On Christmas Eve in Baltimore, the engaged couple Cliff and Brittany celebrate six months of sobriety and head to Brittany’s family gathering. A mishap at Brittany’s house leaves Cliff with a knocked-out tooth, sending them to the dentist, where Didi tends to him. During the treatment, Didi learns that her ex-husband Conway and his girlfriend Patty have had a surprise courthouse wedding, derailing Didi’s carefully laid Christmas Eve plans.
When Cliff discovers his car has been towed and rideshare options are scarce, Didi agrees to drive him to the tow lot. An accidental lock-in turns a routine trip into an unexpected detour, and Cliff calls his friend Marvin for help. Marvin frees him and nudges Cliff toward a late-night comedy show, a venture that tempted Cliff to return to the stage despite years away from stand-up after getting sober following a suicide attempt.
With there being no more food at Brittany’s family’s house, Cliff invites Didi to dinner. She agrees, but at the last moment changes course again, choosing to join Conway and Patty’s wedding celebration, bringing Cliff along as her date. Cliff adopts a confident, flattering front, even spinning stories like that he works for the Baltimore Ravens and could snag them free tickets, all to keep up the illusion of a perfect escort.
Didi later asks to bring Cliff to Marvin’s comedy show, a request that sparks tension with Brittany, who fears Cliff might be regressing. Cliff opens up about his past: he was dismissed from his improv troupe and missed a potential television gig after another performer accused him of bullying. At Marvin’s show, Cliff is asked to perform his beloved sketch, The Baltimorons. The response is mixed, but Cliff pushes through, unable to find a willing partner until Didi steps in and they perform an improvised routine about his dental appointment. The moment grows sweet and intimate, culminating in a kiss, though Cliff pulls away at the last second.
After the show, Didi confronts Cliff about his reaction to the kiss. He explains he panicked because he smelled alcohol on her breath and opens up about his own suicide attempt. Didi forgives him, and the two later steal Conway’s crabbing boat for a late-night harbor cruise. When they return to the dock, Brittany confronts Cliff, expressing concern for his wellbeing and leaving to sleep at her mother’s house. While driving, Cliff encounters Didi being arrested for a DUI; with the help of his uncle, Uncle Frank, he bails her out, and the two spend the night together.
The next morning, Cliff goes home to Brittany and speaks honestly about his father’s suicide and his own fear of repeating the past, assuring her that he has no intention of drinking or harming himself again. He then attends an Alcoholics Anonymous meeting and returns to Didi’s house, presenting her with a crab they caught on Conway’s boat as a Christmas gift. Didi wonders where their relationship is heading, but she invites Cliff inside for Christmas brunch, leaving the future open to possibility and redemption.
