The Bachelor (1999)

In the bustling city of San Francisco, we meet James Shannon III (Chris O'Donnell), a charming yet gullible bachelor who has a knack for fumbling his relationships. His life seems to be a whirl of fleeting romances until he meets the captivating Anne Arden (Renée Zellweger). When he finally gathers the courage to propose, his old habits resurface, and he botches the moment, leaving Anne heartbroken and their future in jeopardy. Suddenly, life takes an unexpected turn when his grandfather, James Shannon (Sir Peter Ustinov), passes away. In an intriguing twist, the old man's will reveals a peculiar condition - Jimmie must marry by 6:05 p.m. on his 30th birthday, which is just around the corner, or he stands to lose his entire inheritance of one hundred million dollars. This would send his pool table company spiraling into bankruptcy, his bank accounts would be frozen, and his employees would face unemployment. With Anne out of town on an assignment and unreachable, a desperate Jimmie finds himself in a race against time. His once carefree bachelor life is replaced by a frantic quest to find a bride, leading him on an amusing journey through his past relationships. He must navigate this chaotic endeavor, learn from his past mistakes, and find true love, all while trying to save his company and his future. The question remains - will Jimmie conquer his commitment issues, tie the knot, and claim his inheritance before the clock strikes 6:05?

The Bachelor is a comedy movie featuring Chris O'Donnell.

It is possible to buy The Bachelor on Amazon Video, Apple TV, DIRECTV, Google Play Movies, Microsoft Store, Vudu and YouTube.