50 free 27 Dresses trivia questions with answers — entertainment quiz, new questions added Aug 2026.
40 free 27 Dresses trivia questions with answers. 27 Dresses is the rom-com that made a closet of hideous bridesmaid gowns into a plot device and gave Katherine Heigl her first solo star vehicle after Knocked Up. This 27 Dresses trivia quiz covers the whole film: Jane Nichols and her Filofax, Kevin Doyle and his 'Malcolm' byline, Tess's lies about being a vegetarian, George and the Boathouse, the slideshow, the beach wedding with all 27 brides as bridesmaids, plus the people who made it: director Anne Fletcher, Devil Wears Prada writer Aline Brosh McKenna, the Rhode Island mansions used as locations, the costume designer who built the dresses, and how it fared at the box office and with critics. The 50 questions run from easy for anyone who has seen it once to hard for people who can quote the reviews, so it suits a girls' night or a movie round. Every answer is checked against documented production records rather than fan sites.
30 of 50 questions with answers and explanations. Play the quiz
Q 01Which actress, then starring in Grey's Anatomy, plays Jane Nichols?
Katherine Heigl
She reportedly received $6 million for the role, fresh off Grey's Anatomy and Knocked Up.
Q 02How many times has Jane been a bridesmaid when the film begins?
27
She keeps every dress in her closet and models them all for Kevin in an impromptu fashion show.
Q 03How old was Jane when she first helped a bride through a wedding-day crisis and got hooked?
Eight
It happened shortly after her mother's death, which is why her parents' wedding looms so large for her.
Q 04How does Jane first meet Kevin Doyle?
Sharing a cab between two weddings on the same night
She is criss-crossing the city to attend both weddings and leaves her Filofax behind in the taxi.
Q 05What does Jane accidentally leave in the cab that Kevin uses to research her?
Her Filofax planner
He returns it later at the engagement party, where she learns the mystery flowers were from him.
Q 06Under what pseudonym does Kevin write the wedding columns Jane adores?
Malcolm
When she finds out he's the cynic and the romantic columnist, she asks which is the real him; he says the cynic.
Q 07Which section of the newspaper does Kevin write for?
Commitments
He is promised a promotion to Features if his story on Jane makes the section's front page.
Q 08Who plays Kevin Doyle?
James Marsden
He came to the role straight after Hairspray and Enchanted, and had played Cyclops in the X-Men films.
Q 09Jane's boss George has just returned from what kind of outing at the start of the film?
Climbing
Her friend Casey slaps her to wipe the goofy look off her face.
Q 10Who plays George, Jane's boss?
Edward Burns
Burns broke through as writer-director of The Brothers McMullen and appeared in Saving Private Ryan.
Q 11What is Jane's younger sister called?
Tess
She sweeps in from a six-month European tour and is engaged to George within weeks.
Q 12Which Swedish-born actress plays Tess?
Malin Akerman
Watchmen, her breakthrough, came the following year.
Q 13Which of these is one of the interests Tess fakes to impress George?
Being a vegetarian
She also pretends to be an outdoors person and to like dogs, all fed to her by Jane.
Q 14How does Jane's friend Casey stop her mooning over George at work?
Q 21Where do Jane and Kevin marry in the film's final scene?
On a beach
All 27 brides she once stood up for serve as her bridesmaids, each wearing the dress Jane wore at their wedding.
Q 22Which choreographer-turned-director made 27 Dresses?
Anne Fletcher
A choreographer turned director, she had just made Step Up and went on to The Proposal and Hocus Pocus 2.
Q 23Which hit film had screenwriter Aline Brosh McKenna written just before 27 Dresses?
The Devil Wears Prada
She later co-created Crazy Ex-Girlfriend and wrote the 2026 Prada sequel.
She slaps her
Judy Greer plays Casey, a variation on the wisecracking best friend she made a career of.
Q 15Which actress plays Casey?
Judy Greer
She had a similar best-friend role in 13 Going on 30 and later in Love Happens.
Q 16What does the sisters' father Hal give Tess when she gets engaged?
Their mother's gown
Tess later drastically alters the dress, which triggers her rift with Jane.
Q 17What is the name of Jane's dream wedding venue, where her parents married?
The Boathouse
Tess reintroduces her to it while sharing plans for model-like bridesmaids and a funny slideshow.
Q 18How much notice does Jane give the busy baker to create Tess's wedding cake?
Three weeks
It is right after that triumph that Kevin introduces himself as Malcolm and she calls him an 'asshole'.
Q 19How does Jane get revenge on her sister at the engagement party?
A slideshow exposing her lies
George calls off the wedding after seeing the deceptions, including Tess paying his young mentee to clean.
Q 20What does Jane do after George praises her for never saying no?
She quits her job
She realises her devotion was unrequited love, kisses him briefly and finds her feelings have faded.
Q 24Which dance film was the director's debut before 27 Dresses?
Step Up
She got her start as Adam Shankman's assistant choreographer after they danced together at the 1990 Oscars.
Q 25In which US state was most of 27 Dresses filmed?
Rhode Island
Two weeks of additional shooting took place in New York City.
Q 26Which two Newport mansions served as locations?
Rosecliff and Marble House
A Charlestown beach and sites in East Greenwich and Providence were also used.
Q 27How did the director want the bridesmaid dresses to look?
Big, ugly and bright
Costume designer Catherine Marie Thomas made about fifty candidates and picked 27.
Q 28Roughly how many candidate dresses did Catherine Marie Thomas create before choosing the final 27?
About fifty
She also designed a few suits for the same selection process.
Q 29When did principal photography begin?
May 10, 2007
Filming ran through July 2007 for a January 2008 release.
Q 30Which studio produced 27 Dresses, with 20th Century Fox distributing?
Spyglass Entertainment
The film opened at number two behind Cloverfield with $23 million.