If you loved the charming romantic comedy How to Lose a Guy in 10 Days, you’re in for a treat! This delightful film follows the antics of a columnist and a businessman as they engage in a playful battle of wits, navigating the ups and downs of love and the lengths people will go to for their careers. With its perfect blend of humor, romance, and heartwarming moments, How to Lose a Guy in 10 Days has become a beloved classic. If you’re looking for more movies that capture the same lighthearted spirit, clever banter, and romantic entanglements, we’ve compiled a list of 15 movies like How to Lose a Guy in 10 Days. These films are guaranteed to entertain and remind you of the joys and pitfalls of love.
1. 10 Things I Hate About You (1999)
Based on Shakespeare’s The Taming of the Shrew, 10 Things I Hate About You is a modern classic that follows the story of Kat Stratford, a headstrong teen, and the charming Patrick, who is paid to date her. The film skillfully combines humor with romance, showcasing the ups and downs of their relationship as Patrick tries to win Kat’s heart while dealing with her tough exterior. With its memorable performances by Heath Ledger and Julia Stiles, the film beautifully captures the spirit of young love and the importance of being true to oneself. Its witty dialogue and romantic twists make it a perfect pick for fans of movies like How to Lose a Guy in 10 Days.
2. The Proposal (2009)
In The Proposal, Sandra Bullock stars as Margaret, a high-powered book editor who forces her assistant Andrew (Ryan Reynolds) to marry her to avoid deportation to Canada. The film is filled with hilarious situations as they travel to Andrew’s hometown to convince his family that their marriage is real. Their chemistry and the outrageous circumstances lead to unexpected romantic developments, making this film a delightful watch. The witty banter and comical misunderstandings mirror the lighthearted fun found in How to Lose a Guy in 10 Days, ensuring that audiences will be entertained from start to finish.
3. Crazy, Stupid, Love (2011)
Crazy, Stupid, Love features an ensemble cast led by Steve Carell, Julianne Moore, and Ryan Gosling. The film revolves around a middle-aged man, Cal, whose life is turned upside down after his wife asks for a divorce. As he navigates the dating scene with the help of a smooth-talking bachelor, Jacob, Cal learns about love and self-discovery. The intertwining stories of love and heartbreak, coupled with sharp humor and genuine moments, make this film an emotional rollercoaster. Its exploration of modern relationships and the comedic mishaps that come with them will resonate with fans of movies like How to Lose a Guy in 10 Days.
4. How to Be Single (2016)
How to Be Single follows the lives of several single women in New York City as they navigate the ups and downs of dating. Starring Dakota Johnson, Rebel Wilson, and Alison Brie, the film offers a humorous look at what it means to be single in a relationship-obsessed world. Each character brings their unique perspective on love, friendship, and self-discovery, making it relatable to a wide audience. The film’s lighthearted approach and comedic moments echo the playful tone of How to Lose a Guy in 10 Days, making it an entertaining addition to this list.
5. Never Been Kissed (1999)
In Never Been Kissed, Drew Barrymore plays a journalist who goes undercover as a high school student to research teenage culture. As she navigates the challenges of high school life, she unexpectedly falls for her English teacher, played by Michael Vartan. The film blends humor with heartwarming moments as Josie learns about love, friendship, and self-acceptance. Its charming storyline and relatable themes of awkwardness and romance resonate with viewers, making it a delightful pick for fans of movies like How to Lose a Guy in 10 Days.
6. 13 Going on 30 (2004)
13 Going on 30 tells the story of Jenna, a 13-year-old girl who wishes to be an adult and wakes up as a 30-year-old woman. As she navigates her new life, Jenna discovers the complexities of adulthood, including love and relationships. The film cleverly balances humor and heart, exploring the importance of staying true to oneself while also highlighting the ups and downs of love. With Jennifer Garner’s charming performance, 13 Going on 30 captures the whimsical yet relatable aspects of romance, making it a great choice for fans of romantic comedies like How to Lose a Guy in 10 Days.
7. The Wedding Planner (2001)
The Wedding Planner stars Jennifer Lopez as Mary, a successful wedding planner who falls for a handsome pediatrician, only to discover he’s engaged to her client. The film blends romance and comedy as Mary navigates the challenges of love, work, and friendship. With its charming performances and delightful storyline, the film offers a lighthearted take on romance and the chaos that can ensue in love. Its engaging plot and comedic situations resonate with the themes found in How to Lose a Guy in 10 Days, ensuring a fun viewing experience.
8. Two Weeks Notice (2002)
In Two Weeks Notice, Sandra Bullock plays Lucy, an environmental lawyer who gives her two weeks’ notice to her wealthy boss, George (Hugh Grant), after becoming overwhelmed by his demands. As she prepares to leave, Lucy and George realize their feelings for each other. The film is filled with witty dialogue and humorous situations as they navigate their professional and personal lives. The chemistry between Bullock and Grant brings a delightful charm to the film, making it a fitting choice for those who enjoy movies like How to Lose a Guy in 10 Days.
9. Sweet Home Alabama (2002)
Sweet Home Alabama follows the story of Melanie, a successful New York fashion designer who returns to her small hometown to finalize her divorce from her childhood sweetheart, Jake. As she navigates her past and her present, Melanie discovers what truly matters in life and love. The film beautifully captures the contrast between city life and small-town charm, showcasing the importance of staying true to oneself. With its heartfelt moments and romantic tensions, Sweet Home Alabama resonates with the playful spirit of How to Lose a Guy in 10 Days, making it a perfect addition to this list.
10. While You Were Sleeping (1995)
In While You Were Sleeping, Sandra Bullock plays Lucy, a lonely transit worker who saves her crush from an oncoming train, only to find herself mistaken for his fiancée while he is in a coma. As Lucy becomes entwined with his family, she discovers love and friendship in unexpected places. The film masterfully combines comedy and romance, capturing the heartwarming moments of connection and self-discovery. Its whimsical premise and charming performances make it a delightful choice for fans of romantic comedies like How to Lose a Guy in 10 Days.
11. The Ugly Truth (2009)
The Ugly Truth stars Katherine Heigl as Abby, a television producer whose romantic life is turned upside down by the arrival of a brash morning show host, Mike (Gerard Butler). Their opposing views on love and relationships lead to hilarious conflicts, yet sparks fly as they learn more about each other. The film balances raunchy humor with genuine moments of connection, providing a fun and engaging exploration of romance. Its playful approach to love and the battle of the sexes resonate with the themes found in How to Lose a Guy in 10 Days.
12. Forgetting Sarah Marshall (2008)
In Forgetting Sarah Marshall, Peter (Jason Segel) is devastated after his girlfriend, Sarah (Kristen Bell), breaks up with him. In an attempt to heal, he travels to Hawaii, only to discover Sarah is staying at the same resort with her new boyfriend. The film hilariously explores themes of heartbreak and self-discovery, with Peter finding unexpected love in the form of Rachel (Mila Kunis). The humor and emotional depth make this film a delightful journey through the complexities of love and relationships, appealing to fans of movies like How to Lose a Guy in 10 Days.
13. My Best Friend’s Wedding (1997)
My Best Friend’s Wedding stars Julia Roberts as Julianne, who realizes she is in love with her best friend, Michael (Dermot Mulroney), just days before his wedding to someone else. Determined to win him back, Julianne embarks on a mission filled with comedic and heartfelt moments. The film explores the complexities of love, friendship, and the lengths one will go to for love. With its memorable performances and iconic scenes, My Best Friend’s Wedding resonates with fans of romantic comedies, making it a delightful addition to this list.
14. Bridget Jones’s Diary (2001)
Bridget Jones’s Diary follows the life of Bridget (Renée Zellweger), a single woman in her 30s navigating love, work, and self-image. The film is based on Helen Fielding’s novel and is filled with humor and relatable moments as Bridget chronicles her romantic misadventures. With the charming chemistry between Bridget, her boss Daniel (Hugh Grant), and her love interest Mark (Colin Firth), the film beautifully captures the ups and downs of relationships. Its humorous take on love and personal growth makes it a must-watch for fans of movies like How to Lose a Guy in 10 Days.
These 15 movies like How to Lose a Guy in 10 Days are filled with laughter, love, and relatable moments that explore the complexities of relationships. From humorous misadventures to heartfelt connections, each film offers a unique perspective on love, making them perfect for fans of romantic comedies. Whether you’re in the mood for a charming story of self-discovery or a hilarious battle of wits, this list has something for everyone. So grab some popcorn, settle in, and enjoy these delightful films! And for more movie recommendations, check out our list of 20 Best Movies Like Fast and Furious | Similar-List for thrilling adventures beyond romance!
