Harriet is an overworked 30-year-old surgical resident originally from Indiana. She struggles with exhaustion and the crushing pressure of her medical career, a path she pursues primarily to validate her parents' financial and emotional sacrifices. As a chronic people-pleaser who avoids conflict at all costs, she harbors a painful secret from her closest friends: her eight-year relationship ended months ago over a brief phone call.

Wyn is Harriet's ex-fiancé, an easygoing man who enjoys the outdoors and cares deeply for those around him. Following his father's death, he moved back to his hometown in Montana to support his mother and work with wood in the family's carpentry shop. He frequently struggles with self-worth, particularly when comparing his modest ambitions to his highly academic sisters or to Harriet's medical career.

Sabrina is a Manhattan heiress and highly organized lawyer with a sharp fashion sense. She acts as the primary planner for the friend group's annual trips to her family's coastal Maine cottage, fiercely guarding their traditions. Driven and direct, she fears the inevitable changes that come with adulthood and uses her wealth and planning skills to keep her chosen family together.

Cleo is an observant farmer with a passion for art and organic agriculture. She presents a calm, grounded demeanor that contrasts sharply with the more high-strung members of the friend group. She is unafraid of setting boundaries and values deep, meaningful conversations over superficial party activities.

Parth is a type-A lawyer and active socialite who shared an apartment with Harriet, Sabrina, Cleo, and Wyn during their college years. He is deeply devoted to Sabrina and matches her strong-willed, competitive nature perfectly.

Kimmy is Cleo's lively and spontaneous girlfriend who helps run their farm. Described as a "human party bus," Kimmy brings a joyful, carefree energy to the group and fiercely supports Cleo when vacation dynamics become strained.

Eloise is Harriet's older, rebellious sister who attended cosmetology school instead of following their parents' strict academic plans. Her loud arguments with their parents heavily influenced Harriet's conflict-avoidant personality.

Hank is Wyn's late father, who ran a family furniture business. Affectionate and welcoming, his sudden passing triggers a deep depression in Wyn and shifts the trajectory of Wyn and Harriet's relationship.

Gloria is Wyn's mother, who lives in Montana and battles Parkinson's disease. She relies on medical marijuana and the care of her son, remaining a warm and steadfast presence in his life.

Martin is a fellow medical resident and friend to Harriet. He inadvertently causes a major rift between Harriet and Wyn when he oversteps physical boundaries during a vulnerable moment.

Lou is one of Wyn's sisters. A highly driven academic who aims to be a famous writer, her success feeds into Wyn's insecurities about his own life path.

Michael is Wyn's other sister. She is an aspiring aerospace engineer whose intense intelligence contrasts heavily with Wyn's laid-back demeanor.