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The eighth season of Will & Grace premiered on September 29, 2005 and concluded on May 18, 2006. Grace tries to tell Tom that she doesn't want to hook up with a married man, but he continues to pursue her. However, NBC later revived the series, with a ninth season of 16 episodes due to premiere in 2017, and a tenth season of 13 episodes in 2018.After talking with Jack, Grace decides to throw caution to the wind, but when Jack realizes what he accidentally talked Grace into, he quickly talks her out of it.Jack is missing an eyebrow from a fire at the premiere of his talk show.However, Will doesn't really trust Jack, so he secretly signs up with a real instructor.When Jack finds out, he's incredibly hurt, and can't believe Will doesn't trust him with this when he trusted him with coming out of the closet.Will realizes Jack is right, and cancels his lesson with the instructor, entrusting his safety back with his friend.Karen sets up Grace on a blind date with one of Malcolm's friends.
Will and Karen end up drunk together, and decide together to put back up their emotional walls.Karen, who is back with Stanley, is still dating Malcolm, because she doesn't want to break his heart.When Grace lets it slip to Malcolm that Karen is back with Stanley, Karen and Malcolm break up, and Grace is left to pick up the pieces of Malcolm, agreeing to be his date to Will's carnival.Will tells Grace about Stan being alive, and the news quickly gets out.Malcolm asks out Karen, and Will is horrified, so to stop the date he tells Karen that Stan is alive.
Will charms a pair of gay flight attendants, and ends up working as a flight attendant himself, to smuggle Grace into first class to talk to Leo.