In 1984, Edna Thornton Ferguson (Sandy Gabriel) pays Tad to date her daughter, Dottie Thornton (Tasia Valenza) at the same time, he falls in love with Hillary Wilson (Carmen Thomas), step-daughter of town matriarch Phoebe Tyler Wallingford (Ruth Warrick) and daughter of Langley Wallingford (Louis Edmonds) Tad's sister Jenny is killed in a jet ski explosion, and Hillary reaches out to help him cope with his loss, but encourages him to do right by Dottie when he gets her pregnant. Tad and Hillary end their relationship, and he marries Dottie. She has miscarried, but hides this from him as she knows he would not marry her otherwise. Meanwhile, Hillary captures the attention of Tad's friend, Bob Georgia (Peter Strong) who soon learns he is terminally ill. She agrees to marry him to make his last days happy. Before the wedding, he discovers he was misdiagnosed and is not going to die, but keeps quiet because he fears losing Hillary to Tad, who is now having his marriage to Dottie annulled after discovering her deception.