Tom (Jason Segel) and Violet (Emily Blunt) meet at a costume New Year's party and hit it off big time. Along with his long-time goofball buddy and co-worker Alex (Chris Pratt), Tom, a successful San Francisco chef, plans an elaborate marriage proposal ritual and then watches it fall apart due to circumstances beyond his control. Violet agrees to wed but their relationship is taken in another direction when she is accepted into the psychology doctoral program at the University of Michigan. Meanwhile, her sister Suzie (Alison Brie) marries Alex and they steal the spotlight.
Tom and Violet move to the winter wonderland in the Midwest where the only job he can get is working in an unconventional sandwich shop. Bored to death and becoming more resentful day by day, Tom takes up hunting deer and is befriended by Bill (Chris Parnell), a stay-at-home dad who loves knitting sweaters. Violet does well in her two-year program and is chosen by Winton Childs (Rhys Ifans), head of the psychology program, to continue her work there for three more years. Even though Violet and Tom have often tried to talk about his leaving a promising career in San Francisco, clearly they haven't gotten to what he really feels. This extension, and a few other factors, lead to a split. Will they be able to work things out in their relationship and finally get married?
Nicholas Stoller directs this comedy that has some funny bits but unlike the raucous Bridesmaids is unable to sustain its humor. The screen chemistry between Emily Blunt and Jason Segel registers high on the romantic scale. Also on the positive side is the story's suggestion that couples not try to work out all of their problems before getting married. There are no perfect husbands and no perfect wives: only vulnerable and flawed human beings trying to keep love alive as a work-in-progress.
Special features on the DVD include a "Making of The Five Year Engagement" with added details; 12 deleted scenes; and a gag reel.