The-Proposal, Sandra Bullock, Ryan Reynolds, Betty White

10 Best Movies Like ‘The Proposal’

2009’s rom-com The Proposal brought two fantastically sarcastic and funny actors together in the form of Sandra Bullock and Ryan Reynolds. These two work wonderfully together in this madcap comedy that sees the two get on smashingly—literally!

Recommended Videos

So, if you are looking for more films like The Proposal, here’s out recommendations. Rom-com is the genre that keeps on giving, and this one certainly gave. Enemies to lovers? Check. A convoluted reason they have to spend time together? Check. Fake engagement? Check. Raunchy Betty White? Check and check. Bullock plays the high-powered Margaret Tate, editor-in-chief of a New York book publishing company who is feared by all her staff; think Miranda Priestly with a long silky ponytail. If Bullock is Miranda Priestly, then that would make Reynolds the suffering personal assistant Andrea, though in this case, he’s called Andrew Paxton.

When Margaret discovers that she could be deported to Canada thanks to a visa violation, she comes up with a solution on the spot: She’s engaged, to Andrew. Andrew is forced along for the sake of his job, but he goes along with it on the terms that he gets promoted, and that she allows him to visit his family, a trip that she must also accompany him on. Through their lies and getting to know one another out of the office, the two, of course, fall in love and decide to get married for real to keep Margaret in New York. Ah, love. It is fickle. It is odd. Here are some other odd and wonderful films you may also enjoy if you love The Proposal.

1. 10 Things I Hate About You

Image of Heath Ledger as Patrick and Julia Stiles as Kat in a scene from '10 Things I Hate About You.' They are both white teenagers sitting on steps staring into each others' eyes. Patrick has wavy, chin-length brown hair and is wearing a black tank top. His hair's pulled back into a short pony tail and there is green paint in his hairline. Kat has wavy blonde hair pulled up into a ponytail, and has various colors of paint in her hair. She's wearing a red shirt.
(Buena Vista Pictures Distribution)

This retelling of the Shakespearian play The Taming of the Shrew became an instant genre classic and is much loved in the rom-com community. With an all-star cast including Heath Ledger, Julia Stiles, and Joseph Gordon-Levitt, this film features deception, betrayal, and the softening of a strong woman’s heart as she learns to love (this is such a trope), all set against the backdrop of Padua High School. Don’t miss out on this film if you want to see Ledger as a leather-wearing bad boy who bursts into “Can’t Take My Eyes Off of You” over the school speaker system whilst avoiding being caught by school security; it’s a must see.

2. Wedding Season

Wedding Season poster: Suraj Sharma, Pallavi Sharda
(Netflix)

A more recent “let’s pretend we’re an item” rom-com comes in the form of 2022’s Wedding Season. Rather than pretending to be there to keep immigration off their backs, economist Asha and DJ Ravi pretend to be an item to keep their family, and all the gossiping aunties off their backs during the wedding season. On top of the usual humor, it also takes a look at the pressures of growing up in an immigrant family that values marriage above all else. It stars Suraj Sharma (Life of Pi) and Pallavi Sharda (Lion) who do have very sweet chemistry together.

3. Definitely, Maybe

Ryan Reynolds and Abigail Breslin, Definitely, Maybe
(Universal Pictures)

If more Reynolds in rom-coms is what you want, then Definitely, Maybe is definitely what you want. Set up a little bit like How I Met Your Mother, Reynolds’ character Will Hayes is spending some time with his daughter, Maya (Abigail Breslin), who demands to know the story of how he met her mom, who he is currently divorcing. The film works through flashbacks, looking at three different women Will dated (though he changes their names): April Hoffman (Isla Fisher), Summer Hartley (Rachel Weisz), and Emily Jones (Elizabeth Banks). It looks at the reasons the relationships fell apart, but Maya deduces that not all is lost, guessing that her father still harbors feelings for one of the three women.

4. Crazy Rich Asians

Michelle Yeoh, from left, Henry Golding and Constance Wu appear in a scene from the film Crazy Rich Asians
(Warner Bros. Pictures)

One of the most successful rom-com films of the last decade comes in the form of Crazy Rich Asians. Much like how Margaret has to meet Andrew’s parents in Alaska, so too does Rachel Chu (Constance Wu) have to visit her boyfriend, Nick Young’s (Henry Golding) parents only this time in Singapore. If Andrew’s parents owned most of the town, Nick’s parents own most of Singapore and are the wealthiest family in the country, which puts Rachel in a very odd and uncomfortable situation. To be with Nick, Rachel must first overcome the fierce dragon mother Eleanor (Michelle Yeoh).

5. Miss Congeniality

Sandra Bullock and William Shatner in 'Miss Congeniality'
(Warner Bros. Pictures)

If you think of Sandra Bullock, it’s hard not to think about one of her most iconic films of all time: Miss Congeniality. Bullock’s comedic talent shines through in this film where she plays FBI special agent Gracie Hart, who has to go undercover at the Miss United States beauty pageant to foil a terrorist plot. Though not necessarily a rom-com, more a comedy with a romantic element, there are similarities between her character here and in The Proposal. Gracie is initially work-obsessed and takes herself too seriously, but through the charade of playing Gracie Lou Freebush, she discovers that there’s more to life than just work. Shoutout to the great performances of Michael Kane and William Shatner here, too.

6. Anyone But You

Glen Powell and Sydney Sweeney staring at each other lovingly
(Sony Pictures)

The most recent one on our list has to be Anyone But You starring Glenn Powell and Sydney Sweeney. Much like 10 Things I Hate About You, this film is based on a Shakespeare story; this time, it’s Much Ado About Nothing. Having spent a night together, Bea (Sweeney) overhears Ben (Powell) essentially talking trash about her. The two meet again six months later, and things are, well, bitterly cold. During a wedding, the two pretend to be together to get people off their backs (Of course they do! They can’t just be civil!) which results in confused and hurt feelings. Hmmm, I wonder how this will end?

7. Two Weeks Notice

Two Weeks Notice, Sandra Bullock and Hugh Grant
(Warner Bros. Pictures)

And we are right back with Bullock in Two Weeks Notice, a 2002 rom-com where she starred opposite Mr. Rom-Com himself (at that time) Hugh Grant. Much like with The Proposal, this is another enemies-to-lovers situation—or rather enemies, to boss and employee, to lovers. Here, Bullock plays intelligent liberal lawyer Lucy Kelson, who is determined to preserve the Coney Island Community Center, which is set to be bought and destroyed by wealthy playboy, George Wade (Grant). When he offers her a job, stating he will protect the center, Lucy takes it but soon realizes that she has become almost a glorified babysitter. Somehow, she still develops feelings for him, and so the drama ensues.

8. Sweet Home Alabama

josh-lucas-reese-witherspoon, Sweet Home Alabama
(Touchstone Pictures)

The classic “girl goes back to her hometown to see what she has been missing” film is, of course, Sweet Home Alabama. Reese Witherspoon plays Melanie Carmichael (formerly Smooter), who is a prominent fashion designer set to marry the wealthy Andrew Hennings. All she needs to do is go home, announce the engagement, and oh yeah, get a divorce from her former sweetheart Jake. Leaving the big city and returning to her Southern roots proves a little more challenging than she first thought, leaving her with more problems than answers. Much like in The Proposal, Melanie’s trip has her questioning what she really wants out of life.

9. How To Lose a Guy in 10 Days

Kate Hudson and Matthew McConaughey on the movie poster for 'How to Lose a Guy in 10 Days.'
(Paramount Pictures)

Starring Kate Hudson and Matthew McConaughey in their rom-com prime, How To Lose a Guy in 10 Days is one of the classics of the ’00s. Released in 2003, writer Andie Anderson (Hudson) states that she can write an article about how women, like her friend (hello Kathyrn Hahn), keep pushing guys away. She states she can get a man, make him like her, and then repel him in 10 days. Advertising executive Benjamin Barry (McConaughey) also makes a similar deal with his boss, only he bets he can get a girl to fall in love with him in 10 days. Cue emotional manipulation, psychological torture, and a gradual falling in love once Andie meets the family, all to come to head in a messy screaming match. Guys, love doesn’t need to be this hard in real life, but man it’s fun to watch.

10. Green Card

1990, Green Card starring Gérard Depardieu and Andie MacDowell
(Touchstone Pictures)

Probably the closest, in regards to the plot of The Proposal, is the 1990 film Green Card. In order to get the apartment of her dreams, Brontë Parrish (Andie MacDowell) must be married. To stay in the country, Georges Fauré (Gérard Depardieu) needs a Green Card marriage. What to do, what to do? The pair marry but live apart, but when immigration gets suspicious, Brontë invites Georges to move in with her. Cue a lot of pretending shenanigans, lying to friends and family, and obviously, getting to know one another on a deeper level that inevitably ends in love.

Aside from the fact that, in reality, starting a relationship with a lie is usually not a good sign, it’s incredibly fun to watch onscreen. Do you have a favorite film featuring this trope that we didn’t mention? Let us know!

(featured image: Touchstone Pictures)


The Mary Sue is supported by our audience. When you purchase through links on our site, we may earn a small affiliate commission. Learn more
related content
Read Article Cannes Standout ‘All We Imagine as Light’ Symbolizes an Independent Filmmaker’s Win Against All Odds
A still from 'All We Imagine as Light'
A still from 'All We Imagine as Light'
A still from 'All We Imagine as Light'
Read Article James Blunt Offers New Insight on Weight Loss Pressure Carrie Fisher Felt for ‘Star Wars’
Carrie Fisher as Leia Organa in Star Wars: The Force Awakens
Carrie Fisher as Leia Organa in Star Wars: The Force Awakens
Carrie Fisher as Leia Organa in Star Wars: The Force Awakens
Read Article Nicholas Galitzine Confirmed as the New He-Man as ‘Masters of the Universe’ Crawls Out of Development Hell
Nicholas Galitzine with a blonde bob haircut sloppily photoshopped atop his head
Nicholas Galitzine with a blonde bob haircut sloppily photoshopped atop his head
Nicholas Galitzine with a blonde bob haircut sloppily photoshopped atop his head
Read Article Glen Powell’s Take on an Iconic Killer in ‘Hit Man’ Is Perfection
glen powell sitting at a table dressed like patrick bateman
glen powell sitting at a table dressed like patrick bateman
glen powell sitting at a table dressed like patrick bateman
Read Article Ryan Gosling Is Returning to Space
Ryan Gosling in 'First Man'
Ryan Gosling in 'First Man'
Ryan Gosling in 'First Man'
Related Content
Read Article Cannes Standout ‘All We Imagine as Light’ Symbolizes an Independent Filmmaker’s Win Against All Odds
A still from 'All We Imagine as Light'
Read Article James Blunt Offers New Insight on Weight Loss Pressure Carrie Fisher Felt for ‘Star Wars’
Carrie Fisher as Leia Organa in Star Wars: The Force Awakens
Read Article Nicholas Galitzine Confirmed as the New He-Man as ‘Masters of the Universe’ Crawls Out of Development Hell
Nicholas Galitzine with a blonde bob haircut sloppily photoshopped atop his head
Read Article Glen Powell’s Take on an Iconic Killer in ‘Hit Man’ Is Perfection
glen powell sitting at a table dressed like patrick bateman
Read Article Ryan Gosling Is Returning to Space
Ryan Gosling in 'First Man'
Author
Laura Pollacco
Laura Pollacco (she/her) is a contributing writer here at The Mary Sue, having written for digital media since 2022 and has a keen interest in all things Marvel, Lord of the Rings, and anime. She has worked for various publications including We Got This Covered, but much of her work can be found gracing the pages of print and online publications in Japan, where she resides. Outside of writing she treads the boards as an actor, is a portrait and documentary photographer, and takes the little free time left to explore Japan.