Guest Stars Samaire Armstrong as Summer Edgecombe David Noroña as Osvaldo "Oscar" Ardiles Monique Gabriela Curnen as Tamsin Wade Troy Ruptash as Matthew Gold Nicole Bilderback as Francesca Ehrlich Susan Gibney as Alice Burns James Jordan as Chuck Calloway Michael Whaley as Elwood Pierce Jack Laufer as Stuart Davis Paul David Story as Carson Co Starring Porter Kelly as Chuck's Sister Ross Mackenzie as Marshall