‘The Baltimorons’ Review: Jay Duplass’ May-December Romance Is a Stealth Charmer With a Low-Key ‘After Hours’ Vibe

After co-directing a handful of no-frills indies with his brother Mark and working for more than a decade in episodic television, Jay Duplass makes an agreeably unassuming solo feature debut behind the camera with The Baltimorons. Marbled with a tender vein of melancholy alongside its unforced comedy, the film follows a thirtysomething, recently sober ex-improv comic who breaks a tooth and requires urgent dental care on Christmas Eve, spawning an unlikely romance. It’s the kind of quirky concept that could easily have been cringe material, but the actors give it a lived-in naturalism that sneaks up on you.

Aside from his acting and producing credits, Duplass’ regular gig since 2015 has been directing TV episodes, notably on Togetherness, Search Party, and most recently, Somebody Somewhere. (I will never stop being mad about that consistently great show getting zero Emmy attention.) Just as Somebody Somewhere was molded with piercing character insight around its star, Bridget Everett, the foundational building block for The Baltimorons is co-writer and lead actor Michael Strassner. He’s teamed with the wonderful Liz Larsen in a May-December romance with genuine heart.

It might sound schematic to describe two wildly dissimilar characters who forge an unexpected connection and discover they can help mend each other in ways they haven’t figured out in their own lives. But there’s a sincerity to the movie that sidesteps the usual potholes of earnestness or sentimentality, thanks to terrific chemistry between the lead actors and the director’s unerringly light touch. It’s also an unabashed love letter to Baltimore, from its blue-collar neighborhoods to its harbor.

The opening scene has Strassner’s Cliff shambling up the stairs to his attic, positioning a chair under a ceiling beam and then fashioning a noose out of a belt. His lethargic body language subtly suggests a run of failures, so even he seems unsurprised that his ineptitude extends to a botched suicide attempt. Cut to six months later, when he sheepishly shows his sobriety anniversary medal to his vigilant fiancée Brittany (Olivia Luccardi).

When Cliff shares that his buddy Marvin (Rob Phoenix) is doing a stand-up set that night and asked him to stop by, Brittany flinches, advising him to stay away from situations that might encourage him to slide back into old habits. He made a promise to her — no more alcohol and no more comedy shows.

It’s on arrival at Brittany’s mother’s house for a family meal that Cliff collides with the door frame and finds himself with a broken tooth and a mouthful of blood. Most dentists are closed for the holiday but eventually he gets a response from Didi (Larsen), a no-nonsense type resistant to both his humor and his flirting, who patches him up with a temporary filling.

Cliff overhears Didi on a phone call when she learns that her daughter is bailing on dinner to celebrate with her father, who divorced Didi and has just been married that morning to his younger girlfriend. When Cliff leaves the dental practice and finds that his car has been towed, she offers to drive him to the tow yard and then helps him out of a jam when he finds it closed.

Duplass establishes the time of year at the start with composer Jordan Seigel’s tinkly piano-bar arrangements of holiday classics like “O Christmas Tree” and “Jingle Bells,” before easing into jazzy cocktail riffs that keep the tone light as Didi slowly lets down her guard and begins warming to terminally awkward, filter-free Cliff.

He reveals that he reluctantly gave up on his comedy aspirations and is now looking to qualify as a mortgage broker, while she shares that she’s a workaholic whose marriage to her high school sweetheart turned out to be a nightmare. Didi politely declines when Cliff invites her to dinner as a thank you. But he gets past her brittle walls, and slowly, as flickers of mutual attraction start to glow, the age difference between them of at least a couple decades seems to shrink.

The low-key After Hours vibe first felt at the tow yard steadily picks up momentum as they strike out on restaurants with Christmas Eve availability. Cliff helps Didi muster the courage to hit the party where her ex-husband Conway (Brian Mendes) and his new wife Patty (Somebody Somewhere alum Mary Catherine Garrison) are celebrating with Didi’s daughter Shelby (Jessie Cohen) and granddaughter Maddie (Zoe Strassner).

In one of the movie’s funniest scenes, Cliff draws on his improv skills in the role of “Didi’s hot young date,” coming up with wild fabrications to make her look good and string along Conway and Patty.

High off that minor victory, Didi and Cliff decide to front up for Marvin’s comedy set — a pop-up improv night in an auto shop — where he reveals the circumstances of his fall from grace and his fears about returning to that environment for the first time since he got sober.

Duplass and Strassner’s script traces the one-step-forward, two-steps-back progress of the main characters’ connection over the course of the night with delicacy, never stretching the boundaries of credibility. That goes even for an impromptu crabbing trip on a borrowed boat.

One particularly lovely scene is Cliff’s inevitable confrontation with Brittany, which de-escalates from anger into affecting emotional candor with equal compassion for both characters. There’s deep regret and a yearning for forgiveness in Cliff’s admission: “I tried to do the normal life thing. Can’t do it. It doesn’t fit.” And there’s grace and dignity in Brittany’s acceptance of him for who he is.

While the wintry tones and abundance of minimally lit outdoor night scenes give the movie a slightly drab, grainy look, it counters with the warm humanity behind its jokey banter.

Duplass is careful not to veer into trite rom-com territory, meaning even a scene in which Cliff asks Didi to dance to her wedding song, “Someone to Watch Over Me,” helping her to reclaim it for herself, feels authentic to the characters and the moment. We have no guarantees at the end as to where Cliff and Didi will end up in each other’s lives. But with gentle brushstrokes, The Baltimorons lets us know that both are in a better place than where they started out.