You know, the type of movie that makes you burst into laughter, feel a little flutter in your heart, and perhaps even be a reason for your happy tears. If you enjoy “How to Lose a Guy in 10 Days,” then you’re in luck!
This article is your guide to finding similar films that are packed with funny situations, undeniable chemistry, and that all-important happily ever after (or at least a happy ending for now!).
What Makes “How to Lose a Guy in 10 Days” So Entertaining?
It’s the classic battle of the sexes with a twist. We’ve got Andie, a woman focused on her career who believes she can drive any man away, and Ben, the charming marketing expert who bets he can make any woman fall for him.
Their amusing schemes and undeniable attraction create a whirlwind romance that’s both funny and heartwarming.
But “How to Lose a Guy in 10 Days” isn’t the only movie out there that can offer that perfect rom-com blend.
Get ready because we’re about to explore a whole world of films that will have you attached to the screen, rooting for the couple, and maybe even taking notes for your own love life (though we don’t recommend trying all of Andie’s tactics!).
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35+ Movies Like “How To Lose A Guy In 10 Days”
#1 Things I Hate About You (1999)
A pretty, popular Bianca (Larisa Oleynik) is forbidden to date until her shrewish older sister Kat (Julia Stiles) does.
To get around this rule, Bianca’s suitor Cameron (Joseph Gordon-Levitt) convinces Patrick Verona (Heath Ledger), a bad boy, to take Kat out. What starts as a scheme turns into something real.
#2 The Wedding Planner (2001)
Mary Fiore (Jennifer Lopez) is a wedding planner who gets engaged to a charming doctor, Steve Edison (Matthew McConaughey).
It turns out Steve is the fiancé of her client, a rich socialite named Fran (Sandra Bullock). Mary must now juggle her client’s wedding plans while dealing with her own conflicting feelings.
#3 The Proposal (2009)
Margaret Tate (Sandra Bullock) is a powerful book editor who faces deportation to Canada. To avoid this, she forces her assistant Andrew Paxton (Ryan Reynolds) to marry her.
They go to Andrew’s hometown in Alaska to meet his family, where funny things happen.
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#4 27 Dresses (2008)
Jane (Katherine Heigl) is a hopeless romantic who loves weddings but has never found her own happily ever after.
She’s been a bridesmaid 27 times and is starting to lose hope. When her younger sister Tess (Malin Åkerman) gets engaged to Jane’s boss, George (Edward Burns), Jane realizes she may be in love with him.
#5 Hitch (2005)
Alex Hitchens (Will Smith) is a “date doctor” who helps men win over the women of their dreams.
He takes on a new client, Albert Brennaman (Kevin James), a shy accountant who is smitten with a celebrity, Allegra Cole (Eva Mendes). However, things get complicated when Hitch falls for Allegra himself.
#6 While You Were Sleeping (1995)
Lucy Moderatz (Sandra Bullock) is a lonely token collector who dreams of a better life. One snowy day, she saves a man named Peter Callaghan (Peter Gallagher) from being mugged.
He falls into a coma, and Lucy is mistaken for his fiancée. She is then swept away by Peter’s wealthy family, but things get complicated when Peter wakes up and can’t remember anything.
#7 You’ve Got Mail (1998)
Kathleen Kelly (Meg Ryan) and Joe Fox (Tom Hanks) are competitors who own rival bookstores. Unbeknownst to each other, they strike up an anonymous online romance. When they discover each other’s true identities, things get interesting.
#8 When Harry Met Sally (1989)
Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) are cynics who believe that men and women can’t be friends. Over 11 years, they keep bumping into each other and their views on love start to change.
#9 Sleepless in Seattle (1993)
Sam Baldwin (Tom Hanks) is a widower who calls a radio talk show to share his grief with his son, Jonah. Jonah puts his dad on air, where he talks about how much he misses his wife.
Annie Reed (Meg Ryan), a Baltimore journalist, hears Sam’s story and is touched. She decides to write a column about him, and soon letters begin pouring in from women all over the country who want to meet Sam.
#10 My Best Friend’s Wedding (1997)
Julianne Potter (Julia Roberts) is a food critic who realizes she is in love with her best friend, Michael O’Neal (Dermot Mulroney), just as he is about to get married to another woman, Kimberly Wallace (Cameron Diaz). Julianne sets out to stop the wedding and win over Michael’s heart.
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#11 Notting Hill (1999)
William Thacker (Hugh Grant) is a travel bookstore owner in Notting Hill, London. His life is turned upside down when famous Hollywood actress Anna Scott (Julia Roberts) walks into his shop.
Even after their different worlds, they strike up an unlikely friendship that soon blossoms into something more.
#12 Crazy Rich Asians (2018)
New York economics professor Rachel Chu (Constance Wu) travels to Singapore with her boyfriend Nick Young (Henry Golding) to attend his best friend’s wedding.
There, Rachel learns that Nick comes from a family of extraordinary wealth and is considered one of Singapore’s most eligible bachelors.
Rachel has to deal with fancy parties, mean rumors, and family members who don’t approve.
#13 The Princess Bride (1987)
Westley (Cary Elwes) must rescue his true love Princess Buttercup (Robin Wright) from the evil Prince Humperdinck (Chris Sarandon).
Along the way, he encounters a host of colorful characters, including a cunning Sicilian with a remarkable memory (Wallace Shawn), a giant with a heart of gold (André the Giant), and a beautiful swordfighter with a mask (Mandy Patinkin).
#14 Clueless (1995)
Cher Horowitz (Alicia Silverstone) is a beautiful, popular Beverly Hills high school student who is as clueless about the real world as she is self-assured.
When she decides to give a new student, Tai (Brittany Murphy), a makeover, Cher’s world is turned upside down.
#15 She’s All That (1999)
Zack Siler (Freddie Prinze Jr.) is a popular high school jock who makes a bet with his friends that he can turn any girl into the school’s prom queen.
He sets his sights on Laney Boggs (Rachael Leigh Cook), a quirky and artistic loner. However, Zack soon finds himself falling for Laney for real.
#16 13 Going on 30 (2004)
Jenna Rink (Jennifer Garner) is a nerdy 13-year-old girl who wishes she could be grown up.
On her birthday, her wish comes true, and she wakes up as a 30-year-old woman (Jennifer Garner). Jenna must now navigate the adult world while trying to find her way back to her childhood.
#17 The Holiday (2006)
Iris (Kate Winslet), a British journalist, and Amanda (Cameron Diaz), an American movie trailer producer, are both heartbroken. They decide to swap homes for the holidays in a bid to escape their troubles.
Iris goes to Amanda’s sunny Los Angeles mansion, while Amanda heads to Iris’s cozy cottage in the English countryside. In their new surroundings, both women find love and happiness
#18 Bridget Jones’s Diary (2001)
Bridget Jones (Renée Zellweger) is a Bridget Jones is a 32-year-old single woman who keeps a diary about her life, loves, and weight struggles.
Things get complicated when she starts dating two men at the same time: the charming but commitment-phobic Daniel Cleaver (Hugh Grant) and the uptight lawyer Mark Darcy (Colin Firth).
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#19 Silver Linings Playbook (2012)
Pat Peoples Jr. (Bradley Cooper) is a former teacher who has been in a mental institution for bipolar disorder. After being released, Pat moves back in with his parents (Robert De Niro and Jacki Weaver) and tries to rebuild his life.
He sets his sights on Tiffany Maxwell (Jennifer Lawrence), a young widow who also has her own emotional baggage. Together, they help each other heal and find love.
#20 Crazy, Stupid, Love. (2011)
Cal Weaver (Steve Carell) is a seemingly happy suburban husband whose life falls apart when his wife, Emily (Julianne Moore), asks for a divorce.
Cal turns to a charming bachelor named Jacob Palmer (Ryan Gosling) for help in navigating the dating scene.
#21 The Apartment (1960)
C.C. Baxter (Jack Lemmon) is a lowly office worker who rises through the ranks by loaning out his apartment for the extramarital affairs of his superiors.
However, things get complicated when he falls in love with Fran Kubelik (Shirley MacLaine), the elevator operator in his building, who is also seeing one of the men using his apartment.
#22 Breakfast at Tiffany’s (1961)
Holly Golightly (Audrey Hepburn) is a charming and eccentric socialite who lives in New York City. She spends her days chasing wealthy men and dreams of a life of luxury.
When down-on-his-luck writer Paul Varjak (George Peppard) moves in downstairs, their lives become intertwined.
#23 Falling for Christmas (2021)
A spoiled hotel heiress, Sierra Belmont (Lindsay Lohan), gets amnesia after a skiing accident and finds herself in the care of a handsome lodge owner, Jake Russell (Chord Overstreet).
With Christmas approaching, Sierra must learn to appreciate the simple things in life and find her way back to herself.
#24 His Girl Friday (1940)
Walter Burns (Cary Grant) is a hard-nosed newspaper editor who is about to lose his ace reporter, Hildy Johnson (Rosalind Russell), to marriage.
To try and stop her from leaving, Walter assigns Hildy to cover a condemned man’s story, hoping to win her back.
#25 Plus One (2019)
Lucy (Lucy Liu) and Alice (Natalie Morales) are best friends who are both single. When they are both invited to the same wedding as plus ones for each other, they decide to go together and have a fun girls’ weekend.
However, their plans are complicated when they both start to develop feelings for the same guy.
#26 Pretty Woman (1990)
Edward Lewis (Richard Gere) is a wealthy businessman who hires Vivian Ward (Julia Roberts), a Hollywood prostitute, to be his escort for a week.
Edward takes Vivian to social events and business meetings, and Vivian begins to transform from a streetwalker into a sophisticated lady. As they spend more time together, Edward starts to develop feelings for Vivian.
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#27 The Big Sick (2017)
Kumail Nanjiani plays a Pakistani comedian who falls in love with Emily Gordon (Zoe Kazan), a graduate student. However, their relationship is complicated by cultural differences and Emily’s illness.
#28 Palm Springs (2020)
Nyles Daytona (Andy Samberg) and Sarah Wilder (Cristin Milioti) meet at a Palm Springs wedding. They soon discover they’re stuck reliving the same day over and over again.
#29 Groundhog Day (1993)
Weatherman Phil Connors (Bill Murray) is sent to cover the annual Groundhog Day celebration in Punxsutawney, Pennsylvania. However, he finds himself reliving the same day over and over again.
Phil must use this time loop to become a better person and win the love of his producer, Rita Hanson (Andie MacDowell).
#30 About Time (2013)
Tim Lake (Domhnall Gleeson) discovers that the men in his family can travel in time. He decides to use this power to improve his love life, but he soon learns that some things are best left unchanged.
#31 Four Weddings and a Funeral (1994)
Hugh Grant stars as a commitment-phobic man who finds himself attending five weddings and a funeral over a year.
Through these events, he grapples with his own ideas about love and relationships.
#32 She’s Having a Baby (1988)
John Hughes classic tells the story of a Chicago architect, Jake (John Cusack), whose life is turned upside down when his girlfriend, Kristy (Molly Ringwald), becomes pregnant. Jake must learn to deal with the responsibilities of fatherhood and navigate the challenges of their relationship.
#33 When We Met (2007)
Noah (Steve Carell) is a cynical architect who meets a young woman named Elisa (Jessica Alba) on a flight to Paris.
They spend a magical night together, but then they lose touch. Five years later, Noah gets a chance encounter with Elisa again and he must decide whether to pursue a relationship with her.
#34 The Hating Game (2021)
Lucy Hutton (Lucy Hale) and Joshua Templeton (Austin Stowell) are co-workers who are constantly at odds with each other. However, their rivalry may be masking a deeper attraction.
#35 A Perfect Pairing (2022)
Lola Alvarez (Victoria Justice) is a passionate wine salesperson who travels to Australia to land a new client. While there, she works with a cynical vineyard manager, Max (Adam Demos), and sparks fly between them.
#36 Your Place or Mine (2023)
Debbie (Reese Witherspoon) and Peter (Ashton Kutcher) are best friends who have lived on opposite coasts for 20 years. They decide to swap houses for a week, and their lives are turned upside down.
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#37 The Half of It (2020)
Ellie Chu (Leah Lewis), a shy high school student, helps the popular football player Paul Munsky (Daniel Diemer) write love letters to Aster Flores (Alexis Demirand), the girl of his dreams. However, Ellie soon finds herself developing feelings for Aster herself.
#38 The Set Up (2018)
Harper (Zoey Deutch) and Charlie (Glen Powell) are assistants to two high-powered executives who are constantly at war with each other.
Harper and Charlie decide to set their bosses up on a date in hopes of improving their working relationship.
However, their plan backfires when Harper and Charlie start to develop feelings for each other.
