Liz encounters the man of her dreams while dealing with the weddings of Cerie, Floyd, and Grizz. Jack is forced to choose between Avery and Nancy. Another woman comes between Jenna and her boyfriend. Kenneth fears receiving a promotion that would move him to Los Angeles.

Jack’s love triangle with Avery and Nancy grows increasingly complicated. Liz gives an old boyfriends a second chance in seeking a date to Floyd’s wedding. Tracy continues his quest to win an Emmy, Grammy, Oscar, and Tony.

Liz Lemon meets her mother’s old flame, while Jack Donaghy’s mother, Colleen, gets tangled in his relationships with Avery Jessup and high school love, Nancy Donovan. Jenna’s mother, Verna, returns, while Tracy learns a lesson from his “mom.”

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 (Jane Krakowski) 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.

Liz discovers that the TGS staff has been excluding her from their weekly hangouts, and strives to prove that she can be fun. Jack must choose between janitors and the shift time they both want, and Kenneth aids Tracy Jordan in being a good husband.

Liz and Jenna attend singles events; Jack is torn between Nancy and news anchor Avery.

Liz reevaluates her feelings for an old flame, Floyd, when he returns with big news. Jack Donaghy teaches Danny Baker the finer points of pranks after the TGS writers play a trick on him. Jenna Maroney and Tracy Jordan see Kenneth Parcell in a disturbing new light after they spend a very long day listening to him tell stories about his childhood.

Jack needs to reestablish himself within the new corporate structure. Liz and Wesley continually run into each other, making them consider fate’s role in their lives. Tracy’s nanny writes an expose.

Liz searches for a man she met in her dentist’s waiting room. Jack fears for the future when he learns a cable company may have its sights on NBC. Jenna helps Tracy try to get a Tony award.

Liz hopes a Valentine’s Day root canal will make her feel better about being alone. Jack goes after an attractive CNBC host. Jenna is crushed when a stalker stops stalking her.