7 Delightfully Witty Rom-Coms Like How to Lose a Guy in 10 Days
If you adore the playful chaos of How to Lose a Guy in 10 Days where love blooms amidst secret bets, over the top antics, and a battle of wits between Kate Hudson’s Andie and Matthew McConaughey’s Benjamin you’re in for a treat. This list dives into seven romantic comedies that capture the same magic: clever schemes, laugh-out-loud misunderstandings, and relationships forged in the fire of hilarious deception. IF you’re craving workplace rivalries, fake relationships, or enemies-to-lovers charm, these picks deliver romance with a side of mischief.
1. The Proposal (2009)
Starring: Sandra Bullock, Ryan Reynolds | Director: Anne Fletcher
Sandra Bullock stars as Margaret Tate, a cutthroat book editor facing deportation to Canada. To stay in the U.S., she blackmails her long-suffering assistant Andrew (Ryan Reynolds) into a fake engagement. What begins as a transactional arrangement spirals into a weekend trip to meet Andrew’s family in Alaska, complete with awkward encounters, a naked collision scene, and Betty White stealing the show as Andrew’s eccentric grandma.
Why Fans of How to Lose a Guy Will Love It:
Like Andie and Benjamin’s secret agendas, Margaret and Andrew’s fake relationship blurs the lines between manipulation and genuine connection. The banter is razor-sharp—Bullock’s icy demeanor clashes perfectly with Reynolds’ sarcastic charm—and the absurd situations (think: a grandma-led ritual dance in the woods) mirror the chaotic energy of How to Lose a Guy. The film’s heart lies in its exploration of vulnerability, proving even the most calculated schemes can’t outrun true feelings.
Stream It On: Prime Video, Apple TV+
2. 10 Things I Hate About You (1999)
Starring: Heath Ledger, Julia Stiles | Director: Gil Junger
This modern retelling of The Taming of the Shrew centers on Kat Stratford (Julia Stiles), a fiercely independent teen, and Patrick Verona (Heath Ledger), the bad boy paid to date her as part of a bet. Kat’s sharp wit and Patrick’s roguish charm collide in a battle of wills, culminating in Ledger’s iconic stadium serenade of “Can’t Take My Eyes Off You.”
Why Fans of How to Lose a Guy Will Love It:
The bet-driven romance parallels Andie and Benjamin’s games, blending humor with heartfelt moments. Kat’s resistance to love and Patrick’s gradual sincerity mirror the tension in How to Lose a Guy, while the supporting cast (including a young Joseph Gordon-Levitt) adds layers of teen drama and wit. It’s a timeless tale of love thriving in spite of pride—and poorly planned schemes.
Stream It On: Disney+, Hulu
3. The Ugly Truth (2009)
Starring: Katherine Heigl, Gerard Butler | Director: Robert Luketic
Abby Richter (Katherine Heigl), a romantically challenged TV producer, reluctantly teams up with chauvinist TV host Mike Chadway (Gerard Butler) to win over her neighbor. Mike’s outrageous dating “advice” leads to cringe-worthy dates, including a vibrating underwear disaster, while their fiery banter slowly uncovers mutual respect—and attraction.
Why Fans of How to Lose a Guy Will Love It:
The battle-of-the-sexes dynamic echoes Andie and Benjamin’s rivalry, with Abby and Mike’s clashing ideologies driving both humor and growth. The film’s raunchy comedy (hello, drone-assisted peep show) is balanced by tender moments, much like How to Lose a Guy’s blend of slapstick and sincerity. Butler’s gruff charm and Heigl’s comedic timing make this a standout for fans of love stories that thrive on chaos.
Stream It On: Hulu, Netflix
4. 27 Dresses (2008)
Starring: Katherine Heigl, James Marsden | Director: Anne Fletcher
Jane Nichols (Katherine Heigl) is a perpetual bridesmaid who secretly loves her boss, George—until her sister Tess swoops in and steals his heart. Enter Kevin Doyle (James Marsden), a cynical reporter writing a piece on Jane’s bridesmaid escapades. As they team up to expose Tess’s lies, Jane’s perfect facade cracks, revealing her true desires.
Why Fans of How to Lose a Guy Will Love It:
Jane’s hidden crush and Kevin’s scheming reporter role mirror Andie’s article-driven deception. The film’s wedding-themed chaos (27 dresses, a spontaneous “Bennie and the Jets” karaoke duet) delivers the same fizzy energy as How to Lose a Guy’s over-the-top dates. Marsden’s wit and Heigl’s relatable earnestness create a dynamic that’s equal parts hilarious and heartwarming.
Stream It On: Apple TV+, Prime Video
5. Crazy, Stupid, Love (2011)
Starring: Steve Carell, Ryan Gosling, Emma Stone | Directors: Glenn Ficarra, John Requa
After Cal Weaver (Steve Carell) is dumped by his wife, he’s taken under the wing of smooth-talking bachelor Jacob (Ryan Gosling), who teaches him how to navigate the dating world. Meanwhile, Jacob’s own playboy ethos is challenged when he meets Hannah (Emma Stone), a law student unimpressed by his charm.
Why Fans of How to Lose a Guy Will Love It:
The mentor-student dynamic between Cal and Jacob mirrors Benjamin’s attempts to “win” Andie, while Jacob’s transformation from player to romantic echoes Benjamin’s journey. The film’s layered storytelling—including a hilarious backyard brawl and a poignant graduation speech—balances humor with emotional depth, much like How to Lose a Guy’s blend of laughs and heartfelt confessions.
Stream It On: Netflix, Amazon Prime
6. Two Weeks Notice (2002)
Starring: Sandra Bullock, Hugh Grant | Director: Marc Lawrence
Lucy Kelson (Sandra Bullock), a passionate environmental lawyer, becomes the long-suffering assistant to billionaire George Wade (Hugh Grant). Their clashing personalities—Lucy’s idealism vs. George’s frivolity—lead to fiery banter, secret crushes, and a climactic public confession of love.
Why Fans of How to Lose a Guy Will Love It:
The workplace rivalry and slow-burn romance mirror Andie and Benjamin’s office-driven tension. Grant’s signature wit (“You’re fired… but not really”) and Bullock’s comedic exasperation create a dynamic reminiscent of McConaughey and Hudson’s chemistry. The film’s mix of slapstick (a destroyed historic building) and sincerity makes it a must-watch for fans of love stories born from chaos.
Stream It On: Netflix, Prime Video
7. Never Been Kissed (1999)
Starring: Drew Barrymore, Michael Vartan | Director: Raja Gosnell
Josie Geller (Drew Barrymore), a shy copy editor, goes undercover as a high school student to write an exposé on teen culture. But her assignment gets complicated when she develops feelings for her English teacher, Sam (Michael Vartan), and rediscovers her own self-confidence.
Why Fans of How to Lose a Guy Will Love It:
Josie’s undercover mission parallels Andie’s deceptive article, blending humor with heartfelt introspection. The film’s exploration of self-acceptance—Josie’s journey from awkward outsider to prom queen—resonates with How to Lose a Guy’s theme of authenticity triumphing over pretense. Barrymore’s endearing performance and the nostalgic ’90s vibe make this a timeless pick.
Stream It On: Apple TV+, Disney+
Conclusion: Love, Lies, and Laughter
From fake engagements to undercover escapades, these seven rom-coms capture the same irresistible blend of humor and heart that made How to Lose a Guy in 10 Days a classic. No matter you’re rooting for scheming assistants (The Proposal), reluctant soulmates (The Ugly Truth), or second-chance romances (Crazy, Stupid, Love), each film proves that love often thrives in the messiest, most unpredictable ways.
Pro Tip for Your Next Movie Night: Pair these picks with a DIY “love fern” (just don’t overwater it!) and lean into the chaos. After all, the best rom-coms remind us that even the most elaborate schemes can’t outsmart the heart.
