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.

The film's story is a modern update of the 1897 play Cyrano de Bergerac by Edmond Rostand.

Ryan Woodman is a bit of a geek with eyes for the school's most popular girl, Ashley Grant.

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.

Then, 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 ends up confessing his feelings for Maggie and admits to her it was him writing her the romantic letters the whole time, not Chris.