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On their one-year anniversary, sous chef Tom Solomon (Jason Segel) plans to surprise his girlfriend, Violet Barnes (Emily Blunt), with an engagement ring. The lovers do end up engaged, but the fact that the proposal does not go exactly as planned proves to be a harbinger of things to come. Each time they try to set a date, various obstacles stand in their way. As more and more time passes, Tom and Violet begin to wonder if perhaps their marriage is not meant to be.