Guest Stars Bree Turner as Sara Co Starring Claire Geare as Janie Peter Katona as Matthew Eijiro Ozaki as Tokyo Tourist Alex Staggs as Todd Jamie Tisdale as Monique Malana Lea as Heather R.F. Daley as Matthew's Dad Liz Alvarado as Divorced Cougar Gregg Brown as Derek #4 Jonah King Church as Bar Mitzvah Boy Todd Lubitsch as Irish Derek Uncredited Ken Marino as Joel Sherilyn Henderson as Zoe the Babysitter