After spending a decade in a failed relationship, successful couples’ therapist Ally is turning 40 and is pushed, kicking and screaming, by her best friend back into the hopeless New York dating scene. But Ally finds her life pulled in opposing directions as she falls into a steamy fling with a 20-something Brooklyn hipster just as she begins a promising, more conventional relationship with Alan, a successful 50-something in Manhattan.

Natalie Portman
as Ally

Mark Ruffalo
as

Role Model
as

Meg Ryan
as

Rashida Jones
as

Tramell Tillman
as

Camden Everett Kwok
as

Christopher Livingstone
as Brent

T. Oliver Reid
as Richie

Francis Jue
as Kent

Matthew Geiler
as Partygoer

Ellie Kim
as Melody

Thomas Evansky
as Partygoer

Katrina Canillas
as Tipsy Girl

Leela Bassuk
as Clara

John Alan Dalton
as Partygoer

Hannah Belle Frankel
as Hostess

Kevin Shiu
as Jason

Jonathan Bender
as Partygoer

Samantha Lee Johnson
as Partygoer

Ethan Raysor
as Partygoer

Genoveva Rossi
as Partygoer
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