Now that Gary and Sasha have taken their relationship to the next level, Gary must decide whether or not putting his career on the line to date his boss is worth it. Meanwhile, Allison tries to teach Tom a lesson in responsibility.

Cast: Jay Mohr, Paula Marshall, Keegan-Michael Key, Brooke D'Orsay, Ryan Malgarini, Kathryn Newton, Anna Curtis, Angee Hughes, Piper Moretti, Dennis Satterfield