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 Nicole Forester as Donna Russell Rodney Rowland as Rodney Bosch 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 Terri Middleton as Funeral Mourner AA Meeting Evan Kole as Jack Bosch Kristy Nolen as Precinct Uniform Cop Kittson O'Neill as Lara Cavallo Kevin Edward Corrigan as Ted Darset Claudia McElhattan as Josie Bosch Aidan Fiske as Young Thomas Mike Massa as Sniper