Tim and his coworkers go on a booze cruise around the island of Manhattan, with Tim's drunken boss at the helm. Tim has no cell signal and needs to get home for "date night," but the boss insists that stay and chug margaritas. Later that night, Amy wakes up to find Tim eating peanut butter on the kitchen floor, and when he characterizes the evening as "a work thing," she suggests he put in for overtime. When he brings it up with Marie from HR the next day, she opens a file, but then the boss is hurt that Tim wants to be paid just to hang out with him. So Tim invites the boss out for drinks, and they head uptown, where they smoke pot with some jazz musicians. During the band's performance, Tim and the boss get onstage to scat, but one musician thinks he heard Tim scat a racist epithet and kicks them out. The next morning at work, Marie announces a random drug test.
Tim's coworker Stan tells an anti-Semitic joke: Three Jews walk into bar - and then buy it. Tim is offended, but his Jewish officemate Herschel doesn't have a problem with it. Jews love to laugh at themselves, he says. For dinner, Tim and Amy join her friends, who repeatedly point out how little he seems to know about his girlfriend. When they ask about his job, he retells the joke and offends the couple. That night, Tim goes to O'Flaherty's, and the guy from dinner, Amy's coworker Adam, shows up with two Jewish friends - and they decide to buy the bar. By the time Tim gets home, Amy has already talked to Adam and heard the whole story. This freaks Tim out, but Amy explains that Adam is her "work husband" and it's totally platonic. When Tim goes back to O'Flaherty's, the place has become kosher. In the back room, Adam is raging over how much money he's losing at the bar, and he explains to Tim that he only bought the place to impress Amy, who he's in unrequited love with. Tim threatens to tell Amy about Adams feelings unless he sells the bar back to O'Flaherty. Adam gives in - losing half his investment but breaking the stereotype that all Jews make great business decisions.
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