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