In an effort to prove to Rita he's not a wimp, Michael tries to convince George Michael to join him in some manly activities, but George Michael is too busy prepping girlfriend Ann for an Inner-beauty Pageant. So Michael and his recently discovered nephew Steve Holt enter a triathlon, only to discover Gob is the one who stumbles at the finish line. Back at work, Michael must deal with a huge mole problem in order to salvage a major real estate deal. But when Gob and Buster team up with George Sr.'s surrogate, Larry, to help Michael save the deal, their plan falls apart in a big way. Meanwhile, Tobias mistakes a CIA agent for a CAA agent and inadvertently betrays the family, and Michael makes Rita a proposal she can't refuse.

After Michael announces he's marrying Rita, George Sr. worries that she's after their family's money. But when Rita's Uncle Trevor tries to stop the wedding by revealing some surprising information about Rita, Michael must decide if he wants to walk down the aisle.