The movie opens with Tom (Segel) proposing to Violet (Emily Blunt), the woman he's been dating for a year. If this were almost any other Apatow film, there would be something glaringly wrong with Tom—he doesn't have a job, say, or he lives with a pack of pot-smoking losers—and the rest of the movie would set out to fix it. But Tom is actually in pretty good shape. He's a talented sous chef at a popular San Francisco restaurant, where he's won the respect of his tough boss. He lives in a simple, tastefully decorated apartment with Violet, who's no slouch, either. She's just completed a Ph.D. in psychology and is waiting on offers for post-doc work.
When the long-awaited job offer comes, it's not from nearby Berkeley, as Violet had hoped, but the University of Michigan. Tom's clearly not excited about the idea of moving, especially when his boss tells him she wants to make him head chef of a new restaurant she's opening. But he resolves to go anyway. "We can handle anything," the two declare.
Michigan turns out to be a trickier relationship snag than arrested development, though. Violet immerses herself in her work at the university, where her boss and colleagues lavish her with praise. Tom, meanwhile, languishes. He can't get a job in any of the local upscale restaurants—which are inferior to San Francisco's anyway, the movie unsubtly implies—so he takes a position as a sandwich-maker at a fancy deli. He quickly becomes miserable. "You have no idea how hard it is to be a man in a relationship and not have a job you're proud of," he tells Violet, in one of the film's few emotionally compelling scenes. (Another involves Violet and her sister talking to each other in Sesame Street voices.)
After a few years in Ann Arbor (how many is unclear—the movie is frustratingly bad at marking time), Tom transforms into a more familiar Apatow leading man: weird, antisocial, and dependent on his male friends. He takes up deer hunting and beekeeping, and pals around with an alcoholic pickle expert and a stay-at-home dad who knits sweaters for fun. He grows some unfortunate facial hair. When Violet's sister and brother-in-law come for a visit, they're afraid to leave their daughter alone with him. It goes without saying that Tom and Violet don't feel much like marrying each other throughout their Michigan sojourn, so the wedding date keeps getting pushed off into the increasingly uncertain future. And without a wedding to plan or a problem to solve (other than the miserableness of Michigan), the film loses its focus. Violet engineers a successful psychology experiment involving stale doughnuts (a too-fitting recurring symbol for a movie as boring as this). Tom works on his bow-and-arrow skills. Members of the audience check their phones.
At this point, the movie's narrative arc is still salvageable. Tom could learn a lesson about the importance of adapting to difficult circumstances. He could get over the fact that Ann Arbor isn't San Francisco and decide to make the best of it anyway—maybe open his own restaurant or start a catering service. Instead, The Five-Year Engagement endorses the idea that Michigan, not Tom's inflexibility, is the problem: When the setting changes, his ambition returns. He goes back to working hard and planning ahead. This only makes the ramble through Michigan that much more infuriating—if Tom wasn't going to learn anything from his unhappiness, why do the filmmakers make us watch so much of it?