10 Movies Like How To Lose A Guy In 10 Days

The 1990s and 2000s were a banner time for big, star-studded romantic comedies, and 2003's "How to Lose a Guy in 10 Days" is a prime example. With Kate Hudson and Matthew McConaughey at the helm — as magazine columnist Andie Anderson and ad executive Benjamin Barry, making for some really satisfying alliterative names — the movie uses basically every rom-com trope in the book, and somehow, it rules. Andie is trying to prove she can drive a man away in just ten days by acting so needy that he wants her gone, while Ben is trying to prove he can make any woman fall in love with him in ten days so he can book a huge account (it involves diamonds and makes a little more sense in context). You can probably guess what actually happens; against all odds, the two actually start to fall for each other before discovering their respective ruses, at which point they part ways only to reunite at the very end of the movie.

Just because the rom-com formula is well-trod doesn't make it any less fun, and thanks to Hudson and McConaughey's full-throated embrace of the material, "How to Lose a Guy in 10 Days" is endlessly charming. So what should you watch next? Luckily, there are plenty of options that are similar enough to this pick, whether they feature two characters involved in opposing schemes or a third-act betrayal that ultimately gets resolved. Here's what you should add to your watchlist after "How to Lose a Guy in 10 Days."

Gil Junger's beloved 1999 Shakespeare adaptation "10 Things I Hate About You" — written by Karen McCullah and Kirsten Smith — shares a title number with "How to Lose a Guy in 10 Days," but the two movies have even more overlap than that. Set in Padua High School as an ode to the Bard's play "The Taming of the Shrew," the modern literary take focuses in on the prickly Kat Stratford (Julia Stiles), whose popular younger sister Bianca (Larisa Oleynik) is desperate to go out on a date. When their overprotective dad Walter (Larry Miller) declares that Bianca can only date if Kat does, Padua's resident popular jerk Joey Donner (Andrew Keegan), who has his eye on Bianca, comes up with a plan: he pays Patrick Verona (Heath Ledger) to take the stubborn Kat out on a date.

This ruse, obviously, brings Patrick and Kat closer despite both of their protestations, while new Padua transfer Cameron James (Joseph Gordon-Levitt) secretly hopes the sweet, beautiful Bianca might realize Joey is an absolute dingus and pick him instead. Kat and Bianca also find out about Joey's scheme, driving Bianca into Cameron's arms while Kat is left furious at Patrick, but just like Shakespeare's comedies, it all ends happily. In the hands of lesser writers and actors, "10 Things I Hate About You" could have just been yet another teen movie; thanks to Ledger, Stiles, Oleynik, and Gordon-Levitt in particular — plus a perfectly deployed David Krumholtz as Cameron's dorky friend Michael Eckman — it's one of the very best of the genre.

Penned by "The Devil Wears Prada" writer Aline Brosh McKenna and directed by rom-com queen Anne Fletcher, "27 Dresses" definitely leans on the "betrayal" aspect of "How to Lose a Guy in 10 Days," but in a totally different sense. When we first meet Jane Nichols (Katherine Heigl, at the height of her "Grey's Anatomy" popularity), she's really living up to that old "always a bridesmaid, never a bride" adage; in fact, Jane has been a bridesmaid a whopping twenty-seven times. (The title makes more sense now, huh?) Jane has been carrying a torch for her boss George (Edward Burns) for years, but when George meets Jane's irresponsible younger sister Tess (Malin Åkerman), he's immediately smitten, much to Jane's dismay; after George and Tess get engaged, Jane ends up spending some unexpected time with newspaper reporter Kevin Doyle (James Marsden), who uses the pseudonym "Malcolm" to cover weddings for a huge publication. 

You can probably see where this is going — Kevin secretly writes a (pretty rough) piece about Jane and her double-digit stats as a bridesmaid, leaving her furious, and Jane meddles with George and Tess' wedding until they call the whole thing off. Throw in a great "best friend" turn from the always-welcome Judy Greer and some excellent chemistry between Marsden and Heigl, and you've got yet another great 2000s romcom. (Also, Marsden should be in way more romantic comedies! He is unbelievably charming! Casting directors, take note!)

Ken Kwapis' 2009 rom-com "He's Just Not That Into You" — written by Abby Kohn and Marc Silverstein and based on one line from one episode of "Sex and the City" — is like, eight romantic comedies folded into one, and there's plenty of backstabbing and betrayal to be found in this ensemble film. In one story, hopeless romantic Gigi (Ginnifer Goodwin) can't figure out why her dates won't call her back until bar manager Alex (Justin Long) delivers some wisdom in the form of the movie's title; if a guy wants to call, Alex tells Gigi, he will. In another, yoga teacher and aspiring singer Anna Marks (Scarlett Johansson) meets a handsome guy named Ben (Bradley Cooper) at the grocery store, but unfortunately, he's married to Gigi's friend and coworker Janine (Jennifer Connolly). (Anna and Ben totally have an affair anyway and the whole thing ends in disaster.) Gigi's other coworker, Beth (Jennifer Aniston) is growing increasingly resentful over the fact that her longtime boyfriend Neil (Ben Affleck), who's friends with Ben, won't propose; they break up for a while but eventually get back together and Neil, as expected, gets down on one knee. Drew Barrymore, Kevin Connolly (from "Entourage"), and Kris Kristofferson are also all sort of floating around aimlessly in this movie.

If you want to watch something that scratches the same itch as "How to Lose a Guy in 10 Days" but a bunch of times in a row, "He's Just Not That Into You" is a solid enough pick. With that said, you can skip the litany of "ensemble movies with overlapping stories" that this movie and "Love Actually" spawned in equal measure ("Valentine's Day," "Mother's Day," and "New Year's Eve," for example, are all duds).

Rom-coms typically involve schemes and ruses of some kind, but it's particularly delightful when everyone is involved in the scheme and/or ruse. That's where "The Proposal" comes in. Directed by Anne Fletcher and written by Peter Chiarelli, the film introduces audiences to Margaret Tate (rom-com queen Sandra Bullock), an uptight publishing executive who happens to be Canadian and live in New York. After committing a minor visa violation, Margaret is in danger of being deported back to Canada unless she gets married, which is where Andrew Paxton (Ryan Reynolds), Margaret's long-suffering assistant, comes in handy. Margaret promises Andrew that if they pretend to be engaged convincingly enough to fool the immigration officer tailing her — a deviously funny Denis O'Hare — she'll give him a promotion and make him an editor for his troubles.

This arrangement gets way more complicated when Andrew brings Margaret home to the small town of Sitka, Alaska to meet his family — and though Andrew's mother Grace (Mary Steenburgen) and grandmother Annie (Betty White) just want to make Margaret feel at home, Andrew's father Joe (Craig T. Nelson) is suspicious about the entire thing. Hijinks, obviously, ensue, and despite the fact that their engagement is very fake, Andrew and Margaret end up falling for each other, at which point Andrew proposes to Margaret simply so she can stay in New York and they can start dating. Reynolds and Bullock make a particularly great pair in "The Proposal," and the late White is a total hoot as a slightly out-there granny ... but perhaps the best part of this movie is the fact that the central couple work together to fool everyone else instead of tricking each other.

Julia Roberts and Richard Gere's second collaboration together — and their reunion with their "Pretty Woman" director Garry Marshall — focuses on Roberts' Maggie Carpenter, a free spirit who shares some similarities with Andie Anderson and also has a bad habit of leaving guys at the altar. That's where Gere comes in; his Ike Graham, a grumpy columnist living in New York, finds out about Maggie's track record of sprinting away from her own nuptials and writes a fairly rude story about her as a result. Unfortunately, all of Ike's details come from one of Maggie's jilted fiancés, so she contacts him to set the record straight ... and he ends up heading to her hometown in Maryland to spend time with her and her fourth hopeful groom, Bob Kelly (Christopher Meloni).

Ike is only in the small town of Hale to write a story about Maggie that's completely and authentically true, but as he spends more time with the flighty Maggie, he starts falling for her despite his initial mistrust. Not only that, but Ike helps Maggie see that she actually has a second bad habit, which is that she loses who she truly is every time she meets a new man; obviously, the two unlikely lovebirds get together in the end. Andie and Ben Barry never make it down the aisle onscreen in "How to Lose a Guy in 10 Days," but if they did, it would probably look a lot like the final scene of "Runaway Bride."

In "How to Lose a Guy in 10 Days," Ben Barry bets that he can make any woman fall in love with him in less than two weeks — and in the 2011 rom-com "Crazy, Stupid, Love," Ryan Gosling's smooth-talking Lothario, Jacob, tells the hapless and recently separated Cal Weaver (Steve Carell) that he can teach him out to pick up women. Cal, who's left reeling when his wife Emily (Julianne Moore) asks for a divorce — and tells him that she had an affair with her coworker David Lindhagen (Kevin Bacon) — resists Jacob's teachings at first, but before long, he'd definitely make Ben proud as he hits the bar every night and meets a different beautiful woman. In an unlikely twist, though, Jacob starts to seriously fall for Hannah — a woman that he meets at a bar played by Gosling's frequent on-screen partner Emma Stone — only to discover that there's a connection between his new paramour and Cal that leads to an absolutely explosive third-act twist.

As with "How to Lose a Guy in 10 Days," "Crazy, Stupid, Love" relies on miscommunication and misunderstandings, although in this particular rom-com, neither Jacob nor Cal sees that aforementioned twist coming at all (so the movie is the one engaging in some light trickery rather than the characters). In any case, if you loved Matthew McConaughey and Kate Hudson's crackling chemistry in the older film, you'll definitely fall for Gosling and Stone's lived-in romance in "Crazy, Stupid, Love."

If you can get past some of the weirdest elements in Garry Marshall's 1999 romantic comedy "Never Been Kissed" — which we'll get to in just a moment — it's a pretty enjoyable staple of the genre, and it shares one major thing in common with "How to Lose a Guy in 10 Days" ... in that the main character is secretly writing an article about her supposed love interest. Drew Barrymore's 25-year-old Josie Geller works as a copy editor at the Chicago Sun-Times but dreams of being a reporter; when her boss Rigfort (Marshall himself) assigns her to a story where she has to go undercover at a local high school and figure out what makes teenagers tick, Josie is acutely aware of the fact that she was deeply unpopular as an actual high schooler. ("Josie Grossie" was her nickname, point in fact.) Josie definitely doesn't make a great impression at first when she tries too hard to fit in, but when her athletic and former popular high-schooler Rob (David Arquette) also starts cosplaying as a teenager, the two basically manage to take over South Glen South High School.

So wait — who does Josie end up writing about for the Sun-Times? That would be her English teacher Sam Coulson ("Alias" alum Michael Vartan), with whom she forms a special bond despite the fact that he thinks she's a high school student. Josie ends up unmasking herself at the senior prom after winning prom queen, crushing Sam and shocking her high school "friends," but ultimately, after reading her article about never truly being "kissed," Sam and Josie reunite in the movie's final moments. (Again, the high schooler and teacher dynamic is weird, but cognitive dissonance helps with this one.)

In the nicest way possible, if "How to Lose a Guy in 10 Days" made you crave another movie about manipulative, borderline lunatics, "My Best Friend's Wedding" is perfect for you. That's not a bad thing, truly; "My Best Friend's Wedding" is a staple of the genre, but Julia Roberts' main character Jules Potter is so unbelievably devious at times that you'll definitely think of all the tactics Andie Anderson uses on Ben Barry. (Frankly, because "My Best Friend's Wedding" came out in 1997, it probably inspired movies like "How to Lose a Guy in 10 Days.") When push comes to shove, Ben Barry and Andie Anderson's tactics are pretty mean, and unfortunately, Jules can also be downright vindictive and cruel when it comes to her best friend Michael O'Neil (Dermot Mulroney), a Chicago sportswriter who calls Jules (a food critic and fellow writer) in New York to reveal that he's getting married. See, Michael and Jules always had a "deal" that they would marry each other if they weren't engaged by the time they turned 28-year-old, a detail that depresses every single millennial who watches this movie; now, Jules is single and has to watch Michael and his young fiancée Kimmy (Cameron Diaz) throughout all their wedding festivities.

Basically everything Jules does in this movie is underhanded and mean, so if you didn't find most of Ben and Andie's antics to be off-putting, you'll be able to handle "My Best Friend's Wedding" with ease. Frankly, the whole thing is worth watching for Rupert Everett as George, Jules' queer best friend who does his best to keep her in check (but usually fails).

Throughout "How to Lose a Guy in 10 Days," both Ben Barry and Andie Anderson are pretending to carry on their relationship for professional gain — and while Will Gluck's 2011 romantic comedy "Friends With Benefits" takes a different approach, the two romantic leads are lying to themselves just like Andie and Ben before them. When art director Dylan Harper (Justin Timberlake) heads to New York City to meet with headhunter Jamie Rellis (Mila Kunis), she convinces him to take a lucrative position at GQ ... but the two end up hitting it off, becoming good friends before agreeing to be, well, "friends with benefits." Here's the problem: after the two start hooking up as platonic friends, they start developing feelings for one another, though they're both loathe to admit it.

Ben and Andie fall for each other without meaning to and resist it for as long as possible, just like Dylan and Jamie — but Gluck's movie gives the two leads a little more depth, introducing us to Jamie's wayward mother Lorna (Patricia Clarkson) and Dylan's father, played by Richard E. Jenkins, who is suffering from the early stages of dementia back in California and is cared for by Dylan's sister Annie (Jenna Elfman). Don't get it twisted, though; "Friends With Benefits" still has plenty of big, silly rom-com tropes amidst all of the familial drama. There's even a flash mob at the end. What more could you ask for?

Andie Anderson and Ben Barry both know about their own individual schemes, but in Gene Stupnitsky's raunchy 2023 comedy "No Hard Feelings," poor Percy Becker (Andrew Barth Feldman) has no idea that he's at the very center of a ruse perpetrated by his own parents. When we first meet Maddie Barker (Jennifer Lawrence), it's an understatement to say she's down on her luck; her car has just been repossessed but she needs it to work as an Uber driver, as she's at risk of losing her late mother's house over the property taxes. An opportunity arises when Percy's parents Allison and Laird — played perfectly by Laura Benanti and Matthew Broderick — offer Maddie a Buick Regal if she'll do one simple thing: "date" their son Percy, a shy and inexperienced high school graduate who's heading to Princeton University in the fall.

Maddie's attempts to, uh, "date" Percy range from awkward to downright traumatizing — like the scene where a fully nude Maddie has to fight off some local kids who stole her and Percy's close while the odd couple went skinny-dipping — and when Percy eventually finds out about his parents' deal with Maddie, he's left furious and heartbroken. Despite all of that, Maddie and Percy's dynamic is legitimately charming, and while the ending doesn't stick to strict romantic comedy standards, the whole venture is unexpectedly touching ... even though Maddie, Allison, and Laird are pulling a pretty mean trick on Percy throughout.