James Shannon III is struggling to cope with his friends' marriages, until his girlfriend catches the bouquet at a wedding, hinting at his own impending marriage. When he botches a proposal, she leaves town, and he discovers a clause in his grandfather's will: he'll inherit a fortune only if he's married by 6:05 pm on his 30th birthday. With time running out, he sets out to find a wife, revisiting past girlfriends in the hopes of securing his future.

The Bachelor
A free-spirited bachelor embarks on a quest to secure a marriage, courting his exasperated girlfriend and other potential partners in a last-ditch effort to claim his grandfather's substantial $100 million inheritance.