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Bullock and Reynolds, who starred as unlikely love interests named Margaret and Andrew, were already established stars when they appeared in the movie. The film also included legendary actress Betty White and "The Office" star Oscar Nuñez.
Here's what the cast has been up to since the movie was released 11 years ago.
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Sandra Bullock starred as Margaret Tate, the editor-in-chief at a book publishing company in New York.
Sandra Bullock in "The Proposal."
Touchstone Pictures
Bullock executive produced and starred in Netflix's 2018 thriller "Bird Box."
Sandra Bullock in January 2020.
Chris Pizzello/AP
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Ryan Reynolds portrayed Andrew Paxton, Margaret's assistant who was blackmailed into marrying her so she could stay in the US.
Ryan Reynolds in "The Proposal."
Touchstone Pictures
In recent years, Reynolds has portrayed Marvel antihero Deadpool.
Ryan Reynolds in December 2019.
(Photo by Charles Sykes/Invision/AP
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Betty White was a scene-stealer as Andrew's grandmother named Annie.
Betty White in "The Proposal."
Touchstone Pictures
After "The Proposal," White starred on her own show called "Hot in Cleveland."
Betty White in September 2018.
ROBYN BECK/AFP via Getty Images
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Mary Steenburgen portrayed Grace Paxton, Andrew's mom.
Mary Steenburgen in "The Proposal."
Touchstone Pictures
Steenburgen stars as Maggie on NBC's musical series "Zoey's Extraordinary Playlist."
Mary Steenburgen in September 2019.
(Photo by Vince Bucci/Invision for the Television Academy/AP
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Craig T. Nelson starred as Joe Paxton, Andrew's dad.
Craig T. Nelson in "The Proposal."
Touchstone Pictures
Nelson stars as Dale Ballard on "Young Sheldon," a spin-off prequel to the hit show "The Big Bang Theory."
Craig T. Nelson in June 2018.
(Photo by Jordan Strauss/Invision/AP
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Malin Akerman played Gertrude, Andrew's ex-girlfriend.
Malin Akerman in "The Proposal."
Touchstone Pictures
Akerman more recently starred on shows like Showtime's "Billions" and Hulu's "Dollface."
Malin Akerman in November 2019.
Mark Von Holden /Invision/AP
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Oscar Nuñez's Ramone had a job as an exotic dancer, among other gigs, in Sitka.
Oscar Nunez in "The Proposal."
Touchstone Pictures
Nuñez is known for his role as Oscar Martinez on NBC's hit show "The Office."
Oscar Nuñez nez in July 2019.
Paul Archuleta/Getty Images
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Denis O'Hare played an immigration investigator named Mr. Gilbertson.
Denis O'Hare in "The Proposal."
Touchstone Pictures
O'Hare appeared as Ira Farber on season two of HBO's "Big Little Lies."
Denis O'Hare in September 2019.
George Pimentel/Getty Images for TIFF