Skip makes small talk with Becca over breakfast until he realizes that it's 11:17 a.m. - the time when the girl he's got a crush on, Stacey Kim, will be making her mail delivery rounds to the President's outer office. Skip rushes through the hallways just in time to "accidentally" bump into her. Their small talk is awkward. Skip eventually summons the courage to tell her he hopes to visit Asia some day. A surprised Stacey agrees and continues on her rounds; she has no idea Skip has designs on her. Skip's proud of himself for taking such an important next step in his imaginary relationship.
The First Lady has an important education reform bill she's trying to push through Congress with the President's help. This morning, they're appearing in support of the bill on the Today Show. Savannah Guthrie asks the President about the bill but then turns her questions to the First Lady's clothing, her workout routine and her background as a dancer earlier in her life.
Over breakfast the next day, the President and First Lady discuss tactics for getting her bill passed. Frohm Thoroughgood, a crusty, racist senior senator from the South is opposed to the bill; the first couple is honoring him with a fancy ball at the White House in an attempt to extract his vote. Becca's dreading going to the ball; Skip thinks it'll be fun, rather like the prom he never attended. Emily encourages Skip to ask the cute girl from the mailroom, Stacey, to be his date. Inspired, Skip heads off to find her. After first asking Stacey's boss for permission, Skip finds Stacey and asks her out. She agrees - as long as they're going just as friends. Overjoyed, Skip races to tell Becca, but she's cool to the idea; she's afraid to see her brother get hurt. Skip is already extolling his dancing skills and fantasizing about his wedding to Stacey.
The President and First Lady invite Senator Thoroughgood to a meeting in the Oval Office; they realize his vote could be the difference between the education bill passing or not. Thoroughgood arrives and immediately insults almost everyone. The senator tells the first couple that he could be open to discussing the education bill, but he'll need help with his own highway bill. He then tells Emily to go fetch him a drink. Incensed, Emily tees off on Thoroughgood, calling him sad and insensitive and someone whose family will be apologizing for him for years to come.
The big night arrives. Skip needs a little help with his bow tie, but otherwise he's on top of his game. He arrives at the mailroom to pick up Stacey, magnificent in her red evening dress. Skip likens her to Queen Amidala, dressed as Padme and ready to take on the Federation. Stacey takes Skip's words as high praise. As they arrive at the ball, Senator Thoroughgood makes a racist remark about Stacey, and Skip calls him out loudly on it. It's a tense moment, but the senator laughs and says he admires Skip's gumption; the moment blows over, but Stacey's impressed that Skip defended her honor.
Thoroughgood is still smarting from Emily dressing him down earlier, but he opens the door to his vote just a crack. If Emily will make a speech tonight lauding him, he tells her, he may just find a way to cast the critical deciding vote at the special late night session of Congress taking place tonight. Emily and the President sneak off to the Oval Office to try to find something nice to say about Thoroughgood. It's a tough assignment.
Skip takes the microphone at the ball and addresses the crowd, thanking Emily for giving him the courage to make tonight happen for him. He then calls everyone's attention to Stacey; he publicly asks if she'll be his girlfriend and then shoves the microphone in front of her face. Stacey is understandably uncomfortable and walks off, leaving Skip dangling with nothing to say in front of an embarrassed crowd.
As the President and First Lady do their best to lionize Thoroughgood in an after-dinner speech, Becca and Marshall escape to the White House lawn. We learn that this is the first time they've hung out together since Marshall broke up with Becca.
After the speech, Thoroughgood thanks the First Lady but tells her she's a fool if she thinks he'll change his vote. Emily devises a plan: she'll delay Thoroughgood at the ball, performing a dancing demonstration that's certain to keep him captive. If he's not on the Senate floor, he can't vote against the education bill. Emily plucks Skip up from his chair, tells the band to strike up a tango and then proceeds to flit her way all around the dance floor with her stepson. When the senator repeatedly attempts to exit in his wheelchair to attend the vote, she glides over to block his path. The cat and mouse game goes on awhile until Thoroughgood is eventually tired out.
The ball over, the first family hangs at their table. Marshall arrives with the good news that the bill passed by a single vote. They look over in the corner where Senator Thoroughgood remains in his wheelchair, hunched over and still sleeping. Victory is theirs.