SpaceMovies Like How to Lose a Guy in 10 Days
Looking for movies like How to Lose a Guy in 10 Days? Here are 10 films with similar playful, charming, competitive vibes, matching themes, and the same emotional impact.
Last updated Oct 1, 2026
Best Movies Like How to Lose a Guy in 10 Days
The best movies like How to Lose a Guy in 10 Days are Anyone But You, The Proposal, 10 Things I Hate About You, Failure to Launch. Each shares the playful, charming, competitive tone and explores similar themes of deception, dating, bets, authenticity, love.
If you loved How to Lose a Guy in 10 Days (2003) for the irresistible battle of wits between Kate Hudson and Matthew McConaughey, the hilarious escalating antics, and the moment the bet stops mattering, these 10 movies deliver a similar experience. We picked each one based on shared tone, themes, and emotional feel — not just surface-level genre tags.
-
1. Anyone But You
2023 RomanceWhere to watch Anyone But YouAnyone But You stars Sydney Sweeney and Glen Powell as two people with a bad history who pretend to be a couple at a destination wedding in Australia. Like How to Lose a Guy in 10 Days, it is built on a fake relationship between two stubborn, attractive leads who are clearly meant for each other. It is raunchier and more of an ensemble comedy, with a modern, loosely Shakespearean setup, but the bickering-into-romance formula is very familiar.
-
2. The Proposal
2009 RomanceWhere to watch The ProposalThe Proposal stars Sandra Bullock as a demanding book editor who forces her assistant, played by Ryan Reynolds, into a fake engagement to avoid deportation, which leads to a weekend with his family in Alaska. It captures the How to Lose a Guy in 10 Days pleasure of a sham romance slowly becoming real. The workplace power dynamic and family setting make it feel different, and much of the comedy comes from his eccentric relatives.
-
3. 10 Things I Hate About You
1999 ComedyWhere to watch 10 Things I Hate About You10 Things I Hate About You follows a high school boy paid to date a famously difficult girl so that her younger sister can start dating, only for him to fall for her. The secret-bet premise is a direct cousin of How to Lose a Guy in 10 Days, complete with the painful reveal. Loosely based on The Taming of the Shrew, it is a teen comedy with Heath Ledger and Julia Stiles, sweeter and more youthful than its adult counterpart.
-
4. Failure to Launch
2006 RomanceWhere to watch Failure to LaunchFailure to Launch stars Matthew McConaughey as a man in his thirties who still lives with his parents, who secretly hire a woman, played by Sarah Jessica Parker, to make him fall for her so he will finally move out. For How to Lose a Guy in 10 Days fans, it offers McConaughey in another romance built on a hidden scheme that is bound to blow up. It is broader and sillier, with more slapstick involving animals and sidekicks.
-
5. The Ugly Truth
2009 RomanceWhere to watch The Ugly TruthThe Ugly Truth pairs Katherine Heigl as an uptight morning-show producer with Gerard Butler as a crude TV personality who claims to know what men really want, and who coaches her through a new romance. Its battle-of-the-sexes sparring echoes How to Lose a Guy in 10 Days, especially the idea of using dating rules as a strategy. It is cruder in its humor, and the deception is more about coaching than sabotage.
-
6. She's the Man
2006 ComedyWhere to watch She's the ManShe's the Man stars Amanda Bynes as a soccer player who disguises herself as her twin brother at a boarding school and falls for her roommate, played by Channing Tatum. Like How to Lose a Guy in 10 Days, it gets its laughs from a lead keeping up an elaborate act while feelings get complicated. It is a teen comedy loosely based on Twelfth Night, more farcical and goofy, with the deception built on mistaken identity rather than a bet.
-
7. Crazy Rich Asians
2018 RomanceWhere to watch Crazy Rich AsiansCrazy Rich Asians follows an economics professor who travels to Singapore with her boyfriend and discovers his family is extraordinarily wealthy and not eager to accept her. It shares How to Lose a Guy in 10 Days' glossy, crowd-pleasing romantic spirit and its charismatic leads. There is no scheme or bet here, though; the conflict comes from class and family expectations, and the film is as much about mothers and culture as about romance.
-
8. What Happens in Vegas
2008 RomanceWhere to watch What Happens in VegasWhat Happens in Vegas stars Cameron Diaz and Ashton Kutcher as strangers who wake up married after a wild night in Las Vegas, then win a jackpot and get stuck trying to outmaneuver each other for the money. The escalating prank war between two people pretending to play nice feels close to How to Lose a Guy in 10 Days. It is broader and more slapstick, and the rivalry is about cash rather than a career-making bet.
-
9. Hitch
2005 RomanceWhere to watch HitchHitch stars Will Smith as a smooth New York dating consultant who helps hopeless men win over women, until he falls for a gossip columnist, played by Eva Mendes, who is digging into his business. It plays with the same idea as How to Lose a Guy in 10 Days: dating as a set of tactics, and what happens when one of the players gets caught. It is more about the coach than the con, with Kevin James adding warm comic relief.
-
10. Ghosts of Girlfriends Past
2009 RomanceWhere to watch Ghosts of Girlfriends PastGhosts of Girlfriends Past stars Matthew McConaughey as a womanizing photographer who is visited by the ghosts of his past relationships on the eve of his brother's wedding, in a riff on A Christmas Carol. It gives How to Lose a Guy in 10 Days fans another dose of McConaughey as a charming player who has to grow up. The supernatural framing makes it more of a fantasy, and Jennifer Garner's old flame is less of a sparring partner than Kate Hudson.
Why These Movies Are Similar to How to Lose a Guy in 10 Days
How to Lose a Guy in 10 Days pits a magazine writer trying to drive a man away for an article against an ad executive who has bet he can make a woman fall for him, with Kate Hudson and Matthew McConaughey sparring until the scheme turns real. Fans love the dueling deceptions and the slapstick sabotage. 10 Things I Hate About You and The Proposal are the closest picks for a fake setup that becomes genuine, Anyone But You is the modern take, and Failure to Launch and Ghosts of Girlfriends Past bring back McConaughey. Crazy Rich Asians is the most glamorous swerve.