Development on the film began in 2005, when Chiarelli wrote the film's script. Principal filming occurred over a period of two months from March to May 2008. The film received mixed reviews from critics, who criticized its script, but praised the chemistry between Bullock and Reynolds. The film was a box office success, grossing over $317 million worldwide, becoming the highest grossing romantic comedy film of 2009.
The couple travels to Sitka, Alaska, Andrew's home town, to meet his family. Margaret meets Andrew's mother Grace and grandmother Annie a.k.a. "Gammy". During the trip to the family home, Margaret notices that nearly every shop in town carries the name Paxton and learns that Andrew's family is in fact very wealthy. During a welcome home party, Andrew confronts his father, Joe, who is angry about Andrew's dating the boss he has so long disliked and thinks he is using her to get ahead in his career. After their argument, Andrew announces the engagement to everyone. Margaret also meets Gertrude, Andrew's ex-girlfriend.
The next day, Grace and Annie take Margaret to a local bar to watch a strip dance by a locally famous but over-the-hill exotic dancer, Ramone. Stepping away from the show, Margaret learns from Gertrude that Andrew wanted to become an editor and make his own life and that Andrew had proposed to Gertrude. However, Gertrude refused because she didn't want to leave Sitka for New York. Returning home, Margaret learns of the conflict between Andrew and Joe. That night, Margaret asks Andrew about his relationship with his father, but Andrew refuses to talk. Instead, Margaret opens up to Andrew.
The next day, the family convinces them to marry while they're in Sitka. After Margaret realizes how close Andrew's family is, she becomes upset, gets on Andrew's boat, and speeds away with him. She tells him she has been alone since she was sixteen years old after her parents died and had forgotten what it felt like to have a family. She lets go of the helm and stumbles to the back of the boat. Andrew makes a sharp turn to avoid hitting a buoy, and Margaret falls out of the boat. Andrew quickly turns the boat around and saves her because she can't swim. At the wedding ceremony, Margaret confesses the truth about the wedding to the guests, including Gilbertson, who informs her she has twenty-four hours to leave for Canada. Margaret returns to the Paxton home to pack her things. Andrew rushes to their room only to find Margaret has already left, leaving the aforementioned book manuscript with a note of praise and a promise to publish it. Gertrude attempts to comfort Andrew and asks if he is going to go after her. As he rushes out to find Margaret, another argument arises between him and Joe. Annie fakes a heart attack and convinces them to reconcile before she "passes away". After she succeeds in getting things moving again, she owns up to faking the attack. Andrew's parents realize he really loves Margaret. He goes to New York and tells Margaret he loves her in front of the entire office staff. They kiss, then go to Gilbertson and inform him they are again engaged, but for real this time. The film ends with Gilbertson asking questions (some of them irrelevant) not only to Andrew and Margaret, but also Joe, Grace, Annie and Ramone.
CastSandra Bullock as Margaret Tate, a chief editor at a major New York City book publisher.
Ryan Reynolds as Andrew Paxton, Margaret's assistant whose ultimate career goal is to become an editor.
Mary Steenburgen as Grace Paxton, Andrew's mother.
Craig T. Nelson as Joe Paxton, Andrew's father who owns the family business that dominates the entire town of Sitka.
Betty White as Grandma Annie "Gammy", Andrew's grandmother and Joe's mother.
Denis O'Hare as Mr. Gilbertson, the immigration agent investigating Margaret's case.
Oscar Nuñez as Ramone, a resident of Sitka who holds many jobs, including waiter, male stripper, shopkeeper, andminister.
Malin Åkerman as Gertrude, Andrew's ex-girlfriend.
Michael Nouri as publisher Bergen, Tate's superior.
Aasif Mandvi as Bob Spaulding, an editor.
Michael Mosley as Chuck, Andrew's friend.
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