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The Five-Year Engagement

In San Francisco, sous-chef Tom, and PhD graduate Violet, are happily engaged. Their wedding plans are interrupted when Tom's best friend Alex gets Violet's sister Suzie pregnant at Tom and Violet's engagement party, and Alex and Suzie quickly marry.

When Violet is accepted into the University of Michigan 's two-year post-doctorate psychology program, Tom agrees to move with her and delay their wedding. Later, he is disheartened to learn his boss planned to make him head chef.

Unable to find a suitable chef's position in Michigan, Tom is resigned to working at Zingerman's deli and takes up hunting with Bill, a fellow university faculty spouse. Violet settles into her new job under professor Winton Childs, working with Doug, Ming, and Vaneetha.

A prank results in Violet being chosen to lead the team's research project, studying people who choose to eat stale donuts rather than wait for fresh ones to arrive. Tom and Violet's nuptials are further delayed when Winton receives funding from the National Institutes of Health with Violet's help and extends her program. Tom is upset by the news, and he and Violet fight over his unhappiness with their new life.

As years pass, Tom becomes disillusioned and obsessed with hunting. Alex, Suzie, and their daughter Vanessa visit, and reveal Suzie is pregnant again. Tom responds that he no longer wants to have a child, surprising Violet, who offers to look after Vanessa with him, but the night turns into a disaster after Vanessa shoots Violet with Tom's crossbow.

Tom's downward spiral becomes evident when Violet sees him eat a stale donut. At a bar with colleagues, a drunken Violet and Winton kiss, which Violet instantly regrets. She tells Tom that she wants to plan their wedding immediately, and he happily agrees. When Violet confesses to kissing Winton, Tom loses faith in their relationship, which reaches a climax when Winton comes to their rehearsal dinner to apologize.

Tom chases Winton away, then leaves to get drunk alone. He runs into Margaret, an amorous co-worker, but opts not to have sex with her, and wakes up half-naked in the snow with a frostbitten toe, which is amputated. Violet visits Tom at the hospital, and they call off their engagement once they arrive home.

Violet starts a relationship with Winton but often reminisces about Tom. He wishes her a happy birthday via email, including a video of Ming's ridiculous experiment on his friend Tarquin. Violet calls Tom, who has returned to San Francisco, working as a sous-chef under Alex and dating the hostess, Audrey. Their friendly-but-awkward conversation takes a turn as they argue over Violet's stale donuts experiment as a metaphor for their relationship, and both end the call upset.

Realizing Tom's unhappiness, Alex fires him out of love, telling him that he is the better chef and should open his own establishment. So, Tom launches a popular taco truck.

Violet receives an assistant professorship but learns she was hired because she is dating Winton, and breaks up with him. After lunch with his parents, Tom decides to win Violet back and breaks up with Audrey. He surprises Violet at her grandmother's funeral in England, and they agree to spend the remainder of the summer together in San Francisco, rekindling their relationship while sharing an apartment and working in the taco truck.

Driving Violet to the airport, Tom offers to take his truck to Michigan and continue their relationship. Violet proposes to Tom at the side of the road, just as he did five years before, and Tom produces the ring he originally gave her, explaining that he was planning to re-propose at the airport.

They head to Alamo Square, where Violet has organized their family and friends for an impromptu wedding. Tom chooses between Violet's various options for the officiant, clothing, and music, and they finally marry.

Tom and Violet share their first kiss as a married couple, and the film flashes back to their first kiss when they first met at a New Year's Eve party. Alex and Suzie sing " Cucurrucucú paloma " on a carriage ride with the newlyweds.