Jack begins to bond with Milton and seeks a way to help him get the kidney he needs. Meanwhile, people start seeking Liz out as a relationship expert as a result of the "That's a Dealbreaker" sketches, and Kenneth helps Tracy deal with his embarrassment over not finishing high school.

Liz concocts a Mamma Mia!-type scenario to help Jack find his father. Pete and Liz feel Tracy's illegitimate child is really a scam artist. Jenna reluctantly shares credit for a new TGS catchphrase with Liz.

Tracy and Liz each agree to give up preferential treatment they receive at work. Colleen visits Jack on the anniversary of his father walking out on them. Jenna takes on a gibbon as a pet.

Liz is turned to by Jack for help finding an engagement ring for Elisa, while Elisa comes to her to confide a secret. Jenna falls for an EMT and goes to great lengths to meet him again.

During her HR-mandated suspension from TGS, Liz gets a taste for how the leisure class lives. Meanwhile, Jenna faces the possible non-release of her 'Janis Joplin' biopic, so Jack tries to get her to generate buzz to get the film back on track.

What should be excitement over the 50th episode of TGS turns to fear when Jack announces budget cuts and layoffs. Liz realizes she needs to do some special negotiating to save jobs, while a request from Kenneth leads to Tracey and Jenna concluding he must be a serial killer.

Jack plans a perfect party for his 50th birthday, but finds it pales to a birthday party of his youth. Liz is tasked to make Tracy think he's going for a trip on a space shuttle. Dennis Duffy tries to make amends to Liz because he has a sex addiction—a revelation that later complicates her friendship with Jenna.

Liz finds out Drew's good looks afford him special treatment from society. Jenna hopes a new hairdo will keep her in the public eye. With Tracy's contract up for renewal, Jack tries to keep him at TGS.

Jack seeks a name for a new mini-microwave that the Legal Department will allow. Liz can't find a way out of jury duty and is forced to leave the staff unmanaged. Tracy sees being able to afford FCC fines as license to swear on television. Jenna gets medication to let her get by with no sleep from Dr. Spaceman so she can continue on both TGS and her 'Janis Joplin' biopic.

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.

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.

When a flu outbreak hits the TGS staff, Jack has to decide who will get a vaccination and who won't.

Amid a health scare that sees him growing close to his mother's nurse, Jack helps Tracy and his wife Angie develop a "post-nup" and gets Jenna an audition to play Janis Joplin. Jenna thinks Liz is only attracted to a midget because she wants a child.

As Christmas approaches, Liz reaches out to children in need, while Jack desperately looks for ways to avoid his mother while she convalesces at his home.

With Jack in tow, a reunion sees Liz finding out her memories of high school differ greatly those of from her classmates. Don Geiss awakens from his coma and makes his choice for the new GE CEO. Tracy and Jenna are threatened by the popularity of Kenneth's elevator jokes.

Liz joins Jack at a party at his friend Gavin Volure's mansion, only to have Gavin fall completely in love with her. Tracy fears his kids have sinister intentions when they become too nice to him. Kenneth entrusts Jack to invest his savings into Gavin's business venture.

Liz and Jenna's friend, Claire Harper, a free-spirited stalker-type, shows up unexpectedly in New York to visit. But once she gets there, she centers her attention on Jack and claims him as her own. Tracy, trying to cheer up Kenneth because of the new page uniforms, invites the cast of Night Court to visit.

Liz, on a return trip from Chicago to get out of jury duty, ends up sitting next to Oprah Winfrey and spills her soul to her for advice. Meanwhile, Tracy and Jenna argue as they attempt to figure out whose life is harder, leading to a wacky "social experiment". Kenneth tests Jack's morality after an Olympics snafu.

Liz tries to get everyone on the TGS staff to be on their best behavior when an adoption agent stops by to observe whether she is fit to be a mother. Jack returns to NBC with plans to go head-to-head against Devin for the top job. Jenna's miffed that Tracy's ignored her contributions to his videogame, The Legend of Dong Slayer.