Guest Stars Rashad Edwards as Jim / Mail Room Clerk Wendell B. Franklin as Ian Lawrence Drew Gehling as Bartender Christine Lahti as Andrea Stevens Rob Reiner as Judge Josh Brickner David Call as Drew Lovatto Cindy Cheung as Lori Ackerman Isabella Farrell as Melanie Clark Ato Blankson-Wood as Associate Lawyer Sullivan Jones as Blake Masters Jeb Brown as Chester Quentin Mare as Tech Client Co Starring Nana Mensah as Kristen Tucker Des Lauriers as Couple #1 (Male) Curran Connor as Elvis Halliday Charlie Pollock as Det. Gifford Tom Titone as Real Estate Client