Is your first breakup the worst? Maybe, maybe not, but I think it’s the most intense. It’s the one where you take the first steps away from childhood, and where you enter into a relationship that exists on a different plane than your family or friends. It’s one where you’re either vulnerable with another person, or another person is vulnerable toward you.

My first breakup was with Roxy (clearly not her real name). Looking back on it, I’m shocked we were together as long as we were, since we had almost nothing whatsoever in common. Possibly because I’m a little dumb, the breakup blindsided me. For perhaps the only time in her teenage life, Roxy was shockingly efficient with The Talk. Inside of ten minutes, she told me that things didn’t feel right, but that she’d always care about me, and that we’d always be friends. One of those things turned out to be accurate.

I find that most movies dealing with breakups don’t tend to linger on the accurate details of breakups. One person is often the bad guy, the hurt and confusion is fast forwarded in a montage, and it all gets resolved with a fresh, new romance. The low-key dramedy Breakup Season doesn’t make any of those mistakes, and it shows a romantic train wreck with intelligence and compassion.

Cassie (Samantha Isler) and Ben (Chandler Riggs) have been seeing each other for a while. It’s been long enough that they’ve gotten a place together in Los Angeles, and while she embarks on what looks to be a successful career in real estate, he struggles to find a job at an architecture firm after earning his master’s degree.* Do they love each other? It doesn’t seem like it, but they care for each other.

A big step is taken when Cassie agrees to spend Christmas with Ben’s family in rural Oregon. They arrive and are (mostly) welcomed by the family. There’s Kirby (James Urbaniak), Ben’s father and a serious railroad enthusiast, Mia (Brook Hogan), Ben’s mother and a serious baking enthusiast, Liz (Carly Stewart), Ben’s younger sister and a budding influencer, and Gordo (Jacob Wysocki), Ben’s surly older brother and a recent divorcee.

The introduction is a little chaotic. Dinner a little moreso. During the dinner, there’s a moment when Gordo and Cassie argue about her vegetarianism (and how Ben forgot to tell the family that she’s a vegetarian). Gordo lectures Cassie about the environmental impact of her flight, and the look in her eyes says it all. I don’t want to be here. With these people. Any of them.

After dinner, Cassie and Ben talk, and it becomes clear that they’re not in sync. They’re so far out of sync they might as well be in different zip codes. Cassie breaks up with him, and wants to leave the next morning. Unfortunately, due to a blizzard and a pileup on the interstate, Cassie is stuck with her new ex and his family for the entirety of Christmas week.

Breakup Season truly is a minor miracle of a film. There are so many ways it could be stupid, insulting, ridden with tropes, and director H. Nelson Tracey sidesteps each narrative pitfall. He knows exactly what kind of a movie he’s making, a bittersweet drama sprinkled with low-key humor. It’s not a misery-fest, nor is it a movie about a house full of misanthropes. All of these are good people, and in their way, they’re trying to deal with an extremely awkward situation. Tracey’s film is more character focused. Instead of, “How will Cassie get out,” Tracey focuses on the character dynamics. He lingers on them long enough so that we understand who we are, but the pacing never becomes dull. Correctly, Tracey has also made a handsome film. Whether it’s inside the family’s rambling house, or around the real La Grande, Oregon, Tracey’s film feels warm and inviting despite the snow.

As the screenwriter, Tracey operates from a place of real compassion. The breakup doesn’t happen because Cassie is a bitch or because Ben is a man-baby. It happens because Cassie has a realization, and we get the sense that her realization took a little time to build. That doesn’t make her a bad person, nor do Ben’s increasingly clumsy attempts to win her back. We understand the hurt coming from both of them. We also understand that Ben’s family, while weirded out by the breakup, want to do what they can to be decent to both parties. Perhaps I’m naive, but experience has taught me that most people operate from a place of decency, and that’s where all of these characters are coming from.

The cast does strong work, particularly when they seem to be playing well-worn archetypes, then zip in a different direction. A good example of this is Jacob Wysocki’s Gordo, who at first glance seems to be the family’s loudmouthed burnout. He’s also one of the most emotionally connected characters, and the advice he gives Ben about dealing with the breakup is wise. I also liked the easy, goofy chemistry between Brook Hogan’s Mia** and James Urbaniak’s Kirby. Ultimately, the film wouldn’t work without the right actors playing Cassie and Ben, since you need to feel for both of them. That casting does work. Watch Samantha Isler, early on, as she works through her feelings toward Ben. What begins as an annoying foible unlocks the door to feelings she might not have realized she had, and ends with her resolved to end the relationship. Similarly, watch Chandler Riggs in the same scene, as he slowly realizes a minor disagreement has snowballed into the end of the relationship. Both of their performances are vulnerable, smart, and sophisticated.

A breakup can be agonizing, liberating, or never ending. The first breakup is something different, a special kind of experience that nearly everyone carries with them. That’s what Breakup Season understands. It’s a perceptive and bittersweet dramedy virtually anyone can relate to.

*A lesser film would imply that Ben is a slacker. Here, he’s hitting a bit of bad luck breaking into a very competitive field.

**This is Hogan’s first film, so bravo!

Tim Brennan Movie Critic

Tim has been alarmingly enthusiastic about movies ever since childhood. He grew up in Boulder and, foolishly, left Colorado to study Communications in Washington State. Making matters worse, he moved to Connecticut after meeting his too-good-for-him wife. Drawn by the Rockies and a mild climate, he triumphantly returned and settled down back in Boulder County. He's written numerous screenplays, loves hiking, and embarrassed himself in front of Samuel L. Jackson. True story.