Eve is a 46-year-old divorcée and the executive director of the Haddington Senior Center. With her son leaving for college, she faces an empty nest and seeks to expand her horizons by enrolling in a community college gender studies class. When an anonymous text message labels her a "MILF," it sparks her curiosity, leading her to explore online pornography and question her established sexual preferences. She is a dedicated but sometimes overly accommodating mother trying to rediscover her own identity.

Brendan is an 18-year-old freshman at Berkshire State University. Accustomed to the easy popularity he enjoyed as a high school athlete, he struggles to adapt to a more diverse and politically aware college environment. He masks his deep insecurities about his parents' divorce behind a superficial macho persona, often resorting to crude language derived from internet pornography to maintain a false sense of control in his relationships.

George is a local plumber dealing with his own recent bereavements, including the death of his wife to cancer and the loss of his parents. He is a stocky, pragmatic man who feels frustrated by the embarrassing actions of his elderly father. Despite a rugged exterior, he attempts to process his grief and sexual frustration through healthier outlets like yoga, presenting a more grounded alternative to the younger men in the story.

Amber is a politically active college sophomore who identifies as an intersectional feminist. She is unconventionally attractive with an athletic build and strong shoulders. Despite her firm political convictions and activism, she feels conflicted by her physical attraction to athletes who do not share her ideology, finding herself repeatedly drawn to men like Brendan.

Amanda is a twenty-something graduate student who reluctantly moved back to her hometown following her mother's death. Sporting Cleopatra bangs and multiple tattoos, she feels entirely out of place among the conservative senior citizens she works with. She struggles with aimlessness, a lack of fulfillment, and an unpredictable dating life as she figures out her next steps.

Ted is Eve's ex-husband who left his marriage to start a new family with a woman he met through an online classified ad. He maintains a veneer of affability but consistently takes the easy way out of parenting responsibilities. He praises Brendan's heavy drinking as typical college behavior rather than addressing his son's underlying emotional struggles, preferring to focus his energy on his new family.

Becca is a high school cheerleader who dated Brendan during their senior year. She presents a meticulously put-together appearance and remains desperately eager to please Brendan even after he breaks up with her right before college. She attempts to adapt to modern sexual expectations by learning from internet tutorials, seeking validation from a largely unappreciative ex-boyfriend.

Zack is a broad-shouldered college freshman from Boxborough who serves as Brendan's roommate at Berkshire State University. He immediately bonds with Brendan over shared interests in drinking, sports, and crude humor, initially seeming to match or exceed Brendan's misogynistic behavior. His social circle slowly shifts when he begins dating a girl who challenges his superficial values.

Sanjay is an Indian-American electrical engineering student with a passion for architecture. Skinny and academically focused, he is quickly dismissed by Brendan as being too nerdy to fit into the popular crowd. Despite this early rejection, Sanjay proves to be observant, grounded, and a surprisingly decent driver when needed.

Dr. Fairchild is a transgender woman and an adjunct professor who dresses in conservative suits and stiletto heels. She projects confidence in the classroom, challenging her adult students to think beyond the rigid gender norms of their upbringings. Outside of her academic authority, she faces ongoing prejudice and personal isolation from her conservative community.

Julian is a thin, sensitive teenage skateboarder enrolled in community college. He is recovering from severe depression and trauma sustained during a bullying incident in high school involving Brendan's friends. Despite his youth, he proves to be thoughtful and respectful toward women, starkly contrasting with his former bullies, and finds himself highly intrigued by his older classmate, Eve.

Dumell is an African-American military veteran enrolled in Dr. Fairchild's evening class. He is open-minded and willing to engage deeply with the progressive curriculum, eventually striking up a close, supportive personal connection with his professor.

Jon-Jon is Ted Fletcher's younger, autistic son from his second marriage. His specific behavioral needs and triggers command the majority of his father's attention during family gatherings, which unintentionally creates a deeper wedge between Ted and Brendan.

Roy is an elderly man whose inappropriate, exhibitionist behavior in the women's restroom results in his permanent banishment from the Haddington Senior Center. His actions cause significant stress and embarrassment for both the center's staff and his son, George.

Jim is a local bartender and Brendan's former childhood soccer coach. He represents the familiar, conventional dating pool of middle-aged, local men that Eve considers while trying to figure out her newly awakened desires.

Wade is a former high school friend of Brendan's with a distinctly macho and aggressive streak. His past physical mistreatment of his girlfriend and his cruel, disproportionate bullying of Julian Spitzer highlight the toxic environment Brendan comes from.

Lexa is a beautiful college student who uses a wheelchair. Her relationship with Zack challenges his superficial frat-boy persona, prompting him to rethink his own behavior and distance himself from more toxic friendships.

Cat is a friend of Amber's and a politically engaged art student at Berkshire State University. She creates provocative installations aimed at holding individuals publicly accountable for problematic and damaging behavior on campus.

Devin is Brendan's academic advisor at Berkshire State University. He attempts to guide Brendan's ambitions while explicitly questioning him about his understanding of sexual consent, serving as an early indicator of the cultural shift Brendan faces at college.

Fiona is Wade's former high school girlfriend. When Julian attempted to intervene as Wade was physically mistreating her, it sparked a severe bullying incident that scarred Julian for years.