Commentary: 'The Boss' Commentator Hollis Gillespie has a friend who is sleeping with her boss, and Hollis keeps telling her it's a bad career move. One time, one of Hollis' fellow waitresses was sleeping with the boss in order to keep her job. She was trying to support a 6-year-old daughter.

Commentary: 'The Boss'

Commentary: 'The Boss'

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Commentator Hollis Gillespie has a friend who is sleeping with her boss, and Hollis keeps telling her it's a bad career move. One time, one of Hollis' fellow waitresses was sleeping with the boss in order to keep her job. She was trying to support a 6-year-old daughter.