Guest Stars Ora Jones as Claire Garland Torrey Hanson as Jack Ziegler Bryan Greenberg as Howard Denton Kelli Simpkins as Dana Worth Jasmine Batchelor as Maxine Keith Kupferer as Mallory "Uncle Mal" Corcoran Kevin Gudahl as Judge Wainright David Darlow as Theo Mountain Keith Powers as Lionel "Nasty Nel" Eldridge Kroydell Galima as Greg Haramoto Gregory Linington as Mark Hadley Dan Waller as Agent McDermott Elizabeth Ledo as Lynda Avery Holliday as Abigail Garland Amir Henderson as Young Talcott Phillip Edward Van Lear as Oliver's Doctor William Dick as Chief Justice Stephen Roosevelt Co Starring Dyllan Yelverton as Bentley Raluca Lazarut as Szuza Phillip Cusic as Young Addison Cheryl Hamada as Judge Reardon Diana Coates as Stephanie Pitts Edward Neequaye as Mason Millie Hurley as Property Manager Tara Mallen as Yvonne Michele Alvarez as Becca Reyes