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Casey (Peter Krause) announces his plans for an upcoming date, as required by Dana (Felicity Huffman) before the two of them can start a romantic relationship. Dan (Josh Charles), intrigued by Casey's date's unique name, asks if he can ask her out after Casey screws up the date. Natalie (Sabrina Lloyd) and Casey suspect that Dana may be a little jealous by this development, with Natalie going a step further and declaring that Dana's plan will most certainly backfire. Dana declares she is not jealous and begins focusing on a larger problem: The following night's broadcast is very short on content and needs about 40 minutes worth of material to fill it out. Meanwhile, Jeremy (Joshua Malina) is up for an industry award and is finding it difficult to write his acceptance speech. As he goes to a number of people for advice, he learns that he will not win the award and that his girlfriend Natalie has known the outcome for some time.