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With Mr. Feeny agreeing to moderate, Cory and Topanga play "The Fiancée Game" to prove how compatible they really are. However, they are stunned to learn that new roommates Eric and Rachel know more about each other than they do. This leads to Topanga making the ultimate decision that she and Cory need to live together on campus.
Cory is thrilled because he thinks that he will finally lose his virginity. But this is not Topanga's intention. She feels that living together will help them to learn more about each other. This plan backfires when they both learn various aspects of each others lives that are not so pleasant. In Topanga's case, she is horrified by Cory's toenail clipping. His newly-trimmed cuticle lands in her facial mask, the attribute that Cory does not like about Topanga.
Meanwhile, Shawn ignores Jack's repeated calls to go through their late father's belongings. Later, the two half-brothers agree to get this important task done. However, they also learn hidden secrets that cause great anger. Shawn comes to learn that Chet went to Jack's stepfather for financial aid to pay for Shawn's college tuition.
After taking some time to "cool down", Shawn decides to take his father's trailer "out on the open road". Cory agrees to join him, but Shawn insists on saying goodbye to Topanga before they set out.
Jack returns to the apartment where he starts to break down emotionally, as he never got to know Chet and now will never get that chance. Rachel tells him to let his feelings out, but Jack refuses, saying he's been bottling it in for Shawn's sake and must continue to do so. A a grieving Jack begins sobbing uncontrollably in Rachel's arms, and after the embrace, the two begin to kiss passionately, with Eric opening the door a moment later. Seeing the pair kissing passionately, he leaves.
- Shawn's trailer in this episode is not the same trailer used in earlier seasons.