10 Movies Like How To Lose A Guy In 10 Days

During the 1990s and 2000s, there was a golden era for grand romantic comedies filled with famous faces, and “How to Lose a Guy in 10 Days,” released in 2003, is a shining example. Starring Kate Hudson as magazine columnist Andie Anderson and Matthew McConaughey as ad executive Benjamin Barry, this movie employs virtually every romantic comedy cliché imaginable, yet manages to stand out. The pairing of their characters, Andie and Ben, creates some delightfully alliterative names that complement each other well. In the film, Andie is on a mission to demonstrate her ability to drive a man away by acting excessively needy for just ten days, while Ben aims to convince any woman to fall in love with him within the same timeframe to secure a significant contract (it involves diamonds and becomes more understandable when viewed in context). As you might expect, they end up developing feelings for each other despite their initial plans. They eventually discover their deceptions, part ways, and reunite at the movie’s conclusion.

As a devoted admirer of romantic comedies, I can confidently say that the familiar formula of “How to Lose a Guy in 10 Days” never fails to amuse. The captivating performances by Hudson and McConaughey make this movie an unending delight. If you’ve already watched it, fret not! There are numerous other movies that share similarities with this gem. Whether they revolve around two characters engaged in conflicting strategies or a heartwarming third-act twist that eventually sets things right, here are some must-watch titles to add to your queue after “How to Lose a Guy in 10 Days.

10 Things I Hate About You

10 Things I Hate About You, a 1999 film adaptation of Shakespeare’s The Taming of the Shrew by Gil Junger, shares its title number with “How to Lose a Guy in 10 Days,” but the similarities between these movies extend beyond that. Set within the halls of Padua High School as a tribute to the Bard’s work, this contemporary retelling revolves around Kat Stratford (Julia Stiles), a prickly character whose younger sister Bianca (Larisa Oleynik) longs for a date. In an effort to protect their daughters, the strict father Walter (Larry Miller) sets a condition: Bianca can only date if Kat does. This rule presents an opportunity for Padua’s most popular jerk, Joey Donner (Andrew Keegan), who has designs on Bianca, as he enlists the help of Patrick Verona (Heath Ledger), a charming but stubborn character, to take Kat out on a date.

Despite their objections, this trick manages to bring Patrick and Kat together, while Cameron James (Joseph Gordon-Levitt), the new transfer at Padua, secretly wishes that sweet and beautiful Bianca might see through Joey’s act and choose him instead. It turns out that both Kat and Bianca discover Joey’s plan, pushing Bianca towards Cameron and leaving Kat angry with Patrick. In a twist reminiscent of Shakespearean comedies, everything ends up working out in the end. If it weren’t for Ledger, Stiles, Oleynik, and Gordon-Levitt, along with David Krumholtz as Michael Eckman, “10 Things I Hate About You” could have been just another run-of-the-mill teen movie. But thanks to their exceptional performances, it stands out as one of the best in the genre.

This trick somehow brings Patrick and Kat together despite their protests, with Cameron James (Joseph Gordon-Levitt) secretly hoping that Bianca might see through Joey’s deception and choose him instead. When both Kat and Bianca find out about Joey’s scheme, it pushes Bianca towards Cameron while making Kat angry at Patrick. The story has a twist similar to Shakespearean comedies, with everything working out in the end. If it weren’t for Ledger, Stiles, Oleynik, and Gordon-Levitt, as well as David Krumholtz as Michael Eckman, “10 Things I Hate About You” could have been just another typical teen movie, but their exceptional performances make it one of the best in the genre.

27 Dresses

Written by Aline Brosh McKenna, famously known for her work on “The Devil Wears Prada,” and directed by Anne Fletcher, the romantic comedy “27 Dresses” shares some similarities with “How to Lose a Guy in 10 Days,” but in an entirely distinct manner. Upon introduction, Jane Nichols (Katherine Heigl, at her peak of popularity from “Grey’s Anatomy”), lives up to the saying “always a bridesmaid, never a bride”; she has been a bridesmaid an astonishing 27 times. As the title suggests, the narrative revolves around Jane’s predicament. Jane harbors long-standing feelings for her boss George (Edward Burns), but when George falls for Jane’s reckless younger sister Tess (Malin Åkerman), Jane is left heartbroken; following George and Tess’ engagement, Jane unexpectedly encounters newspaper reporter Kevin Doyle (James Marsden), who uses the pen name “Malcolm” to write about weddings for a major publication.

It appears a predictable turn of events is unfolding – Kevin covertly pens an unpolished essay about Jane’s bridesmaid duties and impressive stats, causing her to fume. In retaliation, Jane interferes with George and Tess’ wedding until they ultimately decide to cancel it. Add in a fantastic performance by Judy Greer as a best friend, and a captivating chemistry between Marsden and Heigl, and you’ve got another fantastic romantic comedy from the 2000s. (By the way, casting directors, don’t forget Marsden is exceptionally charming – he should star in more romantic comedies!)

He’s Just Not That Into You

The 2009 romantic comedy “He’s Just Not That Into You,” directed by Ken Kwapis and written by Abby Kohn and Marc Silverstein, is essentially eight different rom-com stories combined into one. This ensemble film delves deeply into themes of deception and betrayal. In one narrative, the hopelessly romantic character Gigi (played by Ginnifer Goodwin) struggles to understand why her dates don’t return her calls until the bar manager Alex (Justin Long) offers some advice – if a man wants to call, he will do so. In another storyline, yoga instructor and aspiring singer Anna Marks (Scarlett Johansson) encounters a charming but married man named Ben (Bradley Cooper), who is a friend and coworker of Gigi’s friend Janine (Jennifer Connolly). Despite this complication, Anna and Ben embark on an affair that ultimately leads to disaster. Meanwhile, Gigi’s other coworker, Beth (Jennifer Aniston), becomes increasingly resentful when her long-term boyfriend Neil (Ben Affleck) refuses to propose. After a brief separation, they reconcile, and as expected, Neil eventually proposes. Drew Barrymore, Kevin Connolly, and Kris Kristofferson are among the other characters who make appearances in this movie.

If you’re looking for a series of films similar to “How to Lose a Guy in 10 Days,” consider watching “He’s Just Not That Into You.” However, be aware that many movies like these with interconnected stories, such as “Love Actually” and its sequels like “Valentine’s Day,” “Mother’s Day,” and “New Year’s Eve,” have received mixed reviews. So if you decide to watch them, do so knowing they might not be as enjoyable.

The Proposal

In romantic comedies, there are often intricate plans or deceptions, but it’s especially enjoyable when multiple characters participate in these schemes. That’s where “The Proposal” comes into play. Directed by Anne Fletcher and written by Peter Chiarelli, this film presents audiences with Margaret Tate (portrayed by Sandra Bullock, a queen of rom-coms), a strict publishing executive who is Canadian and resides in New York. When Margaret unintentionally breaches her visa regulations, she faces the possibility of being sent back to Canada unless she gets married, which brings Andrew Paxton (Ryan Reynolds) into the picture, Margaret’s overworked assistant. In exchange for helping them convincingly fake an engagement to fool the immigration officer following them — a cunningly amusing character played by Denis O’Hare — Margaret promises Andrew a promotion and the position of editor.

The situation becomes significantly intricate when Andrew brings Margaret to the quaint town of Sitka, Alaska to introduce her to his family, and although Andrew’s mother Grace (Mary Steenburgen) and grandmother Annie (Betty White) strive to make Margaret feel comfortable, Andrew’s father Joe (Craig T. Nelson) harbors suspicions about the whole affair. Predictably, chaos unfolds, but surprisingly, despite their engagement being entirely staged, Andrew and Margaret find themselves developing genuine feelings for each other. In due course, Andrew proposes to Margaret, enabling her to remain in New York and allowing them to commence a relationship. Reynolds and Bullock form an exceptional duo in “The Proposal,” with the late White providing ample humor as an eccentric grandmother… however, the most delightful aspect of this film may be that the central couple conspire to deceive others rather than deceiving each other.

Runaway Bride

As a devout fan, I can’t help but get excited about the fact that Julia Roberts and Richard Gere are reuniting for their second joint project, this time under the guidance of our beloved “Pretty Woman” director Garry Marshall. In this heartwarming tale, we follow the journey of Julia’s character, Maggie Carpenter, a free-spirited woman who, much like her character Andie Anderson, has a peculiar knack for leaving grooms at the altar.

Enter Richard Gere as Ike Graham, a grumpy New York columnist known for his biting wit. When he stumbles upon Maggie’s checkered past with wedding vows, he penned an unflattering article about her. Unfortunately, his research was based on the accounts of one of Maggie’s jilted suitors, leading to a rather harsh portrayal of our heroine.

Determined to set the record straight, Maggie reaches out to Ike, and in a surprising turn of events, he finds himself traveling to her hometown in Maryland. There, he encounters not only Maggie but also her latest suitor, Bob Kelly, played by Christopher Meloni. The stage is set for an unforgettable encounter between these two unlikely individuals.

In the quaint town of Hale, I find myself, not just penning an accurate tale about Maggie, but becoming deeply entwined in her life. At first, I harbored doubts and mistrust towards this flighty lass, but as our paths crossed more frequently, I found myself irresistibly drawn to her charm. To my surprise, I discovered that Maggie had a hidden habit – she’d lose herself every time she met a new man. As we navigated the ups and downs of our unconventional relationship, it became clear that we were destined for each other. If Andie and Ben Barry ever made it to the altar in “How to Lose a Guy in 10 Days,” their story might mirror the heartwarming conclusion of “Runaway Bride.

Crazy, Stupid, Love.

In the movie “How to Lose a Guy in 10 Days,” Ben Barry challenges himself to win over any woman within two weeks, while in the romantic comedy “Crazy, Stupid, Love” from 2011, Ryan Gosling’s character Jacob boasts that he can instruct any man on how to charm women. Cal Weaver (played by Steve Carell), who is left heartbroken after his wife Emily (Julianne Moore) confesses an affair with her coworker David Lindhagen (Kevin Bacon), initially refuses Jacob’s advice but eventually follows it, going to bars nightly and meeting various attractive women. However, in a surprising turn of events, Jacob develops genuine feelings for Hannah, a woman he meets at the bar and who is often portrayed by Emma Stone, only to learn that she has a connection with Cal that leads to a shocking climax in the third act.

Just like “How to Lose a Guy in 10 Days,” “Crazy, Stupid, Love” uses misunderstandings and miscommunication as its main themes. However, unlike in that movie, neither Jacob nor Cal anticipate the twist, making it the film itself that employs some subtle deception rather than the characters. If you were captivated by Matthew McConaughey and Kate Hudson’s electric chemistry in the previous film, then you are bound to be smitten with Gosling and Stone’s authentic romance in “Crazy, Stupid, Love.

Never Been Kissed

In essence, if you can look past some of the quirky aspects in Garry Marshall’s 1999 romantic comedy “Never Been Kissed,” it offers an enjoyable experience typical of the genre. Notably, much like “How to Lose a Guy in 10 Days,” the protagonist, Drew Barrymore’s character Josie Geller, is secretly writing about her perceived love interest. In this film, Josie, a 25-year-old copy editor at the Chicago Sun-Times with aspirations of being a reporter, is tasked by her boss (played by Marshall himself) to investigate high school life undercover. Being a former outcast herself, Josie struggles initially to fit in, but when athletic and popular high-schooler Rob (David Arquette) also adopts a teenage persona, their shared experience takes over South Glen South High School.

In the end, it turns out that Josie writes an article for the Sun-Times about her English teacher Sam Coulson, who happens to be Michael Vartan from “Alias”. Despite him initially believing she’s a high school student, they develop a unique connection. Later in the story, Josie reveals her true identity at the senior prom after being crowned prom queen, leaving Sam stunned and surprising her fellow students. However, after reading an article about never truly experiencing a kiss, Sam and Josie reconnect in the movie’s conclusion. (Although the relationship between a student and teacher is unusual, understanding contradictions helps explain this situation.)

My Best Friend’s Wedding

If you found “How to Lose a Guy in 10 Days” intriguing due to its portrayal of manipulative characters, then “My Best Friend’s Wedding” might just be the movie for you. It’s not necessarily a negative aspect; “My Best Friend’s Wedding” is a classic in this genre, but the protagonist Jules Potter, played by Julia Roberts, can be remarkably cunning at times, and her actions may remind you of Andie Anderson’s manipulations towards Ben Barry. To be clear, the tactics used by both Ben and Andie are quite unkind, and unfortunately, Jules can also become rather vindictive and harsh when it comes to her best friend Michael O’Neil, a Chicago sportswriter who calls Jules in New York to inform her that he is getting married. The twist here is that they had an agreement to marry each other if neither were engaged by the time they turned 28, a fact that leaves every millennial viewer feeling a pang of nostalgia; now, Jules finds herself single and watching Michael and his fiancée Kimmy throughout all their wedding celebrations.

In essence, the actions of the character Jules throughout this film are sneaky and unkind, so if you didn’t find many of Ben and Andie’s behaviors unpleasant, you should be able to enjoy “My Best Friend’s Wedding” without any issues. To put it simply, the movie is worth watching for Rupert Everett’s portrayal of George, Jules’ gay friend who tries to keep her in line (though often unsuccessfully).

Friends With Benefits

In the movie “How to Lose a Guy in 10 Days” and the romantic comedy “Friends With Benefits” (directed by Will Gluck in 2011), the main characters pretend to be in relationships for professional reasons, similar to Andie Anderson and Ben Barry. However, things take a different turn in “Friends With Benefits.” When art director Dylan Harper travels to New York City to meet with headhunter Jamie Rellis, he ends up landing a lucrative job at GQ and forming a strong friendship with her. As they begin their ‘friends with benefits’ arrangement, they start to develop feelings for each other, although they are reluctant to acknowledge it.

In a similar fashion to Dylan and Jamie, Ben and Andie unintentionally develop feelings for each other and attempt to avoid it for as long as they can. However, the film “Friends With Benefits” adds complexity to their characters, revealing Jamie’s troubled mother Lorna (Patricia Clarkson) and Dylan’s father, portrayed by Richard E. Jenkins, who is battling early stages of dementia in California and is looked after by his sister Annie (Jenna Elfman). Despite the heavy family drama, the movie still maintains the classic, humorous elements of a romantic comedy, culminating in a lively flash mob at its conclusion. What more could one desire?

No Hard Feelings

In Gene Stupnitsky’s 2023 comedy “No Hard Feelings,” it turns out that Percy Becker (Andrew Barth Feldman) is unaware he’s right at the heart of a plot devised by his own parents. At the start, Maddie Barker (Jennifer Lawrence), who is struggling financially as she recently lost her car and faces losing her late mother’s home due to property taxes, finds herself in a predicament. A solution presents itself when Percy’s parents, Allison and Laird (played by Laura Benanti and Matthew Broderick), propose an interesting deal: they will give Maddie a Buick Regal if she agrees to go on a few dates with their son, the timid and inexperienced high school graduate who plans to attend Princeton University in the fall.

Maddie’s attempts at courting Percy, which ranged from uncomfortable to devastating, were as diverse as they were distressing. A striking example was the incident where an embarrassed Maddie had to fend off some mischievous kids who swiped their belongings during a spontaneous skinny-dipping episode – all while the peculiar duo was in the water. When Percy eventually discovered his parents’ arrangement with Maddie, he was left enraged and heartbroken.

However, despite these tumultuous events, Maddie and Percy’s connection was undeniably endearing. The storyline didn’t adhere to traditional romantic comedy tropes, but the overall narrative proved surprisingly moving… even though Maddie, Allison, and Laird were playing a rather cruel prank on Percy in the process.

2025-01-11 20:30