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.

Will and Grace decide to intervene when they discover Grace's niece is dating a bisexual man. Jack gets permission from his husband, Estefan, to sleep with his celebrity hall pass, guest star Ryan Phillippe. Karen struggles to adapt when her assistant, Friday, books them on an economy flight.