Chris O'Donnell's character, Jimmie Shannon, begins by launching into a chauvinistic soliloquy about the "mustanghood" of all bachelors and their perpetual hunt for "sweet grasses" (i.e. women) and proceeds to equate bouquet-tossing at weddings with a death sentence for the boyfriend of the bouquet catcher. When Jimmie fears his relationship with Anne (Renee Zellweger) can go no further without an engagement, his proposal of "you win" barely beats the option of "shit or get off the pot."

It's only after Jimmie is faced with losing his grandfather's $100 million inheritance that a fire is lit under his butt to get the "I do's" over with. Jimmie is utterly surprised that Anne keeps saying no and then leaves town. In an attempt to redeem poor Jimmie, the filmmakers threw in a bit about him having to marry in order to save more than 200 people from losing their jobs in his family's company (like the money is just a bonus for his "good deed"). As heartbroken as he is, the knight in a dusty limo spends the rest of the movie botching proposals to ex-girlfriends, until he finally comes to an "Oh my God" revelation that his only desire is to marry Anne.