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.
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.
Gavin Volure, an eccentric businessman, invites Jack and Liz to a dinner party at his mansion; Tracy thinks his kids are being too nice to him and fears for his life.
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