The movie starts off with Andrew Paxton (Ryan Reynolds) snoozing his alarm clock, and jumping out of bed realizing that hes 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 doesnt leave immediately. Once hes gone, she tells Andrew that shes gonna need him this weekend causing him to break plans to attend his grandmothers 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 hes speaking with a writer, but shes onto him and asks if his family told him to quit. He replies, Everyday.

Later, shes 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? Margarets 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 hes 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 grandmothers party this weekendin Alaska.

Outside of the office, Andrew demands to be promoted immediately and publish a manuscript hes been trying to get noticed or hell 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 Andrews from. When they arrive, Andrews warmly greeted by his mom Grace (Mary Steenburgen) and Grandma Annie Gammy (Betty White). They greet Margaret also, whos noticeably uncomfortable in her new environment. Shes pretty cold with them, and surprised when she learns that Grace cancelled her hotel reservation, so she could stay with them. Shes 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, cant swim. When they arrive at the Paxton manse, Maggie questions why Andy didnt tell her he was rich. He replies that he isnt, but his family is. Andy is surprised to be greeted by the whole town in a Welcome Home party, since hes been gone about 3 years. Maggie and Andy agree that hell 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 Andys 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 theyre in Alaska, its 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 Maggies 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 shes 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 Maggies 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. Shes visibily uncomfortable and heads outside the second hes done. Gertrude joins her and explains that Andy proposed before he left for NYC and she rejected him, but is happy he found Maggie. Shes a local, and always knew it, but Andy was meant for other things. He, meanwhile, has been called to join his father, whos hitting golf balls on the lawn. His father expresses his disappointment with Andys choice to turn away the family biz and work in New York. They argue, and Andy refuses to accept his fathers attempted apology.