Friends with Benefits
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40 free Friends with Benefits trivia questions with answers — trivia quiz, new questions added Oct 2026.
Friends with Benefits took a question people argue about over drinks and turned it into one of the liveliest romantic comedies of 2011. Justin Timberlake and Mila Kunis play Dylan and Jamie, two friends in New York who are sure they can add sex to their friendship without anything getting complicated. The film knows exactly which genre it belongs to, and it pokes fun at the rules while happily following them. This quiz covers the whole story, from the job offer that brings Dylan across the country to the family visit that changes everything and the big public gesture at the end. It also looks at the supporting cast and the famous faces in tiny parts, the songs, the people who made the film, the rival release it kept being compared with, and how critics and audiences received it. The questions start easy for anyone who has seen the film once and get tougher for fans who know the credits by heart. Every answer comes with a short explanation, so you will pick up something new even when you guess.
30 of 40 questions with answers and explanations. Play the quiz
Q 01Which magazine hires Dylan Harper as its new art director when he moves to New York in Friends with Benefits?
GQ
GQ signs Dylan to a one-year contract after a single night exploring the city changes his mind about leaving California.
Q 02Which career first brings Jamie Rellis into contact with Dylan Harper in the film Friends with Benefits?
Executive headhunter
Executive headhunter Jamie brings Dylan over from California for an interview, then spends a night showing him the city to win him over.
Q 03Which illness affects Mr. Harper, the father Dylan visits in California, in the film Friends with Benefits?
Alzheimer's disease
Alzheimer's disease is in its early stages for Mr. Harper, and a moment of confusion at an airport leads to the advice that sends Dylan back to Jamie.
Q 04In which New York landmark does Dylan surprise Jamie with a dancing flash mob in Friends with Benefits?
Grand Central
Grand Central is where Dylan lures Jamie with help from her mother, then asks her for a first real date at a café just across the street.
Q 05Friends with Benefits star Justin Timberlake rose to fame in the late 1990s with which boy band?
NSYNC
NSYNC made Timberlake famous as one of its two lead singers, and the band dissolved as his own stardom grew.
Q 06Mila Kunis, who plays Jamie in Friends with Benefits, spent eight seasons as Jackie Burkhart on which sitcom?
That '70s Show
That '70s Show ran from 1998 to 2006 and overlapped with another long job: Kunis has voiced Meg Griffin on Family Guy since 1999.
Q 07Which romantic comedy with a near-identical premise reached cinemas six months before Friends with Benefits did?
No Strings Attached
No Strings Attached beat it to cinemas in January 2011, and its script had once carried the title Friends with Benefits.
Q 08Over which holiday weekend does Jamie fly west with Dylan to meet his family in Friends with Benefits?
Fourth of July
Fourth of July plans with her mother fall through at the last minute, so Dylan talks Jamie into joining his family trip instead.
Q 09Which former Cheers actor plays Tommy Bollinger, Dylan's gay colleague at the magazine, in Friends with Benefits?
Woody Harrelson
Woody Harrelson won an Emmy as naive bartender Woody Boyd, the role that made his name years before this comic supporting turn.
Q 10Which 1998 hit by the rock band Semisonic plays during the flash mob finale of Friends with Benefits?
Closing Time
Closing Time returned to the charts in three countries in 2011, the year both the film and an episode of The Office featured it.
Q 11Which Pieces of April Oscar nominee plays Lorna, Jamie's free-spirited mother, in the film Friends with Benefits?
Patricia Clarkson
Patricia Clarkson had played another mother for the same director only a year earlier, in his high-school comedy.
Q 12Which star of the sitcom Dharma & Greg plays Annie, Dylan Harper's sister, in the film Friends with Benefits?
Jenna Elfman
Jenna Elfman won a Golden Globe as Dharma in 1999; in this film her character Annie is the mother of Dylan's young nephew Sam.
Q 13Which actor, Oscar-nominated for The Visitor, plays the ailing father of Dylan Harper in Friends with Benefits?
Richard Jenkins
Q 21Which filmmaker, later behind Peter Rabbit and Anyone but You, directed and co-wrote Friends with Benefits?
Will Gluck
Will Gluck rewrote the script around his two leads, then spent more than a month workshopping it with them before the cameras rolled.
Q 22Which high-school comedy inspired by The Scarlet Letter came from the director of Friends with Benefits a year earlier?
Easy A
Easy A lent the later film two of its cast: its young lead returns for a brief cameo, and its screen mother plays another mother.
Q 23Which actor led a rival casual-romance comedy in 2011 and later married Friends with Benefits star Mila Kunis?
Ashton Kutcher
Richard Jenkins earned that Best Actor nomination for a rare lead role, and a second nomination followed for The Shape of Water.
Q 14Which actress makes a brief appearance as Kayla, the girlfriend who dumps Dylan at the start of Friends with Benefits?
Emma Stone
Emma Stone had just led the same director's previous film, so this brief appearance was a quick reunion for the pair.
Q 15Which Saturday Night Live star, who won an Emmy for a Justin Timberlake duet, plays Quincy in Friends with Benefits?
Andy Samberg
Andy Samberg spent seven years in the sketch show's cast, from 2005 to 2012, and helped popularise its Digital Shorts.
Q 16Which Olympic gold medallist makes a cameo appearance as himself in the romantic comedy Friends with Benefits?
Shaun White
Shaun White won his Olympic golds in half-pipe snowboarding, and he went on to play himself again in an episode of American Dad!
Q 17Which How I Met Your Mother star makes an uncredited cameo as Brice in the film Friends with Benefits?
Jason Segel
Jason Segel had already shared the screen with Mila Kunis as the lead of Forgetting Sarah Marshall, a comedy he also wrote.
Q 18Which Parks and Recreation actress makes an uncredited cameo as Madison in the film Friends with Benefits?
Rashida Jones
Rashida Jones, daughter of record producer Quincy Jones, also appeared in The Big Year and Our Idiot Brother in 2011.
Q 19Nolan Gould, who plays Dylan's young nephew in Friends with Benefits, was already known as Luke Dunphy in which sitcom?
Modern Family
Modern Family had made Gould a familiar face by 2011, and that fame helped him land the small film part of Sammy.
Q 20What is the profession of Parker, who leaves Jamie the morning after their fifth date, in Friends with Benefits?
Oncologist
Oncologist Parker treats children, and Jamie holds to her five-date rule with him before he ends things the very next morning.
Ashton Kutcher starred opposite Natalie Portman in the competing film, began dating Kunis in 2012 and married her in 2015.
Q 24Which studio dropped its protest over the title Friends with Benefits after renaming its own competing film?
Paramount Pictures
Paramount Pictures backed down once its own project took a new name; the makers also sped up production for fear of losing the title.
Q 25Which network aired a short-lived sitcom also called Friends with Benefits in the same summer as the film?
NBC
NBC held its unrelated sitcom back from mid-season, then aired it across August and September 2011, a fortnight after the film opened.
Q 26Which Marvel superhero's origin film topped the box office the weekend Friends with Benefits opened in third place?
Captain America
Captain America took first place and the final Harry Potter film second, leaving the comedy third with $18.6 million.
Q 27Which classic Hollywood screen couple did the director of Friends with Benefits cite as a model for Dylan and Jamie?
Hepburn and Tracy
Hepburn and Tracy were the comparison he reached for after rewriting the script as a more adult film about sex and relationships.
Q 28At which ceremony was Friends with Benefits nominated for Favorite Comedy Movie, with a second nod for Mila Kunis?
People's Choice Awards
People's Choice Awards voters nominated both the film and Kunis in 2012, and each of the two leads also drew a Teen Choice nomination.
Q 29In which city does Dylan Harper work as an art director before a job offer takes him east in Friends with Benefits?
Los Angeles
Los Angeles is also where filming wrapped in September 2010, after a summer shoot in Manhattan and Central Park.
Q 30Where does Dylan finally find Jamie after she flies home and ignores his calls in Friends with Benefits?
A skyscraper rooftop
A skyscraper rooftop is the secret spot Jamie showed Dylan on the day they met, and it is where she ends their friendship.