Happiest Season is a 2020 American romantic comedy-drama film directed by Clea DuVall, from a screenplay written by DuVall and Mary Holland. With an ensemble cast consisting of Kristen Stewart, Mackenzie Davis, Alison Brie, Aubrey Plaza, Dan Levy, Mary Holland, Victor Garber, and Mary Steenburgen, the film follows a woman who struggles to come out to her conservative parents while she and her girlfriend visit them during Christmas. DuVall has said the film is a semi-autobiographical take on her own experiences with her family.
Abby Holland and Harper Caldwell are a couple who have been dating nearly a year. Abby has disliked Christmas since her parents passed away, so Harper spontaneously invites Abby to celebrate the holidays with her family in her hometown. Abby sees this as the perfect opportunity to introduce herself to Harper’s parents and propose to her on Christmas morning. However, on their way to the Caldwells’ house, Harper reveals she lied to Abby about coming out to her parents previously; fearing doing so would interfere with her father’s campaign for mayor, she doesn’t want to come out to her family until after Christmas. She asks Abby to pretend to be her straight roommate for the holiday, to which Abby reluctantly agrees.
At the Caldwells’ house, Abby meets Harper’s father, Ted, her perfectionist mother, Tipper, and her wacky artistic sister, Jane. The family welcomes Abby as Harper’s “orphan friend” who has nowhere else to go for Christmas. Abby becomes uncomfortable, especially when she meets Harper’s exes, Connor and Riley. During the visit, she begins questioning how much she knows about her girlfriend when she sees Ted and Tipper’s high expectations and Harper’s competitive relationship with her older sister, Sloane.
Ted is trying to impress a possible donor from the city council to contribute to his campaign, which Abby unwittingly jeopardizes when Sloane’s children put an unpaid necklace into her bag during an outing to the mall. Believing she is a shoplifter, Ted and Tipper think it might be better if they keep Abby away from upcoming social events. From this point, Abby feels even more like an outsider. She also learns from Riley that Harper has publicly denied her sexuality ever since she was a high school freshman, which makes Abby worried about the future of their relationship.
At the Caldwells’ annual Christmas Eve party, Abby, having tired of her current situation but feeling trapped, is relieved when her good friend John arrives unannounced to pick her up. Harper privately begs her to stay and as they are about to kiss, they are caught by Sloane who prepares to expose their relationship to the family. However, it turns out, Sloane has a secret of her own: she and her husband, Eric, are getting a divorce. The sisters get into a public fight, ruining the party. Sloane outs Harper being a lesbian, which Harper denies immediately. Heartbroken by this, Abby leaves the house. John follows her outside, where the two talk about their stories of coming out to their respective families: Abby’s parents were loving and accepting, while John’s dad threw him out of the house and didn’t talk to him for thirteen years. John reminds Abby that coming out can be terrifying for gay people, but has nothing to do with Harper’s love for her.
After realizing that her fear of rejection caused her to hurt Riley and will cause her to lose Abby, Harper finally tells the truth to her parents, confirming that she is a lesbian. This inspires Sloane to reveal her own secret and even Jane tells her parents how neglected she felt throughout the years. Despite all this, Abby still departs with John, feeling that she has been too hurt to give Harper another chance.
Tipper confronts Ted and details the emotional pain their daughters have clearly experienced as a result of their parenting choices, and how Tipper herself has felt constrained by their need to present as a ‘perfect’ family.
Harper goes after Abby to apologize, confessing that she truly loves her and wants to build a life with her. Touched by her words, and with encouragement from John, Abby forgives her and they share a kiss.
Ted apologizes to his daughters for making them feel they always had to meet his standard of perfection. Then he gets a phone call from the donor he’s been trying to impress, who will support him only if Harper suppresses any details about her personal life. Ted rejects the offer. The Caldwells then take a family picture, with Abby included this time.
One year later, Abby and Harper are now engaged, Jane has become a bestselling author with her fantasy novel, The Shadow Dreamers, and Ted has won the mayoral election. On Christmas Eve, the family goes to the cinema to watch It’s a Wonderful Life. As the movie starts, Abby and Harper smile at each other lovingly.
Kristen Stewart as Abby Holland, Harper’s girlfriend
Mackenzie Davis as Harper Caldwell, Abby’s girlfriend
Alison Brie as Sloane, Harper’s eldest sister
Aubrey Plaza as Riley Bennett, Harper’s ex-girlfriend
Dan Levy as John, Abby’s best friend
Mary Holland as Jane Caldwell, Harper’s middle sister
Victor Garber as Ted Caldwell, Harper’s father
Mary Steenburgen as Tipper Caldwell, Harper’s mother
Ana Gasteyer as Harry Levin, a potential campaign donor
Jake McDorman as Connor, Harper’s ex-boyfriend
Burl Moseley as Eric, Sloane’s husband
Sarayu Blue as Carolyn McCoy
Timothy Simons as Mall Security Ed
Lauren Lapkus as Mall Security Crystal
Carla Gallo as Angry Homeowner Lady
Michelle Buteau as Trudy
Jinkx Monsoon as Em K. Ultra
BenDeLaCreme as Miss L’Teau
Jenny Gulley as Ashley, Harper’s friend
Caroline Harris as Kelly, Harper’s friend
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