Nathan and Ray's planned vacation to a tropical island oasis hits a snag after Ray injures his foot on the job, but he convinces Nathan to go alone because he needs to learn how to relax and have fun. While on vacation, Nathan finally starts to give in and relax a bit, but he's taken aback when Carol shows up to join him after buying Ray's ticket off of him. Carol tries to plan out all kinds of events for them, much like she did for vacations when Nathan was younger, and Nathan quickly realizes that he inherited his inability to relax from his mother. With some prodding, Nathan finally convinces Carol to let go and have fun, but they both get so caught up in the island lifestyle and freedom that they decide they never want to leave. Ray, injured foot and all, flies down to talk some sense into them and bring them back home. Meanwhile, Debbie gets upset with Adam after seeing that he used to compose love songs for the special girls in his life in one of his old home videos. Adam spends hours trying to think of a song for Debbie but he ultimately tells her that he can't write one because he used to draw inspiration from his misery; something he hasn't felt in years because she makes him so happy.