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, and was box office success, grossing over $317 million worldwide, becoming the highest-grossing romantic comedy film of 2009.
Margaret Tate (Sandra Bullock) is an executive editor in chief of a book publishing company. After learning she is about to be deported to Canada because she violated the terms of her work visa, she persuades her assistant, Andrew Paxton (Ryan Reynolds), to marry her. She reminds Andrew that if she's deported, the work he put in as her assistant will be lost, and he'll be set back in his dream to become an editor. Mr. Gilbertson, a U.S. immigration agent, informs them that he suspects they are committing fraud to avoid Margaret's deportation. Gilbertson tells them that they'll be asked questions about each other separately. If their answers don't match, Margaret will be deported to Canada permanently and Andrew will be convicted of a felony punishable by a $250,000 fine and five years in prison. Andrew insists that Margaret make him an editor after their marriage and publish the book he's been recommending to her. Margaret agrees.
The couple travels to Sitka, Alaska, Andrew's hometown, to meet his family. Margaret meets Andrew's mother Grace (Mary Steenburgen) and grandmother Annie (Betty White), known as "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 (Craig T. Nelson), 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 as part of her bachelorette party 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 heart attack as it was the only means to get their attention. 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.Sandra 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 dominate 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 and minister.
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.
Peter Chiarelli initially wrote the script for the film in 2005. In May 2007, it was announced that Sandra Bullock had been given a lead role for The Proposal. Julia Roberts was originally approached by producers for a lead role in the film, but later declined. Nearly two months after the announcement, it was reported that negotiations were being finalized for Ryan Reynolds to star opposite to Bullock. In January 2008, Touchstone Pictures signed Anne Fletcher to direct the film. It premiered on June 1, 2009 at the El Capitan Theatre in Hollywood, California.
Filming for The Proposal initiated in April 2008 in Rockport, Massachusetts. In the oncoming days leading to production, areas of the town were temporarily remodeled to represent Sitka, Alaska, the setting of most of the film. Principal photography officially began on April 9 at Bearskin Neck, where it continued over a period of 24 hours. Filming continued at the Motif Number One building on Bradley Wharf (April 14–16), the Haskins Building (April 15–18), and the central business district of Rockport (April 17). Principal photography relocated to Manchester-by-the-Sea, Massachusetts on April 22, where it resumed over an approximate period of two weeks. In response, city officials accommodated the producers by renting out all publicly owned parking lots. Filming for The Proposal was shortly delayed after Bullock and her husband were involved in a car accident. The wedding scene was filmed in a three-story twentieth century Victorian home; photography took place at the residence for three weeks. In an interview with the New York Times, the owners of the home stated that Nelson Coates knocked on their door asking for leaves. Initially, the owners directed Coates to other residences in the area; however, they eventually gave the film's producer a tour of the house. Production occurred on the first floor of the home. Outside of the Cape Ann area, filming took place in Boston, Massachusetts at the State Street Bank Building and in Lower Manhattan in New York City. The Proposal contained 350 special effect shots, and some parts were edited using computer-generated imagery. The score to The Proposal was composed by Aaron Zigman, who recorded his score with the Hollywood Studio Symphony at the Sony Scoring Stage.
As part of an extensive advertising campaign, Reynolds discussed taking part in the production of a nude scene. The scene was filmed in a period of three days, and took approximately twelve takes to complete. Expressing that she was initially nervous, Bullock stated in an interview with Sky News that "when everyone else acts like it's just a normal day it really helps you relax." Although she revealed that producers provided them with fig leaves, Bullock stated that they would continuously fall off. She added, "You could literally see everything." Similar sentiments were expressed by Reynolds, who in an interview with People, stated, "Filming a scene that involves being entirely naked and takes a couple days can be a little awkward." He continued: "Thankfully you're there for so long and you're doing it for so long that you dispense with the awkwardness pretty quickly and start to have mundane, normal conversations – the difference being you're not wearing pants."
The Proposal was released in the United States on June 19, 2009. On its opening day, the film grossed an estimated $12.7 million in 3,056 theaters, becoming the highest-grossing film of the day. It later went on to gross over $34 million during its opening weekend, beating out Year One, Up, and The Hangover. In an exit poll conducted by Disney, nearly 63% of the opening audience consisted of female viewers, 78% were eighteen or older, and 71% were classified as couples. It marked the biggest opening weekend out of any film in Bullock's career, nearly doubling from her previous holder, Premonition. As of October 2011, the film had grossed over $164 million in the United States and Canada.
Box office performances showed similar numbers in international markets. The film was released in Australia on June 18, 2009, grossing over $2.8 million on its opening weekend. In Russia, the film grossed over $2.6 million on its opening weekend, accounting for 34% of all total film revenue in that country. In South Africa the film debuted at number two, losing out to the new release Ice Age: Dawn of the Dinosaurs. It managed to gross over $2.6 million as of October 2011. In the United Kingdom, estimated first opening weekend grosses stand at £3.2 million. The film has grossed over $317 million worldwide, with international grosses standing at $153 million. It is the twentieth highest-grossing film of 2009.
On the review aggregator website Rotten Tomatoes, the film has an approval rating of 44% based on 182 reviews, with an average rating of 5.3/10. The site's critical consensus reads: "Sandra Bullock and Ryan Reynolds exhibit plenty of chemistry, but they're let down by The Proposal's devotion to formula." On Metacritic, which assigns a weighted average rating, the film has a score of 48 out of 100, based on 30 critics from critics, indicating "mixed or average reviews". Audiences polled by CinemaScore gave the film an average grade of "A–" on an A+ to F scale.
Roger Ebert of the Chicago Sun-Times gave a mixed review, giving the film three out of four stars despite complaining that the film "recycles a plot that was already old when Tracy and Hepburn were trying it out". Peter Travers of Rolling Stone was very critical of the film, calling it insipid. He wrote, "Anne Fletcher directs Peter Chiarelli's script like a manufacturer of hard plastic that is guaranteed to ward off intrusion from all recognizable human emotion." New York Times writer Manohla Dargis felt that Bullock's character was awkward in comparison to her previous work. She continued: "She’s always been better in fundamentally independent roles that allow her to grab the wheel [...] and take the spotlight [...], an independence that persists all the way through the last-act coupling. She can smile as brightly at a man as well as the next leading lady, though, like all genuinely big female stars, she’s really more of a solo act." The Telegraph's Tim Robey expressed disappointment towards the film, giving it a two out of five stars.
The interaction between Reynolds and Bullock was well received by critics. Lisa Schwarzbaum of Entertainment Weekly opined that the chemistry between the two actors was "fresh and irresistible." Zorianna Kit of The Huffington Post exclaimed that "what [kept] audiences of this lite-fare comedy in their seats is the undeniable on-screen chemistry between leads Sandra Bullock and Ryan Reynolds." She continued: "The two are so adept at comedy and have so much fun with one another, viewers watching The Proposal won't be able to resist their charms, even when some of the plot veers in to unnecessarily silliness." Betsey Sharkley of the Los Angeles Times felt that their relationship was a "cheeky update of The Taming of the Shrew." She opined, "Bullock's deft physical comedy, one of her most endearing qualities, is given a full run. [...] Reynolds' ability to deliver a line, or a look, with withering, surgical precision is there at every turn." Giving it a one out of five stars, The Guardian writer Peter Bradshaw gave a negative reaction to the interaction between Reynolds and Bullock. Bradshaw stated: "Their initial sparky detestation isn't convincing, and neither is their later thawing and romance. In each scene, it looks as if they have never met before. And Margaret isn't permitted to be a convincing cow, because that would make her unsympathetic [...]. Andrew can't be a total wimp, because that would be unsexy, so the fundamental comic premises of the film are fudged."
The Proposal was released by Touchstone Home Entertainment on DVD and Blu-ray on October 13, 2009. It sold over 2.4 million units within its first week, translating to an addition of $39.3 million in the box office. In its second week, sales numbers declined by 70% to 623,744 units, ranking second among DVD sales of the week. By July 2013, The Proposal had sold over 5.6 million units and earned over $90 million in sales.
The 2012 Malayalam-language Indian film My Boss is a remake of The Proposal. Set in Mumbai and Kerala, the remade version has many differences from the original although the basic storyline remains the same. Popular actors Dileep and Mamta Mohandas played the lead roles in this version. The remake was also a hit.
A Chinese remake co-produced by Walt Disney Pictures and Linmon Pictures and directed by Yee Chin-yen was announced in June 2016.