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Who Are Bosses, Boats and Eckhart Tolle?

Chuck’s new purchase of a boat creates a rift between Dan and his longtime friend. Meanwhile, Darlene hires her first assistant at Wellman Plastics but soon realizes she is anything but helpful, leading Darlene to question her decision. Elsewhere, Jackie is laser-focused on her dream of being a contestant on “JEOPARDY!” and believes the late, great Alex Trebek wants her to go all the way.

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Name Type Role
Erica Montolfo-Bura Writer
Alexandra Billings Guest Star Robin
Emily Pendergast Guest Star Assistant Lisa
James Pickens Jr. Guest Star Chuck
Milo Manheim Guest Star Josh
Lynda Tarryk Director