Phoebe is a 29-year-old pre-K teacher living in Los Angeles who manages debilitating intimacy anxiety and emetophobia (a clinical fear of vomiting). Approaching her 30th birthday, she feels immense pressure from a letter she wrote to herself as a teenager demanding she lose her virginity before turning 30. She frequently relies on lists and organization to control the unpredictable nature of human connection, leading her to create a systematic checklist to force herself into romantic encounters.

Jonathan is Phoebe's long-time best friend and roommate, whom she met during their freshman year at UCLA. He is confident, conventionally attractive, and acts as a constant source of stability for Phoebe, often rescuing her from difficult situations. Though outgoing and friendly, he remains notably private about his own dating life, spending many nights away from their apartment and causing tension in his friendship with Phoebe.

Matthew is a professional photographer based in Rochester, New York, who sat behind Phoebe in high school calculus. He reconnected with Phoebe on a dating app and maintains a steady, long-distance friendship built around daily online word games. He exhibits extreme patience and understanding, offering Phoebe a low-pressure connection that still triggers her severe anxiety when transitioning to an in-person meeting.

Nora is a core member of Phoebe's college friend group. She is sexually liberated, outwardly confident, and effortlessly secures dates—traits that represent an aspirational ideal for Phoebe. Despite her bold exterior, she harbors her own insecurities about her life's direction and deeply values the emotional security her friends provide.

Meg is a deeply empathetic and nurturing member of Phoebe's friend group. She often relies on romantic platitudes to stay positive, maintaining a supportive presence for her friends even while managing her own emotional struggles and returning to the dating scene.

Alex is an aspiring actor and a sensitive, romantic member of Phoebe's inner circle. He shares Phoebe's tendency to fall hard and fast in relationships, and his insecurities occasionally make him critical of himself. He remains a steadfast supporter of Phoebe's endeavors.

Finn is a handsome, kind, and capable new teacher at the Brentwood Friends Academy. He quickly impresses Phoebe with his calm demeanor around the children, prompting her to view him as a straightforward romantic candidate for her checklist. He shares flirtatious, friendly moments with Phoebe as they adjust to the new school year.

Sandy is Phoebe's therapist, providing a clinical framework for Phoebe's panic disorder, OCD, and emetophobia. She acts as a voice of reason, challenging Phoebe's reliance on arbitrary timelines and encouraging her to focus on internal accomplishments rather than manufactured romantic checklists.

Jamie is Phoebe's younger sister, currently planning her upcoming wedding to her high school sweetheart. Her adherence to traditional social timelines and relationship milestones inadvertently intensifies Phoebe's feelings of being left behind romantically, though Jamie remains deeply supportive of her sister.

Ethan is Jamie's high school sweetheart and fiancé. He is warmly integrated into the Berman family and readily supports his future sister-in-law when family tensions arise during wedding events.

Jodi is Phoebe's mother. She can be demanding about appearances, particularly during stressful family events like weddings, but ultimately demonstrates pride in her daughter's ability to stand up for herself.

Phoebe's father is a supportive parent who shares some of Phoebe's nervous tendencies. He provides crucial emotional validation by assuring her that their family comes from a long line of nervous individuals, helping her normalize her physical anxiety symptoms.

Aunt Carol is an outspoken and often inappropriate relative. She dismisses Phoebe's anxiety, suggesting it is merely a cover for her being a lesbian, which provokes Phoebe into finally advocating for herself in front of her family.

Lucas is Phoebe's former middle school crush. A traumatic incident involving him—when Phoebe suffered a panic attack and vomited on him just before their first kiss—cemented her deep-seated fear of physical intimacy.

Noah is Finn's roommate. He hosts an upcoming birthday party and begins dating Phoebe's friend Meg, expanding the social circle between the teachers and Phoebe's friends.

Sydney is Jonathan's coworker. Phoebe tracks Jonathan's location to her neighborhood, leading to assumptions about their romantic involvement and causing Phoebe to worry about losing her best friend to a new girlfriend.

Teacher Rob is an older colleague at the Brentwood Friends Academy. He becomes the unwitting and awkward target of the first task on Phoebe's romance checklist, resulting in a disastrous attempt at flirting.

Cheryl is a fellow teacher who previously helped Phoebe secure her job at the academy after witnessing Phoebe skillfully de-escalate a conflict during a field trip.

Dan is the principal of the school where Phoebe teaches. He implements strict rules for the Fall Ball based on past incidents and encourages Phoebe to interview for an assistant principal position.

Also known as Nick, DJ Spider offers Phoebe a ride home from the dance alongside Teacher Rob. During the car ride, he lights a joint that triggers a severe, catastrophic panic attack for Phoebe.

Danny is one of Finn's fourth-grade students who lacks a filter, asking highly personal and inappropriate questions about Phoebe and Finn's relationship during school activities.