If you’re a fan of the romantic comedy genre, then odds are you’ve watched the 2003 film How to Lose a Guy in 10 Days more times than you can count. The movie has everything you want in a good rom-com: humor, hijinks, and, of course, love ferns. That’s why you might be in the market to find a few more movies like How to Lose a Guy in 10 Days to add to your repertoire. Not that there’s anything wrong with watching this classic on repeat for days — or even weeks — at a time. (Hey, no judgments here! You like what you like.) But just in case you’re looking to switch it up a bit while still quenching that rom-com thirst, you’re going to need a few fun options at your disposal.
First, let’s take a quick trip down memory lane to revisit the OG. Starring Matthew McConaughey and Kate Hudson, How to Lose a Guy in 10 Days centers around their characters, Benjamin Barry and Andie Anderson, respectively. They both place secret bets on their relationship in an attempt to advance their careers because, well, Ben is sure he can make a woman fall in love with him in 10 days. Little does he know that his target, Andie, is also using him as the subject of her latest column — about how to lose a guy in that much time. But what neither one of them could’ve predicted was that they’d actually start to fall for each other. Doesn’t reading that just make you want to cue up Carly Simon’s “You’re So Vain” and watch Ben and Andie’s shenanigans for the umpteenth time?
Then again, it’s always a solid idea to shake things up now and then. So, just sit back, relax, and fall for these tried and true classics.
Movies Like How to Lose a Guy in 10 Days
1. 10 Things I Hate About You (1999)
What do you do when your dad says you can only start dating once your antisocial sister does? Find someone willing to ask said sister out, no matter the cost. Starring Julia Stiles and Heath Ledger, 10 Things I Hate About You carries out a lot of the same themes as How to Lose a Guy in 10 Days in that it involves some sort of dating wager that ends up with both parties developing actual feelings for one another. There’s even still a number 10 in the title — how’s that for similarities?!
2. The Proposal (2009)
Sandra Bullock and Ryan Reynolds star in this 2009 flick about a boss who gets engaged to her assistant to evade deportation. Yet much to their surprise, this charade proves not to be as fictitious as they initially thought when they start to develop real feelings for each other. Sound familiar?
3. The Ugly Truth (2009)
What makes men and women tick? Katherine Heigl and Gerard Butler have very different theories on the matter in this film. But while they initially butt heads on, well, everything, they end up getting some firsthand experience on the subject — with each other.
4. 27 Dresses (2008)
Katherine Heigl plays Jane, the ultimate embodiment of the expression “always a bridesmaid, never a bride.” That is until she meets Kevin, a handsome reporter played by James Marsden. Much like Andie in How to Lose a Guy in 10 Days, Kevin’s drive as a journalist is what initially inspires him to hang around with Jane and her 27 bridesmaid dresses. However, the better he gets to know her, the more his feelings for her continue to grow. (Anyone else sensing a pattern here?) And similar to Andie and Ben’s “You’re So Vain” sing-off, there’s an entertaining bar scene between Jane and Kevin where they belt out their own rendition of Elton John’s “Benny and the Jets.”
5. Friends With Benefits (2011)
Unlike How To Lose a Guy in 10 Days, this arrangement is more out in the open than the secret bets Andie and Ben make. However, the story does center around two people Jamie (Mila Kunis) and Dylan (Justin Timberlake), who go into their relationship with one expectation — adding sex to their relationship with zero romantic feelings involved — and end up falling for each other in the process. It’s a classic rom-com move and one that Friends with Benefits makes sure to utilize.
6. Two Weeks Notice (2002)
The film centers around passionate environmentalist lawyer Lucy Kelson (Sandra Bullock), who believes her talents are being wasted on trivial tasks by her boss George Wade (Hugh Grant). So, she decides to give him her two weeks’ notice. Just as their time together comes to a close, though, they realize how much they need each other — not professionally but personally.
7. While You Were Sleeping (1995)
From a pure plot standpoint, this film doesn’t really appear to have much in common with How to Lose a Guy in 10 Days. In fact, transit worker Lucy (Sandra Bullock) doesn’t even know Peter (Peter Gallagher) when she saves him from an oncoming subway train and allows his family to believe that they are engaged while he lies unconscious in a hospital bed. That said, How to Lose a Guy in 10 Days involves finding love in unlikely places, which is precisely what happens when Lucy falls for Peter’s brother Jack (Bill Pullman). It’s a romance she never saw coming, and that’s what makes it all the more exciting.
8. Music and Lyrics (2007)
Alex Fletcher (Hugh Grant) and Sophie Fisher (Drew Barrymore) seem to have nothing in common. He’s a former ‘80s pop star, and she’s just there to water his plants (or could it be a love fern?). But that doesn’t stop them from creating a hit song together. Between his music and her lyrics (hence the title), their partnership could finally revitalize Alex’s career — that is, if their chemistry doesn’t get in the way.
9. My Best Friend’s Wedding (1997)
You can’t help who you end up falling in love with, whether it be the subject of your latest writing assignment or your best friend… on the week of his wedding. Talk about bad timing, and Julia Roberts’ character Julianne Potter has it in spades when she attempts to win the love of her BFF Michael O’Neal (Dermot Mulroney) now that he’s literally days from the altar. You’ll laugh. You’ll cry. You’ll say a little prayer that this never happens to you.
10. The Wedding Date (2004)
The charming film stars Debra Messing as Kat Ellis, who hires a male escort (Dermot Mulroney) to pose as her boyfriend at her sister’s wedding. Why? Well, she’s attempting to save face in front of her ex, who is also part of the big day. But much like on How to Lose a Guy in 10 Days, the lie of their relationship starts to feel much more real than either anticipated.
11. You’ve Got Mail (1998)
This Meg Ryan and Tom Hanks classic about two mortal enemies falling in love (over email, no less) has the perfect blend of humor and romance guaranteed to give you all the rom-com feels you crave. It’s got playful bickering. It’s got heartfelt gestures. It’s got mail.
12. Failure to Launch (2006)
Let’s start with the obvious connection here — the film stars Matthew McConaughey. But it also centers around a couple meeting each other under false pretenses. Tripp, a 30-something grown adult man, still lives with his parents. At a loss over what to do, Tripp’s parents hire Paula (Sarah Jessica Parker) to help motivate him to leave the nest. However, things start to get complicated when Paula begins to (you guessed it) fall for Tripp for real.
13. The Wedding Planner (2001)
What’s the number one rule of any good wedding planner? Never, under any circumstances, fall for one of the grooms. And yet, that’s precisely what Mary Fiore (Jennifer Lopez) does when she meets Steve Edison (Matthew McConaughey). Am I just going to name every Matthew McConaughey rom-com out there? Possibly! But that still doesn’t make this flick any less worth watching.
14. She’s All That (1999)
Like so many movies that have come before and after it, She’s All That is a love story that started with a bet. After his girlfriend publicly dumps him for an older guy, popular jock Zach Siler (Freddie Prinze Jr.) wagers that he could turn any girl into the prom queen, including Laney Boggs (Rachael Leigh Cook). But the more he gets to know her, the more he starts to like her. All bets are off.
15. Never Been Kissed (1999)
For her next assignment as a reporter, Josie Geller (Drew Barrymore) gets tasked with enrolling in high school and pretending to be one of the students, which leads to some pretty interesting results. Going undercover in the name of journalism? Andie Anderson would be so proud!
16. Fool’s Gold (2008)
This one doesn’t technically qualify as a romantic comedy, but it reunites Matthew McConaughey and Kate Hudson as love interests who team up to find a lost treasure. Need I say more?
17. 50 First Dates (2004)
If you love Adam Sandler movies, this is a classic you’ve got to see. After a freak accident, a young woman loses her memory each day. And when she meets a man who falls head over heels for her, things get even more complicated. When he learns of her condition, he tries his best to make the relationship work, despite having to reintroduce himself on each date. It’s an exciting tale that teaches its audience that love truly has no bounds.
More Classics to Add to Your Rom-Com Queue
- Hitch (2005)
- What Happens in Vegas (2008)
- Just Go With It (2011)
- Made of Honor (2008)
- The Holiday (2006)
- Leap Year (2010)
- Definitely, Maybe (2008)
- When in Rome (2010)
- Pretty Woman (1990)
- What Women Want (2000)
- Ghosts of Girlfriends Past (2009)
- Only You (1994)
- My Best Friend’s Girl (2008)
- Someone Like You (2001)
- He’s Just Not That Into You (2009)
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