Amy Myer [Kimberly Williams-Paisley] is a woman who has lived by a precise timeline laid out by her dying mother when Amy was seven. The plan directs her to become an attorney and to marry her seventh boyfriend, a rule she takes to heart. She defines a “boyfriend” as the seventh man who calls her his girlfriend, a definition that locks the marriage slot into the future. She quietly tests the path by breaking up with boyfriend #5 and then encounters Daniel McCandless [Brad Rowe], whom she initially believes could be the perfect seventh. Yet she remains obsessed with making him the seventh, not the sixth, and sets out to find a genuine #6 who could precipitate the shift she craves.
Enter Peter Connor [Patrick Dempsey], a local bagel shop owner who also carries the shadow of a fortune earned as an ex Bear Stearns trader. Peter loves Amy and invites her to accompany him to a wedding on Orcas Island. At first she resists, but soon sees him as a potential #6 who could unsettle the carefully laid plan. The couple travels together to the island wedding, where Peter bluntly tells his friends they are dating and even calls Amy his girlfriend, thereby locking Peter into the #6 slot in Amy’s scheme. They begin to behave as a couple around Peter’s social circle and his ex-girlfriend, who appears with her new husband, adding a dash of complication and a spark of chemistry.
The connection between Amy and Peter intensifies, and they share a night of hot, undeniable chemistry. Yet Amy pulls back, insisting that what happened felt like a mistake because it challenges the timeline she lives by. Peter, probing the future, asks what would happen after marriage since the plan ostensibly ends there, and the pair return to the city with unresolved tension and new questions about what they truly want.
Back in the workplace, Daniel reveals to his boss that he and Amy are dating, which technically places Daniel as the seventh by Amy’s own rules. This public declaration tests the entire premise, pressing Amy to confront the reality of her feelings rather than the rigid structure she constructed.
Realizing she has developed real feelings for Peter, Amy faces a pivotal truth: she and Daniel have never even held hands, and the happiness she longs for lies beyond the timeline she’s followed for so long. She makes the bold choice to quit her job and start fresh, setting out to find Peter. Though he isn’t at work, she discovers him at the island—the wedding venue they had attended together—apparently now connected to his life in a new way. They meet, embrace, and a new chapter begins as Amy leaves her old life behind.
The story culminates with Peter offering Amy a job at the bagel shop, and the two sharing a quiet moment in Amy’s apartment, both seemingly ready for a future that might lead to marriage, but this time on their own terms rather than a meticulously plotted timeline. The film leaves them standing on the cusp of a self-authored destiny, where love decides the outcome rather than a list of predefined steps.
