Grace reveals a secret from her past to her father, changing their relationship forever; legendary drag queen Miss Coco Peru emcees a lip-sync monologue throwdown to determine who will be Jack's best man, Will or Karen.

Jack and Estefan's wedding takes a detour when they're forced to get married at the airport by their friend Miss Coco. Will's worried his relationship may turn long-distance. Grace meets a charming guy. Karen reconsiders her commitment to Nikki.

Grace and her neighbor, James give their romance another shot – even after she slept with his son and his father. But an embarrassing incident puts Grace’s relationship, and her dignity, in jeopardy. Will decides it’s time for Jack to grow up, and cuts him off financially. But unlikely wisdom from Jack’s husband, Estefan, makes Will reconsider.

Karen introduces Will and Grace to the new love of her life, Phil. But Will and Grace become increasingly suspicious that Phil has sinister intentions for their friend. When Miss Coco Peru tells Jack that he's closing down his bar for good, Estefan encourages Jack to become its new owner.

Will and Grace become convinced Karen is in danger when her new boyfriend, Phil, takes her to a cabin in the woods. With the help of Karen's assistant, Friday, Will and Grace race to save her. Jack makes up a story to a snobby reporter in order to keep his new bar relevant after its previous owner, Miss Coco Peru, steps down.