After getting her ex-husband John's approval, Jill Abbott launched a new men's line of products under the Jabot banner. Although Jill approached her new project with enthusiasm, her personal life was in a shambles. To Jill's disappointment, Phillip made it clear that he was interested in remaining at Katherine Chancellor's home. Jill waged a custody battle for Phillip, which caused several unseemly details to surface, such as Katherine's move to take away Phillip's hefty inheritance when he was still a small boy. Despite what happened in the past, Phillip chose to stay with Katherine because she provided him with a level of security and attention that he had never received from Jill. To get back at Katherine, Jill hired a homeless man--whom she christened Rex Sterling-- to pose as a wealthy gentleman and romance her nemesis. Meanwhile, Katherine also bribed a photographer to lavish Jill with attention.

Phillip was befriended by Cricket Blair and Nina Webster. Eventually, Phillip's feelings for Cricket went beyond friendship. But Cricket didn't return his affections because she was dating Danny Romalotti. Meanwhile, Nina waged an aggressive campaign to win Phillip's heart. She soon had competition. Cricket and Danny agreed to date other people for the summer, and Cricket fell in love with Phillip.

During Phillip's and Cricket's romance, Phillip began drinking to give himself confidence. One evening, while driving Cricket home, Phillip got into an accident. Cricket told authorities that she was driving so that Phillip, who was under the influence of alcohol, wouldn't be arrested. The negative publicity nearly cost Cricket her job as a model at Jabot. But Phillip, who had no recollection of the accident, ultimately assumed responsibility after Danny told him what actually had happened. Cricket temporarily moved into Katherine's home to lend Phillip emotional support as he struggled to quit drinking. But the circumstances created tension and the young lovers found themselves quarreling. One evening, while Cricket was enjoying an innocent visit with Danny, Nina got Phillip drunk and seduced him.

Cricket was forced to make a decision between Phillip and Danny when both young men proposed marriage to her. While Cricket was struggling to make up her mind, Nina schemed to win Phillip. Shortly after Cricket resolved to accept Phillip's proposal, Nina broke the news about their sexual encounter. The ploy nearly worked. Hurt by Phillip's infidelity, Cricket arranged to return his engagement ring. At the last moment, Cricket realized how deeply she loved Phillip and she proceeded with plans to marry him. Both Katherine and Jill were delighted by the news. Nina, however, still had a trump card she hadn't played. To Katherine's and Jill's horror, Nina announced that she was pregnant with Phillip's baby.

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