Most romantic comedies (rom-coms) follow a similar structure, with their own unique twists. Ordinarily, in a rom-com, an unlikely duo are brought together, a conflict arises that pulls them apart and a heartfelt and unforgettable declaration of love brings them back together.
Even though rom-coms do often feature cliché and a predictable ending here and there, they also make for great comfort films that never get old. A memorable rom-com will make you laugh, and maybe even make you cry.
Below are 10 classic rom-coms that can be enjoyed time and time again – without getting old.
Kate Hudson and Matthew McConaughey starred in the popular rom-com “How to Lose a Guy in 10 Days.” (Jim Spellman/WireImage)
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- “How to Lose a Guy in 10 Days”
- “When Harry Met Sally”
- “10 Things I Hate About You”
- “Jerry Maguire”
- “The Proposal”
- “Bridesmaids”
- “Crazy, Stupid, Love”
- “My Best Friend’s Wedding”
- “You’ve Got Mail”
- “My Big Fat Greek Wedding”
1. “How to Lose a Guy in 10 Days”
In “How to Lose a Guy in 10 Days,” two individuals working in New York City are brought together by their places of employment. Andie Anderson, a journalist played by Kate Hudson, pitches a magazine storyline which turns into the title “How to Lose a Guy in 10 Days.” In order to complete the assignment, she needs to find a man to date.
Benjamin Barry, an advertiser played by Matthew McConaughey, bets his co-workers he can make a woman fall in love with him in 10 days in order to win the lead in a huge campaign.
The pair unknowingly uses each other to complete their tasks, but feelings eventually begin to get in the way of their end goals.
2. “When Harry Met Sally”
The 1989 movie “When Harry Met Sally” is a display of the age-old question: can a man and a woman be platonic friends?
Billy Crystal and Meg Ryan star in this movie as Harry and Sally respectively.
At the start of the film, Harry is dating Sally’s friend Amanda. When both Harry and Sally need to get to New York City, the two wind up carpooling to their destination.
“When Harry Met Sally” explores the idea of whether a man and a woman can just be friends. (Hulton Archive/Getty Images)
After hours of car conversation, the two go their separate ways, but this is not the last time they see each other.
The movie takes place over many years, and through this time, Harry and Sally bump into each other on various occasions, growing closer with each new meeting.
3. “10 Things I Hate About You”
Not to be confused with “How to Lose a Guy in 10 Days,” “10 Things I Hate About You” stars Julia Stiles and Heath Ledger as Kat Stratford and Patrick Verona.
Cameron James, played by Joseph Gordon-Levitt, is the new kid in school. He wants to go out with Bianca Stratford, played by Larisa Oleynik, who tells him she is not allowed to date until her older sister Kat does.
Kat is very anti-social and not interested in dating, making Cameron’s task a tricky one. He ends up enlisting Patrick to charm Kat into going out with him so that he can date Bianca.
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In “10 Things I Hate About You,” Patrick Verona (Heath Ledger) is paid to go out with Kat Stratford (Julia Stiles). (Buena Vista/Getty Images)
4. “Jerry Maguire”
This 1996 movie is about Jerry Maguire, a sports agent played by Tom Cruise who pairs up with single mother Dorothy Boyd, played by Renée Zellweger. Dorothy has a young son named Ray, who Jerry grows quite close to. The two earn one client, Rod Tidwell, played by Cuba Gooding Jr.
Jerry and Dorothy have a lot in the balance, between work, Ray and their own budding relationship.
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5. “The Proposal”
When Margaret Tate, played by Sandra Bullock, is about to lose her job upon trouble with her visa renewal application, she must think fast to save her career.
In an attempt to keep her job, she claims to be engaged to her assistant, Andrew, played by Ryan Reynolds.
After a meeting with an immigration officer who clearly suspects fraud, the fake couple heads to Sitka, Alaska, to meet Andrew’s family.
The late Betty White also stars in this movie as Andrew’s grandma.
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6. “Bridesmaids”
The “Bridesmaids” movie is a battle between old friends and new.
Lillian, played by Maya Rudolph, enlists old friend Annie, played by Kristen Wiig, as her maid of honor. Her other bridesmaids are played by A-listers including Melissa McCarthy, Rebel Wilson, Ellie Kemper and Rose Byrne.
Wiig and Byrne’s characters quickly become competitive over their own individual relationships with the bride to be. While Annie tries to create a perfect wedding for her friend, she runs into a long line of misfortunes, causing chaos to brew.
7. “Crazy, Stupid, Love”
In “Crazy, Stupid, Love,” Steve Carell plays Cal. When Cal is in his 40s, he is thrust back into the world of dating after his wife is unfaithful.
While reciting his sad story in a bar, Jacob, played by Ryan Gosling, overhears and pledges to help Cal get back into the game. As he helps Cal regain his dating confidence, his own relationship with Hannah, Emma Stone, begins to blossom.
Ryan Gosling’s character in “Crazy Stupid, Love” goes on his own love journey with Hannah (Emma Stone) while also guiding Cal (Steve Carell) to find love. (D Dipasupil/FilmMagic)
8. “My Best Friend’s Wedding”
In “My Best Friend’s Wedding,” Julianne Potter, played by Julia Roberts, and her best friend Michael O’Neal, played by Dermot Mulroney, kick off this film in quite a pickle.
Potter and O’Neal make a pact with one another to marry each other if neither are married by a certain age. While initially a fun game between friends, in the days leading up to Potter’s 28th birthday, she wonders if they will go through with their marriage.
That is, until she receives a shocking call from Michael that he has met someone and intends to get married in just a few days.
When Potter flies to Chicago for the wedding, she meets his future wife, Kimberly Wallace, played by Cameron Diaz, and becomes her maid of honor. From there, drama ensues.
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Julia Robert’s character tries to break up her friend’s marriage in “My Best Friend’s Wedding.” (Ronald Siemoneit/Sygma/Sygma via Getty Images)
9. “You’ve Got Mail”
Almost 10 years after “When Harry Met Sally,” Ryan starred in another classic rom-com, this time opposite Tom Hanks.
In “You’ve Got Mail,” Kathleen Kelly, played by Ryan, a boutique bookstore owner, and Joe Fox, played by Hanks, a corporate businessman, are rivals in the real world.
Online, though, the two develop a relationship, unknowing of the others’ true identity.
10. “My Big Fat Greek Wedding”
This 2002 movie is the first of three in the series. Following “My Big Fat Greek Wedding” was “My Big Fat Greek Wedding 2” in 2016 and “My Big Fat Greek Wedding 3” in 2023.
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In this initial film, Toula Portokalos, a Greek woman played by Nia Vardalos, falls in love with Ian Miller, a non-Greek man played by John Corbett. The two must deal with the struggle with Toula’s family and their disappointment that he is not Greek.