28 Movies Like How To Lose A Guy In 10 Days You Can't Miss - Endless Popcorn
Scene from Clueless for movies like How To Lose A Guy In 10 Days post.

28 Movies Like How To Lose A Guy In 10 Days You Can’t Miss

Scene from Clueless for movies like How To Lose A Guy In 10 Days post.

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Did ‘How To Lose A Guy In 10 Days’ have you laughing out loud and secretly rooting for Andie and Ben, amidst all their romantic shenanigans? Oh, the rollercoaster of love, laughter, and a little bit of mischief! If that film left you craving more of those hilariously unpredictable romantic plots, then brace yourself!

We’ve combed through the vast universe of romantic comedies to find movies that resonate with the charm, wit, and unpredictability of ‘How To Lose A Guy In 10 Days’. Ready to dive into a world where love rules, but with a twist? Pour yourself a glass of wine, get that tub of ice cream, and let’s journey together through the world of romance, sprinkled generously with humor and unexpected turns!

1.  Easy A

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Easy A Movie Description

Olive, a shy and timid teenage girl, is prompted by her best friend to share details of her uneventful weekend. Making an attempt to seem more interesting, she fabricates a story about her supposedly wild weekend.

Little does she know that the high school’s busybody has overheard the conversation and quickly spreads this untruth around her school. With the exaggerated story about her now circulating, Olive quickly becomes notorious but for all the wrong reasons.

2.  You've Got Mail

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You’ve Got Mail Movie Description

Kathleen Kelly, a hardworking boutique bookseller, is struggling to make ends meet in the wake of the arrival of Joe Fox and his corporate Foxbooks chain across the street.

When they meet online, however, their initial animosity fades away as an intense anonymous romance blossoms between them. Unaware of each other’s true identity, they continue their online relationship until Joe learns that his beloved cyber lover is actually his business rival.

3.  The Ugly Truth

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The Ugly Truth Movie Description

Abby Richter is an ambitious TV producer who has spent far too much time searching for the right partner and still remains single.

When her employers team her up with Mike Chadway, a notorious TV celebrity and chauvinist, he sets out to prove his theories on the differences between men and women by putting Abby through a series of tests.

4.  Love Happens

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Love Happens Movie Description

Dr. Burke Ryan is an acclaimed self-help guru on the brink of a major success, but he’s held back by his unresolved grief over the death of his wife.

Eloise Chandler is a successful businesswoman who has grown tired of dating and is instead focusing all her energy on her flourishing flower shop. When these two seemingly unlikely people meet, a spark is ignited.

5.  Clueless

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Clueless Movie Description

Cher, the quintessential queen bee of her Beverly Hills high school, is always eager to meddle in the lives of others. Obsessed by the idea of being able to make perfect matches for those around her, she sets her sights on two teachers whom she attempts to bring together.

After experiencing success with this endeavor, Cher turns her attention to Tai, a clumsy and awkward new student who is desperately in need of a makeover. Cher lavishes her with attention and helps transform her into an ultra-chic fashionista.

6.  Mean Girls

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Mean Girls Movie Description

Cady Heron is a teenage girl who spent her formative years in Africa, being educated by her scientist parents. As fate would have it, Cady and her family eventually move to the suburbs of Illinois, giving her the chance to finally experience public school.

She quickly learns about the complicated social hierarchy that exists between different groups of students, and eventually finds herself welcomed into the ranks of an elite clique known as “the Plastics”. Despite her newfound popularity, Cady soon discovers that her new friends are not always what they seem.

7.  Just Go with It

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Just Go with It Movie Description

Danny Maccabee, a plastic surgeon with a recently broken heart, is determined to enjoy future dates without any strings attached. To do this, he creates an elaborate web of lies and tells everyone that he is married.

His plan works until he meets Palmer – the ideal woman for him that he has been searching for – and she resists involvement. Rather than coming clean and confessing his lies, Danny enlists the help of Katherine – his assistant – to pretend that she is his soon-to-be ex-wife.

8.  13 Going on 30

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13 Going On 30 Movie Description

Jenna, a young teen fed up with the perils of junior high school, wishes desperately to be an adult. Little does she know that her wish will soon become reality when she is miraculously transformed overnight into a thirty-year-old version of herself (Jennifer Garner).

Although Jenna is excited by the newfound freedom that adulthood brings, she quickly discovers that the real world is not only quite different from her adolescent dreams but also far more complicated.

9.  50 First Dates

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50 First Dates Movie Description

Henry, a doting Playboy, is enamored with Lucy and determined to win her affection. However, she is afflicted with short-term memory loss and cannot remember anything from the day before. Every morning, Henry must prove his commitment to her anew.

While her friends and family are skeptical of his intentions, Henry persistently showers her with attention and affection in order to demonstrate the depth of his affection.

10.  The Princess Diaries

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The Princess Diaries Movie Description

Mia Thermopolis is an ordinary teenage girl living in San Francisco, but her life is soon thrown into chaos when she learns that she is actually a princess of the small European principality of Genovia.

With the help of her formidable grandmother, Queen Clarisse Renaldi, Mia embarks on a comical journey to learn what it means to be royalty. Along the way, she must face numerous challenges such as handling her mother’s new fiancé and coping with a scheming rival for the throne.

11.  Two Weeks Notice

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Two Weeks Notice Movie Description

Lucy Kelson, a driven and dedicated environmental lawyer, is determined to preserve a local community center and decides to go to work for the indecisive and weak-willed billionaire George Wade as part of the deal. Working as his legal advisor, she soon finds herself not only handling his legal matters but also helping him dress himself properly.

When the time comes for her to leave the firm, she finds herself growing jealous of his new legal advisor June Carter, a Harvard graduate. Despite being ready to move on, Lucy starts having second thoughts about leaving George and faces a difficult decision.

12.  Freaky Friday

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Freaky Friday Movie Description

Tess Coleman and her daughter Anna are complete opposites – Tess is a single mother, while Anna is a teenage girl. But when they receive mysterious fortunes at a Chinese restaurant, their lives get turned upside down.

After an eerie overnight transformation, the two wake up to find that they have switched bodies! Forced to take on each others’ lives, they soon discover the power of empathy and gain a newfound appreciation for one another.

13.  What Happens in Vegas

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What Happens in Vegas Movie Description

Joy McNally and Jack Fuller are two complete strangers who find themselves in the surreal position of being married after a wild night in Las Vegas.

When the judge refuses to grant an annulment, the couple is forced to make their impromptu marriage work. With a huge jackpot at stake, they embark on a tumultuous journey of self-discovery as they attempt to come to terms with their unlikely union.

14.  27 Dresses

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27 Dresses Movie Description

Jane, a single woman who puts others before herself, has been the go-to for brides needing help with wedding planning since she was young. When Jane’s younger sister Tess captures the heart of the man Jane had secretly been in love with for years, Jane is left questioning her role as a perpetual bridesmaid.

At the same time, a dashing reporter (James Marsden) sees Jane’s unique situation as the perfect story he needs to get off the bridal beat and into his dream job.

15.  What Women Want

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What Women Want Movie Description

When John, a chauvinistic advertising executive, discovers that he has acquired the miraculous power to hear what women are thinking, his first thought is to use it to bring about the downfall of his powerful female boss.

Armed with this newfound knowledge, John begins plotting her demise. As John increasingly gets more and more ambitious in his scheming, he begins to develop an unlikely admiration for his boss and even starts to fall in love with her.

16.  Friends with Benefits

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Friends With Benefits Movie Description

Jamie and Dylan are two friends who have both experienced a series of broken romances. Having had enough, they decide to take a break from looking for true love and instead focus on having fun.

When Jamie, an executive recruiter from New York, lures Dylan, an art director from Los Angeles, to take a job at GQ magazine in New York, the two of them quickly become fast friends. But when they decide to add sex to their friendship, things start to get complicated.

17.  What a Girl Wants

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What a Girl Wants Movie Description

Daphne, an adventurous and curious American teenager, decides to take a risk and board a plane to England without warning or informing anyone.

Upon arriving at her destination, she discovers the surprising truth – her father is Lord Henry Dashwood, a member of the British upper class who is running for political office. Unaware of her existence, Lord Henry warmly welcomes Daphne into his life, but his family and current betrothed are unimpressed.

18.  The Proposal

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The Proposal Movie Description

High-powered book editor Margaret Tate finds herself in the unfortunate predicament of being deported to Canada. Desperate to stay, she turns to her hapless assistant Andrew Paxton for help.

Faced with no other option, Andrew reluctantly agrees to pretend they are engaged, though he imposes a few conditions of his own. Embarking on a roller-coaster ride of unforeseen complications, the unlikely couple is forced to confront their true feelings for each other and the looming question of whether or not they should get married.

Movies Like The Proposal

19.  Failure to Launch

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Failure To Launch Movie Description

Tripp, a 35-year-old professional layabout, is content to stay at home and be cared for by his doting mother Sue. But enough is enough for Sue and her husband Al, who devise a plan to get Tripp out of the house – they enlist the help of Paula, who employs her womanly charms to encourage Tripp to move out.

20.  She's All That

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She’s All That Movie Description

High school star Zach Siler is used to being the envy of his peers, but his reputation takes a drastic turn when his long-time girlfriend, Taylor, leaves him for sleazy reality television star Brock Hudson.

Desperate to regain the admiration of his peers, Zach agrees to an unlikely challenge, he must win over nerdy outcast Laney Boggs and help her become the school’s next prom queen.

21.  Legally Blonde

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Legally Blonde Movie Description

Elle Woods (Reese Witherspoon) is a stunningly beautiful and intelligent woman who has achieved it all. She is the most popular girl on campus, top of her graduating class, and has a glamorous job waiting for her after college.

However, there is one thing missing from her perfect picture of success – a proposal from her long-time boyfriend Warner (Matthew Davis). When he goes off to Harvard Law School, Elle is determined to follow him and win his heart forever.

22.  My Best Friend's Wedding

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My Best Friend’s Wedding Movie Description

Julianne Potter and Michael O’Neal have been childhood friends since they were just kids. They made a deal to marry each other if they were both still single by the age of 28.

But days before Julianne’s 28th birthday, Michael suddenly announces his engagement to a stunningly beautiful 20-year-old named Kimberly.

Upon hearing the news, Julianne realizes that she is actually in love with Michael and makes it her mission to stop the wedding.

23.  He's Just Not That Into You

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He’s Just Not That Into You Movie Description

Beth, Neil, Gigi, Mary and Janine are all friends living in Baltimore in their 20s and 30s who find themselves tangled in a web of complicated relationships.

Beth, ever the romantic, longs for commitment from Neil but he isn’t on the same page; Gigi’s tired of waiting by the phone for someone to call; Mary’s surrounded by supportive friends who all happen to be men, none of whom she’s interested in; and Janine finds her husband tempted by his ex-girlfriend Anna.

24.  The Wedding Planner

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The Wedding Planner Movie Description

Mary and Steve’s fateful encounter is only the beginning of a whirlwind romance. Meeting while Mary is celebrating her most successful event to date, the wedding of Internet tycoon Fran Donelly (Bridgette Wilson-Sampras), their connection is almost instant.

When a near-fatal accident involving a runaway dumpster threatens Mary’s life, Steve races to her aid, saving her from a certain death.

25.  17 Again

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17 Again Movie Description

Mike O’Donnell is a middle-aged man haunted by his past mistakes and longing for a better future. Years ago, as a high-school basketball star, he gave up his promising prospects to marry his girlfriend and raise their child – only to see his marriage fall apart years later, leaving him feeling like a failure on all accounts.

When he is inexplicably given a second chance to relive his teenage years, Mike jumps at the opportunity to fix the mistakes of his past – but in doing so, he may be jeopardizing his present and future.

26.  She's the Man

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She’s the Man Movie Description

Viola Johnson (Amanda Bynes) finds herself in a tricky situation when she makes the rash decision to disguise herself as her twin brother, Sebastian, and enroll at a prestigious boarding school in his place.

With her true identity concealed, Viola quickly finds herself involved in a tangle of complications when her roommate Duke falls for her, unaware that she is actually a girl. Meanwhile, Olivia, another student at the school, has also fallen for Sebastian believing him to be Viola’s twin.

27.  Fool's Gold

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Fools Gold Movie Description

Ben Finnegan, a passionate treasure hunter, is on a mission to find the legendary Queen’s Dowry. But his obsession with the search has cost him both his marriage to Tess and his treasured boat.

After stumbling upon a vital clue hinting at the whereabouts of the treasure, Ben takes Tess and her billionaire employer Nigel Honeycutt along for the ride.

28.  10 Things I Hate About You

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10 Things I Hate About You Movie Description

Kat Stratford is a beautiful and intelligent teenage girl, though her sharp wit and abrasive attitude make it difficult for her to find a boyfriend. This poses a problem for her sister Bianca, whose strict parents won’t let her date until Kat finds someone first.

When new arrival Patrick Verona enters the picture, Kat begins to open up to the possibility of romance. Patrick is a classic bad boy with a heart of gold, so it’s no surprise when his effortless charm slowly begins to win her over. Will Kat take a chance on love and let down her guard? Can Patrick prove that he is more than meets the eye?

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