Guess the rom-com film these cinematic couples came from!

By: Olivia Cantor
Image: Castle Rock Entertainment Nelson Entertainment

About This Quiz

Movie couples are fun to watch, whether they're just falling in love, are already in love, or making a comedy out of their love life. Think you can guess which rom-com films these couples came from? Then take this quiz and challenge yourself, loves!

This film shows a series of chance encounters between Harry Burns and Sally Albright, who showed him how to fake an orgasm -- while they were in a restaurant. In which film can you find these two?

"When Harry Met Sally" starred Billy Crystal and Meg Ryan. This film is hailed as one of the best-written rom-com films ever.

Online, they're friendly chatmates NY152 and Shopgirl. Offline, they're big bookstore chain owner, Joe Fox, and independent bookstore owner, Kathleen Kelly, who are rivals in their industry. In which film can you see these two?

"You've Got Mail" was one of the first rom-com films to heavily use the online storyline. It starred Tom Hanks and Meg Ryan.

When wannabe New York socialite Holly Golightly bumps into writer-turned-kept man Paul Varjak, their chemistry sparkles like diamonds on display. In which film will you find these two lovers?

"Breakfast at Tiffany's" was originally a novella written by Truman Capote. Audrey Hepburn's iconic image is based on her character in this film.

Rich and handsome businessman Edward Lewis hires the hooker with the proverbial heart of gold, Vivian Ward, but their quickie night turns into a longer transaction, which leads into a more romantic dealing. In which film can you find these two?

"Pretty Woman" starred Julia Roberts and Richard Gere. It wasn't originally intended as a rom-com, but we're all glad it was rewritten!

Commitment-phobic marine veterinarian​ Henry Roth tries to take out Lucy Whitmore again and again, because her short-term memory loss can't seem to remember each romantic episode. Which film is this?

"50 First Dates" was a hit with rom-com lovers. It starred Adam Sandler and Drew Barrymore.

At the end of the day, American Hollywood star, Anna Scott, is just a girl standing in front of British independent bookstore owner, Will Thacker, asking him to love her. In which film can you find these two?

"Notting Hill" came out in 1999. It starred Julia Roberts and Hugh Grant.

Taking a page from Jane Austen's "Pride and Prejudice," this British gal writes her love life frustration in her journal, narrating about her crush, Daniel Cleaver, and her eventual love, Mark Darcy. What film is this?

"Bridget Jones's Diary" had a sequel. They both starred Renee Zellweger.

Lonely Lucy, who works as a Chicago Transit employee, accidentally rescues her crush, handsome passenger, Peter, who falls into a coma. In the process, she meets Peter's brother, Jack, and falls for him. What Sandra Bullock film is this?

"While You Were Sleeping" was but one of Sandra Bullock's rom-com works. She likes appearing in them, obviously.

You could say greeting card writer, Tom Hansen, seasonally fell in love with a girl named Summer. Which Joseph Gordon-Levitt movie is this?

"500 Days of Summer" was a small film but a big hit for rom-com fanatics. It's still being talked about today, and its storyline was even being mimicked by other films.

When Julianne tries to cash in on a college oath she made with BFF and secret love, Michael, to marry each other if they were still single at age 28, she gets the surprise of her love life to find out that he is in love with another girl, and is about to get married. Which Julia Roberts movie is this?

"My Best Friend's Wedding" was a hit for Julia Roberts. She played a restaurant critic.

When former pop idol, Alex Fletcher, and wannabe melody writer, Sophie Fisher, compose a song together, they find their "way back into love." Which film is this?

"Music and Lyrics" starred Hugh Grant and Drew Barrymore. Grant seems to love appearing in rom-coms.

There's married couple Julie and Peter and his best man, Mark, who is in love with the wife. There's brokenhearted writer, Jamie, smitten with Portuguese housekeeper, Aurelia. There's the UK Prime Minister bachelor falling for a 10 Downing Street staffer. There are also other couples along the way. In this collection of multiple rom-com stories woven together seamlessly in one ultimate rom-com flick, you'll end up singing "Love is All Around" at the end of it all. Which film is this?

"Love, Actually" is a Richard Curtis film. The stories are set in London.

When jazz musician, Sebastian, meets aspiring actress, Mia, on a Hollywood backlot, they started to play beautiful music together... In which movie musical can you find these two?

"La-La Land" stars Ryan Gosling and Emma Stone. They sing and dance their hearts out in this one.

Taking a page from Shakespeare is Heath Ledger's, Patrick, hired to woo the shrew named Kat, played by Julia Stiles, only he falls for real. In which film can you find these two?

"10 Things I Hate About You" is actually following the Shakespearean structure of 'Taming of the Shrew.' Hollywood loves borrowing the Bard's original rom-com-ic material...

In the 1954 version, millionaire bachelor Linus Larrabee was played by Humphrey Bogart while the chauffeur's daughter was played by Audrey Hepburn. In the 1995 version, it's Harrison Ford and Julia Ormond stepping in the role of lovebirds. Which film is this?

"Sabrina" was a good rom-com film for Audrey Hepburn. But in the '90s remake, Harrison Ford was the hotshot in it. Go figure.

There's definitely an intriguing fact about a girl played by Cameron Diaz who is the love of the life of Ben Stiller's, Ted, and apparently some other guys around the vicinity. Which film is this?

"There's Something About Mary" is the quintessential "boy gets to date his dream girl" rom-com. Cameron Diaz seems to be the object of desire in many rom-coms.

When Mila Kunis' character, Jamie, tries to have a "no strings attached" sex only relationship with Justin Timberlake's character, Dylan, it's a sure thing that this sex-com will later turn into a rom-com, with feelings attached. Which film is this?

"Friends with Benefits" is similar to "No Strings Attached" in terms of the sex-com turned rom-com storyline. But this one is cuter!

When you're American foreigner, Margaret, whose work visa is about to expire, and you kind of force your American assistant, Andrew, to marry you to save your legal status, then you know you're in this Sandra Bullock-Ryan Reynolds film. Which one is this?

"The Proposal" stars Sandra Bullock as a Canadian citizen. In reality, Ryan Reynolds is the Canadian.

For Joseph Fiennes', the Bard character, it is the east but Juliet isn't the sun, as Gwyneth Paltrow's character, Viola, provides his inspiration while sustaining his admiration. In which period film can you find these two?

"Shakespeare in Love" imagined Shakespeare being inspired by a woman while he was writing what would be 'Romeo and Juliet.' Records are unclear if this really happened.

Nora Ephron takes a page out--or a frame off--of "An Affair to Remember" so the world can't forget this love story between grieving widower architect, Sam Baldwin, and newspaper reporter, Annie Reed, who both trade insomnia and states to have an empire state of mind (and heart) in New York. Which film is this?

"Sleepless in Seattle" starred Tom Hanks and Meg Ryan, again. These two really love teaming up for rom-coms!

This quintessential Gen X-er rom-com starred Winona Ryder and Ethan Hawke as the are-you-or-aren't-you-gonna couple housemates struggling to find their place in the world after college. Which film is this?

"Reality Bites" is actually more of a Gen X reflection tale, with love thrown in. It's what young people felt during the changing '90s.

When thirtysomething Toula Portokalos gets pressured by her European-descended family to get married and have babies like the other women in their clan, little did they expect that she'd fall for a cute teacher who's just your average American Joe -- until they heard bells ringing. Which rom-com is this?

"My Big Fat Greek Wedding" was a huge rom-com hit. It starred Nia Vardalos, who also wrote the screenplay.

No rom-com list is complete without the mention of this '80s John Hughes classic, where Molly Ringwald's, Andie, and Andrew McCarthy's, Blane, are kind of a thing, but her BFF, Duckie, played by Jon Cryer, is loving her silently, waiting on the sidelines. Which film is this?

"Pretty in Pink" was written by John Hughes. Its title shares the name of an '80s song by the group, The Psychedelic Furs.

When high school kids, Danny and Sandy, sing their way into finding each other, coming from a season of Summer Loving, then losing each other, and finding each other again, it's a heck of a lightning ride for this couple -- as depicted in this movie musical. Which film is this?

"Grease" was a huge hit at the movies. It was also a hit on stage.

When lifestyle magazine writer, Andie, researches to write a "listicle" of ditching dudes and ad exec, Benjamin, takes a bet about wooing women within a short time frame, and their paths cross, you get this film. What is it?

"How to Lose a Guy in 10 Days" starred Kate Hudson and Matthew McConaughey. The tandem worked here.

In this Will Smith movie, he plays a dating coach who teaches men how to woo women. But his own styles dissipate when he falls for gossip writer, Sara, played by Eva Mendes. Which film is this?

"Hitch" was a cute rom-com where the featured Romeo's tactics backfired on him because his Juliet was just as sassy. Hitch and Sara ended up together, eventually.

Cameron Crowe's directorial debut features John Cusack's average student, Lloyd, and Ione Skye's student achiever, Diane, weaving a life right after high school, hopefully ending up together. What film is this?

"Say Anything" had a classic moment when Lloyd raised a boombox to woo Diane. Well, it was the '80s, so what the heck.

Catherine Zeta-Jones' New York head chef character, Kate, can stand the heat in the kitchen, but gets professionally and romantically challenged when Aaron Eckhart's sous chef character, Nick, enters the picture. What film is this?

"No Reservations" set the rom-com story in a New York kitchen. Naturally, things will heat up in there!

Hugh Jackman is an accidental time traveling duke who meets modern-day Meg Ryan's cynical corporate character, and they eventually fall in love in New York. Which film is this?

"Kate and Leopold" came out in 2001. Meg still has the rom-com charm!

When single mom and hotel staffer, Marisa Ventura, gets mistaken as a socialite by young politician, Christopher Marshall, they are smitten with each other as she tries to hide her real persona while he tries to enjoy New York with her. What J.Lo movie is this?

"Maid in Manhattan" starred Jennifer Lopez and Ralph Fiennes. Who said rom-coms are solely for teens? This one works!

Jack Black's superficial character falls in love with an obese girl played by Gwyneth Paltrow, whom he sees as sexy and slender -- because he was put under hypnosis. Which film is this?

"Shallow Hal" was an interesting rom-com for Jack Black. Gwyneth also researched the role by actually wearing a fat suit, and roamed around unrecognized.

When Mel Gibson's sleazy chauvinistic ad exec character, Nick, suddenly gets magical powers to listen in on women's thoughts, he uses it for career advancement while inadvertently falling for rival female ad exec, Darcy, played by Helen Hunt. What film is this?

"What Women Want" featured yet another advertising executive as a character in a rom-com.

In this Woody Allen opus, stand-up comedian Alvy Singer narrates his love life and his eventual relationship with the titular character, all taking place in 1970s New York. Who is she?

"Annie Hall" is a classic Woody Allen opus. They said it began the rom-com genre, but some critics disagree.

Could you imagine a love affair between a teenager with a morbid curiosity and a senior citizen who encourages him to appreciate life more? In which cult '70s rom-com/black comedy can you find this unlikely couple?

"Harold and Maude" is a rather dark tale but also comedic and, yes, romantic. Never mind the age gap!

When you have Tom Hanks playing a man in love with a mermaid, and you have Daryl Hannah playing that mermaid, perhaps love could be fantastic as well as comedic! What '80s film is this?

"Splash" is a fantastic tale indeed. However, Hollywood is not the first one to make a story about a mermaid falling in love with an average human.

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