Chuck and Blair/Cruel Intentions parallel

Yesterday night I watched “Cruel Intentions” for the first time, a 1999 movie based on the  “Dangerous Liaisons” book by Laclos.

Here’s a quick summary:

Kathryn and Sebastian, two wealthy, manipulative teenage step-siblings from Manhattan’s upper-crust, conspire in Cruel Intentions, a wickedly entertaining tale of seduction and betrayal. The stakes are high when the duo agrees upon a deliciously diabolical wager of sexual conquest without consequences. The pawns? The naive Celcile Caldwell and the virginal Annette Hargrove. Its summer break, and Kathryn has been dumped by her beau, Court Reynolds, for the innocent Cecile. Desperate to get even, Kathryn challenges Sebastian to ruin Celcile by deflowering her and turning her into a tramp-thus humiliating Court by delivering Cecile to him as damaged goods. Sebastian has pretty much ‘had’ all of the girls in New York City up to this point, and he’s gotten a bit bored of it all. Though this is too easy a conquest for him, he obliges. He sets his sights on a greater challenge-the new headmaster’s daughter, Annette, who recently wrote an article in Seventeen Magazine about how she intends to stay pure until she marries her boyfriend. Sebastian bets Kathryn that he can seduce the chaste and pristine Annette before school begins in the fall. Kathryn thinks this feat impossible and quickly agrees to the wager. The stakes: if Sebastian succeeds, Kathryn must give him a night of unbridled pleasure, something’s he’s wanted since their parents got married. If he fails, he must forfeit his priceless 1956 Jaguar to Kathryn and suffer the shame of defeat.

Now, don’t you think the plot has something to do with Chuck and Blair? If you have watched the movie, you’ll see the plot reminds of episode 2×07, Chuck in real life. Let’s make some parallels.


The leading girl asks the playboy to seduce a girl for her, to completely destroy her good reputation.

In CI case, the girl is a virgin, while in GG, is Vanessa. We know Vanessa is not a virgin anymore (I mean, I think it’s logical because at that time she already had a relationship with Nate on the show and I think they had sex).

The bitch of the situation wants to destroy the good girl (casuality is that tagline for CI is Seduce and destroy, just like Blair’s line to Chuck in the first scene pictured).

But all has a price. What will be the boy’s prize if they win?

Well, Sarah Michelle Gellar’s character Katheryn promises Sebastian “what he has wanted since their parents married”, that is,  her body. She is the only one he never had sex with. Funny.

On the other hand, Blair in the beginning only says to Chuck that he will get “the thrill of the impossible”. Then, when she sees that Chuck doesn’t want to do the dirty work anymore because let’s face it, it’s not worth seducing Vanessa Abrams without anything in return, and we all know that – Blair rises the stakes, making clear to him, he not only will have the thrill of seducing a Brooklyn hobo (EWWW) but he will have her (Blair) too if he’ll succed V.

A difference is that Kathryn asks for Seb’s Jaguar if he fails, while Blair apparently only wants to sleep with Chuck again, that I think is even better. This detail was though used in 2×12, when C&B made the deal for the best date at the ball.


Sebastian meets Annette at his aunt’s house, while Chuck meets V on the place of her new goal: trying not to make some rich men close an old bar (or something, can’t remember exactly).

They try to impress them, Seb tries to be kind and offers the girl to help her in the new city, while Chuck tells Vanessa he’ll buy the place so it won’t be changed into a cheap place. Both girls know they’re bad news, so Annette makes it clear to Sebastian that she wants nothing to do with him, and so does Vanessa. Chuck receives a watermelon drink on his suit as a bonus too. LOL.


They both failed, but this doesn’t mean they won’t try it again.

Sebastian tries to seduce Annette at the swimming pool, but he gets rejected again, even if he tries to tell her what people said about him wasn’t the truth, and he has changed. The girl is too pure. Chuck doesn’t do anything, on the contrary. In GG’s case, Vanessa is the one that comes to him few hours later. She thought about his offer and wants to accept it, because it’s the only thing she could do to save that bar. But, quoting V “this doesn’t mean I trust you”, and Chuck knows it, but this is at least a start. (But you know, GG times are shorter so all goes faster).


Both guys want to succeed, so they have to impress the victim to show her she can trust them.

Sebastian calls a friend that is friends with the girl and threatens him to tell everyone his secret (the guy is gay) if he won’t help him. So the guy meets Annette, they talk, and she starts to think that maybe Sebastian has really changed. Sebastian calls Annette after a few hours telling her he was thinking about her, and she really seems to believe him now.

In GG we see Chuck going to the old bar and meeting the barman that believes him, and is Chuck that tells V “he trusts me”, and V too seems to trust Chuck. And Chuck is really serious about that. He really likes the place, he wants to buy it. So, to “seal the deal” Chuck asks V to come to his house that night because there will be a party.

In both CI and GG, the bitch checks how things are going with the playboys. Sebastian and Katheryn meet at their house and she asks him, and then she teases him, while Blair sends a simple text to Chuck. She then asks him about the progresses when both are at the party. [continues in the next point]

This is the part of the story where all is starting to become too serious than the players thought, because both playboys in the end have a heart, and both situations are worth for them.


Both guys arrive at the point that this is no more game for them. Feelings are now involved, and in GG’s case, business too.

Blair meets Chuck at the party and asks him how things are going. Chuck is honest with her, isn’t a game anymore. He likes the place V showed him, and it could really become a good business. Blair obviously thinks he’s kidding, but Chuck’s expression shows how he isn’t. Blair then asks if he’s gonna crush Vanessa anyway, but Chuck doesn’t answer. He’s caught by Vanessa’s entrance in the room. He excuses himself and goes to greet her, leaving Blair alone. (I felt so bad for B in this scene that I wanted to crush Vanessa on the spot, lol).

In CI happens the same. Sebastian is spying Annette and Katheryn gets in. She’s jealous because she sees Seb slowly getting far from her, and she tries to kiss him to make him change his mind, but he doesn’t. He gets out of the room and decides to go where Annette is, leaving Katheryn alone.

Both bitches have been ditched, and they’re jealous and angry at the same time. Revenge is coming.


Chuck greets V. He’s happy to see her, and she’s happy she came. Before doing the next move C and V are interrupted by Bart. V listens to their convo and understands how Chuck is feeling, while Blair spies from a corner in the room. Vanessa reaches Chuck after she listens to the convo, and he’s alone sitting on a couch. They talk and all, and when Vanessa turns to leave, Chuck takes her hand and begs her to stay. Blair catches them and she’s upset. She knows she has to act soon if she doesn’t want Chuck to get into V’s pants.

Vanessa has now full trust in Chuck.

Same for CI. Seb goes with A and shows her he is a good guy because he cares about visiting old people for his aunt. On the trip home, she holds his hand while he’s driving. Sebastian gets to kiss Annette  later, while Katheryn spies, but this time he gets rejected. This is the beginning.  [continues into the next point]


Both bitches have enough because they’re seeing their men going too far than they expected. They’re losing them.

Blair goes to Chuck and tells him the girl is not worth the game, and that she’s bored. Chuck only thinks that she’s only afraid to give him what she promised if he wins. What Chuck doesn’t know is that Blair is actually jealous because she saw that there was something more between them when they looked into each other’s eyes minutes before. She doesn’t want them to get intimate now, because maybe something could start.

Katheryn does the same. She goes to Seb’s room in the morning and asks him about the situation, noticing he’s becoming way too interested in the girl. He admits that he was going to close the deal the night before, but then he stopped because he felt he didn’t want to do it, he wanted to respect the girl. Katheryn jokes about that. She thinks Seb is whipped, and she doesn’t like this. He then decides to go to the girl, but she left. This won’t stop him.


Blair tells Vanessa the truth. They used her. Chuck to get to Dan, and she, to destroy her. Vanessa doesn’t believe her, but that’s the truth, and when Chuck comes in between their conversation, he doesn’t say anything. He was interested in that place, but he was playing a game too. Vanessa then leaves, humiliated. Even if Chuck didn’t seduce her, for Blair, he won. In one hour he’ll receive his prize in Blair’s room. Just a little detail: he really doesn’t seem thrilled.

CI has deeper consequences on the other hand.

Sebastian in the end goes to Annette, they have sex, he realizes he loves her and he starts to become the caring boyfriend, but then Katheryn opens his eyes again, making him go to Annette’s Hotel to break up with her few days later. He comes to get his prize, then. He waits for Katheryn to come home and tells he wants her, but she won’t yield to him. Yet, she confessed that all was a plan to humiliate him too. Sebastian is furious, and leaves her alone again.


Chuck goes to Blair’s room to have what she promised him. She’s hot as ever in her red lingerie. He starts kissing her and they fall on her bed. All is going as planned until Chuck stops, asking for those three words. Blair answers with “Are you kidding”, and Chuck realizes she’s not ready to say anything. Maybe she really doesn’t feel anything for him, and wants only to have sex, and Chuck is not really in the mood that night to play games. He doesn’t care she’s “prepared to settle”, he wants to know the truth, and he wants to know it now to give meaning to the act. After the whole Vanessa thing I think he wanted to know if he was just a pawn for her or not. Seeing that she’s reluctant to say the words, he stops. Now she has to chase him if she really wants him. And we know what happens next.

In CI things are complicated. After the break up, Annette is offended and goes away, but Seb sends her his journal, to let her know what was going on, the deal and all. She finds out the truth and after hours she decides to go to him again. (He waited the whole night outside her Hotel). He’s beating another of the characters on the sidewalk, and Annette doesn’t see a taxi coming. The car almost hits her, but Sebastian saves her and tells her he loves her before he, sadly, dies there. Annette decides to make copies of Seb’s journal so in the end everybody knows the truth about Katheryn, that in the very last minutes of the movie she is humiliated.

xoxo, T

(please don’t copy this into your blogs without linking here).

About purplebass

hey, you! Thank you for stopping by. I'm Tweety, and I am a girl who loves writing, reading, and watching stuff on TV and write reviews about it. I currently study languages (English and Spanish) @ University here where I live in Italy. I dream to become a teacher or something more impossible, like a writer. For the moment I only write stories on my laptop and review a lot of books. Speaking of which, I'm really into YA despite I am not a teenager anymore, and if you have suggestions, I am always open to hear your book advice! :D

9 thoughts on “Chuck and Blair/Cruel Intentions parallel

  1. Maedy says:

    wow what an amazing parrarel!!!
    you know i disgust so much when Chuck took vanessa hand.. i hope he brought disinfectan.

    and what makes chuck run from blair to vanessa?
    ugh just stop right there.

    and CI is a brilliant movie. i felt bad for katherine at the end of the movie. and sebastian died too. well it’s not a happy ending movie. but you can’t deny sexual chemistry between katherine and seb. they are much much hotter than seb and annete.

    • You know, I really don’t know.
      It’s weird, because Chuck didn’t care much about V until that episode. Maybe he just wanted to close the deal and that’s all, like Blair asked.
      I don’t think that it would have started something later, like in 2×20 when he succeeds to sleep with her

  2. ronan03 says:

    i started watching gg at the beginning because some critic compared the show to one of my favorite movies-cruel intentions. all your comparisions were so apt. what a thoughtful post.

  3. I love this! I haven’t the movie since 2000 and I almost forgot the whole movie (thanks to GG I remember bits and parts).

    I’m happy that GG didn’t go in the same exact direction as CI becasue then this show would have ended right then and there.

    I hated how they protroyal Vanessa as this saint, please.

    But love this and picspasm.

    • thank you 🙂
      well, I’m glad too. I couldn’t bear Chuck falling in love with V and forget Blair so easily.
      It would have been wrong and there would have been no S3 since people would have been so disgusted to see this couple together.

  4. kjewls says:

    Amazing post! The comparisons, the picspam, the writing, everything was fabulous!

    I loved the movie Cruel Intentions! So much so, that I actually bought the DVD! (Ryan Phillippe was SO gorgeous, before he became a d-bag and started cheating on Reese! Wasn’t he?)

    And now that you mention it, the parallels between the plot and characters of Gossip Girl and Cruel Intentions ARE remarkably similar! I think a lot of the reasons I loved Cruel Intentions are the same reasons I love Gossip Girl. (Hot actors, great acting, Upper East Side opulence, fabulous style, ingenious banter and double entendre usage, complex characters, cat and mouse games, and sexual tension galore).

    Come to think of it, rewatching Cruel Intentions might be the perfect way to tide myself over, while I wait for the new season of Gossip Girl to begin. Thanks again for the fabulous post!

  5. Je t'adore says:

    Wonderful post bb. You’re awesome. Thank God Chuck didn’t end up with that hobo. I wanted Seb and Kat to end up in the movie, maybe because I don’t usually like good girls. And let’s be honest now, Mannessa can’t even compare with Reese. I agree with Jules about Ryan too, I use to love him before he end up being such a d-bag. Who would cheat on Reese? WHO?

  6. a says:

    this is a really good post, i was looking for an analysis on cruel intentions and came across this. many i have talked to about CI is that kat was the bitch, which is true in a sense but at the same time i felt like it she was betrayed by seb because they were close and he was the only person she confined in, at the end i find it funny when she has her speech and she says “he would say kathryn im sorry” because she was hurt. also it’s humoring with ryan cheating on reese and then cheating on abby with another girl, sounds like sebastian valmont where is sarah michelle gellar anwyay.

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