Overview
Whatever It Takes is a 2000 American teen comedy film directed by David Raynr and starring Shane West, Marla Sokoloff, Jodi Lyn O'Keefe, and James Franco. It was released in the United States on March 24, 2000. The film's story is a modern update of the 1897 play Cyrano de Bergerac by Edmond Rostand.
Plot
Ryan Woodman is a bit of a geek with eyes for the school's most popular girl, Ashley Grant. This induces cringing in his neighbor and best friend, Maggie Carter, a cute, intellectual girl. Football jock Chris Campbell, who happens to be Ashley's cousin, has his eye on Maggie, and he offers to help Ryan get the girl of his dreams if Ryan does the same for him. Ryan and Chris agree on the deal, which has Ryan compose soulful e-mails for Chris to use on Maggie, while Chris advises Ryan to treat Ashley like dirt, with the reasoning it's the only way to get her attention.
At first, neither guy finds it easy to change their ways; Chris comes on too strong for Maggie's liking, and Ryan is too nervous to be a jerk to Ashley. But as they start to succeed, Ryan begins to see Maggie in a new light and wonders if he's pursuing the right girl. He realizes Ashley is not meant for him just as he tries to convince Maggie of Chris's affection for her. Meanwhile, Maggie questions her own interest in the narcissistic Chris. Ryan's change in behavior, which includes insulting his geeky friends, also sinks Maggie's opinion of him. Ryan learns Chris plans to “nail and bail” Maggie on the night of the school prom, a strategy he's done with every girl he's dated. Ryan tells Chris that this won't work because Maggie is too good for that, but he blithely ignores him.
Ryan ends up confessing his feelings for Maggie and admits to her it was him writing her the romantic letters the whole time, not Chris. Feeling let down by the dishonesty, Maggie is hesitant to reciprocate his feelings. She ends up going to the prom with Chris while Ryan begrudgingly goes with Ashley. At an afterparty in a hotel, before Chris can get Maggie into bed, Maggie insists on tying him to the bed and blindfolding him, which he obliges. When Chris is fully restrained, Maggie tells him she has just played him and takes a Polaroid of him in the humiliating position. She leaves Chris in the room to be taunted and drawn on by other partygoers. Ryan ends up ditching Ashley and goes after Maggie. Back at their homes, Ryan tries to talk to Maggie over the balcony and apologizes for his wrongdoings.
From Wikipedia (CC BY-SA 4.0).