Guest Stars Aidan Devine as Martin Bayley Trevor Hayes as Dennis Masterson Oliver Becker as Alan Zuker Alexandra Castillo as Jacqueline Caleb Cosman as Chicago Lister Interviewer Co Starring Briony Glassco as Susan King Bill Lake as Carson Lewis Olivia Jones as Megan Tellis James Gilbert as Jack Shaun Benson as Ryan Drew Nelson as Jim Kinsler Kevin Hanchard as Jim Slater Matthew Edison as Co-Worker Allison Hossack as Financial Advisor Tyler Hynes as Greg Kristian Bruun as Client #2 Emily Piggford as Lawyer Marcelo Arroyo as Cam Client Duane Murray as Broker Jonathan Seinen as Justin Grevillius Frank Chiesurin as Chris Lannin David Tompa as Assistant D.A. Stanley Jonathan Nathaniel as Waiter