In the fourth set premiere, Derek is still trying to find a missing Esther. Gladys continues to spend time with Rupert, May becomes too curious which requires her to confront Gladys on the matter and ask why she has taken such an interest in her nephew. Gladys then tearfully reveals that she had a son once, but lost him, and Rupert reminds her of him. May then appologizes and says she can come see Rupert whenever she likes. Floyd and Gillian;s relationship gets right back on track. However, with Gladys back in town Floyd can't help but have second thoughts. Wendy is excited that Esther is gone as Derek can now seek a divorce from her as she is missing and they can reunite.
Kendra misses Guy and finds raising Elsie to be stressful, she almost has some coffee, but ultimatley witholds. When Wendy goes to see Derek and tries to kiss him, he pulls back. He then tells her that he does love her, but he loves his wife as well. His first priority is to find her and ensure that she is all right. Wendy leaves devestated. Kendra then recieves help when her cousin Orlando arrives in town for a visit. Gladys and Rupert's relationship continues to grow, Kline then expresses his feelings to May that he doesn't like Gladys spending so much time with a stranger. Norma becomes saddened when she learns that Steven doesn't have much time left as his age is getting the better of him.
Orlando helps Kendra with Elsie and in the process meets Wendy, whom he develops a crush on. Gladys and Floyd then have lunch with ends with an awkward kiss. Gregg sees the from a distance. He and Max are now happiliy married. They hit a bump in the road when Gregg expresses his desire to be a parent and adopt and Max informs him that he doesn't feel that he is ready for children. A new neighbor, but an old face to Gladys, moves to Ribbon heights, Basil Barcroft. What could be his relationship to Gladys?