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 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.

Mother’s Day sees TGS cast and crew deal with visits from their mothers.

Grizz’s announcement of his engagement leaves Liz dealing with both Tracy and Dotcom wanting to be his best man. Liz and Pete are suspect about Jenna’s new boyfriend. Jack learns that he’s been left a gift by Don Geiss.

Liz tries to be more fun when she learns she’s been excluded from weekly staff parties. Tracy gets Kenneth to help him be a better husband to Angie. Jack has to decide which janitor gets the shift they want.

Liz attends a singles event with Jenna. Jack’s torn between Avery Jessup and Nancy Donovan. A racist remark in the TGS offices sees Toofer contemplating if he has a future with the show.

Liz has to deal with both Floyd’s return and the news he brings in the process. After the writers prank Danny, Jack helps him get his revenge. Jenna and Tracy are horrified after listening to tales of Kenneth’s 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 exposé.

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.

Jenna’s mother comes to visit, and she looks to Jack to help. Frank moves in with Liz as a boarder, and they decide to aid one another stop some bad habits.