Honestly, looking back at 2012, we didn’t deserve Jason Segel and Emily Blunt. When The Five-Year Engagement hit theaters, people sort of expected another Forgetting Sarah Marshall. They wanted the easy laughs, the slapstick, and a tidy ninety-minute bow on a wedding. Instead, what we got was a messy, awkward, and surprisingly painful autopsy of a relationship that just... wouldn't... end. It’s a movie about the space between "I do" and the actual ceremony, and it turns out that space is where a lot of life happens.
I rewatched it recently. It’s longer than it needs to be, sure. But that length is kind of the point.
The film follows Tom Solomon (Segel) and Violet Barnes (Blunt). They get engaged quickly. It’s cute. There are balloons. Then, life intervenes. A career opportunity for Violet in Michigan pulls them away from Tom’s rising chef career in San Francisco. What was supposed to be a short delay turns into a half-decade of resentment, stale cookies, and Tom hunting deer in the Michigan wilderness while wearing a sweater he definitely didn't own in California. It’s a specific kind of purgatory that anyone who has ever "put their life on hold" for a partner knows all too well.
Why the Five-Year Engagement feels like a documentary for Millennials
Most romantic comedies treat the wedding as the finish line. The Five-Year Engagement treats the engagement as the starting gun for a marathon that nobody trained for. It’s one of the few films that captures the "trailing spouse" syndrome with any real honesty.
Tom goes from being a sous-chef at a high-end San Francisco restaurant to making sandwiches in a deli. He’s miserable. But he’s "supportive." That’s the lie the movie picks apart—the idea that you can swallow your own ambitions for years without it turning into a toxic sludge that eventually poisons the relationship.
Director Nicholas Stoller and Segel (who co-wrote it) leaned into the discomfort. You remember the scene where Violet and her sister, played by a pre-superstardom Dakota Johnson, have a conversation in Elmo and Cookie Monster voices? It’s absurd. It’s also exactly how siblings talk when they’re trying to avoid a massive, life-altering confrontation. The film is littered with these moments where the comedy is just a thin veil for the fact that these two people are drifting apart in slow motion.
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The Michigan factor and the ego
Let’s talk about the setting. Moving from San Francisco to Ann Arbor is a classic cinematic trope for "the end of excitement," but for Tom, it’s a total ego death. There’s a specific psychological weight to being the partner who moved.
- Tom’s identity was tied to his kitchen.
- In Michigan, he becomes "the guy who’s with the professor."
- His hobby becomes increasingly bizarre (the aforementioned hunting and mead-making) because he has no professional outlet.
It’s a cautionary tale about the "happily ever after" delay. The longer the engagement lasts, the more the wedding stops being a celebration of love and starts being a deadline they’re both dreading. You see it in the way they keep changing the date. Each postponement is a tiny brick in a wall.
The supporting cast was a fever dream of talent
Looking at the call sheet for this movie today is wild. You’ve got Chris Pratt before he was "Marvel's Chris Pratt." He plays Alex, Tom’s best friend, who is basically the chaotic mirror to Tom’s stagnation. While Tom and Violet are overthinking every detail of their future, Alex is out there accidentally getting Violet’s sister pregnant and getting married immediately.
It’s a hilarious, frustrating contrast. Alex’s life is a mess, but it’s a mess that’s moving forward. Tom’s life is "perfectly planned" but standing still.
Then you have Alison Brie, Mindy Kaling, Randall Park, and Kevin Hart. It’s an embarrassment of riches. Most of them are playing characters who are just as confused as the leads, which helps ground the movie. It’s not just Tom and Violet who are struggling; everyone in their thirties is basically just winging it and pretending they have a plan.
Real talk about the 124-minute runtime
One of the biggest complaints at the time was that the movie was too long. People said it felt like a five-year engagement.
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That was a deliberate choice by Stoller. He wanted the audience to feel the fatigue. He wanted you to get a little tired of Tom and Violet’s circular arguments. In a world of TikTok-paced content, a two-hour-plus rom-com feels like a vintage epic. But that sprawl allows for scenes that a tighter edit would have cut—like the awkwardness of Tom’s parents' various divorces and remarriages, or the slow-burn realization that Violet’s professor (Rhys Ifans) is a predatory jerk.
It’s a movie that rewards patience. It’s not a "first date" movie. It’s a "we’ve been together three years and need to talk about our future" movie.
What we can learn from Tom and Violet’s mistakes
If you’re in a long-term engagement right now, this movie is basically a PSA. The central conflict isn't that they don't love each other. They clearly do. The conflict is that they stopped being a team and started being two people living parallel lives that happened to share a kitchen.
Tom’s mistake wasn't moving to Michigan. It was failing to find a new version of himself once he got there. He held onto his San Francisco identity like a shield, using it to justify his bitterness. Violet’s mistake was assuming that Tom’s sacrifice was a one-time transaction rather than an ongoing debt she needed to acknowledge.
Tactical takeaways for the "Long Engagement" crowd
If you find yourself in a situation where the wedding keeps getting pushed back, take a page out of the Tom Solomon playbook of what not to do.
Don't let your hobbies become a substitute for your personality. Tom's descent into "mountain man" territory was a cry for help that he masked as a rugged new persona. Honestly, if you're starting to make your own pickles and knit your own sweaters out of spite, it’s time to sit down and have the "Are we actually doing this?" talk.
Also, watch the "supportive" trap. Being a supportive partner doesn't mean being a martyr. Martyrs are eventually burned at the stake, and in this movie, that stake is a giant taco truck at the end of the film.
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The ending is the most honest part
Without spoiling the beat-by-beat, the way the film concludes is surprisingly low-key. It acknowledges that a wedding doesn't fix the five years of baggage you just accumulated. It’s just a ceremony. The real work is the stuff that happened in the snow in Michigan, the fights over the guest list, and the realization that your partner is a flawed, annoying, wonderful person who is also struggling.
The movie didn't break records at the box office. It didn't win Oscars. But it has aged better than almost any other comedy from that era because it’s so grounded in the reality of how hard it is to actually stay together.
Actionable Insights for Navigating Relationship Stagnation:
- Audit the "Why": If the wedding date has moved more than twice, stop looking at venues and start looking at the relationship. Is the delay logistical or emotional?
- The Trailing Spouse Plan: If moving for a partner’s career, the "trailing" partner needs a concrete, 90-day plan to establish their own community and goals. Do not wait for your partner to provide your social life.
- Communication over "Support": Replace "I’m fine with whatever you need" with "I am willing to do this, but I am worried about X, Y, and Z."
- Identity Check: Ensure your self-worth isn't tied to a specific city or job title. If those things change, who are you? Tom didn't know, and it nearly cost him everything.
Stop viewing The Five-Year Engagement as a simple comedy and start viewing it as a roadmap of the potholes to avoid in a long-term commitment. It’s messy, it’s too long, and it’s occasionally frustrating—just like a real relationship.