Bill (2007)

Bill is unhappy: he's married a banker's daughter and has a non-job at the bank; his wife Jess is tied to daddy's purse-strings; and, Bill is developing a gut from lack of exercise and constantly eating candy bars. He dreams of buying a donut franchise to be independent of Jess's dad. Bill is roped into a mentoring program at his old prep school, assigned a smart-mouthed kid who pops up when least expected. When Jess starts an affair with Chip, a local TV personality and vain Rob Lowe look-alike, it sends Bill, the kid, and a young sales clerk from a lingerie shop on a quest to win back Jess and get the donuts. What about self-respect?