Dave Chappelle plays a crack addict who visits an elementary school to give an anti drug speech.
Liz befriends a pregnant teenager from a donut shop she visits in the hopes to adopt her baby. Kenneth plans a combined birthday party for Tracy and Jenna, but Jenna wants all of the attention and a party of her own. Jack agrees to go out with the guys to keep his mind off Elisa and ends up bonding with Frank over their father issues.
Tracy does an interview with Larry King and causes mayhem throughout New York City. Jack wonders if his career will get in the way of taking his relationship with Elisa to the next level. Liz loses her cell phone in a cab and recruits Kenneth to go out with her to Queens to retrieve it.
Dave Chappelle plays America’s most vicious blind white supremacist and unveils racy “bootie” videos starring Nat King Cole.
Liz insists that she and Drew have their first official date on Valentine’s Day. Elisa brings Jack to church to celebrate the day, which is very different from the way he traditionally celebrates. Kenneth employs the help of Tracy to try to win the affection of a new worker.
Jack’s resemblance to an evil telenovela character has him on the outs with Elisa’s grandmother. Liz tries to begin a relationship with a new neighbor after accidentally receiving his mail. Tracy has trouble maintaining the party lifestyle of ex-Wall Street execs now working as interns.
Not wanting to go alone, Jack asks Liz to go on a GE corporate retreat with him. Jenna finds that method acting in preparation for her upcoming role as Janis Joplin allows Frank to take advantage of her. Kenneth helps Tracy understand how diabetes affects him.