Joanne Whalley as Lainie / Joanne (segments "Two for Dinner" and "Late Lunch")

Chris Messina as Jack (segment "Two for Dinner")

Kathy Baker as Diana (segment "Sailing Lesson")

Marshall Bell as John (segment "Sailing Lesson")

Polly Draper as Milly / Marlene (segments "Sailing Lesson" and "Late Lunch")

Maya Kazan as Caroline (segment "Late Lunch")

Rosanna Arquette as Anne (segment "Late Lunch")

Cybill Shepherd as Nancy (segment "Late Lunch")

Rita Wilson as Mary Kay (segment "Late Lunch")

Nancy Carlin as Patty (segment "Late Lunch")

Elea Oberon as Rose (segment "Late Lunch")

Valarie Pettiford as Wendy (segment "Late Lunch")

Alyson Reed as Jackie (segment "Late Lunch")

Gloria Garcia Stanley as Gloria (segment "Late Lunch")

Jeremy Kahn as Robert (segment "Late Lunch")

Mitzi Zamarripa as Cheryl (segment "Two for Dinner")

Dave Zamarripa as Raphael (segment "Two for Dinner")

Sebastian Pacheco as French Maitre d' (segment "Two for Dinner")

Kenton Smith as French Bartender (segment "Two for Dinner")

Isabelle Nogueras as French Waiter (segment "Two for Dinner")

Doug White as French Patron (segment "Two for Dinner")

Derek Wintermote as Montana Waiter (segment "Two for Dinner")

Regina Coppola as Montana Patron (segment "Two for Dinner")

Stephanie Gamble as Montana Patron (segment "Two for Dinner")

John Polley as Montana Patron (segment "Two for Dinner")

Todd DeVincenzi as Single Man (segment "Two for Dinner")

Ali Hall as Single Woman (segment "Two for Dinner")

Jovani Silva as Taxi Driver (segment "Two for Dinner")

Caleb Cabrera as Dock Boy (segment "Sailing Lesson")

Justin Ashforth as Man on Boat (segment "Sailing Lesson")

Brittany Wagner as Boat Driver (segment "Sailing Lesson")

Chelsea Bond as Boat Passenger (segment "Sailing Lesson")