Guest Stars Trevor Hayes as Dennis Masterson Aidan Devine as Martin Bayley 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 Kristian Bruun as Client #2 Tyler Hynes as Greg Emily Piggford as Lawyer Marcelo Arroyo as Cam Client Frank Chiesurin as Chris Lannin Duane Murray as Broker Jonathan Seinen as Justin Grevillius David Tompa as Assistant D.A. Stanley Jonathan Nathaniel as Waiter
