A professional hockey player for a Boston team, John Logan manages the physical and public demands of his rookie season. His rigorous travel schedule creates physical and emotional distance between him and his girlfriend, Grace Ivers. He actively seeks creative methods to reconnect with her, ranging from playful bar bets to planned getaways in Vermont.

Grace is a senior at Briar University who manages the campus radio station. She handles a heavy academic and professional workload while maintaining a long-distance relationship with John Logan. She is practical and intelligent, often using her quirky sense of humor to lighten stressful situations.

A high school teacher and hockey coach who comes from a wealthy family. He lives in New York with his girlfriend, Allie Hayes, and desires to formalize their commitment. Eager to take the next step in their relationship, he often relies on the advice of his former college roommates, though he sometimes fails to listen to Allie's explicitly stated wishes.

A successful actress starring in the cable drama The Delaneys. She is methodical, preferring to take life decisions at her own pace. While deeply committed to her boyfriend, Dean, she feels anxious about rushing into an engagement and views major life milestones as a rigid sequence she is not quite ready to begin.

A dedicated husband, father, and successful bar owner. He provides steady support to his wife, Sabrina, and their young daughter, Jamie. Beneath his easygoing exterior, he experiences feelings of restlessness and professional boredom, which he initially keeps hidden to avoid adding stress to his household.

A highly intelligent, ambitious recent graduate of Harvard Law School. She balances her high-powered career aspirations with her responsibilities as a wife and mother. She struggles to relax, bringing her intensive planning mindset even to her vacation in St. Barth's.

A star professional hockey player whose public success contrasts with his private struggles. He carries deep psychological scars from his abusive childhood, making him fiercely protective of his independence and fearful of repeating his father's mistakes. He relies heavily on the support of his partner, Hannah Wells.

A talented music producer building a successful career in the music industry. She provides unconditional support to her boyfriend, Garrett Graham, often prioritizing his emotional well-being above her own needs. She finds herself carrying a significant secret that she hesitates to share due to his ongoing family stress.

A celebrated hockey legend and Garrett's estranged father. He cultivates a public image as a supportive parent, completely at odds with his private behavior. He continually uses his fame and media influence to manipulate appearances and force public interactions with his son.

Allie's father, who lives in Brooklyn and manages the daily challenges of multiple sclerosis. He presents a gruff, sarcastic exterior but deeply cares about his daughter's happiness, expecting any partner to prove their genuine commitment to her.

A senior partner at a New York law firm specializing in wrongful-conviction cases. He and his partner, Bruce, are wealthy neighbors who offer practical assistance and career connections to Tucker and Sabrina during their honeymoon.

A successful fitness influencer vacationing in St. Barth's. Alongside his partner, Kevin, he offers practical assistance and unexpected business opportunities to Tucker and Sabrina when their honeymoon encounters a series of mishaps.

A creepy antique porcelain doll supposedly haunted by the spirit of a young boy who died on the California Trail. The doll serves as a long-running, macabre inside joke among the friend group, repeatedly shipped from one couple to another as a prank gift to interrupt important life milestones.

Grace's father, who hosts her and Logan during the holidays. He is fascinated by the haunted doll Alexander when it arrives at his house, noting its fine craftsmanship before storing it in the attic.

Grace's former college roommate. She provides a listening ear as Grace vents about the difficulties of maintaining a long-distance relationship, offering practical suggestions for achieving stability.

Garrett's sports agent. He manages Garrett's public relations and fields media requests, often finding himself caught between his client's desire for privacy and the lucrative opportunities presented by Garrett's fame.

The three-year-old daughter of Tucker and Sabrina. She is well-loved by her parents and extended 'aunts' and 'uncles' in the friend group, bringing joy to their social gatherings.

Tucker's mother. She steps in to care for her granddaughter, Jamie, while Tucker and Sabrina leave for their honeymoon in St. Barth's, patiently enduring Sabrina's anxious instructions.

Dean's sister. She participates in the friend group's social events and casually discusses her own relationship frustrations, comparing her situation to those of the other women.

Dean's mother, who works as a lawyer in Manhattan. She and her husband own the luxurious family vacation villa in St. Barth's that they lend to Tucker and Sabrina.

Dean's wealthy father. He provides his son with access to significant financial resources, including a private plane and a luxury vacation home.

An actress starring alongside Allie in The Delaneys. She offers Allie a helpful "relationship ladder" analogy that provides a new perspective on emotional security and commitment.

One of Allie's costars on the television show The Delaneys. He represents the close bond and active social life shared among the cast members.

An actor on The Delaneys who joins Allie and Seraphina during their night out. His personal connections inadvertently help Allie locate Dean during a conflict.

A young rapper who goes by the stage name "Nice." He records his album at the studio where Hannah works as a producer, representing her growing professional success.

A producer for the ESPN program The Legacy. He attempts to organize a television special documenting Garrett and Phil Graham's family history for a sports audience.

The owner of a bed-and-breakfast in Vermont where Logan and Grace stay after surviving a blizzard. He also operates as a local pastor capable of officiating weddings.

The co-host of a Vermont bed-and-breakfast alongside her husband, Pastor Steve. She helps provide comfort to guests arriving after treacherous travel conditions.