29 and Holding (2004)

Mike Lesley and Jeff Smith are turning 30 and believe their carefree days are about to be over Mike is the likeable slacker of the two He is a substitute teacher who works well with kids but would rather live on the golf course than be working This infuriates his scheming longtime girlfriend Cathy and his banker father Jack They both want Mike to become a banker at Jacks office Cathys anger at Mikes inability to commit to the job drives her into another mans bed in an act of spite Finding her in the act shocks Mike into a life crisis hes never faced before In stark contrast to Mike is his highstrung friend Jeff who is a conservative pharmaceutical representative whose traditional nature finds him struggling with the values of modern society