Walter announces that he is leaving Hillman to take a job at a community center in Philadelphia. A roast is organized to give everyone a chance to say goodbye to him. Ron learns that he cannot graduate because he failed to take a European history course. Walter lobbies the dean on his behalf and convinces him to let Ron take the final. Although his friends help him cram for the test, Ron cannot learn enough in one night to pass the difficult exam. He wants to drop out of school, until Walter reminds him of his father's probable reaction. Kim receives a grant to study medicine in London over the summer. She and Matthew must head their separate ways, as he is going to spend the summer with an acting company in Seattle.

After graduating, Ron elects to work on his music full-time. Dwayne complains about his inability to pay his share of the bills. Ron insists that X-Pression will win a record contract through a talent competition. The group loses to a talented but smart-alecky adolescent singing group (which taunts them after the contest). The other band members grow frustrated at their lack of financial success and decide to quit. Dwayne picks that moment to throw Ron out of the apartment. Ron finally takes another job, so Dwayne agrees to cover for him for a few more months. Freddie neglects her friends, job and studies as she becomes completely obsessed with Shazza. Even Shazza begins to grow tired of her constant fawning. Whitley, Kim and Lena conduct a sort of intervention to discuss her behavior.

Ron struggles with his new job at a car dealership. A female con artist gets him fired. She apologizes, and they hatch a scheme to get the boss to let them develop an ad campaign. Although things do not quite go as planned, Ron proposes a business partnership. Kim worries that she will not get into medical school after her least-desired choice rejects her. However, she soon has several offers to weigh--including one from Hillman.

Col. Taylor recommends that Dwayne apply for a summer job with Kinishewa. Dwayne follows Col. Taylor's suggestion by inviting the company vice president over for dinner (for an interview in a less formal setting). Dwayne and Whitley are stunned when the man's assistant, Kinu, arrives in his place. Although Kinu seems friendly and gracious, Whitley warns Dwayne that she is out for revenge. Dwayne comes to agree with Whitley after Kinu informs him that another applicant received the job. Kinu angrily points out that she is also married, and outlines the qualifications of the man who was hired. Dwayne realizes that he was not the best candidate for the job, and has a very hard time dealing with the disappointment. Whitley assures him that she still believes in him.

Dwayne and Whitley decide to rent a cabin in the mountains for a second honeymoon. They cannot afford the trip on their own, and Mr. and Mrs. Gaines are the only couple willing to join them. Mr. Gaines ends up getting them free use of a friend's run-down old cabin. At his wife's urging, he leaves their son Darnell in charge of the Pit. He screws everything up, behaves rudely to customers, and tries to fire Lena and Charmaine. Mr. and Mrs. Gaines get into an argument about his attitude toward their son and refuse to sleep in the same room. Dwayne and Whitley try to sneak outside, only to get sprayed by a skunk. Darnell promises his father that he is going to get himself together.