Season 5 of the show explores Cooper’s attempts to come to terms with his circumstances — which are far more restrictive than ever before.
In “Encourage, Discourage,” Cooper tells Oliver that his attempts to learn how to be “Otto poor” have led him to cancel every one of his weekly deliveries, including the “Gucci loafers of the week,” “the seafood tower of the week,” and the “foot scrub of the week.” As a beneficiary, Oliver doesn’t take all that well to the shocking news.
In another scene of the episode, Cooper tells Oliver that his father may have spoiled him with all the riches of the world — but he failed to take care of some of his basic needs. As he tells Oliver, he never learned how to ride a bike. Likewise, his dad never lent him a hand with schoolwork or showed up for major life events.
The episode titled “The Heist” sheds light on another aspect of Cooper’s hardships. Having lost all money, he is no longer able to invest in Oliver’s startup — which renders him useless in a group project.
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