The Baltimorons (2025)

The best summation I can offer for the tone (and therefore the experience) of The Baltimorons is a cross between a '70s dramedy and When Harry Met Sally. This is an independent production from director Jay Duplass and comedian Michael Strassner. They scripted the movie together, and Strassner plays a character whose backstory is loosely based on his own life, including struggles with alcoholism, attempted suicide, and disappointment stemming from nearly making it big. There's some real drama here, but the movie finds humor within it. This is, after all, ultimately a romantic comedy, albeit one grounded in believable emotion. The leads are deeply flawed, and - like When Harry Met Sally - this understands the goal is to help them come to terms with those flaws and find a way forward together, rather than pretend they can (or should) be wiped away.

All of which is a longwinded way of saying I liked it a great deal and absolutely recommend it as a funny, melancholy alternative to the usual upbeat holiday offerings. This one's quite good, so feel free to stop reading and stream the movie before I go and spoil the hell out of it.

The film's other lead is Liz Larsen, who plays Didi, an aging, divorced dentist who Strassner's Cliff meets after knocking out a tooth on Christmas Eve. For those squeamish, rest assured this isn't a major component of the movie, and Duplass doesn't dwell on the procedure, only the characters. After the tooth is back in place, Cliff emerges to find his car's been towed. Didi gives him a ride to the impound lot, where a series of comedic events result in him being locked inside and eventually stealing his car back with her help.

They keep almost going their separate ways, but something - usually Cliff - pulls them back together to keep the fun going. And they really are both having fun. Didi's plans were already ruined, because her ex-husband eloped that morning, causing their daughter (and granddaughter) to agree to spend Christmas Eve with him. Didi's invited, as well, but she's frightened of making an appearance for a variety of reasons.

But as luck would have it, Didi and Cliff wind up in the neighborhood, anyway, and - in keeping with the bizarre day so far - she decides to stop by, after all. Cliff offers to go with her, and she brings him along. He uses his improv skills to humiliate her ex-husband, which of course pleases Didi to no end.

All of this understandably draws Cliff away from his fiancé, Brittany (Olivia Luccardi), who at first comes off as overly pushy and controlling... until we learn she's been living in constant fear of Cliff relapsing. Conventional romantic comedies would usually introduce a character like this to serve as a foil who needs to be overcome, but that's not her role in the narrative. The movie plays with our assumption that there's a flaw in her personality, but it's all for the twist that her fears are genuine and understandable. When her and Cliff finally break up because he wants a life different from the one she needs and she's no longer able to carry the emotional baggage of worrying about him at all times, we're left empathizing with both characters, who in turn empathize with each other. That's not how these movies usually go, and it's truly refreshing.

But I'm getting ahead of myself. First, Didi and Cliff attend a comedy show, where Cliff is pulled up on stage. This is the first time he's attempted to do standup since becoming sober, and he's petrified. Didi accompanies him, and - after a rocky start - they manage to make it through a scene. It's awkward and confusing for both of them, but Didi realizes she has feelings for Cliff and he realizes he's capable of performing without alcohol.

Not wanting the night to end, Didi and Cliff steal her ex's boat to steal softshell crabs... or at least attempt to do so. They eventually do locate one crab before returning to the dock, where Cliff runs into Brittany, who's been tracking him on her phone and was worried he'd drowned himself. Everyone goes their separate ways, but Cliff sees Didi pulled over for driving under the influence. He bails her out, takes her home, and they spend the night together.

The next morning, she tells him they both know he needs to go make things right with Brittany. This culminates in the aforementioned sequence where we're given a glimpse into what that character's been going through and why a breakup really is the best way forward for both of them. He then returns to Didi's, and the two head in to spend the holidays with her daughter and granddaughter.

So it resolves happily, but doesn't conclude with any kind of fairytale ending. Didi and Cliff don't profess their love for each other, they don't kiss in the last scene (though they kiss earlier in the movie), and there's certainly no guarantee they'll be together forever. The movie tells us they like each other a lot, they enjoy spending time together, and they're going to continue seeing each other. Neither seems to have any expectations, which is probably for the best, as neither seems sure what they want, either. But regardless of whether they get married or break up after a few weeks, they're happy in the moment, and - more significantly - being together seems to have a positive effect on their mental health. You're left with the sense that even if this ends the next day, the experience will have been a net positive for everyone involved.

The movie as a whole being grounded (in spite of some fairly absurd coincidences and shenanigans) extends to the casting and setting. Neither Strassner nor Larsen look or act like the stars you'd associate with a typical romantic comedy. Instead, these feel like the kind of people you'd expect to pass on the street in Baltimore (or any city for that matter). They're funny and likeable in a believable way, and don't feel polished or fake.

Likewise, the movie is playing with the old trope of treating the city as a sort of third character, though unlike countless artificial versions of New York strategically photographed to make it seem cleaner than it's ever been, they portray Baltimore as a realistic city with rough edges. It's a city that doesn't initially fill you with confidence, but over time the movie reveals its charm. In that respect, it mirrors the film's portrayal of its actual characters. This is a study of those who are more than they seem.

I also appreciate this movie's willingness to invert the usual dynamics surrounding age and gender. While I don't recall the movie explicitly telling us Didi's age, she's a grandmother who logically must be a couple decades older than Cliff, a man in his mid-thirties. This joins last year's Babygirl in challenging sexist stereotypes surrounding age and attraction.

I don't have a great deal to say about the holiday elements here. The movie leverages the tonal dissonance common in holiday media to highlight the story being at once happy and sad. The music choices make this apparent: mostly we're hearing melancholy Christmas instrumentals. This also seems to be playing with traditions surrounding the holidays as a sort of break in normality, almost existing outside the normal flow of time. This Christmas Eve is a bizarre adventure for both these characters, one that wouldn't be possible on a normal day.

While I wouldn't describe this as being similar to movies like White Reindeer or The Holdovers, fans of those kinds of bittersweet spins on the holidays would be particularly rewarded to give The Baltimorons a shot. This is one of the better new Christmas movies I've seen this year - I can absolutely recommend it.