Friends with Benefits (2011) gave us sharp dialogue, great chemistry between Mila Kunis and Justin Timberlake, and a refreshing take on romance in the digital age. It pokes fun at the clichés of romantic comedies — while secretly embracing them — and somehow makes falling in love with your best friend feel brand new again.
Think you remember every sarcastic line, steamy scene, and fake rom-com reference? Take this 10-question trivia quiz and see if your memory of this modern classic holds up — no strings attached.
Friends with Benefits (2011) Trivia Questions & Answers
- Who plays Dylan in Friends with Benefits?
Correct Answer: Justin Timberlake
Justin Timberlake stars as Dylan, a charismatic L.A. art director who moves to New York for a new job. His charm and chemistry with Mila Kunis anchor the film, blending humor with unexpected emotional depth.
- Who plays Jamie, Dylan’s counterpart in the film?
Correct Answer: Mila Kunis
Mila Kunis shines as Jamie, a savvy New York headhunter with a sharp tongue and a hidden romantic streak. Her banter with Dylan drives the film’s playful, self-aware tone, balancing cynicism with sincerity.
- What city does Dylan move to for his new job?
Correct Answer: New York City
Dylan relocates from L.A. to New York after Jamie recruits him for a position at GQ. The city’s energy and romantic backdrops set the stage for their evolving “no-strings” relationship.
- What job is Dylan hired for?
Correct Answer: Art director at GQ
Dylan lands a creative director role at GQ, marking a career boost and a lifestyle change. The fast-paced media world contrasts with his easygoing nature — and serves as the backdrop for his deeper connection with Jamie.
- What kind of relationship do Dylan and Jamie initially agree to have?
Correct Answer: Physical with no emotional attachment
Swearing off love, they make a pact for purely physical intimacy. But despite their rules, real feelings develop — proving their relationship can’t be kept “just physical” for long.
- Which romantic comedy do Dylan and Jamie mock throughout the film?
Correct Answer: Fictional rom-com within the movie
They laugh at a fake rom-com starring Jason Segel and Rashida Jones, poking fun at cheesy tropes — all while their own story slowly mirrors them. This meta-humor is part of the film’s charm.
- Who plays Dylan’s eccentric father suffering from early Alzheimer’s?
Correct Answer: Richard Jenkins
Richard Jenkins gives a moving performance as Dylan’s father. His gentle decline adds emotional layers to the story, especially when Dylan is reminded of life’s brevity and what really matters.
- What recurring location becomes meaningful to Dylan and Jamie?
Correct Answer: The rooftop of Jamie’s apartment
The rooftop, with its homemade “Hollywood” sign, becomes their shared haven. It represents vulnerability, comfort, and the quiet moments that gradually pull them closer.
- How do Dylan and Jamie finally confess their feelings?
Correct Answer: Through a grand gesture in a public place
Despite mocking rom-com clichés, Dylan wins Jamie back with a dramatic confession at Grand Central. His flash mob-like speech is heartfelt and symbolic — embracing the very tropes they laughed at.
- What song plays during the film’s final kiss scene?
Correct Answer: “Closing Time” by Semisonic
“Closing Time,” which first played during a flirty bonding scene, returns at the end. This callback redefines the song as a beginning — closing the door on casual flings, and opening one to something real.
