Office Management for Beginners

When Jane tells Chelsea that there is no budget for her new super-equipped van, Chelsea's arrogant lawyer Bobby convinces her to cut the staff's holiday bonuses to free up the funds. But after Jane offers the alternative solution of dropping Bobby from retainer and putting him on his hourly rate, Bobby retaliates by playing a series of practical jokes on her. Jane refuses to stoop to his level by responding to his tactics, until he finally pushes her too far -- and Jane proves that she can out-prank the prankster.

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S01E05 - Chelsea's Ex