If you’re a fan of How to Lose a Guy in 10 Days, you already know the charm of a great romantic comedy with a twist. This classic film brings together humor, romance, and a bit of mischief as Andie and Ben try to trick each other while sparks inevitably fly. For those who love the mix of humor, love, and complex relationships, this list of films like How to Lose a Guy in 10 Days offers all the heartwarming vibes you’re looking for. Whether it’s fake relationships, hilariously awkward situations, or undeniable chemistry, these movies promise to deliver a romantic journey filled with laughter. Dive in for more picks that will keep you entertained and laughing!
1. 10 Things I Hate About You (1999)
This modern adaptation of Shakespeare’s The Taming of the Shrew stars Julia Stiles and Heath Ledger in a high school setting where romance and rebellion collide. When Cameron tries to win over Bianca, he must first find a way to get her prickly older sister, Kat, to date. This film’s mix of romance, tension, and laughs makes it a great pick for fans of How to Lose a Guy in 10 Days.
2. The Proposal (2009)
In The Proposal, Margaret Tate (Sandra Bullock) and Andrew Paxton (Ryan Reynolds) find themselves in a sham engagement to avoid deportation. Their comedic clash of personalities, set against the backdrop of a remote Alaskan family trip, turns into genuine chemistry. Like How to Lose a Guy in 10 Days, this film is packed with laughter, romance, and unforgettable moments.
3. 27 Dresses (2008)
Always the bridesmaid but never the bride, Jane (Katherine Heigl) has been in 27 weddings. Her own romantic struggles take a turn when a handsome journalist, Kevin, takes an interest in her. With its humor and insights into love and relationships, 27 Dresses is a must-watch for fans of rom-coms like How to Lose a Guy in 10 Days.
4. Failure to Launch (2006)
In this rom-com, Tripp (Matthew McConaughey) still lives with his parents, who hire Paula (Sarah Jessica Parker) to get him to finally move out. The clash between Paula’s “mission” and their unexpected connection adds humor and warmth. Fans of How to Lose a Guy in 10 Days will enjoy the similar dynamic of romance with a goal-driven twist.
5. She’s All That (1999)
In a high school setting, popular guy Zack takes on a bet to transform artsy loner Laney into prom queen. As he begins to fall for her, the lines blur between the bet and genuine affection. With its themes of love, transformation, and unexpected chemistry, She’s All That is another gem for rom-com enthusiasts.
6. Crazy, Stupid, Love. (2011)
With an all-star cast, Crazy, Stupid, Love. explores multiple love stories, centering on Cal (Steve Carell) as he re-enters the dating world with help from ladies’ man Jacob (Ryan Gosling). The film’s humor, heart, and genuine romance make it a standout in the genre, ideal for fans of complex love stories.
7. The Wedding Planner (2001)
Jennifer Lopez stars as Mary, a wedding planner who falls for a charming doctor (Matthew McConaughey) – who turns out to be the groom in the wedding she’s planning. The chemistry between the leads and the romantic dilemma at the heart of the story makes this a delightful watch for anyone who loves films like How to Lose a Guy in 10 Days.
8. Friends with Benefits (2011)
In Friends with Benefits, Dylan (Justin Timberlake) and Jamie (Mila Kunis) try to maintain a “no strings attached” relationship, only to realize they might have real feelings for each other. The witty dialogue, modern take on relationships, and undeniable chemistry between the leads make this film another rom-com classic.
9. No Strings Attached (2011)
Starring Ashton Kutcher and Natalie Portman, this film follows a pair who agree to a casual, no-strings relationship. Of course, feelings get in the way. Similar to Friends with Benefits, this movie offers plenty of laughs, romance, and twists – perfect for fans of lighthearted love stories with a humorous edge.
10. Hitch (2005)
Will Smith stars as Alex “Hitch” Hitchens, a dating consultant who can help anyone find love—except himself. When he meets Sara (Eva Mendes), his own rules get put to the test. This film’s mix of humor, romance, and charm is ideal for fans of How to Lose a Guy in 10 Days who enjoy watching romantic schemes unfold.
11. Bride Wars (2009)
Two best friends, Liv and Emma, have their friendship tested when their weddings are booked on the same day. As they fight over the perfect wedding venue, their relationship and love lives are hilariously challenged. Bride Wars is a delightful watch for anyone who loves rom-coms with a bit of friendly rivalry.
12. What Happens in Vegas (2008)
After a wild night in Vegas, Jack (Ashton Kutcher) and Joy (Cameron Diaz) wake up married – and they both want to keep the jackpot winnings from the night before. Forced to stay married for the cash, they go through ups and downs that eventually bring them closer. This film’s mix of wild romance and comedy makes it a perfect choice for fans of How to Lose a Guy in 10 Days.
13. Leap Year (2010)
Anna (Amy Adams) heads to Ireland to propose to her boyfriend, but along the way, she finds herself stuck with an irritable local (Matthew Goode) who might just be the one she’s meant to be with. With its charming romance and scenic backdrop, Leap Year offers the type of unexpected love story that How to Lose a Guy in 10 Days fans will adore.
14. Legally Blonde (2001)
While not a traditional romantic comedy, Legally Blonde follows Elle Woods (Reese Witherspoon) as she heads to Harvard Law to win back her ex. As she proves her worth and finds her true calling, Elle’s journey is full of laughs, heart, and empowerment. Fans of How to Lose a Guy in 10 Days will enjoy Elle’s fun personality and determination.
15. The Ugly Truth (2009)
Katherine Heigl and Gerard Butler star in this rom-com about a TV producer and a chauvinistic TV host whose love advice to her ends up having unexpected results. The clash of personalities, witty banter, and surprising chemistry between the leads make The Ugly Truth a great pick for fans of opposites-attract romances.
These 15 films like How to Lose a Guy in 10 Days offer plenty of romance, humor, and unexpected connections. From classic fake-relationship tropes to heartwarming love stories, there’s something here for every rom-com fan. Whether you’re in the mood for laughter, rivalry, or a charming meet-cute, these films are sure to deliver the entertainment you’re looking for. For even more romantic and entertaining picks, visit > More Info and discover more favorites for your watchlist!
