- Liv's skateboard pro boyfriend is coming to Wisconsin for a competition.
- Liv's boyfriend from Hollywood is professional skateboarder Miller White, and is in town to participate in a local competition to which Liv is asked to sit on the panel as a celebrity judge, along with local weatherman Johnny Nimbus and another pro-skateboarder named Spike Bickle. Liv's only qualification for being a judge though was being in the movie "The Skateboard Bandit" between seasons of "Sing It Loud," which Miller trained her for. When most of the Rooney family meets him (the exception being Maddie who is assigned basketball practice by Pete), they find out how utterly stupid her beau is, something that Liv already knows. Miller somehow assumes Karen is a psychic, rather than a psychologist, and that her brother Joey is her identical twin. After the visit, Liv dresses up for her judging appearance and subsequent date with Miller and is filled with excitement as one would expect. The excitement of the moment is shattered though, when she receives a text from him ending their relationship.
Too heartbroken to participate in her judging position, as well as doing everything else, Liv spends most of her time sulking on her bed. After Karen learns about the text message, she tries to help her daughter deal with it by using two pillows; one to deal with her depression, and the other to deal with her anger. Karen even claims she had to use these pillows herself when she was dating Pete, and quite often. Maddie, however, tells her that the best way to get over a breakup is to seek revenge, something Karen desperately tries to talk her out of. Before the competition, Miller starts to have second thoughts about breaking up with Liv, and unknowingly tells Maddie that he wants to reconcile. In reality he only wanted to get back together because Liv is a judge and could determine his score. Just as he's about to perform some of his tricks, Liv gets up from the judge's table and prepares to smash the homemade skateboard Stanley that he carries around for good luck, only for Maddie to try to stop him from doing so, Their attempt at revenge against Miller gets Liv disqualified as a judge. However, when he decides to break up with her anyway, Maddie grabs Miller and a pair of garden shears and cuts off his ponytail. The two girls are grounded for their revenge plots, and Liv tries to occupy their shared time by giving a verbal description of her movie "The Skateboard Bandit," since neither of the girls have permission to watch the movie on DVD.
Meanwhile, Joey and Parker meet another professional skateboarder who calls himself "The Masked Shredder," only to discover that he is a childhood friend of Joey's; none other than Skippy Ramirez, who actually credits Joey for getting him into skateboarding when they were in pre-school. Ramirez's claim to fame is his outlandish wipeouts, but when he injures himself during one of his stunts, he urges Joey to wear his mask and take his place, at the added behest of his little brother Parker. His meager attempts to impersonate the shredder keep the reputation of Ramirez in tact, but the elder Rooney brother doesn't fare so well after his wipeout either.
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