While Jack puts together the perfect 50th birthday party for himself, home videos inspire him to try to recreate his happiest moment. Dennis decides to tell Liz about his addiction. Meanwhile, Kenneth and Pete work to make Tracy's childhood dream come true.

Wedding fever hits TGS, leaving Liz to sort out Grizz's dilemma when both Tracy and Dot Com want to be his best man. Jenna's new boyfriend, Paul, raises Liz and Pete's suspicions, while Jack is finally forced to deal with the death of his mentor, Don Geiss, when Geiss leaves him a strange but meaningful inheritance.