Romantic comedies know that true love usually needs one awkward first meeting, two misunderstandings, and a perfectly timed dash to the airport.
These romantic comedy movie trivia questions hop across decades to test characters, settings, meet-cutes, and plot clues.
Classic Rom-Coms Before the 1980s
The genre had sparkling banter and complicated courtship long before anyone sent a risky text.
- Which 1934 comedy follows runaway heiress Ellie Andrews and reporter Peter Warne?
Answer: It Happened One Night - Who played Ellie Andrews in It Happened One Night?
Answer: Claudette Colbert - Which 1938 screwball comedy features a pet leopard named Baby?
Answer: Bringing Up Baby - Who stars opposite Katharine Hepburn in Bringing Up Baby?
Answer: Cary Grant - Which 1940 comedy reunites Tracy Lord with her ex-husband C. K. Dexter Haven?
Answer: The Philadelphia Story - Who played Tracy Lord?
Answer: Katharine Hepburn - Which 1953 romance follows a princess who slips away to explore Rome?
Answer: Roman Holiday - Who plays reporter Joe Bradley in Roman Holiday?
Answer: Gregory Peck - Which 1954 film pairs chauffeur's daughter Sabrina with the wealthy Larrabee brothers?
Answer: Sabrina - Who plays Sabrina in the 1954 film?
Answer: Audrey Hepburn - Which 1959 comedy has musicians Joe and Jerry disguising themselves as women?
Answer: Some Like It Hot - Who plays singer Sugar Kane in Some Like It Hot?
Answer: Marilyn Monroe - Which 1961 comedy centers on insurance clerk C. C. Baxter lending out his home?
Answer: The Apartment - Who directed The Apartment?
Answer: Billy Wilder - Which 1977 film stars Woody Allen and Diane Keaton as a mismatched New York couple?
Answer: Annie Hall
The 1980s Build the Modern Rom-Com
Big hair, boom boxes, and Nora Ephron-style conversation set the template for decades to come.
- Which 1984 film follows a mermaid named Madison who falls for Allen Bauer?
Answer: Splash - Who plays Madison in Splash?
Answer: Daryl Hannah - Which 1985 comedy follows bored housewife Roberta as she becomes fascinated with Susan?
Answer: Desperately Seeking Susan - In which 1987 film does Westley tell Buttercup, 'As you wish'?
Answer: The Princess Bride - Who plays Buttercup in The Princess Bride?
Answer: Robin Wright - Which 1987 film features Cher as widowed bookkeeper Loretta Castorini?
Answer: Moonstruck - Who plays Ronny Cammareri in Moonstruck?
Answer: Nicolas Cage - Which 1988 comedy stars Eddie Murphy as Prince Akeem?
Answer: Coming to America - What New York borough does Prince Akeem choose in Coming to America?
Answer: Queens - Which 1989 film asks whether men and women can ever be just friends?
Answer: When Harry Met Sally... - Who plays Sally Albright?
Answer: Meg Ryan - At which New York deli does Sally stage her famous performance?
Answer: Katz's Delicatessen - Who directed When Harry Met Sally...?
Answer: Rob Reiner - Who wrote When Harry Met Sally...?
Answer: Nora Ephron - What song do Lloyd Dobler and Diane Court hear from the raised boom box in Say Anything...?
Answer: In Your Eyes
1990s Rom-Com Royalty
The nineties delivered bookstores, radio shows, weddings, and enough grand gestures to fill a video store.
- Which 1990 film pairs businessman Edward Lewis with Vivian Ward?
Answer: Pretty Woman - Who plays Vivian Ward?
Answer: Julia Roberts - Which city is the main setting of Pretty Woman?
Answer: Los Angeles - Which 1993 film connects Sam Baldwin and Annie Reed through a radio call-in show?
Answer: Sleepless in Seattle - Who plays Sam Baldwin?
Answer: Tom Hanks - At which landmark do Sam and Annie finally meet?
Answer: The Empire State Building - Which 1994 film begins with Charles running late to a wedding?
Answer: Four Weddings and a Funeral - Who plays Charles in Four Weddings and a Funeral?
Answer: Hugh Grant - Which 1995 film modernizes Jane Austen's Emma in Beverly Hills?
Answer: Clueless - Who plays Cher Horowitz?
Answer: Alicia Silverstone - Which 1997 film has food critic Julianne trying to stop her best friend Michael's wedding?
Answer: My Best Friend's Wedding - Who plays Julianne Potter?
Answer: Julia Roberts - Which 1998 film pairs bookseller Kathleen Kelly with businessman Joe Fox?
Answer: You've Got Mail - What is Kathleen's bookstore called?
Answer: The Shop Around the Corner - Which 1999 film pairs movie star Anna Scott with travel bookseller William Thacker?
Answer: Notting Hill
2000s Favorites and Complicated Couples
Flip phones and glossy magazines may have dated, but these meet-cutes still know exactly what they are doing.
- Which 2001 film follows wedding planner Mary Fiore?
Answer: The Wedding Planner - Who plays Mary Fiore?
Answer: Jennifer Lopez - Which 2001 film features Elle Woods following Warner to Harvard Law School?
Answer: Legally Blonde - Which 2002 film pairs Melanie Carmichael with her estranged Alabama husband Jake?
Answer: Sweet Home Alabama - Who plays Melanie?
Answer: Reese Witherspoon - Which 2003 film challenges Andie Anderson and Benjamin Barry with opposing bets?
Answer: How to Lose a Guy in 10 Days - What magazine employs Andie Anderson?
Answer: Composure - Which 2003 ensemble film opens and closes at Heathrow Airport?
Answer: Love Actually - Who plays the British prime minister in Love Actually?
Answer: Hugh Grant - Which 2004 film has Henry Roth repeatedly wooing Lucy Whitmore?
Answer: 50 First Dates - What condition affects Lucy's memory?
Answer: Anterograde amnesia as portrayed in the film - Which 2005 film stars Will Smith as dating consultant Alex Hitchens?
Answer: Hitch - Which 2006 film swaps the homes of Amanda Woods and Iris Simpkins?
Answer: The Holiday - Which two locations are exchanged in The Holiday?
Answer: Los Angeles and Surrey, England - Which 2008 film turns a Hawaii vacation into a painful reunion for Peter Bretter?
Answer: Forgetting Sarah Marshall
Rom-Coms from 2010 Onward
Modern favorites refresh the formula with new voices, sharper family stories, and a few questionable dating apps.
- Which 2011 film follows best friends Dylan and Jamie trying to avoid romance?
Answer: Friends with Benefits - Who plays Jamie in Friends with Benefits?
Answer: Mila Kunis - Which 2011 film stars Emma Stone as Hannah, whose father seeks dating advice?
Answer: Crazy, Stupid, Love. - Who plays dating expert Jacob Palmer?
Answer: Ryan Gosling - Which 2013 film gives Tim Lake the ability to travel through his own life?
Answer: About Time - Who plays Tim Lake?
Answer: Domhnall Gleeson - Which 2015 film stars Amy Schumer as magazine writer Amy Townsend?
Answer: Trainwreck - Which 2017 film dramatizes the courtship of Kumail and Emily?
Answer: The Big Sick - Who co-wrote The Big Sick with Kumail Nanjiani?
Answer: Emily V. Gordon - Which 2018 film follows Rachel Chu to a lavish wedding in Singapore?
Answer: Crazy Rich Asians - Who plays Rachel Chu?
Answer: Constance Wu - Which 2018 Netflix film pairs assistants Harper and Charlie as matchmakers?
Answer: Set It Up - Which 2020 film traps Nyles and Sarah in a wedding-day time loop?
Answer: Palm Springs - Which 2022 film pairs divorced parents David and Georgia at their daughter's Bali wedding?
Answer: Ticket to Paradise - Which 2023 film stars Sydney Sweeney and Glen Powell as Bea and Ben?
Answer: Anyone but You
Meet-Cutes, Mix-Ups, and Secret Identities
Identify the film from the setup that pushes two people into the same story.
- In which film do Lucy and George meet after he falls onto Chicago train tracks?
Answer: While You Were Sleeping - Which film begins with Lucy Kelson working for billionaire George Wade?
Answer: Two Weeks Notice - In which film does journalist Josie Geller return to high school undercover?
Answer: Never Been Kissed - Which film has advertising executive Nick Marshall begin hearing women's thoughts?
Answer: What Women Want - In which film does Sam Montgomery exchange anonymous messages with Austin Ames?
Answer: A Cinderella Story - Which film features Alex Fletcher writing a song with plant caretaker Sophie Fisher?
Answer: Music and Lyrics - In which film does Anna pretend to be engaged while traveling across Ireland?
Answer: Leap Year - Which film has Margaret Tate claim she is engaged to assistant Andrew Paxton?
Answer: The Proposal - In which film does Jenna Rink wake up as a 30-year-old magazine editor?
Answer: 13 Going on 30 - Which film follows a prince posing as a college student in Wisconsin?
Answer: The Prince & Me - In which film is Viola Hastings mistaken for her twin brother at boarding school?
Answer: She's the Man - Which film has Daphne Reynolds travel to London to find her father?
Answer: What a Girl Wants - In which film does Kate McKay fall for a duke who travels from 1876?
Answer: Kate & Leopold - Which film pairs a morning-show producer with an opinionated TV personality named Mike Chadway?
Answer: The Ugly Truth - In which film does a professional escort pose as Kat Ellis's boyfriend at a wedding?
Answer: The Wedding Date
Weddings, Workplaces, and Faraway Settings
A rom-com location is never just scenery, especially when it contains a wedding cake or a corner office.
- Which film follows Jane Nichols, who has served as a bridesmaid 27 times?
Answer: 27 Dresses - Which newspaper does Kevin Doyle write for in 27 Dresses?
Answer: The New York Journal - Which film sends Sophie Hall to Verona to answer an old love letter?
Answer: Letters to Juliet - Which country hosts the central wedding in Mamma Mia!?
Answer: Greece - Which film centers on Toula Portokalos and Ian Miller's cross-cultural wedding?
Answer: My Big Fat Greek Wedding - What kind of family business employs Toula at the start?
Answer: A Greek restaurant - Which film has rival morning TV producers Becky Fuller and Mike Pomeroy?
Answer: Morning Glory - Which film pairs fashion executive Melanie with childhood sweetheart Jake in Alabama?
Answer: Sweet Home Alabama - Which film follows chef Rachel and restaurant owner Nick to Singapore?
Answer: Crazy Rich Asians - Which film takes place largely at the Kellerman's resort in the Catskills?
Answer: Dirty Dancing - Which film pairs bookstore owner William Thacker with an actress in London's Notting Hill?
Answer: Notting Hill - Which film has Sophie and Sky planning their wedding on Kalokairi?
Answer: Mamma Mia! - Which film follows two women exchanging homes for Christmas?
Answer: The Holiday - Which film brings Margaret and Andrew to Sitka, Alaska?
Answer: The Proposal - Which film follows columnist Carrie Bradshaw and Mr. Big toward a New York Public Library wedding?
Answer: Sex and the City
Stars, Sources, and Rom-Com Connections
Close with actors, literary inspirations, directors, and pairings that made repeat chemistry look easy.
- Which actress stars opposite Tom Hanks in both Sleepless in Seattle and You've Got Mail?
Answer: Meg Ryan - Which actress stars opposite Hugh Grant in Notting Hill?
Answer: Julia Roberts - Who directed Clueless?
Answer: Amy Heckerling - Which Jane Austen novel inspired Clueless?
Answer: Emma - Which Shakespeare play inspired 10 Things I Hate About You?
Answer: The Taming of the Shrew - Who plays Kat Stratford in 10 Things I Hate About You?
Answer: Julia Stiles - Who plays Patrick Verona?
Answer: Heath Ledger - Who directed Crazy Rich Asians?
Answer: Jon M. Chu - Which author wrote the novel Crazy Rich Asians?
Answer: Kevin Kwan - Who directed Love & Basketball?
Answer: Gina Prince-Bythewood - Which writer-director made Something's Gotta Give?
Answer: Nancy Meyers - Who directed The Big Sick?
Answer: Michael Showalter - Which actress plays Bridget Jones?
Answer: Renée Zellweger - Which Jane Austen novel loosely inspires Bridget Jones's Diary?
Answer: Pride and Prejudice - Which actor plays Mark Darcy in Bridget Jones's Diary?
Answer: Colin Firth
Keep the game going with movie trivia, Valentine's Day trivia, Clueless trivia, and Legally Blonde trivia.
Sources and Further Reading
- American Film Institute: 100 Years, 100 Passions
- British Film Institute romantic comedy features
- Academy Awards official database
- Library of Congress National Film Registry
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