Perennial co-stars Tom Hanks and Meg Ryan teamed up again for the 1998 film You’ve Got Mail. The two played IRL business rivals who spent a lot of time flirting online. What early internet email service did the two use?
Who could forget the iconic “You’ve got mail” AOL alert voice? I guess…anyone under the age of 30. While the use of the technology in the film is dated, the chemistry between the co-stars is timeless.
The film The 40-Year-Old Virgin was almost stopped one week into filming. What was the reason?
The 40-Year Old Virgin was almost stopped one week into filming because the studio was worried star Steve Carell looked like a serial killer in the scenes that had been shot so far. Not exactly a compliment.
What song does Holly Golightly play on the ukulele in Breakfast at Tiffany’s?
Henry Mancini wrote “Moon River” specifically for Audrey Hepburn and Breakfast at Tiffany’s. Once the film was completed, a film exec tried to cut the scene featuring the song, but Hepburn insisted that it remain in the film.
Siblings from which acting family appear alongside Julia Roberts in both Runaway Bride and America’s Sweethearts?
In Runaway Bride, Joan Cusack plays Julia Roberts’ character’s best friend, while in America’s Sweethearts, John Cusack plays her love interest.
What Ivy League school does Elle Woods attend in Legally Blonde?
Elle, played by Reese Witherspoon, enrolls in Harvard Law alongside her ex-boyfriend and his new fiancée, but finds out that she’s a much better law student than he is.
What move/attention-getting flirting technique does Elle Woods encourage her manicurist to try in Legally Blonde?
As Elle Woods says, when used appropriately, the Bend and snap has an 82% rate of return on dinner invitations.
Which actress played the lead role in Clueless?
Alicia Silverstone made her mark as the unforgettable Cher in Clueless. Both Gellar and Witherspoon were considered for the role, but director Amy Heckerling said her ideal actress would be the girl from “those Aerosmith videos,” and Cher’s blonde, so I guess Tyler was out of the question.
In Notting Hill, Julia Roberts starred opposite Hugh Grant, her playing an actress, he playing a travel bookstore owner. Everyone knows that. But do you remember who played her on- and off-actor boyfriend in the film?
Alec Baldwin is actually uncredited for his role as movie star Jeff King in Notting Hill. Makes sense. Would you want to be known as the guy who kept Anna Scott and Will Thacker apart?
Which Jason Segel-starring rom-com was also written by Jason Segel himself?
Forgetting Sarah Marshall was Jason Segel’s first time doing double duty as lead actor and writer (and also co-producer, with Judd Apatow). The infamous nude break-up scene in Forgetting Sarah Marshall was apparently based on one of Jason Segel’s real-life experiences.
Coyote Ugly and Eat Pray Love have a strange connection—what is it?
Elizabeth Gilbert wrote a GQ article about working at the real Coyote Ugly bar in New York City which later became the basis for the film. She is also the author of the memoir Eat Pray Love, which was made into a film starring Julia Roberts.
Which quirky 2001 film resulted in a boom of copycat baby names?
In 2000, there were 12 babies in England and Wales named Amélie. After the 2001 film Amélie, that number would skyrocket and by 2007, there was an average of 1,100 new Amélies per year. One can assume that a few parents may have named their babies Donnie, Hannibal, or Shrek following the release of those films, but certainly not in the same numbers as Amelie.
Who played Julia Stiles’ character’s love interest in 10 Things I Hate About You, famously serenading her with “Can’t Take My Eyes Off You”?
While the late, great Heath Ledger played the abovementioned character, named Patrick Verona in the film, the three actors mentioned in B, C, and D all also appeared in the film.
Which of these rom-coms is NOT a modern retelling of a Shakespeare play?
Emma is actually a modern adaptation of the Jane Austen novel of the same name, making it the only non-Shakespeare adaptation here. 10 Things I Hate About You, Kiss Me, Kate, and Deliver Us From Eva are all actually adaptations of the same play: The Taming of the Shrew.
What celebrity chef did Melissa McCarthy base her brash Bridesmaids character Megan on?
Melissa McCarthy may have gone a bit far in her desire to make her character like Guy Fieri—she actually wanted to wear a platinum blonde wig for the part, but she settled for ill-fitting pants and golf shirts in order to reflect the unique style of the celebrity chef.
In You’ve Got Mail, Tom Hanks and Meg Ryan’s characters each own the same type of business—what is it?
While Kathleen (Ryan) owns a small bookstore, Joe (Hanks) runs Fox Books, a chain of mega bookstores.
Love Actually featured an ensemble cast of some of the U.K.’s greatest acting talents (and Laura Linney). Who played the Prime Minister in the film?
Hugh Grant played David, the last-nameless Prime Minister in Love Actually who stands us to the US president, played by Billy Bob Thornton.
In Bridget Jones’s Diary, Bridget is pursued by two suitors. One is played by Hugh Grant—who plays the other?
Colin Firth is unforgettable as Mark Darcy in the trilogy of Bridget Jones films, opposite Renee Zellweger—especially in the awkward brawl he gets into with Hugh Grant’s character outside the Greek restaurant at the conclusion of the first film.
Which Cameron Diaz rom-com featured the infamous “hair gel” scene?
Who could forget the hair gel scene in There’s Something About Mary? Diaz initially worried that it was too disgusting and would ruin her acting career, but at the end of the day, the idea was simply too funny not to go ahead with.
Who plays the main character, Lucy, in While You Were Sleeping? (Refresher: she’s a fare collector for the Chicago Transit Authority who falls in love with a passenger, saves him, and when he wakes up from a coma, tells his family that she’s his fiancée).
Although Sandra Bullock ultimately got the role of Lucy, the role was originally written for Demi Moore and was later offered to Julia Roberts, who refused.
Speaking of Julia Roberts, what was the name of her character in Pretty Woman?
In the original script for Pretty Woman, the character of Vivian was supposed to be much darker, and featured her trying to stay clean for one week so that she could go to Disneyland. In a rewrite, the film took a much more fairytale approach, and it paid off.
What’s the name of the movie which features Julia Roberts starring opposite Rupert Everett and Dermot Mulroney?
My Best Friend’s Wedding was a huge hit when it came out in 1997, coming in second place that weekend to a superhero film (Batman & Robin)—a familiar fate for many rom-coms in the 21st century!
The Holiday is a Christmas rom-com starring Jude Law, Cameron Diaz, Jack Black, and which other star?
Kate Winslet played Iris in the film, a recently dumped English woman who swaps her home with Amanda, played by Cameron Diaz.
13 Going on 30 features a memorable dance sequence set at a magazine party. Which ‘80s artist performs the song?
When the Poise magazine party falls flat, Jennifer Garner’s character gets the DJ to put on “Thriller” by Michael Jackson and starts to re-enact the dance from the famous video, creating one of the more memorable scenes of the film.
What was the name of Jenna’s best friend/love interest in 13 Going on 30, played by Mark Ruffalo?
While Mark Ruffalo played the adult version of Matty, the teen version was played by Sean Marquette, who now has a recurring role on The Goldbergs.
13 Going on 30 was sort of a female-centric take on Big. In it, a junior high student named Jenna is transformed into a 30-year-old magazine editor overnight. Who plays the adult version of Jenna?
Jennifer Garner was given the part of Jenna because of her extra-endearing 2002 Golden Globes acceptance speech when she won for her role in Alias.
Meg Ryan was basically the queen of rom-coms in the late ‘80s and early ‘90s. In 1993, she starred in Sleepless in Seattle—who played her widower love interest in that film?
You could say that this instance co-starring with Tom Hanks was the beginning of a beautiful thing for Ryan—after all, they also went on to co-star in the hit You’ve Got Mail, but they actually first appeared in Joe Versus the Volcano together three years before Sleepless.
Director Rob Reiner based part of When Harry Met Sally off his friendship with one of the film’s writers, who wrote the book Heartburn and also directed Sleepless in Seattle and You’ve Got Mail. What is the writer/director’s name?
Nora Ephron was known for her many books and her work on a number of hit films, including many rom-coms. The last film she wrote, produced, and directed before her death in 2012 was Julie & Julia.
In When Harry Met Sally, Meg Ryan’s character famously makes a scene by faking an orgasm in a public place. Where did the scene take place?
After Ryan’s Sally Albright makes her performance in the diner, a woman nearby famously says “I’ll have what she’s having.” That woman was director Rob Reiner’s mother.
In When Harry Met Sally, what funnyman stars opposite Meg Ryan?
Harry Burns was famously played by the wise-cracking Billy Crystal, who also appeared in one of the other great romantic movies of the ‘80s, The Princess Bride.
What is the name of the Pointer Sisters song that the Prime Minister is caught dancing and lip-syncing to in Love Actually?
Grant definitely showed he could “Jump” for love in the famous solo dance scene in Love Actually—one he didn’t initially want to film, because he thought it would undermine the Prime Minister’s authority.
Your Results
Fairly Flirty
Wow! Your knowledge of rom-coms is pretty impressive, but there’s also still a lot more out there for you to watch—may we recommend a Netflix marathon weekend? Retry this quiz afterward and double your score!
Pretty Passionate
Whether it’s classics like Breakfast at Tiffany’s, golden age fare like When Harry Met Sally, or contemporary instant classics like Bridesmaids, you know your way around a rom-com. Way to go!
Really Romantic
Congrats! You’re basically rom-com royalty—you could easily rub elbows with fellow queens Julia Roberts and Meg Ryan, or go toe-to-toe with Reese Witherspoon and Sandra Bullock. Is there even a rom-com you haven’t seen?
Happy With Your Test Score? This video can help you do better on any quiz... even if you know ABSOLUTELY NOTHING about the topic.
Quiz
Even if they pretend they don’t, everyone’s got a favorite romantic comedy. Who in their right mind could deny the charms of Julia Roberts in Pretty Woman, or Tom Hanks in Sleepless in Seattle? Rom-coms have a little something for everyone—A-list casts, meet-cutes, friendships, tears, family, and laughs. What’s not to love? There’s so many classic rom-coms out there that even the most ardent fan may not have seen them all—test your knowledge with this quiz and see if you’re among the elite few rom-com superfans!
