Jerry worked as a part-time security guard/usher/whatever was needed at a concert venue. He didn't really want to work there, but Jessica (the host) kind of made him. That might explain why he had numerous mishaps during his short tenure.

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Sarah's job in an adult store was like a dream – at first. Her store sold high-quality products, offered educational classes, and was all-around sex positive. Then a new owner arrived, determined to make the place as cheap and skeevy as possible.

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Julie worked in marketing at a law firm where she encountered an intense micromanager. And the micromanager didn't even technically work there. Awkwardly, it was the boss's wife.

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When Brittany's boss became fixated on escape rooms, things got a little weird. At one point, Brittany found herself handcuffed next to her co-workers. Then people started busting into her office in the middle of the day to rifle through her desk for clues. Soon, she wanted to escape for real.

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Dr. Angela Toscano was a social media manager for a small marketing company whose executives didn't know how the internet worked. And they insisted they were like a family, a foreboding phrase that really meant they were weird and intense (which, to be fair, is like a family).

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Robert worked in fast food and had a boss who collected – of all things – fire trucks. And was afraid of heights. Robert also had run-ins with customers who asked for some seriously strange things, like dried-off pickles.

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Larry worked as "chauffeur," driving funeral directors to pick up the recently deceased for exactly one day.

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Madeline Jarvis quit her telemarketing job. It wasn't easy, considering she had no idea who her boss was. She's fairly certain grey filters were installed over the lightbulbs, which complemented the workplace's overall dejected vibes.

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