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On a flight back from Chicago, Liz spills her soul to Oprah Winfrey. Meanwhile, Tracy and Jenna butt heads as they try to determine whose life is harder and Jack's morality is tested by Kenneth after an Olympics snafu.
Liz tries to keep the TGS staff from ruining her chances at adoption when an evaluator (Megan Mullally) drops by the job. Jack is back at 30 Rock to reclaim his position from Devin Banks (Will Arnett), but quickly learns the task won't be easy when he is given a sizeable demotion.
Liz and Jenna's free-spirited friend Claire (Jennifer Aniston) visits New York and falls hard for Jack. Kenneth, distressed over the new page uniforms, turns to Tracy who cheers him up with a surprise involving the cast of Night Court.
Jack tries to get his job - and his promotion - back. Meanwhile, Liz tries to adopt a baby, while Tracy enjoys the success of his pornographic videogame as Jenna sues him for not properly compensating her.