The Baltimorons explores an unexpected romance between two misfits

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Jay Duplass (The Puffy Chair; Cyrus; Jeff, Who Lives at Home) directs this screenplay cowritten with Michael Strassner about Cliff (played by Strassner), a six-months-sober former improv comedian whose Christmas Eve cracked tooth leads him to Dr. Didi Dahl, D.D.S. (Liz Larsen) and a May/December romance as they explore Baltimore over one night. (100 min.)

Glen: Cliff is struggling to find his footing. He just earned his six-month Alcoholics Anonymous chip, but his life feels offtrack. He’s got a girlfriend (Olivia Luccardi) who loves him but doesn’t really support him. He loves improv comedy, but it triggers his alcoholism, so his girlfriend laid down the law: No alcohol and no comedy. Basically, no fun. He’s a lost soul who, thanks to a dental emergency, meets another lost soul, Didi, whose husband left her for a younger woman. It’s Christmas Eve, and the thought of facing her children and ex with his new woman at a family gathering is unenticing. When Cliff discovers his car has been towed outside of Didi’s office, she offers him a ride to the impound lot, setting in motion a 24-hour adventure as the pair gets to know each other and discover that though they’re each broken, they just might fit together. It’s very sweet, very melancholic, and very naturalistic. You feel like you’re witnessing real life.

Anna: I absolutely love stories like this. Something about misfits finding their match gives me all the good feels. Cliff’s just trying to keep himself out of a rut so deep that he drinks again, and Didi is so stuck in her own rut that she isn’t even looking for the sunlight anymore. The messiness of imperfection is played so well by Strassner and Larsen in this “slice of life” film. The two don’t feel like a fit, but somehow, they’re just what each other needs in that weird window of time that they find each other. At one point, the two end up at a comedy show, and Cliff is peer-pressured back onstage. In what first seems to be a humiliating attempt by his improv peers to knock Cliff down, the two find a way to play with each other when Didi joins him onstage. It’s so sweet, but these two can’t seem to stop getting in their own way.

Glen: I didn’t recognize any of these actors, which I think helps add to the realism. I looked at Strassner’s and Larsen’s IMDb pages, and they’ve each done a lot of supporting actor work, but here they are front and center, and they both turn in amazing and natural performances. Strassner is scruffy but loveable, and Larsen projects a protective hardened exterior that begins to crack under Cliff’s charm—they’re perfect for these roles, which makes sense since Strassner—drawing from his own life—co-wrote the screenplay with Duplass. Likewise, Duplass explained that Larsen’s personal history was also incorporated into the screenplay. With its light, jazzy score and cinema verité-style location filming in Baltimore, this is the anti-Hallmark Christmas movie. It’s a love story that feels real and a shared adventure that feels spontaneous. Are they going to make it? You don’t know, but their hopefulness is palpable. 

Anna: I applaud Duplass, Strassner, and Larsen—this is a little film that manages to make the small things feel big and reminds us that life-changing moments sometimes tumble like rocks down a hill, one right after the other and all in a great big pile. You might as well enjoy the fall.

New Times Arts Editor Glen Starkey and freelancer Anna Starkey write Sun Screen. Comment at gstarkey@newtimesslo.com.

This article appears in Apr 24 – May 4, 2025.