27 Dresses Trivia
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49 free 27 Dresses trivia questions with answers — entertainment quiz, new questions added Oct 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 49 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 49 questions with answers and explanations. Play the quiz
Q 01Which actress plays perpetual bridesmaid Jane Nichols in 27 Dresses?
Katherine Heigl
Katherine Heigl. Her Jane has stood beside 27 brides and kept every outfit, on the theory that one day, when it is finally her turn, all those people will be there for her.
Q 02Which Elton John song do a tipsy Jane and Kevin belt out on top of a bar, mangling the lyrics?
Bennie and the Jets
Bennie and the Jets. Neither of them knows the words, the whole bar joins in anyway, and the next morning a customer in a diner hails the pair as Bennie and the Jets.
Q 03In 27 Dresses, what does eight-year-old Jane use to mend a bride's torn dress?
A hair ribbon
A hair ribbon. She borrows it from her little sister at a cousin's wedding, the family's first big event since their mother died, and the grateful bride lets Jane carry her train.
Q 04On the night 27 Dresses opens, what will cost Jane's cab driver money every time he does it?
Glancing in his mirror
Glancing in his mirror. Jane offers $300 for the night, less a fine for every look, because she is changing clothes on the back seat as she shuttles between a wedding in Manhattan and another in Brooklyn.
Q 05What does Jane leave behind on the night she meets Kevin, which he then uses to research her?
Her Filofax planner
Her Filofax planner. Before handing it back Kevin rips out a week, writes himself into every Saturday for the rest of the year and adds his phone number, so that she has to call him.
Q 06Under what first name does Kevin Doyle sign the wedding columns that Jane adores?
Malcolm
Malcolm. He tells a stunned Jane that he keeps his own first name off the byline so that he doesn't get stalked by crazy brides.
Q 07In 27 Dresses, which section of the newspaper does Kevin write for?
Commitments
Commitments. A colleague calls it the gold standard of wedding announcements, the page brides-to-be rip open first every Sunday, and its star writer says he is dying back there.
Q 08Who plays cynical reporter Kevin Doyle in 27 Dresses?
James Marsden
James Marsden. The director had just worked with him on Hairspray, where he played TV dance-show host Corny Collins, and cast him here as a romantic lead for a change.
Q 09In 27 Dresses, Jane's boss George strolls back into the office fresh from what kind of trip?
Climbing
Climbing. He has just been up and down Mount Whitney in ten hours, and the smitten Jane startles him by remembering that it was his eighth time.
Q 10Who plays George, Jane's boss, in 27 Dresses?
Edward Burns
Edward Burns. He made his name writing, directing and starring in the indie hit The Brothers McMullen, and joked that George, a self-made saint of a boss, is a kind of man who doesn't really exist.
Q 11Jane's sister arrives in New York in 27 Dresses after six months working as a model in which fashion capital?
Milan
Milan. She breezes in as if between fashion shows, and only after her wedding is called off does she admit that she had been fired there and dumped by her Italian boyfriend.
Q 12Which actress plays Jane's younger sister Tess in 27 Dresses?
Malin Akerman
Malin Akerman. Her Tess has so few friends of her own (girls, she admits, just don't like her) that she has to borrow Jane's best friend to make up her bridesmaids.
Q 13Which lifestyle does Tess pretend to follow in order to impress George?
Being a vegetarian
Q 21Where do Jane and Kevin marry in the final scene of 27 Dresses?
On a beach
On a beach. A year has passed, and among the guests George meets Tess all over again, this time as her real self: broke, cheerful and designing her own handbags.
Q 22Which choreographer-turned-director made 27 Dresses?
Anne Fletcher
Anne Fletcher. She said she identified with Jane completely, as 'a full-blown co-dependent' whose own nickname is Mama, and she went on to direct Sandra Bullock in The Proposal.
Q 23Which hit film had screenwriter Aline Brosh McKenna written just before 27 Dresses?
The Devil Wears Prada
Being a vegetarian. She waves away a chili dog at a ball game unless it is a tofu one, and a year after the lie comes out she reintroduces herself to George as someone who eats a hamburger a day.
Q 14How does Jane's friend Casey stop her mooning over George at work?
She slaps her
She slaps her. The idea is to wipe the goofy look off Jane's face before George walks in, since, as Casey points out, everybody in the office knows about the crush except him.
Q 15Which actress plays Jane's wisecracking best friend Casey in 27 Dresses?
Judy Greer
Judy Greer. Her brassy Casey also gets the film's wisest line: when Jane's revenge on her sister leaves her miserable, Casey says that if it had been the right thing to do, she would feel better.
Q 16In 27 Dresses, what does the sisters' father Hal give Tess when she gets engaged?
Their mother's gown
Their mother's gown. Jane had always hoped to wear it herself, and when Tess finds it old-fashioned and has it cut up for parts, Jane's years of patience finally run out.
Q 17In 27 Dresses, what is the name of Jane's dream wedding venue, where her parents married?
The Boathouse
The Boathouse. Her parents' ceremony there, with a big band at sunset, is the wedding Jane has always dreamed of copying, which is why it stings when Tess books the place for herself.
Q 18After a cancellation at her chosen venue, how long does Tess give Jane to organise the whole wedding?
Three weeks
Three weeks. The venue's usual wait is a year and a half, but Tess rings nine times until another couple's wedding falls through, then tells Jane she knows she can pull it together quickly.
Q 19How does Jane take revenge on her sister at the rehearsal dinner in 27 Dresses?
A slideshow exposing her lies
A slideshow exposing her lies. Tess hands her a script to read over the family photos; Jane reads every word as written but swaps the pictures, among them young Tess dangling a cat upside down.
Q 20In 27 Dresses, what does Jane do after George praises her for never saying no?
She quits her job
She quits her job. Hearing her own doormat habit praised is the last straw: she tells George that she got too comfortable to leave and never bothered to get a life of her own.
The Devil Wears Prada. McKenna modelled Jane on a friend who had been a bridesmaid about a dozen times, and that friend got engaged just before the film was given the go-ahead.
Q 24Which dance film was the director's debut before 27 Dresses?
Step Up
Step Up. It was produced by Adam Shankman, the choreographer-director who had given her her start years earlier by taking her on to help stage his dance numbers.
Q 2527 Dresses is set in New York City, but in which state was most of it actually shot?
Rhode Island
Rhode Island. Providence doubled for Manhattan, Newport's Gilded Age mansions hosted the grand weddings, and the bar where Jane and Kevin sing was a real dive in Pawtucket.
Q 26In 27 Dresses, Jane compares unmasking her favourite columnist as a cynic to learning her favourite love song is about what?
A sandwich
A sandwich. She has clipped and saved his tender wedding columns for years, so hearing from their author that the cynic is the real him knocks the romance flat.
Q 27Which classic film was the theme of the wedding behind Jane's hoop-skirted, parasol-twirling bridesmaid outfit in 27 Dresses?
Gone with the Wind
Gone with the Wind. When Kevin protests that nobody holds such weddings, Jane replies that she has been to three, and the costume team built eight giant hoop dresses for the scene.
Q 28Kevin's cynicism about weddings in 27 Dresses dates from his own: who did his wife leave him for?
His college roommate
His college roommate. Jane guesses it while needling him in a gift registry, asking whether his own wife left him or something, and he answers 'Bingo', with an extra bingo for the roommate.
Q 29Which nickname does Kevin's newspaper article pin on Tess, sending her into a rage?
Bridezilla
Bridezilla. Tess screams down the phone at Kevin about lawyers she doesn't have, then storms out telling Jane to alert Traffic Control because Bridezilla is on the loose.
Q 30What is the name of George's dog, who carries the ring when he proposes to Tess?
Gatsby
Gatsby. Tess gushes over dogs to win George round, although, as Jane reminds her in private, she could not stand the family's own dog when they were children.