Polly Draper
Milly / Marlene (segments "Sailing Lesson" and "Late Lunch")
Marshall Bell
John (segment "Sailing Lesson")
Kathy Baker
Diana (segment "Sailing Lesson")
Cybill Shepherd
Nancy (segment "Late Lunch")
Rosanna Arquette
Anne (segment "Late Lunch")
Rita Wilson
Mary Kay (segment "Late Lunch")
Justin Ashforth
Man on Boat (segment "Sailing Lesson")
Chris Messina
Jack (segment "Two for Dinner")
Alyson Reed
Jackie (segment "Late Lunch")
Chelsea Bond
Boat Passenger (segment "Sailing Lesson")
Joanne Whalley
Lainie / Joanne (segments "Two for Dinner" and "Late Lunch")
Maya Kazan
Caroline (segment "Late Lunch")
Nancy Carlin
Patty (segment "Late Lunch")
Elea Oberon
Rose (segment "Late Lunch")
Valarie Pettiford
Wendy (segment "Late Lunch")
Gloria Garcia Stanley
Gloria (segment "Late Lunch")
Jeremy Kahn
Robert (segment "Late Lunch")
Mitzi Zamarripa
Cheryl (segment "Two for Dinner")
Dave Zamarripa
Raphael (segment "Two for Dinner")
Sebastian Pacheco
French Maitre d' (segment "Two for Dinner")
Kenton Smith
French Bartender (segment "Two for Dinner")
Isabelle Nogueras
French Waiter (segment "Two for Dinner")
Doug White
French Patron (segment "Two for Dinner")
Derek Wintermote
Montana Waiter (segment "Two for Dinner")
Regina Coppola
Montana Patron (segment "Two for Dinner")
Stephanie Gamble
Montana Patron (segment "Two for Dinner")
John Polley
Montana Patron (segment "Two for Dinner")
Todd DeVincenzi
Single Man (segment "Two for Dinner")
Ali Hall
Single Woman (segment "Two for Dinner")
Jovani Silva
Taxi Driver (segment "Two for Dinner")
Caleb Cabrera
Dock Boy (segment "Sailing Lesson")
Brittany Wagner
Boat Driver (segment "Sailing Lesson")
