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Tracy and his fake son Donald go to Jack to get him to invest in Donald's newest idea, a themed restaurant in Time Square. When Jack goes for a site visit, and sees that Donald's "Staples" is a joke, he backs out of investing. Jack originally convinces Tracy to cut Donald off, but then tells him to support him after reliving some of his own father issues.
Jenna is trying to keep things fresh with her boyfriend Paul, who continues to dress up like Jenna. She wants to make a sex tape and leak it on the internet, but he wants her to meet his parents. This causes them to fight and break up.
Liz thinks that maybe her and Carol's relationship might be getting stale as well, so Jack tells her to see a therapist. Kenneth takes on the role but goes a little crazy after hearing all of Liz's problems.