The Ultimate 90's Chick Flick Trivia Quiz

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The 90's is a nostalgic era with the bizarre fashion trends and terrible haircuts but many millennials return to it because it marks the beginning of their conscious taste in music, movies, and style. Even if certain iconic elements were not initially celebrated they have been remembered far beyond their original sortie as cultural classics. In this era came the emergence of the "chickflick" where Julia Roberts and Drew Barrymore tie for starring in the most melodramatic movies of the decade. (You know you love Pretty Woman and Never Been Kissed.)

But what constitutes a "chickflick"? They are generally light, fun movies with heavy overlap from the romantic comedy genre. These are the films you stay in to watch, saying you "have plans" when people invite you clubbing. Some have exhausted the Austenian trope-- following two characters who initially despise each other only to end up falling in love. Others rely on a celebration of  femininity, relatable mistakes, and feel-good scenarios. But chickflicks should not be trivialized as if narrative messages targeting women are inherently shallow and silly.

Many of the following films provide valid advice, imperfect heroines, and relatable contexts that young and old women alike can appreciate and learn from. How well do you remember the classic chickflicks of the 90's?

Question 1

Who does Cher from Clueless end up with?

Little else better represents the culture of 90's chickflicks than Clueless, an endlessly quotable movie released in 1995. Cher epitomizes a 15 year-old teenage girl who is a bit naive, materialistic and takes everything too seriously. In her search for a boyfriend she reminds us how important it is to be selective and is not afraid to say no to unwanted prospects. In true Austenian style however, she ends up falling for someone she was repulsed with in the beginning.

Question 2

Who does Nicole ask to take her to Centennial?

In Drive Me Crazy popular socialite Nicole is overlooked by her dream date the school's basketball star. She teams up with an unlikely accomplice to fuel jealously in her original date. Her shaggy haired counterpart similarly joins with her to make his previous girlfriend jealous. Once they publicize their relationship and are viewed together by fellow high schoolers their respective partners want them back before prom. Though this was the original plan it doesn't end up being what they wanted.

Question 3

When does Jack first approach Rose?

Jack falls for Rose since he first glimpses her sulking on the first class balcony. She is frustrated with her lack of choice in marrying a rich and controlling fiancé Cal. Rose is similarly bored with the monotony of high-class life; she wants to escape from the rigid mannerisms and expectations but sees no way out. When she meets Jack he opens a door to another lifestyle, he has different perceptions and aspirations that inspire her to dream for herself.

Question 4

In Romy and Michele's High School Reunion who do they pretend to be?

When Romy(Mira Sorvino) and Michele (Lisa Kudrow!) first decide to attend their ten year high school reunion they are extremely excited. However, they later realize they don't have big careerist titles to hold over everyone. Frightened of being bullied by the A-Group popular girls all over again, they decide to lie to impress everyone. Their plan backfires but they eventually concede they shouldn't have to try to impress anyone. A few months later they have opened their own boutique and are completely content with themselves.

Question 5

Who does groom Michael end up with in My Best Friend's Wedding?

My Best Friend's Wedding is a wonderfully funny dramatic romcom that came out in 1997. The plot swivels around an obsessed Julianne who realizes she's head over heels for Michael, her college best friend, just when he decides to get engaged. Jules uses every dirty trick in the book to push him into realizing his true love for her, but is it enough to tear him away from his bubbly young fiancée Kimmy? Also who can forget the spontaneous brunch rendition of Dionne Warwick's "I Say a Little Prayer For You".

Question 6

In Parent Trap where do the lost twin sisters meet?

British Annie and Californian Hallie couldn't have more distinct personalities. While one is refined and speaks French, the other is down to earth and horseback rides. However once they realize they share the biological parents they have a reason to unite forces and bring their mom and dad face to face. This reunification plan becomes a race against time as the freckled duo (both played by Lindsey Lohan) soon find out Nick Parker is soon to be remarried to a younger "Cruella de Ville".

Question 7

In 10 Things I Hate About You how does Patrick gain Katarina's forgiveness?

In a modern "Taming of the Shrew" the popular high schooler Bianca can only begin to date when her older standoffish sister Katarina does. Two boys plot to get Katarina a date so her sister will be eligible. They encourage bad boy Patrick Verona because he is the only one who would dare ask Katarina on a date. 10 Things I Hate About You has witty dialogue that spruces up the predictable plot, it also has ultimate rewatch value because Heath Ledger.

Question 8

How does Josie (Barrymore) become popular in Never Been Kissed?

Josie is a perfectionist copywriter and the youngest editor at the Chicago Sun-Times at 25. She is given a journalist assignment and infiltrates South Glen High School to complete it. However, she's having issues in her personal life and vows that the next person she kisses will be the one. On the first day of school she befriends friendly geek Aldys, but needs to get in the popular group for her story content. Also given this unfortunate set up she falls for Hot and Cool English teacher Sam Coulson, will she blow her career cover to pursue the relationship?

Question 9

Who does Tai end up with?

Tai comes to Beverly Hills high school with little social know-how or fashion sense. However, Cher and Dionne transform her into a beautiful new "it" girl and push her towards some of the most eligible bachelors at their school. While the first boy they push her towards turns out to be a creep, she soon becomes more confident and eager to pursue others.Tai actually ends up with the guy she was attracted to in the beginning-- you can't change taste.

Question 10

In She's All That what must Zack do if he loses the bet?

A modern readaption of My Fair Lady, She's All That depicts a high school drama where a popular jock bets he can transform any geeky girl into a prom queen (the nerve!). In typical 90's romantic comedy style athletic Zack is surprised when he finds himself genuinely attracted to the artistic introvert, Laney. Of course Laney gets a makeover and is now worthy of male attention-- making her eligible for prom queen. Also, the impromptu choreographed dancing make She's All That just off-brand enough to fit in with 90's style.

Question 11

What is Will Thacker's (Grant) profession in Notting Hill?

Another Julia Robert's classic, in Notting Hill famous American actress Anna Scott (Roberts) runs into Will Thacker (Hugh Grant) in England. In a series of coincidental mistakes they meet several times and something sparks between them. She stays at his place and he helps her practice line delivery, just as their relationship begins to blossom the perils of fame get in the way. Paparazzi and movie promotions make her omnipresent and Will is not sure he can handle her fame. The movie ends in a classic 90's race where the boy realizes he's made a stupid mistake.

Question 12

When does Zack first impress Laney?

She's All That is the typical '90s teenage film about a boy simultaneously underestimating girls and overestimating himself. Jockey popular boy Zack asks out introverted artistic Laney in an attempt to make a bet with his friend Dean. She is immediately unimpressed by his arrogance and suspicious about his interests. He learns more about her from a mutual friend and tries to mirror her interests, joining her at a local art lounge. He is not ready to perform anything but Laney thinks the surprise of calling him on stage is the price of his earlier arrogance.

Question 13

Why does Prince Henry reject Danielle at the ball in Ever After?

In the beginning different aspects of Cinderella are being debated by the Brothers Grimm. They frame Ever After as a tale set in Renaissance France, with Cinderella as a central decision maker. It features all sorts of cultural content, from Thomas More's Utopia to Leonardo Da Vinci's Mona Lisa. Moreover, Danielle is given a personality and often portrayed as stronger and smarter than Prince Henry. She has endured her step family, chases away gypsies, and defends herself against Pierre le Pieu.

Question 14

Which movie is inspired by a classic fairy tale?

Many of the movies on this list have found themselves inspired by Shakespeare comedies. This particular film starring Drew Barrymore is actually based on a classic fairy tale. Though it takes somewhat of a detour from the original story and actually gives the prince some semblance of a personality, it's still found its way into the hearts of women all around the world. And Drew looks absolutely dazzling in her dress, maybe rivalling the recent Disney reboot based on the same fairy tale.

Question 15

How does Katerina express her forgiveness for Patrick in 10 Things I Hate About You?

Katarina initially does not want to go to prom and is only antisocial because she has vowed not to be forced into anything by peer pressure. In high school this automatically makes you a pariah. Patrick, a boy she's decided to give a chance, asks her to prom and she reluctantly concedes because her sister Bianca encourages her that it is her decision. Once Kat finds out Patrick was paid to take her to prom she is infuriated but realizes it is ultimately what she wanted.

Question 16

What prompts Amanda (Jennifer Love Hewitt) to find Preston in Can't Hardly Wait?

Can't Hardly Wait became the archetype for high school party movies. Most of us have never really experienced anything quite like that, and those who have might not actually remember the experience. Still, at the heart of this movie are a boy, Preston, and a girl, Amanda, who are finally mature enough to know what they want out of life. As it turns out, it's each other. Through some crazy antics and misunderstandings, they finally do hook up. What makes Amanda like him in the first place?

Question 17

What is Julia's (Barrymore) profession in The Wedding Singer?

The Wedding Singer pairs Adam Sandler and Drew Barrymore in the ultimate 90's romantic comedy. Robbie (Sandler), an aspiring rockstar from New Jersey, has lowered his career expectations to finding the next gig or getting a "real job". His longtime girlfriend breaks up with him because of this but Julia (Barrymore) cheers him up and slowly their relationship begins to test the lines between platonic or more. However, Julia is set to marry shmuck boyfriend Glenn in Vegas when Robbie decides he loves her.

Question 18

How does Maggie most specifically mirror the tastes of her fiancés?

Runaway Bride is a case of Maggie Carpenter who has left three men at the alter. It's not that she is allergic to commitment, she just caters too much to the man she is dating. When ex-reporter Ike finds her he tries to help her pinpoint why she can't commit to these marriages at the last minute. Ike meets her when her soon-to-be husband is an athletic director and tries to coach her down the isle. She then realizes she is in love with Ike but runs away from him as well.

Question 19

In Clueless who delivers the diss "you're a virgin who can't drive"?

Clueless provides endlessly quotable content from this era, and the creative burn above is a poignant example of how cruel high school girls can be. (the only response to this is an acknowledged, "way harsh") When Tai joins Cher and Dionne in a Beverly Hills high school she picks up all of the colloquial expressions of the hip upper-crust. However Cher has only "adopted" her as a pet project because she was so tragically uncool to begin with. At the low point in the movie, Cher reflects on her responsibilities to people and reorganizes her goals.

Question 20

Once Chase and Nicole decide to be together what do they discover once they return home?

Chase and Nicole have rejected their original lovers in favour of each other. Little did they know that despite their opposite personalities they actually get along quite well. In the beginning they only thought they shared jealousy but they also share the experience of growing up with single parents. They also share aspects of their individualities with each other. Since they are neighbours they decide to share a ride home together after the big night of declaring their love for each other.

Question 21

What do the popular kids constantly do to Michele?

Romy and Michele's High School Reunion is a classic not only thanks to its main stars who are absolutely fantastic, but because of its over the top portrayal of high school (and the fact that the actors all play themselves despite being significantly older). The cool girls in the class have a habit of doing something to Michele, making fun of an unfortunate physical issue she has. Luckily, by the time the reunion comes around, she's sporting a rocking hot bod and a ton of confidence.

Question 22

How does Titanic begin?

This 1997 masterpiece redefined the notion of romance. It combines fictional romance with historic tragedy. By making audiences once again relive the desperation and horror of the sinkage through personal attachments to characters Rose and Jack, it pays homage to the original wreckage. The director Cameron infuses joyous scenes like the panoramic of Rose and Jack on the stern with a knowing fragility. The story of lust and vengeance adds to the epic story of the human disaster, even if it focuses less on technical mishaps than it does on Rose and Jack.

Question 23

In Shakespeare in Love what play is Shakespeare inspired to write?

Shakespeare in Love is a tale of how the playwright was inspired by a love interest who shares his love for the stage. They meet as she auditions in disguise, reciting Shakespeare's own Two Gentlemen of Verona. Unfortunately she is engaged to lowly aristocrat Lord Wessex who notices Shakespeare's interest and threatens to kill him. Shakespeare continues to visit his muse Viola, visiting her on her balcony and unknowingly casting her as the lead in the play he is writing.

Question 24

In My Best Friend's Wedding how does Jules attempt to embarrass Kim?

Jules (Julia Roberts) is flabbergasted to find Kim (Cameron Diaz) is a naive and energetic twenty year-old. She judges Kim is the exact wrong type of girl for her college buddy Michael and attempts to show him why. Kim embodies the paradox of the perfect girl- she is detestable because she has no flaws but her pure intentions make it impossible to detest her. So, endearing Kim waltzes through these traps unscathed. Even when Jules preys on her confessed weakness it results in the entire bar cheering Kim on. Tough luck, Jules.

Question 25

Where do Romeo and Juliet first share a kiss?

This modern rendition of Romeo and Juliet takes place in Verona Beach. It retains character names and the original Shakespearean dialogue is also kept but the ire of the feuding families is due to gang rivalry. Romeo decides to crash the Capulet party with a group of his friends, there he first glimpses Juliet and they share a moment staring each other through a fish tank at the costume party. However Juliet is dragged away to dance with Paris, her family's chosen fiancé.

Question 26

What does Vivian teach Edward in Pretty Woman?

Pretty Woman provides a not entirely negative perspective into the sex industry and at least gives some sort of recognition the respect sex workers deserve-- the same as anyone else. However, Edward realizes that actually him and Vivian are both in the profession of "scr*wing people for money". His way of doing this is just sanctioned by capitalism and the law. In a pivotal scene at the horse races, she teaches him how to be human and realize who he is surrounding himself with.

Question 27

In Never Been Kissed what immediately happens to Josie on her first day at school?

Josie seems a little tone-deaf arriving to her first day back in high school sporting a white feathered boa. Following this a series of mishaps solidifies her uncool status and Josie has an uphill battle to reach the peer group her Chicago Sun-Times editor wants her to infiltrate. Also her younger brother drop-out Rob comes to the school and immediately gets the attention of the in-crowd by eating an entire tub of coleslaw. He next pretends they used to date and boom! Josie's in.

Question 28

In Pretty Woman what does Vivian do when she locks herself in the Hills Regent Hotel Bathroom?

Fantastic 90's duo Julia Roberts and Richard Gere collaborate to make one of the most successful box office hits of 1990. When successful lawyer Edward (Gere) strays down Hollywood Boulevard and picks up Vivian (Julia). Their chemistry is palatable in his high end Lotus car and he proposes she stay the evening at his hotel. There they connect on a human level as she symbolically removes her wig and he sees another side of Vivian the sex worker. For a compensation of $3000 stays with him for a week and they begin to change each other.

Question 29

Where do the parents reunite in the Parent Trap?

The twins Annie and Hallie accompanied by butler Martin and Nick's helper Chessy scheme to have the ex's meet. These two counterparts begin a romance as soon as they meet. Once Elizabeth, Chessy, and Martin have figured out the twins have switched places they need to exchange them. However, father Nick is not in on the plan and is completely blindsided after not seeing nor hearing from Elizabeth in over eleven years. Their arrival is also a surprise to Meridith, the pending stepmother who the twins hate.

Question 30

In Romy and Michele's High School Reunion how does popular boy Billy end up?

Romy and Michele attend their ten year high school reunion in Arizona pretending to be the businesswomen who invented Post-it. After pretending for a while they realize even though many of their old rivalries are still aflame, they don't care what their old high school peers think. Romy gets back at Billy by pretending to be interested in him and telling him she will meet him in his hotel room if he waits for her up there naked. This is her revenge for when he left her hanging at prom.

Question 31

In Notting Hill Will pretends to work for what magazine to see Anna?

Famous actress Anna invites Will to the Ritz Hotel for their first planned date. However Anna is caught up in an interview session with fellows production crowd and cast members are answering questions about a new Sci-Fi film. Will is forced to interview Anna and her costars about a out of the blue. He randomly chooses a magazine he can pretend to write for, but unfortunately it is extremely inappropriate given the film takes place in space. He pulls it off in an only slightly cringeworthy scene- well done Will.

Question 32

What does Mike learn from Trip in Can't Hardly Wait?

In the setting of a high school graduation party jocky Mike has dumped his girlfriend Amanda and convinced his bros to do likewise. He is anticipating all of the girls who will be interested in college, but unfortunately he receives some daunting insight from a former stud. Amanda is now uninterested in high school boys and their attitudes, instead finding value in a secret lover and his intellect. Can't Hardly Wait is about the life that comes after high school, it is a tribute to all nerds.

Question 33

In The Wedding Singer where does Robbie confess his love for Julia?

Both Robbie and Julia are initially engaged to other people when they meet. However when Robbie's relationship fails and new girl Julia helps cheer him up he begins to fall for her. With an elderly lady's encouragement Robbie realizes he needs to halt Julia's wedding before it occurs. He has finally decided he wants to have Julia by his side when he is growing old. Robbie catches Julia with fiancé and unabashedly confesses his love for her, she accepts his feelings and admits her own.

Question 34

How does Shakespeare in Love end for Viola?

In Shakespeare in Love the famous playwright has been inspired to write a play that depicts the true nature of love. His muse and leading "man" Viola is enamoured with him but both recognize the futility of the situation since Shakespeare is currently married though separated. Viola's identity is unmasked and she is banned from playing the lead role because of the laws against female actors. However, the night before the performance the replacement's voice has broken and Viola must step in for him before the Queen.

Question 35

Who dies first in Romeo and Juliet?

This Shakespearean adaptation (as well as the original) is a story of miscommunication, between families and within relationships. Juliet is planning to elope with Romeo and has hatched an elaborate plan with Father Lawrence to fall into a comatose and is taken to the church, presumed dead. Romeo falls into a depressed state and buys poison for himself, he seeks Juliet's body out to have his final resting place be in her arms. No one has told Romeo his Juliet will be fine and well.

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