Will is more interested in finding the perfect gift for his son Nathan's (Jake Johnson) 13th birthday than in doing his job selling insurance. His best friend, sensitive soul Craig (Christopher Moynihan), still pines for his college ex, Lisa. Will's brother-in-law, Kenny (Dan Fogler), clamps down on his anger and asks himself, "What would Tobey Maguire do?," when his ex-wife, Brenda (Amanda Detmer), starts seeing a guy who is everything he's not and much better looking (Henry Simmons). After Craig crashes Lisa's wedding to try to win her back, they are all faced with an opportunity to "man up" and be like their forefathers.

Cast: Amanda Detmer, Dan Fogler, Grant Garry, Armani Jackson, Jake Johnson, Charlotte Labadie, Christopher Moynihan, Teri Polo, Henry Simmons, Mather Zickel