The Bachelor (1999 film)

The Bachelor is a 1999 romantic comedy film directed by Gary Sinyor and written by Steve Cohen. It is a remake of the 1925 film Seven Chances and stars Chris ODonnell and Rene Zellweger. The film was also the debut of RampB singer Grammywinner Mariah Carey as an actress.

Jimmie proposes to Anne again, but she is able to see his core reticence, and leaves for Greece. Jimmie, unable to give up inheriting the money due to the lives that would be ruined if the family business closes, decides to pursue exgirlfriends to propose to. Meanwhile, Anne has second thoughts and returns to her apartment, which she shares with her sister Natalie Marley Shelton. Natalie talks Anne into going home to go visit their parents in Napa for the night.Jimmie, on his desperate quest, opens a shoebox full of photos of old girlfriends, and begins to track them down one by one. First he sees Stacey Rebecca Cross, an oil futures trader, who, as it turns out, is engaged already. Second is Zoe Stacy Edwards, a clingy window dresser. When Jimmie goes to see her, just after promising hed never leave her for another woman, he runs off after a woman in the street whom he thinks is Anne which turns out not to be. He returns to find Zoe has set a mannequin on fire in effigy of him. He also strikes out with a melodramatic opera singer Mariah Carey and a toughasnails cop Jennifer Esposito. Soon his list is depleted, but his last choice accepts brittle, chainsmoking socialite Buckley Brooke Shields, who detests Jimmie but wants his money to prop up her waning family fortune. As the priest tries to conduct the ceremony, she gradually learns the other conditions of the will she and Jimmie must have children within five years, spend no more than one night apart per month, and need to stay married for at least ten years. Horrified, she drives off in a convertible. ........

Source: Wikipedia