Former mobster, Nathan Hastings, who became a detective with the Paul Williams Detective Agency, caught a shoplifter while working security for Fenmore's Department Store. Nathan ended up talking the judge into releasing Drucilla Barber into his custody and took her in once he realized another thing they shared-Nathan was once illiterate, too. Nathan taught Dru to read and be more ladylike, and eventually Dru fell in love with him. But lo and behold, who was Nathan's girlfriend? Dr. Olivia Barber, Drucilla's "perfect" sister. The sisters were reunited, but it was obvious no love was lost between them. Nathan explained that his heart was with Olivia. Dru plotted to win him away by seducing him, but that didn't work. Olivia informed their parents of Dru's presence in Genoa City. They came to see Dru, but were rebuffed, so returned home.
Pushed by Olivia to produce her mystery "boyfriend," Drucilla talked Jabot executive trainee Neil Winters into playing the part. Neil ended up falling in love with Olivia himself. Olivia decided that Dru was setting them up, so moved up her wedding date. This was the year of the grand masquerade ball. Olivia had to work, so Nathan dressed as an Arabian and took Dru, dressed as the Firebird ballerina. Nathan and Olivia married with Dru as reluctant maid of honor. Dru and Neil commiserated, and ended up falling in love. It was obvious both couples were mismatched. The scholarly Olivia was married to the former criminal Nathan, and the former criminal Dru was with the well-educated Neil Winters. Neil supported Dru in her rise to ballerina stardom. But she turned down a chance to tour with the ballet for a modeling career. Neil thought it unforgivable, to be giving up art for self-gratification and big money, so they broke up.
A pregnant Olivia was found to have ovarian cancer, but refused to abort the baby to save her life. After the birth, Liv was to have a hysterectomy, but it and the cancer subject were dropped. But in later years they did try to have another baby. Nathan Jr., "Nate," was delivered early to save Liv's life.
Shortly after Dru and Neil were married at the Chancellor Estate, Lillie Belle left Walter and showed up in Genoa City. She stayed with Liv and Nathan, and drove a huge wedge between them with her bizarre behavior due to clinical depression. Dru tried to talk Lillie Belle into staying with them in hopes of giving Liv and Nathan space to repair their marriage. But as always, Dru's mother rebuffed her in favor of her chosen daughter Olivia. Walter ended up claiming his wife and returning home with Lillie Belle in tow.
Nathan and Olivia were still on the outs since Olivia took her mentally ill mother's side against Nathan. So Nathan began an affair with the beautiful Keesha Monroe. Olivia became suspicious, and both Dru and Neil tried to caution Nathan after they caught him with Keesha. Each time Nathan tried to end the affair, Olivia did something to drive Nathan back to Keesha's arms. Nathan finally ended the affair, and he and Liv began trying for another child. Just as Keesha was falling in love with Malcolm, he found out about the affair with Nathan and dumped her. Then Keesha began getting persistent calls from old boyfriend, Stan, who later died of AIDS. Keesha went to Dr. Liv, turned out to be HIV positive, and had to tell Nathan. It was about this time that Dru decided to tell Olivia about Nathan's affair with Keesha. Liv was furious, not only that Nathan had betrayed her, but also that he had endangered her and Nate with HIV. She kicked Nathan out and forbade him to ever see their son again. All three of them were HIV negative, but Keesha was doomed with full-blown AIDS. The compassionate Malcolm began seeing her again, helping her through the difficult times as she grew weaker and thinner, and would have otherwise been left all alone to die. Malcolm cared for her so he brought her flowers and a veil and married her on her deathbed, so she could at least die happy. Nathan became desperate to see his son, and ended up kidnapping him. Life on the run was rough on Nate, so Nathan finally did the right thing, and was returning Nate to Olivia when he was struck by a car and killed.