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Perry goes to Rebecca’s sister Lisa for advice, but this results into an awkward moment for him. Shawn is forced to help Justin with a school paper. Instead of helping him though, he gives Justin an old paper he has written himself, and is offended when it turns out the paper did not earn an A grade for Justin.

Rebecca is appalled that her sister is dumping a guy she spent a date with because he is too nice. Rebecca tries to set them up again, but soon finds out it is maybe for the better that Lisa is not seeing him any longer. Meanwhile, Shawn forgets to pick up Perry from the dentist because he has met a girl on the streets. As a result, Perry feels neglected and breaks off their friendship.

Rebecca intends to confront the guy who stood her up for the senior prom, but Perry makes up a lie so she won’t find out the real reason why she was stood up. Shawn can’t watch the championship games on his cable company, so he romances Lisa’s friend, Vanessa, who’s cable company is airing the games.

Lisa finally convinces Rebecca to have her first one night stand. But the always polite Rebecca violates Lisa’s number-one rule by calling her date, Leo, the morning after. Now Leo is into Rebecca, so Lisa gives her sister her own unusual brand of dating advice so Rebecca can break up with him. Meanwhile, an overworked Perry decides to take a stay-cation. But doing so gets on the nerves of his unemployed roommate, Shawn, to the point that Shawn decides to get a job.

Rebecca tries to take her relationship to the next level but when she discovers a giant tattoo, she changes her mind. Perry tries to fire Erin, his assistant but ends up in a relationship with her. Shawn doesn’t want to watch Lisa’s coworkers cute dog, until he discovers what a great chick magnet the dog is.