Summary

• The Proposal, a timeless rom-com, blends enemies-to-lovers & fake-dating tropes, offering a believable & engaging romance.
• Like The Proposal, 27 Dresses features personal sacrifice and romantic misunderstandings within wedding preparations.
• Two Weeks Notice, akin to The Proposal, explores workplace romance with witty banter & unexpected love blossoming.

The Proposal is one of the timeless romantic comedies of the 2000s, and there are many other movies like The Proposal for fans of the romcoms. Released in 2009, the movie follows the story of Margaret Tate, a high-powered book editor who must fake an engagement with her assistant, Andrew Paxton, to avoid deportation to Canada. As they head to Alaska to visit Andrew's family, the duo's initially contentious relationship starts to soften, unfolding into a series of comedic and romantic misadventures. The Proposal masterfully combines two beloved rom-com tropes: the enemies-to-lovers narrative and the fake-dating/marriage storyline.

What makes The Proposal particularly endearing to fans is its ability to balance witty dialogue with situational comedy, all while building a believable romance. The film's success lies in its universal appeal—viewers enjoy watching the evolution of Margaret and Andrew's relationship from professional and strained to intimate and cooperative. This transition, powered by engaging performances and a well-crafted script, ensures the movie's place as a favorite among rom-com enthusiasts. Thanks to the tried-and-true tropes, there are many other movies like The Proposal for fans to seek out.

20 27 Dresses (2008)

Another Rom-Com Hit From The Proposal Director Anne Fletcher

27 Dresses centers on Jane, a perpetual bridesmaid whose love life is non-existent. She faces her biggest challenge when her sister announces her engagement to Jane's boss, whom she secretly loves. Similar to The Proposal, this film thrives on the themes of personal sacrifice and romantic misunderstandings within the context of wedding preparations. 27 Dresses shines with its mix of humor and heartache as Jane navigates her complex relationships and learns to put her own happiness first. Its blend of comedic scenarios and emotional depth make it a compelling watch for fans of The Proposal and character-driven rom-coms.

19 The Wedding Planner (2001)

Mary Finds Herself In A Complicated Workplace Romance

The Wedding Planner stars Jennifer Lopez as Mary, a successful wedding planner whose meticulous life is thrown into disarray when she falls for a charming doctor, only to discover he is the groom in the most important wedding of her career. Echoing The Proposal, the film explores the complications of workplace romance and unexpected love under professional circumstances. The Wedding Planner excels with its engaging mix of romance and comedy, showcasing the chaos and charm of love that collides with career aspirations, making it a delightful pick for those who enjoy a well-crafted rom-com with a twist.

18 Just Friends (2005)

Another Classic Ryan Reynolds Romantic Comedy

Just Friends features Ryan Reynolds as Chris, a formerly overweight and unpopular teen who returns to his hometown as a successful music executive. He attempts to win over his high school crush, Jamie, but finds that old habits die hard. Similar to The Proposal, the movie utilizes a comedic approach to unrequited love and the transformation of personal relationships over time. Just Friends combines slapstick humor with touching moments of self-realization, making it a riotously funny yet heartfelt journey through past and present affections. The movie features one of Ryan Reynolds' best roles and good laughs intertwined with romantic nostalgia.

Just Friends is available to rent on Amazon Prime Video, Apple TV, YouTube, and Google Play.

17 Sweet Home Alabama (2002)

New York-Based Career-Focused Melanie Confronts Her Past

Sweet Home Alabama stars Reese Witherspoon as Melanie, a New York fashion designer who must confront her past in the Alabama countryside. She returns home to finalize a divorce from her childhood sweetheart before she can marry her upscale New York fiancé. Echoing The Proposal, this film navigates themes of identity, love, and belonging, blending Southern charm with city sophistication. Sweet Home Alabama offers a heartwarming exploration of rediscovering roots and rekindling old flames, delivered with humor and warmth. Sweet Home Alabama is perfectly cast and full of self-discovery and second chances.

Watch on Fubo

16 How To Lose A Guy In 10 Days (2003)

Ben & Andie's Relationship Is Built Entirely On Deceit

How to Lose a Guy in 10 Days features Andie (Kate Hudson), a magazine writer who takes on a challenge to make a man break up with her within 10 days for an article she's writing. Unbeknownst to her, the man, Ben (Matthew McConaughey), has his own bet to make a woman fall in love with him in the same timeframe. Similar to The Proposal, the film revels in the humor and complications of a relationship based on deceit. The 2003 release excels with its dynamic lead performances and engaging plot, making it a quintessential rom-com.

Watch on AppleTV+

15 The Ugly Truth (2009)

TV Producer Abby & Celebrity Mike Have A Battle-Of-The-Sexes Relationship

The Ugly Truth is about Abby, a romantically challenged morning show producer whose views on love are challenged by her chauvinistic correspondent, Mike. Tasked with helping Abby attract her neighbor, their professional relationship takes a turn as they begin to influence each other's love lives. Much like The Proposal, the movie explores the enemies-to-lovers trope through a battle of the sexes, combining risqué humor and romantic developments. The Ugly Truth thrives on its sharp wit, making it a hit for those who enjoy a rom-com with a modern, edgy twist.

Watch on TBS

14 Leap Year (2010)

Anna Falls For An Irish Innkeeper After Initially Locking Horns

Leap Year follows Anna, a woman who travels to Ireland to propose to her boyfriend on Leap Day, an Irish tradition where women propose to men. However, her plans get derailed by a series of misadventures and the surly yet charming local innkeeper Declan. Like The Proposal, the film sees Declan and Anna lock horns until they inevitably fall for each other, set against the backdrop of a picturesque journey and blending cultural quirks with romantic mishaps. Leap Year captivates with its beautiful Irish settings and evolving, playful chemistry, making it one of the most heartwarming romantic comedies.

Watch on AppleTV+

13 Two Weeks Notice (2002)

Another Sandra Bullock Work-Based Romantic Comedy

Two Weeks Notice is another Sandra Bullock romantic comedy, as she plays Lucy, an idealistic lawyer who ends up working for George (Hugh Grant), a charming but self-centered billionaire. As Lucy becomes frustrated with George's lack of consideration and ethics, she resigns, prompting both to realize their true feelings. Similar to The Proposal, this film revolves around a workplace romance where initial antagonism and professional demands lead to unexpected romantic developments. Two Weeks Notice shines with witty banter and the charismatic performances of the bankable stars, making it a delightful rom-com about finding love in the least-expected places.

Two Weeks Notice is available to rent on Apple TV, Amazon Prime Video, YouTube, and Google Play.

12 Just Go With It (2011)

Danny & Katherine Pose As A Married Couple Only To Fall In Love

Just Go With It stars Adam Sandler as Danny, a plastic surgeon who enlists his office manager, Katherine (Jennifer Aniston), to pose as his soon-to-be-divorced wife to cover up a careless lie he told his much younger girlfriend. This leads to a series of comedic and unexpectedly romantic adventures in Hawaii. Echoing The Proposal, the first collaboration between Aniston and Sandler uses the fake-relationship trope to comedic effect, as pretense gradually morphs into genuine affection. Just Go With It combines picturesque settings with a blend of slapstick and heartfelt moments, making it one of the best 2010s romcoms.

11 You’ve Got Mail (1998)

Joe & Kathleen Fall For Each Other Online But Hate Each Other In Real Life

You've Got Mail stars Tom Hanks and Meg Ryan as Joe and Kathleen, rival bookstore owners who unknowingly fall in love over the internet while despising each other in real life. This classic rom-com masterfully uses the enemies-to-lovers trope, blending it with the then-emerging world of online dating. Similar to The Proposal, it explores how two seemingly incompatible individuals can find common ground and romance amidst ongoing conflicts. You've Got Mail stands out for its charming leads, witty dialogue, and how it captures the romantic zeitgeist of the late '90s, making it a beloved staple for rom-com enthusiasts.

Watch on Netflix

10 Red, White, & Royal Blue (2023)

Alex Claremont-Diaz & Prince Henry Are International Rivals

Red, White, & Royal Blue adapts the novel where Alex Claremont-Diaz, the First Son of the United States, and Prince Henry of Wales start as international rivals forced into a staged friendship to smooth over a diplomatic incident. Echoing The Proposal, this setup blossoms into an intense romantic relationship, navigating the complexities of their public roles and personal desires. With its high-stakes political backdrop, the movie blends humor, heartfelt moments, and the thrill of a forbidden romance. Red, White & Royal Blue captivates with its banter and the poignant exploration of identity and duty.

9 The Accidental Husband (2008)

Emma Is Engaged To A Man She's Never Met Due To An Ex-Lover's Revenge Plot

The Accidental Husband follows Emma, a successful radio talk show host and relationship expert whose plans for a perfect wedding are disrupted when she finds out she's already married to a man she's never met. This mishap results from a revenge plot hatched by a jilted lover. Like The Proposal, the film plays with the theme of unintended relationships leading to genuine affection, employing the fake marriage trope with a comedic twist. The Accidental Husband glows with its blend of humorous misunderstandings and romantic entanglements, offering a lively and engaging take on the chaos that love can bring.

Watch on Fubo

8 Green Card (1990)

Brontë Marries A Frenchman So He Can Get A U.S. Visa

Green Card follows a Frenchman who enters into a marriage of convenience with Brontë, an American horticulturist, so that he can stay in the U.S. Initially, their relationship is purely pragmatic and filled with mutual irritation, but as they continue to feign marriage, they slowly start uncovering each other's true selves, leading to unexpected feelings. Much like The Proposal, Green Card thrives on the fake marriage trope, providing comedic situations and romantic developments as the couple navigates their complex arrangement. The film blends is a delightful exploration of how love can grow from the most convenient of arrangements.

Green Card is available to rent on Apple TV, Amazon Prime Video, YouTube, and Google Play.

7 Happiest Season (2020)

Abby & Harper Are Thrown Into Awkward Situations At Family Events

Happiest Season is a holiday romantic comedy that captures the challenges and warmth of coming out to one's family during Christmas. Abby plans to propose to her girlfriend, Harper, during her family's annual holiday party. Still, Abby learns that Harper has not yet come out to her conservative parents, leading to a series of comedic misunderstandings and tension-filled scenarios. Echoing The Proposal, the film uses the themes of hidden truths and forced pretenses in a family setting while blending humor with serious emotional undertones. Additionally, Happiest Season stands out for its LGBTQ+ relationships with depth and authenticity.

6 Something New (2006)

Kenya Is Reluctant To Get Serious With Brian Because Of Her Personal Boundaries

Something New follows a successful Black career woman who struggles with her desire for a "perfect" Black partner until she meets Brian, a White landscape architect. Initially, Kenya hesitates due to their racial and cultural differences, leading to a tumultuous start. Similar to The Proposal, the movie explores the challenges of embracing unexpected love and breaking personal boundaries, all within a context that tests societal norms and personal expectations. Something New excels in its nuanced approach to interracial romance, delivering a blend of heartfelt romance and social commentary, making it a compelling and insightful romantic comedy.

Something New is available to stream on Starz through Apple TV.

5 Two Can Play That Game (2001)

Shante Uses Mindgame To Keep Her Boyfriend In Check

Two Can Play That Game follows Shante Smith, a successful career woman who prides herself on her ability to manipulate her relationships to keep her man in check. When her boyfriend strays, Shante launches a ten-day plan to get him back under her control. Much like The Proposal, the film delves into the dynamics of power and control within relationships but with a comedic twist. Two Can Play That Game cleverly uses mind games and battle-of-the-sexes humor to explore romantic entanglements, making it an engaging and witty rom-com that offers a fresh take on dating strategies and love.

Two Can Play That Game is available to rent on Apple TV, Amazon Prime Video, YouTube, and Google Play.

4 The Lovebirds (2020)

Jibran & Leilani Resolve Their Relationship While Solving A Murder Mystery

The Lovebirds is about a couple on the brink of breaking up who inadvertently become embroiled in a bizarre murder mystery. As they work together to clear their names, they encounter one ridiculous obstacle after another, forcing them to address the issues in their relationship. Like The Proposal, the movie combines high-stakes scenarios with comedic elements and explores how extreme circumstances can bring a couple closer together. The Lovebirds excels in its fast-paced humor, making it a unique blend of rom-com and action-packed adventure, with a refreshing take on love and partnership under pressure.

3 The Hating Game (2021)

Lucy & Joshua's Professional Rivalry Turns Romantic