The movie starts off with Andrew Paxton (Ryan Reynolds) snoozing his alarm clock, and jumping out of bed realizing that he’s overslept and could be late for work. He rushes out and gets to the office in the nick of time. Just as he gets to his desk, Margaret Tate (Sandra Bullock) walks into the office. Everyone either stutters or looks away as she coldly, hurriedly walks past them and directly into her office. Margaret is a book editor for a big NYC Publishing company and Andrew is her assistant/secretary.
Margaret fires an editor named Bob Spaulding, who tries to embarrass her by yelling at her in front of the entire office. She takes the abuse then threatens to have security escort him out if he doesn’t leave immediately. Once he’s gone, she tells Andrew that she’s gonna need him this weekend causing him to break plans to attend his grandmother’s 90th birthday party. His father berates him over the phone and urges him to quit. When he senses Margaret coming towards him, he makes it seem like he’s speaking with a writer, but she’s onto him and asks if his family told him to quit. He replies, “Everyday.”
Later, she’s called into the office of her bosses who tell her that because she left the country to woo a new writer a few months before, she voided her visa and will be deported shortly. This would mean that she would lose her job, which would be given to the only other editor in the building Bob, who she just fired. At that moment, Andrew interrupts with a phone call from a writer, Margaret tells him to take a message, so he asks if he should say she is otherwise “engaged?” Margaret’s eyes light with an idea. She calls Andrew into the office and announces to her bosses that she and Andrew are getting married. He tries to deny it, but she convinces them otherwise.
After they leave the office, she blackmails Andrew to keep the ruse until she gains her citizenship. He reluctantly agrees and heads over to Immigration with her. At the office, they meet Mr. Gilbertson, who immediately recognizes their situation, and tries to intimidate them into confessing. Andrew seems like he’s going to crack, but decides against it and inturn blackmails her into promoting him. They tell him that they are going to announce their engagement at his grandmother’s party this weekend…in Alaska.
Outside of the office, Andrew demands to be promoted immediately and publish a manuscript he’s been trying to get noticed or he’ll make a deal and confess. She, realizing she needs him, agrees and, upon his request, gets down on her knees and proposes. He teases her for a moment before accepting.
They travel first class for the first part of their journey, then take a smaller, less comfortable plane to Sitka, where Andrew’s from. When they arrive, Andrew’s warmly greeted by his mom Grace (Mary Steenburgen) and Grandma Annie “Gammy” (Betty White). They greet Margaret also, who’s noticeably uncomfortable in her new environment. She’s pretty cold with them, and surprised when she learns that Grace cancelled her hotel reservation, so she could stay with them. She’s shocked to see that Andrew comes from a wealthy family, who own many businesses in town. She gets scared when they climb into a dinghy to head to their house; Maggie, as they call her, can’t swim. When they arrive at the Paxton manse, Maggie questions why Andy didn’t tell her he was rich. He replies that he isn’t, but his family is. Andy is surprised to be greeted by the whole town in a “Welcome Home” party, since he’s been gone about 3 years. Maggie and Andy agree that he’ll decide how and when to announce the engagement, but are interrupted by his father, who belittles Andy in front of everyone. Andy and his father Joe (Craig T. Nelson) are estranged and to defy Joe, Andy announces the engagement immediately. He and Maggie have an awkward moment where they describe his “proposal.” The gist of it is that they dated, she thought he was cheating, but instead was surprised to find him in a tuxedo in a hotel room on a blanket of rose petals and handcut hearts, where he sobbingly proposed. (Very funny scene) The crowd clang glasses until Andy and Maggie kiss, to which they oblige. Afterwards, Maggie is introduced to Andy’s high school/college sweetie Gertrude (Malin Akerman), who still lives and works in Sitka.
That night, Maggie and Andy are shown to their room, a large, beautiful bedroom with a gorgeous view of the nearby lake, where Gammy gives them the “Babymaker,” a quilt known for its magical powers. Maggie tosses it aside, as Grace and Gammy leave them to “rest.” Andy makes his bed on the floor and Maggie sleeps on the bed. Because they’re in Alaska, it’s bright, even at night, so Grace tries to find a comfortable way to sleep. Andy hearing her rustling around, activates remote controlled curtains, which darken the room.
The next morning they are awakened by Maggie’s phone ringing. She answers and moves about the room, searching for a signal. Andy yells at her to leave, so she heads downstairs and out the front door, followed by the family puppy. As she’s talking, she realizes her mistake of leaving the door open, and runs to protect the pup from a hungry eagle. The eagle grabs the dog, but releases him shortly after. Maggie catches the dog and tries to continue her conversation, but the eagle grabs the phone when trying to get the puppy again. Grace and Gammy smile thinking that Maggie is playing with the puppy, when she is in fact trying to entice the eagle into releasing the phone. Andy comes outside and tells Maggie to get dressed because his family wants to bring her somewhere.
Turns out that Maggie’s been taken to a bar, where Ramone, a local and waiter from the party, is also a stripper. Grace puts a veil on Maggie, and forces her to go on stage where she is given a lap dance. She’s visibily uncomfortable and heads outside the second he’s done. Gertrude joins her and explains that Andy proposed before he left for NYC and she rejected him, but is happy he found Maggie. She’s a local, and always knew it, but Andy was meant for other things. He, meanwhile, has been called to join his father, who’s hitting golf balls on the lawn. His father expresses his disappointment with Andy’s choice to turn away the family biz and work in New York. They argue, and Andy refuses to accept his father’s attempted apology.
When Gammy, Grace, and Maggie arrive at the house, they find Andy hacking away at an old canoe. Grace rushes inside to yell at Joe and urges him to accept Andy’s decisions before they never hear from him again. Grace eavesdrops before heading upstairs for a shower. Andy doesn’t realize that they’ve arrived. He’s listening to his mp3 player very loudly, while he undresses on the balcony. Maggie realizes that she forgot to grab a towel. She and Andrew bash into each other as she attempts to grab a towel and he attempts to head to the bathroom. They are both completely naked (hilarious scene; no way they couldn’t be naked!), and shocked to see the other. They run into separate corners trying to cover up, while explaining why the other is naked/wet. Later that evening, Maggie asks what is going on between Joe and Andy, who refuses to answer and instead asks Maggie about a tatoo on her back. She explains that she got it when she was 16, after her parents died in an accident. She also reveals that she’s not as tough as she seems; after Bob yelled at her and called her names, she wept in the bathroom at work. Andy listens attentively before breaking the seriousness with a joke.
The next morning, Maggie frantically tries to awaken Andy before his mother enters the room with breakfast. He jumps into bed and they pretend to snuggle, when Grace comes in with Joe. They announce that they’d like Andy and Maggie to marry the next day in the same barn they were married. Andy and Maggie try to refuse, when Gammy enters and guilts them into agreeing so she could see her only grandchild wed before she dies. (Who’s gonna say no to that?) After they leave, Maggie immediately falls into a domestic role, bringing Andy muffins and coffee in bed. She realizes her enjoyment of this and hurries to dress and leave wile Andy is ignorant to her behavior.
She grabs a bicycle and heads into the forest, where she comes upon Gammy chanting to Mother Earth. Gammy urges Maggie to join her and gets Maggie to begin chanting herself. As she gets into it, Maggie begins singing, bumping and grinding to “Get Low" by Ying Yang Twins, which is witnessed by Andy, who was walking nearby. He informs her that her replacement phone has arrived and is going into town to pick it up. He invites her along and she complies after getting the okay from Gammy to end their chanting. She’s surprised to find Ramone working in the Paxton convenience store. He programmed and charged her phone and toys with her a little before handing it to her. Andy takes her to the internet café to check her email. She has to put dimes into a meter for one-minute of dial-up service. She watches jealously as he talks to Gertrude outside.
Later, Grace and Gammy “kidnap” Maggie and take her to a dress shop, wear she tries on Gammy’s wedding dress. Gammy makes alterations and presents Maggie with a necklace that he mother gave her. Maggie is visibly moved by this and tries to reject the gift, but cannot because of Gammy’s persistance. She hurriedly meets Andy at the marina and speeds off into the lake. Andy tries to find out what’s wrong, while she begins to panic and freak out about their arrangement. She explains that she’s panicked by his loving family and fears that Gammy and the family will be crushed if they ever learn the truth. He tries to calm her and accidently causes her to fall overboard when he takes over the wheel. He rescues her and promises that they’ll be okay.
When they arrive home, his father leads them into the barn, where Mr. Gilbertson, the INS agent, is waiting. He explains that he contacted Mr. Paxton and explained what he believes to be the reason for their hurried engagement. Joe urges Andy to take the deal while it’s available. Andy, realizing what this would mean for Maggie, stands by his word and insists that they’re relationship is valid and they’ll wed tomorrow. Maggie insists that Andy consider his options when they are alone later, but he insists they continue with their plans. Gammy interrupts and drags Andy away to avoid bad luck (the groom can’t see the bride before the wedding).
At the wedding, Maggie is walked down the aisle by Gammy as Andy waits at the altar. They turn to face the minister Ramone (another of his jobs). He begins the ceremony, but is quickly interrupted by Maggie, who confesses. Mr. Gilbertson rejoices in being proven right as Maggie heads out of the barn. Andy is about to follow when he is stopped by his family, who demand he explain. He heads up to the bedroom, but Maggie’s already left. Gertrude arrives and makes him realize that he’s fallen for her. He tries to chase after Maggie, but is stopped by his father, who expresses his disapproval. They argue, but stop when Gammy falls to the ground with a heart attack. They carry her aboard a plane to take her to the hospital. On the plane, she makes them promise to bury the hatchet. They agree, and she gets up and asks the pilot to take them to the airport; she was faking! Aboard another plane, Mr. Gilbertson explains that Maggie has 24 hours to pack and head to Canada. Andy arrives and tries to have an old friend stop the plane, but he’s too late and the plane takes off.
Back in NYC, Maggie begins to pack her office. No one pays her mind or helps as she tries to have her boxes shipped to Canada. Andy arrives out of breath, and begs her to stay. He professes his love and proposes marriage, so he can court her. She tries to hide her feelings, but can’t and accepts. They kiss and are applauded by the entire office.
The credits roll as they, the entire Paxton family and Ramone are interviewed by Mr. Gilbertson.
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