Guest Stars Danny Murphy as Herb Eliza Coupe as Julia Lauren Bowles as Annie Ben Giroux as Tim Johnny Knoxville as Chuck Erinn Bartlett as Nikki Kate Hodge as Katherine Bonnie Hellman as Midwestern Woman Kenneth Cusack as Joe The Usher Nathalie Johnson as Amy Gerard Facchini as Waiter #1 Tommy Michael Gonzales as Waiter #2 Matt Clark as Waiter #3 Sandra Eloani as Jennifer Spenishton