15 Movies Like How To Lose A Guy In 10 Days: Hilarious Rom-Coms You Can’t Miss

15 Movies Like How To Lose A Guy In 10 Days: Hilarious Rom-Coms You Can't Miss

If you loved How to Lose a Guy in 10 Days, you’re in for a treat. This rom-com classic, starring Kate Hudson and Matthew McConaughey, delivers a perfect mix of humor, romance, and heart, making it one of the most beloved romantic comedies of all time. The film’s witty premise—where a woman tries to drive her boyfriend away within 10 days while he tries to make her fall in love with him—has inspired countless fans to search for more films in the same genre. In this article, we explore movies like How to Lose a Guy in 10 Days, each offering its own twist on love, relationships, and the unpredictable chaos that often accompanies them. Whether you’re looking for lighthearted comedy or charming chemistry between the leads, these films will have you laughing, crying, and maybe even swooning.


1. The Proposal (2009)

Starring Sandra Bullock and Ryan Reynolds, The Proposal tells the story of a high-powered book editor, Margaret Tate, who forces her assistant, Andrew Paxton, into a fake marriage to avoid being deported to Canada. As they prepare for their wedding, they must travel to Andrew’s hometown, where sparks fly and unexpected feelings emerge. The chemistry between Bullock and Reynolds drives the film, with plenty of laughs and heartfelt moments.

Why it’s similar to How to Lose a Guy in 10 Days: Like How to Lose a Guy in 10 Days, The Proposal centers around an unlikely romance, where two people initially fake a relationship, only to discover real feelings along the way. Both films use humor to navigate misunderstandings, unexpected chemistry, and romantic growth.


2. 13 Going on 30 (2004)

In 13 Going on 30, Jenna Rink (Jennifer Garner) is a 13-year-old girl who magically wakes up 30 years old. As she tries to navigate her adult life, she discovers that her choices in her teenage years have shaped her future in unexpected ways. Alongside her best friend, Matt (Mark Ruffalo), Jenna must figure out what really matters in life, love, and friendship.

Why it’s similar to How to Lose a Guy in 10 Days: While not a traditional rom-com, 13 Going on 30 deals with the themes of self-discovery, love, and the humorous complications of romance. Both films blend humor with heartfelt moments as characters navigate love and personal growth.


3. Notting Hill (1999)

This iconic rom-com stars Julia Roberts as Anna Scott, a famous actress who falls in love with William Thacker (Hugh Grant), a humble bookstore owner in London. Their relationship is tested by their different worlds, with Anna’s fame creating plenty of comedic and dramatic challenges. Filled with witty dialogue and memorable moments, Notting Hill is a timeless romantic comedy.

Why it’s similar to How to Lose a Guy in 10 Days: Like How to Lose a Guy in 10 Days, Notting Hill explores the theme of an unlikely romance that faces challenges from external pressures. The chemistry between the leads, combined with the quirky humor, makes this film a standout in the rom-com genre.


4. Crazy, Stupid, Love (2011)

In Crazy, Stupid, Love, Cal Weaver (Steve Carell) navigates the challenges of dating after his wife, Emily (Julianne Moore), asks for a divorce. With the help of the charming playboy Jacob (Ryan Gosling), Cal embarks on a series of humorous adventures to rediscover his own romantic confidence. The film weaves together multiple love stories with plenty of laughs and heartwarming moments.

Why it’s similar to How to Lose a Guy in 10 Days: Both films feature romantic misadventures, humorous dating scenarios, and characters who must navigate the tricky waters of love, relationships, and personal growth. Crazy, Stupid, Love adds a little more complexity with intertwining relationships, but it delivers the same mix of humor and romance.


5. The Wedding Planner (2001)

Jennifer Lopez stars in this rom-com as Mary Fiore, a successful wedding planner who finds herself falling in love with the groom of one of her clients, Steve Edison (Matthew McConaughey). As their romantic relationship develops, Mary must navigate the complications of her professional life and personal feelings, leading to a series of comedic and heartfelt moments.

Why it’s similar to How to Lose a Guy in 10 Days: The shared chemistry between the lead characters, combined with a plot that centers around a complicated romance, makes The Wedding Planner a great match for fans of How to Lose a Guy in 10 Days. Both films feature the charming McConaughey in a romance with a strong-willed woman.


6. Legally Blonde (2001)

Elle Woods (Reese Witherspoon), a fashion-loving sorority girl, follows her ex-boyfriend to law school in a quest to win him back. However, she soon discovers that she’s more than capable of excelling on her own, defying stereotypes and proving her worth. With plenty of humor and inspiring moments, Legally Blonde became a beloved classic.

Why it’s similar to How to Lose a Guy in 10 Days: Both films feature strong-willed women who undergo personal transformations and ultimately learn important lessons about love, relationships, and self-worth. Legally Blonde mixes humor with empowerment, much like the charm of How to Lose a Guy in 10 Days.


7. The Holiday (2006)

In The Holiday, two women—Cameron Diaz and Kate Winslet—swap homes for the holidays to escape their romantic troubles. While in their new locations, both women meet men who challenge their views on love and relationships. The film is full of beautiful settings, hilarious moments, and touching developments.

Why it’s similar to How to Lose a Guy in 10 Days: Both films focus on romance and personal growth, with characters learning life-changing lessons about love and relationships through unexpected circumstances. The Holiday shares the light-hearted humor and romantic energy found in How to Lose a Guy in 10 Days.


8. Sweet Home Alabama (2002)

Sweet Home Alabama follows the story of Melanie Carmichael (Reese Witherspoon), a fashion designer in New York who returns to her small hometown in Alabama to divorce her estranged husband, Jake (Josh Lucas). However, as she reconnects with her roots, she realizes that her heart may not be as ready to move on as she thought.

Why it’s similar to How to Lose a Guy in 10 Days: Both films explore the theme of love and relationships in unexpected ways, combining humor with heartfelt emotions. Sweet Home Alabama offers a romantic twist that centers on rediscovering lost love, much like the quirky romance in How to Lose a Guy in 10 Days.


9. When Harry Met Sally… (1989)

This classic rom-com follows Harry (Billy Crystal) and Sally (Meg Ryan), two friends who debate whether men and women can truly be friends without romance getting in the way. Over the years, their relationship evolves, leading to a beautiful, heartfelt ending.

Why it’s similar to How to Lose a Guy in 10 Days: Both films explore the dynamics of romantic relationships and love through humor, with When Harry Met Sally offering timeless insight into the intricacies of romance, while How to Lose a Guy in 10 Days focuses on the more comedic side of love.


10. My Best Friend’s Wedding (1997)

My Best Friend’s Wedding stars Julia Roberts as Julianne, a woman who realizes she’s in love with her best friend Michael (Dermot Mulroney) just as he’s about to marry someone else. Determined to stop the wedding, Julianne uses humor and schemes to try and win Michael’s heart before it’s too late.

Why it’s similar to How to Lose a Guy in 10 Days: Both films explore love and the complexities of relationships through humorous situations and schemes, with characters engaging in dramatic antics in pursuit of love.


11. Friends with Benefits (2011)

In Friends with Benefits, Jamie (Mila Kunis) and Dylan (Justin Timberlake) agree to start a casual relationship without any emotional attachment. However, they soon find themselves developing deeper feelings for one another, leading to comedic situations and heartwarming moments.

Why it’s similar to How to Lose a Guy in 10 Days: Both films explore the complications of relationships and love, with humor rooted in the characters’ initial misunderstandings of their feelings and the consequences of their actions.


12. Two Weeks Notice (2002)

Sandra Bullock stars as Lucy Kelson, a lawyer who has been working for a wealthy businessman, George Wade (Hugh Grant). After years of work, she decides to quit, but as the two grow closer, they develop an unexpected and complicated romance.

Why it’s similar to How to Lose a Guy in 10 Days: Two Weeks Notice shares the themes of opposites attracting and workplace romance, along with the comedic moments and growing chemistry between the characters.


13. The Ugly Truth (2009)

This rom-com stars Katherine Heigl as Abby, a TV producer who reluctantly teams up with Mike (Gerard Butler), a cynical relationship expert. Their on-screen chemistry quickly sparks, leading to hilarious and romantic situations as they each learn more about love and relationships.

Why it’s similar to How to Lose a Guy in 10 Days: The Ugly Truth features a similar dynamic where characters start off at odds but slowly develop romantic feelings amidst humorous situations. Both films also play on the tension between opposite personalities.


14. 27 Dresses (2008)

27 Dresses follows Jane (Katherine Heigl), a perpetual bridesmaid who is secretly in love with her boss. When her younger sister announces her engagement to the same man, Jane’s world is turned upside down, leading to a series of humorous and heartfelt moments.

Why it’s similar to How to Lose a Guy in 10 Days: Both films center around romantic misadventures and the ups and downs of love, filled with humorous situations and the gradual growth of relationships.


15. The Sweetest Thing (2002)

The Sweetest Thing stars Cameron Diaz, Christina Applegate, and Selma Blair as three women who navigate love, friendship, and complicated romantic entanglements. With plenty of laughs and steamy chemistry, the film explores what it means to fall in love in unexpected ways.

Why it’s similar to How to Lose a Guy in 10 Days: Both films focus on love, misunderstandings, and relationships, with characters learning important lessons about life and romance along the way.


If you loved How to Lose a Guy in 10 Days, these 15 films are a perfect follow-up. From zany romantic escapades to complicated relationships, they all provide the humor, charm, and heart that make romantic comedies so irresistible. Whether you’re looking for laughs, love, or life lessons, these movies like lie with me will keep you entertained from start to finish. So grab your popcorn, relax, and enjoy these films that offer just the right balance of romance and comedy.

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