Guest Stars Anne Dudek as Benedicte Schaeffer Michael Rispoli as Wilkie Dino Rende as John Schaeffer Kyle Bornheimer as Paul Kathy Baker as Marie Burgess Rodney Rowland as Rodney Bosch Nicole Forester as Donna Russell Tony Marino as Brian Russell Kaleigh Loughridge as Molly Russell Christian Keiber as Toby Gunder Aubree Stone as Amy Cavallo Devin Druid as Young Nathan Kelley Davis as Ruth Posch Kittson O'Neill as Lara Cavallo Aidan Fiske as Young Thomas Evan Kole as Jack Bosch Terri Middleton as Funeral Mourner AA Meeting Kristy Nolen as Precinct Uniform Cop Kevin Edward Corrigan as Ted Darset Claudia McElhattan as Josie Bosch Mike Massa as Sniper