Paul Giamatti as Miles

Thomas Haden Church as Jack

Virginia Madsen as Maya

Sandra Oh as Stephanie

Marylouise Burke as Miles's Mother

Jessica Hecht as Victoria

Missy Doty as Cammi

M.C. Gainey as Cammi's Husband

Alysia Reiner as Christine Erganian

Shake Tukhmanyan as Mrs. Erganian

Shaun Duke as Mike Erganian

Robert Covarrubias as Miles's Building Manager

Patrick Gallagher as Gary the Bartender

Stephanie Faracy as Stephanie's Mother

Joe Marinelli as Frass Canyon Pourer

Chris Burroughs as Chris at Stanford

Toni Howard as Evelyn Berman-Silverman (voice)

Khoren Babouchian as Armenian Priest

Lee Brooks as Ken Cortland

Peter Dennis as Leslie Brough

Alison Herson as Foxen Winery Pourer

Phil Reeves as Vacationing Dr. Walt Hendricks

Rob Trow as Obnoxious Golfer

Lacey Rae as Los Olivos Waitress

Cesar Ramos as Barista

Daniel Rogers as Reciting Eighth Grader

Natalie Carter as Siena

Simon Kassis as Mini-Mart Owner

Sevag Kendirjian as Armenian Deacon

Jaren Coler as Acoustic Guitarist

Chris Astoyan as Mrs. Erganian's Son (uncredited)

JR Garcia as Little Boy (uncredited)

Gregory Heath as Tasting Room Customer (uncredited)

Alex Kalognomos as Alex (uncredited)

Parker Quinn as Customer in Shoe Store (uncredited)

Mikael Sharafyan as Armenian Wedding Guest (uncredited)