The Bachelor begins with an analogy that men, like wild mustangs, are driven to various sweet patches of grass -- tall, short, dark and blonde grasses. Over grand aerial views of wild horses on the open plains, we hear Jimmie Shannon (Chris O'Donnell) explaining that both want their freedom and "have an endless quest for..." -- cut to a close-up of many shapely female legs perched at a bar.
Jimmy's philosophies may stem from spending time with a group of buddies he works with at his grandfather's sporting goods company. All the boys are bachelors, but in the first few minutes, Jimmy watches his friends fall like dominoes. At each wedding the bride's bouquet is thrown to one of the guy's girlfriends. Immediately we see the poor male superimposed over the running mustangs. Suddenly a lasso encircles him and pulls 'em down. Sure enough, Jimmy's girlfriend Anne (Renee Zellweger) nets the nosegay, and like a horse who knows he's headed for the noose, he offers an obligatory proposal, saying simply, "You win".
Not the proposal Anne had in mind, she rejects his offer, and Jimmy is confused. However, after the death of his grandfather, his confusion turns to panic. Grandpa's will states that unless Jimmy is married by his thirtieth birthday (conveniently tomorrow) and stays married for ten years, he has no claim to the $100 million estate. Even though he doesn't tell Anne of the predicament, she rejects his second overture, leaving Jimmy to ask every girls he's hardly even slept with if they will marry him. Desperate to help, Jimmy's buddy Marco (Artie Lang) heads to the newspaper to place an ad.
That leads to the extended finale with scads of women dressed in white chasing Jimmy through San Francisco, willing to marry for money alone. Insulting toward marriage, men, and women, the script offers a myriad of profanities and sexual innuendo including a discourse on how a flower represents a plant's vagina. With the exception of one beautiful moment when a priest tells Jimmy what marriage is really about, this movie should have been taken behind the barn and shot.