I had never seen this movie before, and truth be told, had never really even heard about it, either. It rang a vague bell when I heard the name, but I could not quite place it. Plus, the description made it sound rather like what is commonly called a "chick flick", so I approached with caution.
But it was actually a pretty good movie, once I finally saw it.
There is this guy, named Sebastian (played capably by Ryan Phillippe), is essentially a very highly successful young man, but he is very immature, making a sport of conquering as many women as he can. This behavior has become such a pattern, such a routine, that he thinks nothing of it, and schemes for more conquests without so much as a pause for thought as to how it might be affecting others.
He makes a bet with his sister by marriage, Kathryn (played by Sarah Michelle Gellar, who was very good in the role), who has watched all of this with a passing interest, almost with a sense of competition, since she is largely doing the same thing in her own life. She decides to make a bet with her semi brother, Sebastian, a kind of indecent proposal, if you will. He has to conquer the consumate good girl, an avid Christian by the name of Annette Hargrove (played very nicely by Reese Witherspoon, who lends the character the right kind of innocent feel).
The prize for her, if he fails, is his 1956 Jaguar XK140, a very valuable car, and his pride and joy. If Sebastian wins, she promises to have sex with him, knowing that she is especially enticing to him because she is the one thing that he cannot have. She promises that he can have her, or do her, any way that he wants to, and wherever he wants to. Full access, if you will.
So, he plays his smooth game, trying to win her trust, and acting shocked -shocked! - when she mentions that his reputation is that of a player, for all intents and purposes.
He is convincing and, little by little, he does indeed break down the barriers she has placed in relation to him, and she begins to trust him more, and eventually, of course, to fall for him.
From that point onward, he is consumed by a struggle within himself. In pursuing Annette so vigorously, he in fact falls in love with her. He has the opportunity to go the distance with her and win his bet, yet cannot bring himself to do it.
In the meantime, Kathryn not only observes and understands all of this but, she reveals, has planned all of this. She seems to have known exactly what would happen, and there is a sense that she has been the driving force of everything that happens behind the scenes. By the time that she reveals all of this to Sebastian, he is going crazy. He feels strongly enough about her to warn her away from him, revealing that he is, indeed, not someone that she can ever trust. Clearly used to conquests of women before, he obviously never expected to fall for "the one", or that "the one" might end up being Annette.
Despite how torn up he is by all of this, Kathryn views it all with humor. While Sebastian is initially seen as the immature womanizer who does not understand the full extent of the pain he is causing people, we find that it is Kathryn who is more like that than anybody else.
Sebastian, in the meantime, struggles and tries to come to terms with his feelings, playing it off as just another girl that he has conquered, but he has pushed her away, and now cannot deny that he loves her. He does things that are ill-advised, constantly trying to get in contact with her (but her friends protect her, and do not allow this guy who has caused her so much pain to go anywhere near her). Increasingly desperate, he then hovers around her apartment, and she finally notices just as he walks away. She goes out and follows him toward the park, but he is confronted by one of the guys that he has used in one of his little schemes, and a physical fight breaks out between the two of them.
She runs to intervene, to break up the fight, and in the process of trying, she is thrown in the middle of the road nearby. Sebastian sees this, sees the car approach, and throws himself in the street, getting her safely out of the way, but sacrificing himself in the process, getting struck by the car and receiving wounds that will prove fatal.
It is then that Annette finally avenges Kathryn by revealing the book of private thoughts of Sebastian's during his funeral. Kathryn was giving a speech at the time, and is surprised by the reaction, or rather the lack of reaction, which is clearly not what she expects. When everyone starts walking out right in the middle of her speech, she goes outside and follows them, and it is there that she finds out that the book of Sebastian's, where Kathryn is portrayed as essentially an evil schemer, is now widely circulated, so that everyone present has a copy, and knows all of the unsavory details about Kathryn. She even has cocaine inside of her necklace.
This is a good movie, and kind of draws you in. It came on television the first time that I saw any of it, and it seemed like a chick flick, and I was about to turn it off. Yet, somehow, I kept it on, but hardly paid attention to it. But little by little, I found myself watching it more and more, and paying attention. When I got the chance to see it more fully, and uncensored and without commercials to boot, it was even more addictive.
It is a comedy, although there are points where it becomes a serious movie. it is also quite sexy, without being over the top with it, like some other movies. Done in good taste, but being weighed down by overly serious pretensions, or anything. A fun movie that might even be seen as a tear jerker towards the end. But a good movie, all in all, and I recommend it.
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