Heather Graham as Pippa McGee

David Sutcliffe as Ian

Taye Diggs as Hemingway Jones

Sarah Chalke as Jane

Cheryl Hines as Roxanne

Keram Malicki-Sánchez as Frank

Sabrina Grdevich as Rachel

Bruce Gray as Malcolm McGee

Sandra Oh as Lulu

Michael McMurtry as Luke

Amy Price-Francis as Sasha

Reagan Pasternak as Sydney

Jefferson Brown as Clifford

Suzanne Cyr as Suzanne

Frank Chiesurin as Chad

Carlo Rota as Bob Jackman

Jonathan Keltz as Valet

Kasia Vassos as Lane

Martin Roach as Bartender