The arduousness of planning a wedding is undeniably time-consuming, but the amount of time that goes into unmaking the plans is the source of Tom Solomon (Jason Segel) and Violet Barnes' (Emily Blunt) relationship discord. Directed by Nicholas Stoller (who previously worked with Segel on The Muppets), The Five Year Engagement takes us on a tour of two vastly different places (San Francisco and Ann Arbor) and, likewise, two vastly different people trying to succeed in the delicate art of compromise.
Co-written by Stoller and Segel, the majority of The Five Year Engagement balances physical and verbal comedy. Unfortunately, there are pockets of time when both mediums fall flat/feel too awkward to sit through. Where Stoller and Segel most strongly flourish in their crafting of the narrative is in the constant flashback to the moment Tom and Violet first met: At a New Year's Eve party with the theme "Create Your Own Super Hero." Tom created Super Bunny, Violet decided Princess Diana counted as a superhero and went with that (I actually really think she should be cast in a Princess Di biopic as a result of this costume). The flashback is told in increments, slowly revealing to the audience just how magical of an encounter it was (Van Morrison song included).
Appropriately, the film opens with Tom fumbling to get through his proposal with the help of his best friend, Alex (Chris Pratt), who secures the roof of the restaurant they work at for Tom to ask the question. When their families learn of the engagement, they are, for the most part, thrilled. Even Violet's sister, Suzie (Alison Brie, who you know better as Trudy on Mad Men), a woman who could never imagine getting married, is delighted for them. At their engagement party, the worlds of uptight Britishism and open-minded Americanism collide in the best possible ways, including Alex somehow convincing Suzie to sleep with him.
In the meantime, Violet has been waiting to hear from Berkeley about her acceptance into the post-doctorate psych program. When she finally receives their response, it is a rejection. Not wanting to break the news to Tom yet, she tells Suzie instead, who then blurts out that she is pregnant with Alex's child. This then segues into Alex and Suzie's wedding, baffling both Tom and Violet, who can't believe that they've been beaten in the race to marriage by their best friend and sister, respectively.
Because Violet was accepted to the psych program at the University of Michigan, Tom graciously agrees to quit his high-paying sous-chef job (even after his eccentric boss offers him the position as head chef at her new restaurant, Clam Bar) and move there with her for the two years it will take for her to complete the coursework. While Violet instantly takes a liking to her fellow students, Doug (Kevin Hart), Vanetha (Mindy Kaling, who I always expect to talk with a thick Mumbai accent), and Ming (Randall Park), and her professor, Winton Childs (Rhys Ifans, who I'll always see as Spike from Notting Hill), Tom struggles just to get a job at a Jewish deli after being laughed at by several other restaurant owners for voluntarily moving to Michigan from San Francisco.
As time wears on, the dissonance between Tom and Violet becomes increasingly palpable, with Tom turning to hunting and knitting as his sole means of entertainment. Eventually, both Tom and Violet end up cheating on each other (though Tom does so in a much more full-fledged way). It is at this point that they are both forced to recognize that the career goals they have for themselves are too divergent to ignore any longer. Of course, Tom has to lose a toe to frost bite in the process of getting to this conclusion.
And so, Tom returns to San Francisco, opens up a popular taco truck (Californians are obsessed with that shit), and starts dating a much younger girl he had previously met at the restaurant where he was a sous-chef. Violet has also gotten involved with Winton and has been offered an assistant teaching position at the university (an offer she later learns was merely the result of Winton's nepotism). Even so, the more they try to move on from one another, the more they discover that they can't. Thus, when Violet's final grandparent dies (a running joke throughout the movie is, "At least no one died," after which the scene cuts to a grandparent's funeral), Tom seizes the opportunity to fly to London and tell her how he feels.
After a passionate reunion beneath the Wham! posters of Violet's childhood bedroom, Tom suggests that she comes back to San Francisco with him during the time she has off from work. Violet gladly agrees, knowing full well that all of their problems will still be the same. When her vacation is over and Tom is driving her to the airport in his Taco-mergency truck (a converted ambulance), she proposes to him. Tom's response is to pull their old engagement ring out of his pocket and show that he was going to re-propose to her.
With this, Violet instructs Tom to drive to the park, where they proceed to run up the hill making snap decisions about music for the ceremony (string quartet or New Orleans brass band), tuxedos (vintage or traditional), and officiators (Jewish, Christian, extreme Christian, or Justice of the Peace). In the end, it is optimistically romantic to believe that Tom and Violet's issues will dissolve because of how much they love one another. In reality, after another five years, who knows if they would be able to endure one another? Then again, sometimes you just have to say "fuck it" and go with what that infernal organ, the heart, tells you to do.