17. Grace Marries James
(“The Definition of Marriage,” season 8, episode 15)
Grace and Leo’s marriage has now fallen apart (they got divorced, though briefly reconnected in a one-night stand). But that means Grace is free to marry James (Taye Diggs), Will’s Canadian love interest who needs a green card to stay in the U.S. Of course, in true Will & Grace fashion, she also finds out she’s pregnant with Leo’s baby as she is marrying Will’s boyfriend.
This show really got insane in the final season, huh? (The marriage is eventually annulled.)