Cal Weaver is living the American dream. He has a good job, a beautiful house, great children and a beautiful wife, named Emily. Cal's seemingly perfect life unravels, however, when he learns that Emily has been unfaithful and wants a divorce. Over 40 and suddenly single, Cal is adrift in the fickle world of dating. Enter, Jacob Palmer, a self-styled player who takes Cal under his wing and teaches him how to be a hit with the ladies.
Steve Carell Cal
Ryan Gosling Jacob
Julianne Moore Emily
Emma Stone Hannah
Lio Tipton Jessica
Jonah Bobo Robbie
Joey King Molly
Marisa Tomei Kate
Beth Littleford Claire
John Carroll Lynch Bernie
Kevin Bacon David Lindhagen
Liza Lapira Liz
Josh Groban Richard
Mekia Cox Hip Hairdresser aka Tiffany
Julianna Guill Madison
Zayne Emory Robbie's Friend (Eric)
Crystal Reed Amy Johnson
Joanne Brooks Waitress for Cal and Kate
Reggie Lee Officer Huang
Caitlin Thompson Taylor
Karolina Wydra Jordyn
Tracy Mulholland Megan
Katerina Mikailenko Stephanie
Janine Barris Heather
Jenny Mollen Lisa
Charlie Hartsock Sad Sack
AlgeRita Wynn Robbie's Principal
Wendy Worthington Woman (Who Gives Cal Tour)
Dan Butler Cal's Boss
Tiara Parker Gabby
Laurel Coppock Sophia
Rasika Mathur Emily's Assistant
Joshua Sternlicht Bartender
Jasen Salvatore Bartender #2
Michael John Long Bartender #3
Dillon Neaman Bartender #4
J-Ray Bartender #5
Janae Nicole Caudillo Bartender #6
Christopher Darga Lowe's Salesman #1
Rich Hutchman Lowe's Salesman #2
Richard Steven Horvitz Lowe's Salesman #3
Lauren Stone Mall Clerk
Megan James Hannah's Colleague #1
Rebecca Flinn-White Hannah's Colleague #2
Billy Atchison Hannah's Colleague #3
Ehrin Marlow Hannah's Colleague #4
David Orosz Hannah's Colleague #5
Camille Abelow Hannah's Colleague #6
Maija Polsley Jacob's Date
Christian Pitre Waitress with Check
Heather La Bella Female Bartender
Georgia Hurd Jacob's Girl
Lisa Brown Jacob's Girl #2
Tingting Yu Jacob's Girl #3
Raena Cassidy Raena
Ami Haruna Ami
Jessica Diz Olivia
Tania Wagner Tania
Georgia Treantafelles Georgia
Holly Daniels Assistant Principal
Olga Fonda Danielle (uncredited)