Liz asks Oprah Winfrey for advice when they are seated next to each other on a flight; Jenna and Tracy try to determine whose life is harder; Kenneth tests Jack's morality.
Liz tries to stop the staff from ruining her chances at adopting a child when an adoption agent (Megan Mullally) makes a visit to the set; Jack returns from D.C. with a plan to reclaim his position from Devin Banks (Will Arnett).
Liz and Jenna's friend Claire (Jennifer Aniston) visits and falls for Jack; Tracy tries to cheer up Kenneth by turning one of his dreams into a reality.
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