Nikki starts admiring and complimenting with the customers at the Khaki Barn so she can earn more money to buy Jonesy new skates, but when she accidentally calls Jonesy on the one of the new cell phones Caitlin gave all of them, he overhears her flirting with one of the customers and thinks she's cheating on him. Meanwhile, Jen gets stuck in a question booth, and Wyatt lets the gang endlessly prank him so he can finish his new album from humiliation. (The title of the episode refers to Oops, I Did It Again, a single by Britney Spears.)
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