Lindsay

Estella Warren

A.J.

Justin Kirk

Monica

Liza Lapira

Lindsay's Therapist (uncredited)

Whoopi Goldberg

Max

David Eigenberg

Charlotte

Sandra Bernhard

Terrence

Michael Rispoli

Roger

Maulik Pancholy

Lewis

James McDaniel

Eve

Michael Hyatt

Dagney

Lindsey Kraft

Ralph

Joel Marsh Garland

Stevie

Jason Kravits

Cop

Brian Anthony Wilson

Trish

Raushanah Simmons

Bartender

Nate Lombardi

Liz

Brianne Berkson

Steven

Christopher Sieber

Yoga Teacher

Elizabeth Fountain

Simone

Whitney Sugarman

Jazz Club Singer

Gregory Generet

Stylist

Stella Blanc

Fairy Princess

Gabrielle Cilibrasi

Jazz Club Guitarist

Jair Cohelio

Snow Cone Girl 2

Kendall Draughn

Henry

Henry Hodges

Spencer

Spraga

Snow Cone Girl

Rachel Mower