Liz is dealing with being a stay-at-home mom while Jack tries to find true happiness. Kenneth and Tracy are both adjusting to Kenneth's new position as President of NBC.
Jack brings in several famous musical artists to perform a benefit song so his biological father can get a kidney, Tracy is afraid to speak at his high school's graduation, and Liz finds a talent in giving irresponsible relationship advice.
Liz is upset because nobody remembers her 40th birthday, Jack tries to give up drinking to support his pregnant girlfriend, and Tracy threatens to break character during TGS.
After Don Geiss wakes from his coma and tells Jack that he plans to remain as CEO, a snow-in forces Jack to go with Liz to her high school reunion--where Liz learns, much to her surprise, that she was the class bully.
Elisa's grandmother hates Jack because he looks like an evil character in a telenovela. Meanwhile, Liz uses that character's underhanded moves to pick up on a sexy neighbor.
Liz can't get anyone to give her a ride home from her oral surgery, which is scheduled for Valentine's Day. Meanwhile, Jack goes out on a date with a sexy, smart journalist, and Jenna discovers that her stalker has moved on.
Liz believes she's found her perfect man while between weddings with Wesley, Jack has to make a decision after Nancy meets Avery, Kenneth gets fired while trying to avoid a promotion, and Jenna's boyfriend becomes a Cher impersonator.
Jack asks Liz to accompany him to a societal event, the birthday party of a royal. When Jack's ex-wife arrives, he introduces Liz as a girlfriend. To help Pete reclaim his manhood, Tracy holds a party in the office, inviting girl dancers.