Brian and Michael grow further apart as Brian struggles to save Liberty Avenue from gentrification and Michael embraces domestic life. The street may never be the same when Debbie decides to retire from the diner and newcomer Loretta Pye takes over.

Brian remains steadfast in his belief that marriage is the death of a relationship. Debbie has a difficult time accepting her role as a lady of leisure – especially when she discovers that Loretta has stolen her act including the button-clad vest right down to the wisecracks. Ted decides to undergo an extreme makeover.

Debbie tries to let Loretta down easy. Brian must refrain from sex after he contracts syphilis. Hunter has to deal with the aftermath of his classmates and their parents discovering how he got HIV. Ted regrets having plastic surgery. Justin and Daphne discuss the possibility (or impossibility) of Brian embracing domestic life. Michael, Melanie, and Lindsey are forced to reevaluate their parenting arrangement when the fight over JR reaches its climax.