The ultimate Cruel Intentions quiz

By: J.P. Naomi
Estimated Completion Time
3 min
The ultimate Cruel Intentions quiz
Image: tmdb

About This Quiz

Two step-siblings, one headmaster's daughter and a whole lot of drama! Take this Cruel Intentions quiz to remember the cruelest and most provocative moments from this late '90s drama!
In which year was the premiere of Cruel Intentions?
1995
1999
Cruel Intentions was released on March 5, 1999. It grossed more than $13 million in its opening weekend at the box office.
2002
2005
In which US city is Cruel Intentions based?
Miami
Los Angeles
New York City
Cruel Intentions was mainly filmed in New York, although some scenes were filmed in Canada and California. There were 28 filming locations in total!
Chicago
Who is the main male character in Cruel Intentions?
Jeremiah
Sebastian
Cruel Intentions was rated R for strong sexual dialogue and sexual situations involving teens, language and drug use. "In the game of seduction, there is only one rule: Never fall in love."
Ronald
Gordan

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What is Sebastian's last name?
Buckingham
Beaudreau
Baudmont
Valmont
Cruel Intentions was written by Roger Kumble. He is said to have written the screenplay in only 12 days. He also directed the film.
Which famous actor plays the role of Sebastian Valmont?
Edward Shearmur
Ryan Phillippe
Ryan Phillippe was born on September 10, 1974. He appeared on One Life to Live early in his career, then went on to star in films such as I Know What You Did Last Summer, 54 and Cruel Intentions.
Neal Moritz
Matt Damon
What is the name of Sebastian's therapist?
Dr. Greenbaum
Dr. Regina Greenbaum is portrayed by actress Swoosie Kurtz. She is an Emmy Award winner and two-time Tony Award Winner. She also appeared in Liar Liar.
Dr. Phil
Dr. Withers
Dr. Marvin

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Sebastian is incapable of sustaining...
Healthy weight
Good grades
Serious relationships with women
Sebastian is out for quick satisfaction and always has been. He is apparently in therapy to cure him of this, so he can have longer and more serious relationships with women.
Interest in his extracurriculars
What is the name of Dr. Greenbaum's daughter?
Jenny
Carol
Marci
Actress Tara Reid plays the small role of Marci Greenbaum. Reid has appeared in multiple films since the start of her career in 1987. She is best known for her role as Vicky in the American Pie films.
Mary
Why did Marci call her mother crying?
Her boyfriend broke up with her and posted a nude photo of her on the internet
Marci calls her mother, hysterically crying. Dr. Greenbaum realizes that the ex-boyfriend is actually Sebastian and she goes after him, yelling!
Her boyfriend broke up with her and is dating her friend
Her boyfriend physically abused her
Her boyfriend stood her up on date night

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What is Sebastian's relation to Kathryn?
Cousins
Uncle
Step-siblings
Cruel Intentions won Choice Movie: Drama Teen Choice Award in the year 2000. It was also nominated in other ceremonies, including MTV Movie Awards, Golden Slate Awards and Blockbuster Entertainment Awards.
Younger brother
Which actress plays the role of Kathryn Merteuil?
Katie Holmes
Selma Blair
Reese Witherspoon
Sarah Michelle Gellar
Sarah Michelle Gellar was born on April 14, 1977, in New York. She is married to Freddie Prinze Jr. and they have two children together.
Who is Kathryn's ex-lover?
Ronald
James
Court
Sarah Michelle Gellar landed her first leading part in the 1992 miniseries, Swans Crossing, and her television breakthrough came in 1993, with the role of Kendall Hart on All My Children.
Sebastian

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What is the last name of Court?
Reynolds
Court Reynolds is played by actor Charlie O'Connell. He was born on April 21, 1975, and in 2005, he appeared on the seventh season of the reality television series, The Bachelor.
Berman
Genesis
Brady
Who is dating Court Reynolds now?
Cecile
Charlie O'Connell was born in New York City and had a small career in film and television. His maternal grandfather, Charles Witkowski, was the mayor of Jersey City, NJ, from 1957 to 1961.
Annette
Bunny
Blaine
Which actress plays the role of Cecile Caldwell?
Katie Holmes
Cameron Diaz
Selma Blair
Selma Blair was born on June 23, 1972, in Michigan. She graduated from the University of Michigan in 1994, with degrees in photography, psychology, fine arts and English.
Tara Reid

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Why does Kathryn take Cecile under her wing?
She wants revenge on Court
Cecile is now dating Court, who dumped Kathryn. Kathryn thinks if she befriends Cecile, she'll be able to manipulate her and get back at Court.
She needs help with her grades
She needs fashion advice
She wishes she had a sister
Who is Sebastian's new love interest?
Carly
Annette
Sebastian is always interested in a new and different female. But the movie reveals there is something different about his feelings toward Annette this time.
Samantha
Jessica
What is Annette's last name?
Bening
Hargrove
Annette Hargrove is a sweet and innocent girl with short blond hair. She is an optimist at heart and a bit naive when it comes to boys.
Jasmine
Palmetta

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Which famous actress plays the role of Annette Hargrove?
Candace Cameron
Cameron Diaz
Reese Witherspoon
Reese Witherspoon was born on March 22, 1976, in Louisiana. She and Ryan Phillippe were actually dating during the filming of Cruel Intentions and were married in 1999. They divorced in 2007.
Katie Holmes
Sebastian views Annette as what?
A baby
A promiscuous girl
A conquest
Sebastian keeps a diary of his "conquests" - innocent, naive girls that he hopes to break, while making them fall in love with him. He leaves them shortly thereafter.
A shoe-in
What is the occupation of Annette's father?
Headmaster of their school
Headmaster Hargrove is portrayed by actor Drew Snyder. Snyder was born in Buffalo, NY, on September 25, 1946. He is also known for his roles in Commando and Universal Soldier.
Attorney
Paramedic
Librarian

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What is the name of the prep school that Kathryn, Sebastian, Cecile and Annette attend?
King Arthur Prep
Phillips Prep
Manchester Prep
The students at Manchester Prep are on their summer break for the majority of this film. We see the students back in school at the end of the film.
St. John Prep
Where is Annette staying during the summer break?
At the Hampton Inn
At Helen Rosemond's in the Hamptons
She stays with Helen in the Hamptons on Long Island. The Hamptons are also called the "East End" of Long Island.
At her father's house
At her mother's house
Who is Helen Rosemond?
The headmaster's assistant
Kathryn's mother
Sebastian's aunt
Helen is portrayed by actress Louise Fletcher. She was born on July 22, 1934, in Birmingham, Alabama. She began her acting career in 1958 and is still active as of 2017.
Sebastian's ex-girlfriend

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Who bets Sebastian that he can't successfully seduce Annette?
Kathryn
If she wins the bet, she wants his car. If he wins the bet, she offers him one night of passion with her.
His Aunt Helen
Court
Blaine
What kind of car does Sebastian drive?
Mercedes
BMW
Ferrari
Jaguar
Sebastian drives a vintage Jaguar 1956 XK140 Roadster. We see Kathryn driving it at the end of the film, with her sunglasses on.
Who is Annette's ex-boyfriend?
Blaine
Greg
Greg O'Connell was portrayed by actor Eric Mabius. Mabius was born on April 21, 1971, in Harrisburg, PA, and has been an actor since 1995.
Jack
Ronald

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Who is Greg currently dating?
Blaine
Blaine Tuttle was portrayed by actor Joshua Jackson. Jackson is best known for his roles as Pacey Witter on Dawson's Creek and Charlie Conway in The Mighty Ducks.
Cecile
Kathryn
Marci
Who is Cecile's music teacher?
Mrs. Sugarman
Marci Greenbaum
Ronald Clifford
Ronald Clifford is portrayed by actor Sean Patrick Thomas. He is best known for his co-starring role in the 2001 film, Save the Last Dance, with actress Julie Stiles.
Annette Hargrove
Who does Sebastian send his diary to?
His mother
His favorite teacher
Annette
He sends it to her because he wants her to read it and understand that he truly did fall in love with her, unlike the other "conquests" that he details in his diary.
Kathryn

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To stir up trouble, who does Kathryn tell that Sebastian had an affair with Cecile?
Sebastian's mother
Annette
Dr. Greenbaum
Ronald
Ronald does not like this piece of information and goes after Sebastian to let him hear it! He ends up in a street fight with him, where Sebastian ultimately gets killed by an oncoming car.
When does Sebastian profess his love to Annette?
At her graduation
Right before he dies
Sebastian tells Annette that he loves her and she says it back to him. He then falls limp in her arms and she cries in agony over his death.
On their first date
In the hospital
Outside of his funeral service, who is handing out copies of Sebastian's journal to the student body?
Kathryn
Annette
Cecile
Cecile wants to make sure that everyone knows the truth about Sebastian. This follows Kathryn's "eulogy" where she rants about how she tried to make Sebastian a better person - but the students walked out instead.
Ronald

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What is the title of Sebastian's journal?
Cruel Intentions
Cruel Intentions ultimately earned more than $75 million at the box office. After being made with a $10 million budget, it was widely successful and was followed by two subsequent films: Cruel Intentions 2 and Cruel Intentions 3.
Dirty Secrets
My Wish
Best Practices to Dating a Virgin
What is revealed in Kathryn's crucifix at the end of the film?
Water
Juice
Cocaine
At the end of the film, the headmaster takes Kathryn's crucifix from the rosary beads she wears around her wrist, and her troubled character is revealed as he discovers it is filled with cocaine.
Marijuana
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