Maddie is a 26-year-old woman struggling with the recent death of her older brother, Josh. She uses sarcasm, morbid humor, and a heavy workload to protect herself from emotional vulnerability and a deep-seated fear of abandonment caused by her neglectful upbringing. Tasked with traveling the country to spread her brother's ashes alongside a man she wants to avoid, she is forced out of her comfort zone.

Dominic is Josh's best friend and the executor of his will. Known for his responsible nature and need for control, he often sacrifices his own desires to do what he feels is right. He is steady, patient, and quietly grieving the loss of his best friend, remaining dedicated to fulfilling Josh's final travel requests despite Maddie's initial hostility.

Josh is Maddie's late brother who recently died from cancer just before his 30th birthday. In life, he was a natural comedian and a protective buffer for Maddie against their toxic family. In death, he orchestrates a cross-country scavenger hunt, leaving specific instructions that force his sister and his best friend to seize the moment and confront their grief.

Rosaline is Dominic's elegant and poised ex-wife, possessing a natural affinity for people that exacerbates Maddie's insecurities. She is deeply affected by Josh's death and handles her grief with a grace that Maddie finds both awe-inspiring and intimidating.

Jeremy is Maddie's ex-boyfriend turned best friend who trains for marathons as a hobby. He is emotionally available, funny, and deeply loyal, offering a safe space for Maddie when she feels overwhelmed, even as she tries to hide the specifics of her travel arrangements from him.

Tula is one of Maddie's closest friends. She is a supportive presence who lovingly calls out Maddie's tendency to avoid her emotions, pushing her to take time off work and properly engage with her grief.

Cecilia is Maddie and Josh's mother. An influencer who monetizes her life, she views her son's funeral primarily as an opportunity for social media engagement, prioritizing her online presence over her daughter's genuine need for comfort.

Florence is Maddie and Josh's stern grandmother. She is a punitive, rule-bound guardian who raised the siblings with a lack of compassion, frequently locking them out of the house as punishment during their childhood.

Adam is one of Dominic's younger twin brothers. He is an aspiring Olympic swimmer who looks up to Dominic for advice, though he has always harbored a lingering crush and deep admiration for Maddie since she babysat him during a summer years ago.

Carter is Dominic's younger twin brother who swims for the UPenn swim team. With Maddie's help during his childhood, he discovered a love for graphic novels that helped him manage his dyslexia, leading to his aspirations of becoming a writer.

Emilia is Dominic's mother. Years ago, after she suffered a car crash that limited her mobility, Maddie spent the summer helping her around the house, forging a bond of genuine warmth that contrasts sharply with Maddie's own mother.

Nathanial is Dominic's father. A dedicated neurosurgeon, his demanding career sometimes keeps him away from family events, though he maintains a warm household alongside his wife.

Pamela is Maddie's boss. She relies heavily on Maddie to keep the company running smoothly, inadvertently feeding into Maddie's need to feel indispensable and causing her to overwork herself rather than properly process her grief.

Reggie is the owner of a tattoo shop in Topeka, Kansas. He and his wife owe Josh a favor after Josh photographed Reggie's proposal for free, a debt they repay by giving Maddie and Dominic their requested tattoos.

Carmen is Reggie's wife. She shares the story of how Josh kindly photographed her husband's proposal to her at Multnomah Falls, shedding tears at the news of Josh's passing.

Carlisle is Jeremy's boyfriend. He supports Jeremy and integrates into Maddie's close-knit friend group during their gatherings in Seattle.