, highlighting the boundaries she sets even as they engage in physical acts. Darla writes her blog in secrecy, carefully documenting her thoughts while keeping her personal life hidden from Bailey.
An emotional crescendo occurs when the two find themselves in Dallas, meeting Bailey's unsupportive parents. They share a romantic evening and recreate a meaningful moment from his past with Elizabeth, but not everything is smooth sailing; secrets unravel as Elizabeth unintentionally exposes Bailey’s use of Darla to make her jealous, leading to conflict that tests their newfound connection.
As their separate struggles unfold, Darla confronts demons from her past, taught by her mother, Betty, who reflects the same destructive patterns. In the end, after facing their truths and combining efforts for personal growth, both Darla and Bailey emerge from their experiences transformed. Bailey realizes his relationship with Elizabeth has come to a natural conclusion, while Darla embraces recovery and accepts a publishing opportunity she initially turned down.
Fast forward a year, Bailey’s cancer is in remission, and Darla has successfully navigated her path to recovery. With a promise to support each other in their newfound friendship, they decide to go on a date, a hopeful step towards a brighter future.
