Written and directed by Clea DuVall, this romcom is groundbreaking in that it's one of the few LGBTQ+-themed films made for the holiday season. But Happiest Season ultimately hits many of the same beats that a holiday film about a heterosexual, cisgender couple would. For better or worse, this makes it feel immediately comfortable and familiar. The cast does a great job at keeping the film feeling light, funny, and heartwarming. And the film's humor also ensures that the tough, complex subject of coming out never gets too dramatic or possibly triggering. But the retreading of popular holiday movie/romcom themes does prevent the film from breaking out of traditional Hollywood modes. For instance, Levy's character, John, embodies several too-familiar "gay male best friend" stereotypes -- i.e. characters who are often mysteriously devoid of familial ties, always have snappy comebacks ready, and are the emotional backup for their best friend when needed. John does have a more serious, expansive moment when he counsels Abby on Harper's reticence to come out to her family, citing how some families disown or disapprove of children who identify within the LGBQ spectrum and talking about his own traumatic coming-out experience. But beyond this, John remains a character of cliches, which is unfortunate in a film like this, which overall aims to break stereotypes.
Davis does well with Harper, who could be read as unlikable or even manipulative. Harper's fear of her parents' reaction to her sexuality is understandable, and the regretful actions she takes can be put into the context of that fear. But compared to Stewart's likable Abby, who's comfortable with herself, Harper can seem like she's taking advantage of Abby's love and devotion. Things only ramp up when viewers learn more about what Harper did to Riley in the past, making you wonder whether Abby and Riley should be together instead. But Harper's fear is only part of the problem with her dysfunctional family, and her courage to be herself eventually helps the rest of her family members be themselves, too, bringing the film back to its ;roots of togetherness, happiness, and holiday cheer. Despite its flaws, Happiest Season does remind audiences that, for many people, the point of the holidays is to be with family and celebrate love and joy. And the film's message that everyone deserves love, understanding, and empathy rings true.