Part four opens with Basil arguing with Gladys and almost getting violent until Derek intervenes. Gladys and Derek then talk and Derek realizes that while Esther is gone, he shouldn't miss out on life. Floyd and Gillian have an engagement party where Floyd sees Derek and Gladys getting very close. Wendy and Floyd notice this and become upset. Gillian notices Floyd's frusteration and begins to have second thoughts abouth their engagement. May along with Basil also notice their sudden closeness, May then decides to probe Basil for answers about Glady's past, again. He then tells her that Gladys left him because he made a mistake but then did something terrible to her.
Wendy thought she moved on with her life, but realizes that she is still hopelessly in love with Derek. Floyd and Gillian argue over the status of his relationship with Gladys. Kendra is reunited with Guy when Andre comes to town for a visit. Andre then blind-sights Kendra with the announcement that he is getting re-married. She becomes upset and then tells Andre she is seeing someone, which she isn't. Ruth, Kendra's mother, returns once again to Ribbon Heights. This time she stays for good. she notices that Kendra and Andre still have lingering feelings for each other but will never acknowledge them. Gregg and Max then begin the adoption process.
Derek and Gladys then decide to go on a date. The evening goes well and ends with Gladys going home with Derek. Kendra then meets, an elder age sim who take an interest in her. His name is Vladamir Color. Andre's jealousy is obvious. Kendra and Vlad begin dating, to spite Andre's engagement. May then begins to piece Gladys's past together. Gillian then accuses Floyd of only asking her to marry him to make her happy. Floyd then begins to realize the truth in the statement but tells her that he does have feelings for Gladys but loves her. They decide to remain engaged but "take a break."