25 Movies Like How to Lose a Guy in 10 Days: You might be looking for more movies like How to Lose a Guy in 10 Days if you like romantic comedies with funny romantic situations, familiar characters and situations, and a focus on the complexities of relationships and dating.
In this 2003 movie, Matthew McConaughey and Kate Hudson play a couple who secretly bet on their relationship to help their jobs but end up falling in love along the way.
Here are 25 movies that are like How to Lose a Guy in 10 Days in terms of genre, theme, story, or tone. Some of them even have the same players or the same people running them. You’re sure to find something that fits your taste, whether you want to laugh, cry, or look at love ferns.
25. How Do You Know (2010)
Reese Witherspoon plays a former softball player who gets cut from her team and has to figure out what to do with her life. She has relationships with two men: a charming baseball player (Owen Wilson) and an unhappy businessman (Paul Rudd).
- How Do You Know (2010)
She has to choose which one is best for her and figure out how she knows. This movie is like How to Lose a Guy in 10 Days in that it has a sports theme, a love triangle, and an emotional problem.
These are some movies like How to Lose a Guy in 10 Days that you can watch if you want some sweet romance and some laughs. All of them are fun and interesting in their own ways, and they will make you feel good about love and life.
24. What Happens in Vegas (2008)
Cameron Diaz and Ashton Kutcher play two people who don’t know each other but end up getting married in Las Vegas after a night of partying.
- what happens in Vegas (2008)
They want to end their marriage, but then they find out they’ve won $3 million. To get their share of the money, they have to stay married for six months and go to counseling classes. Along the way, they also try to make each other’s lives worse. This movie is like How to Lose a Guy in 10 Days in which they get married by chance, there’s a problem with money, and it’s funny as hell.
23. The Holiday (2006)
Cameron Diaz and Kate Winslet play two women who break up with their boyfriends and decide to swap houses for Christmas. Winslet goes to Los Angeles to meet Diaz’s friend, Jack Black, while Diaz goes to England to meet Winslet’s brother, Jude Law.
- The Holiday (2006)
Both of them find love and happiness in places they didn’t expect. This movie is like How to Lose a Guy in 10 Days in that it has a holiday theme, a love story between people from different cultures, and a happy ending.
22. The Bounty Hunter (2010)
Jennifer Aniston and Gerard Butler play a divorced pair who get back together when he is hired as a bounty hunter to bring her in for skipping bail.
- The Bounty Hunter (2010)
They end up going on a road trip together, where they face different risks and get back together. This movie is like How to Lose a Guy in 10 Days in that it has a lot of action, a tense relationship, and stars who get along well.
21. Just Go With It (2011)
Adam Sandler plays a plastic surgeon who acts like he’s married so he doesn’t have to make a commitment. He wants to date a young woman named Brooklyn Decker, but she finds out about his fake wife, Jennifer Aniston, and wants to meet her.
- Just Go With It (2011)
He gets Aniston and her kids to believe his lie, and they all go on vacation with him. This movie is like How to Lose a Guy in 10 Days in that there is a romantic lie, the story is hard to follow, and there are funny parts.
20. Monster-in-Law (2005)
Jennifer Lopez plays a woman who falls in love with a handsome doctor (Michael Vartan) whose jealous and manipulative mother (Jane Fonda) tries to ruin their relationship.
- monster-in-law (2005)
This movie is like How to Lose a Guy in 10 Days in that there are fights in the family, funny situations, and competition between the women.
19. Ghosts of Girlfriends Past (2009)
On the night before his brother’s wedding, Matthew McConaughey plays a womanizer who sees the ghosts of his past, present, and future lovers.
- Ghosts of Girlfriends Past (2009)
They show him what happens when he does bad things and what love is really about. This movie is like How to Lose a Guy in 10 Days in that it has a supernatural factor, a story arc about redemption, and a romantic comedy.
18. 27 Dresses (2008)
Katherine Heigl plays a woman who is always a bridesmaid. She has a crush on her boss, Edward Burns, who is engaged to Malin Akerman’s younger sister. She also meets James Marsden, a cynical reporter who wants to write a story about her obsession with weddings.
- 27 dresses (2008)
This movie is like How to Lose a Guy in 10 Days in that it’s about a wedding, the two main characters are in love with each other, and they’re both very nice.
17. Fool’s Gold (2008)
In the movie Fool’s Gold, Matthew McConaughey and Kate Hudson play a divorced couple who work together to find a lost Spanish galleon with a lot of gold on board.
- fool’s gold (2008)
Along the way, they face danger from a cruel gangster (Kevin Hart), a rival wealth hunter (Ray Winstone), and their own unresolved feelings for each other. Andy Tennant is in charge of the movie, which is set in a foreign place and has action, comedy, and romance.
16. A Little Bit of Heaven (2011)
Kate Hudson plays a carefree woman with cancer who falls in love with her doctor, who is played by Gael Garcia Bernal.
- A Little Bit of Heaven (2011)
God (Whoopi Goldberg) also comes to visit her and gives her three wishes. This movie is like How to Lose a Guy in 10 Days because of the life-changing event, the unlikely marriage, and the spiritual theme.
15. The Break-Up (2006)
Jennifer Aniston and Vince Vaughn play a couple that breaks up but stays in the apartment they used to share. They plan and play jokes on each other to make each other unhappy and force each other to leave.
- the break-up (2006)
But they also know that even though they are different, they still care about each other. This movie is like How to Lose a Guy in 10 Days in that the main characters don’t like each other and there are funny and sad parts.
14. Bridget Jones’s Diary (2001)
Based on the book by Helen Fielding, this movie stars Renee Zellweger as a single woman who decides to keep a diary of her personal and work life as she tries to improve herself and find love. She gets connected with two men: her charming boss (Hugh Grant) and a quiet lawyer (Colin Firth).
- Bridget Jones’s Diary (2001)
This movie is like How to Lose a Guy in 10 Days in that it has a funny narrator, a woman who is easy to relate to, and British humor.
13. No Strings Attached (2011)
Natalie Portman and Ashton Kutcher play two friends who decide to have a casual s*xual relationship with no emotional connection or commitment.
- No Strings Attached (2011)
But they soon figure out that they want more from each other than just sex. This movie is like How to Lose a Guy in 10 Days in that it is about two people who are friends but also have feelings for each other.
12. Crazy, Stupid, Love (2011)
Steve Carell plays a middle-aged man whose wife (Julianne Moore) comes out of the blue and asks for a divorce. He meets a smooth-talking ladies’ man, played by Ryan Gosling, who takes him under his wing and shows him how to be a better man and a better lover.
- Crazy, Stupid, Love (2011)
His teen son, Jonah Bobo, has a crush on his babysitter, Analeigh Tipton, who has a crush on Gosling’s character. And Gosling’s character falls in love with a lawyer (Emma Stone) who is already in a relationship with someone else. This movie is a lot like How to Lose a Guy in 10 Days in terms of how funny it is, how sad it is, and how it takes surprising turns.
11. He’s Just Not That Into You (2009)
This movie is based on the self-help book by Greg Behrendt and Liz Tuccillo. It tells the stories of several men and women in Baltimore who are having trouble with dating and relationships.
- He’s Just Not That Into You (2009)
Ben Affleck, Jennifer Aniston, Drew Barrymore, Bradley Cooper, Scarlett Johansson, Jennifer Connelly, Ginnifer Goodwin, Justin Long, and many others are in the group. If you like How to Lose a Guy in 10 Days because it shows love from different points of view and shows how hard dating can be, you might also like He’s Just Not That Into You.
10. Just Like Heaven (2005)
In this movie, Reese Witherspoon and Mark Ruffalo play a lonely engineer who moves into a new apartment where the ghost of a young doctor (Witherspoon) used to live.
- Just Like Heaven (2005)
Soon, they become friends and try to figure out what happened to her and why she can’t cross over. This movie is like How to Lose a Guy in 10 Days in that it has a magical element, strange humor, and a sweet love story.
9. Sweet Home Alabama (2002)
Reese Witherspoon plays a famous fashion designer who goes back to her hometown in Alabama to get a divorce from her husband (Josh Lucas) so she can marry her rich fiance (Patrick Dempsey) in New York.
- Sweet Home Alabama (2002)
She soon finds out, though, that she still cares about her old flame and that her past is not so easy to leave behind. This movie is like How to Lose a Guy in 10 Days in that there is a big difference between the city and the country, love is found again, and it is set in the beautiful South.
8. Failure to Launch (2006)
Matthew McConaughey plays a 35-year-old man who still lives with his parents (Kathy Bates and Terry Bradshaw) and has no plans to leave. His parents hire a trained interventionist (Sarah Jessica Parker) to get him into a relationship and get him to leave home.
- Failure to Launch (2006)
But when they start to like each other, things get harder. This movie is like How to Lose a Guy in 10 Days in that there is a love lie, the characters are weird, and funny things happen.
7. Something Borrowed (2011)
The book that this movie is based on was written by Emily Giffin. Ginnifer Goodwin plays a lawyer who has a crush on her best friend’s (Kate Hudson) fiance (Colin Egglesfield).
- Something Borrowed (2011)
She ends up sleeping with him after her birthday party, starting a hidden relationship that hurts her friendships and makes her feel bad about herself. This movie is like How to Lose a Guy in 10 Days in that it has a complicated love triangle, a moral problem, and a lot of emotional drama.
6. Bride Wars (2009)
Kate Hudson and Anne Hathaway play best friends whose relationship changes when they find out that they are both getting married on the same day at the same place. They go to great lengths to ruin each other’s big day, even though they are having problems in their own relationships.
- bride wars (2009)
This movie is a lot like How to Lose a Guy in 10 Days in terms of the friendship between the women, the theme of a wedding, and the funny things that happen.
5. Love Actually (2003)
During the Christmas season in London, this movie follows the lives of a number of pairs and single people. It looks at many different things about love, like romance, friendship, family, cheating, and sadness.
- Love Actually (2003)
Hugh Grant, Emma Thompson, Colin Firth, Keira Knightley, Liam Neeson, Alan Rickman, and many more stars are in the movie. If you like How to Lose a Guy in 10 Days because it shows different kinds of relationships and makes you feel good, you might also like Love Actually.
4. The Ugly Truth (2009)
Katherine Heigl and Gerard Butler play two TV stars who have very different ideas about love and relationships. Heigl is the producer of a morning show, and she hires Butler to lead a segment on dating that is blunt and sexist.
- The Ugly Truth (2009)
At first, they don’t agree on anything, but in the end, they learn a lot about the subject from each other. This movie is like How to Lose a Guy in 10 Days in that it has witty dialogue, a story about how opposites meet, and a setting in the media.
3. The Proposal (2009)
In this movie, Sandra Bullock and Ryan Reynolds play a boss and her helper. The boss gets engaged to her assistant to keep from being deported.
- The Proposal (2009)
But, much to their surprise, when they start to feel real feelings for each other, they realize that this act isn’t as fake as they thought it was at first. This movie is a lot like How to Lose a Guy in 10 Days in terms of plot and tone. There is a lot of fun and romance in it.
2. 10 Things I Hate About You (1999)
In this modern version of Shakespeare’s The Taming of the Shrew, Julia Stiles, and Heath Ledger play two opposites who are set up by a scheming high school student (Joseph Gordon-Levitt) who wants to date Stiles’ younger sister (Larisa Oleynik).
- 10 Things I Hate About You (1999)
Like How to Lose a Guy in 10 Days, this movie is about a dating bet that leads to real feelings between the two people involved.
1. The Wedding Planner (2001)
Jennifer Lopez plays a successful wedding planner who falls in love with a beautiful doctor (Matthew McConaughey) who is the groom of one of her clients.
- The Wedding Planner (2001)
This movie has a lot in common with How to Lose a Guy in 10 Days. For example, the main characters are both focused on their careers, there is a love lie, and the main characters get along well.
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Conclusion
These are some movies like How to Lose a Guy in 10 Days that you can watch if you want some sweet romance and some laughs. All of them are fun and interesting in their own ways, and they will make you feel good about love and life.
There’s something for everyone, whether you want action, comedy, drama, or magic. So get some popcorn, kick back, and watch these movies like “How to Lose a Guy in 10 Days.”
Source: Season Release