Cruel Intentions

Cruel Intentions

Year: 1999

Runtime: 97 min

Language: English

Director: Roger Kumble

DramaThrillerRomance

In the cutthroat world of privileged youth, a trio of manipulative acquaintances - including Kathryn (Sarah Michelle Gellar), Sebastian (Ryan Phillippe), and Annette (Reese Witherspoon) - engage in a dangerous game of emotional manipulation, exploiting the vulnerabilities of those around them to satisfy their own twisted desires.

Warning: spoilers below!

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Timeline – Cruel Intentions (1999)
Trace every key event in Cruel Intentions (1999) with our detailed, chronological timeline. Perfect for unpacking nonlinear stories, spotting hidden connections, and understanding how each scene builds toward the film’s climax. Whether you're revisiting or decoding for the first time, this timeline gives you the full picture.
1

Sebastian's Search for Challenge

Sebastian Valmont, a wealthy and charismatic teen, grows weary of his usual manipulative games with women. He decides to seek someone who can challenge his seductive prowess, leading him to the principled Annette Hargrove, who desires true love above all else.

New York City
2

The Bet is Proposed

Sebastian proposes a risky bet to his stepsister, Kathryn Merteuil. The wager states that if he fails to seduce Annette, he will give up his vintage Jaguar XK140, but if he succeeds, Kathryn must yield to his desires.

3

Kathryn's Revenge Scheme

Kathryn is motivated by vengeance against her ex-boyfriend, Court Reynolds, and manipulates Sebastian into using innocent Cecile Caldwell to lead Ronald Clifford, a kind-hearted music teacher, into a romantic trap. This layered scheme serves both Sebastian's and Kathryn's agendas.

4

Sebastian's Struggle

Initially, Sebastian finds it difficult to seduce Annette as she has been warned about his notorious reputation. To rectify this, he blackmails football player Greg and uncovers that it was Cecile's mother who informed Annette, complicating his mission further.

5

The Seduction Plan

With Kathryn’s assistance, Cecile becomes bold, leading to a well-laid plan for her to seduce Sebastian. However, as Sebastian spends more time with Annette, he begins to experience genuine feelings for her, complicating his original intentions.

6

Annette Resists

Sebastian attempts to kiss Annette, but she resists, fearing that he will take away her sense of control. This leads to a moment of self-evaluation for both characters, who realize they share profound feelings but are hindered by their own fears.

7

Sebastian's Confession

In a moment of clarity, Sebastian confesses his true emotions to Annette, igniting a passionate connection between them. However, Kathryn threatens Sebastian, warning him that revealing his feelings could ruin their reputations.

8

Betrayal and Heartache

Sebastian’s deception weighs heavily on Annette, leaving her heartbroken after she learns of his betrayal. As their relationship crumbles, Sebastian struggles to mend things with Kathryn but is consistently rebuffed.

9

Kathryn's True Intentions

Kathryn reveals that her manipulations have a darker purpose: to destroy Sebastian’s pride and spirit through his love for Annette. This revelation leads to Sebastian attempting reconciliation but receiving only rejection.

10

Apology and Exposure

Sebastian leaves Annette a heartfelt apology and shares his innermost thoughts through his journal, which ultimately exposes Kathryn's cruel manipulations. This act not only seeks redemption but also reveals the truth to everyone's eyes.

11

Confrontation and Tragedy

As tensions mount, Ronald confronts Sebastian in a fit of anger, leading to a chaotic encounter. In a heroic effort to save Annette, Sebastian pushes her away from danger but tragically gets struck by a taxi in the process.

New York City
12

Moments Before Death

In the heartbreaking moments leading up to his death, Sebastian and Annette share their true feelings for one another. This emotional exchange highlights the devastating consequences of Kathryn's manipulative cruelty.

13

Sebastian's Funeral

During Sebastian's funeral, Kathryn's eulogy falls flat amidst the support for Cecile, who circulates copies of Sebastian's journal, *Cruel Intentions*. This act further enshrines Sebastian's truth and reveals Kathryn's wickedness.

14

Kathryn's Downfall

With the contents of Sebastian's journal exposing her vices and manipulations, Kathryn faces public scrutiny and the collapse of her carefully constructed image. Her actions lead her into a dark place of reflection and remorse.

15

Annette's Final Remembrance

In a poignant conclusion, Annette drives away in Sebastian's car, wearing his sunglasses and clutching his journal. This final moment symbolizes her enduring love for him, despite the cruel fate that bound their lives together.

Last Updated: November 19, 2024 at 20:44

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