Jill had a brief fling with wealthy newspaperman Stuart Brooks, who dumped Jill and wed a widowed Liz after Jill lied about being pregnant. Next, Jill set her sights on wealthy divorcé John Abbott of Jabot Cosmetics. Jill's affair with her stepson Jack led to her break-up with John. Jill's feud with Kay re-ignited and she came upon a homeless man, whom she named Rex Sterling, and hired to romance Kay. Rex and Kay eventually married.

Jill and Kay were united in their goal of keeping Nina Webster, whom young Phillip impregnated, from ruining Phillip's future with Cricket Blair. Jill was devastated when an alcoholic Phillip died after sustaining injuries in a car accident. After having a fling with Victor Newman, Jill re-married John Abbott and gave birth to their son Billy. An exasperated Jill had to battle Mamie Johnson, the longtime Abbott maid, for John's affections. Later, John and Jill divorced a second time.

Other romantic dalliances include hairdresser Derek Thurston, private eye Andy Richards, Dina's stepson Marc Mergeron, secretary David Kimble, pool boy-turned-executive Brad Carlton, renovator Jed Sanders, attorney John Silva, businessman Keith Dennison, webmaster Sean Bridges, ex-con Larry Warton and embezzler Elliot Hampton. Sven, Jill's masseur, shot his former client and later kidnapped her. Jack and lawman Carl Williams rescued Jill.

Kay and Jill's battle took on a new level after a long-lost document from Phillip revealed that Phillip willed Jill the Chancellor mansion. A judge ordered that both Kay and Jill could live in the lavish home. Next, Liz visited Jill and gently informed her that she was adopted. After mistakenly believing that crafty Charlotte Ramsey was her birth mother, Jill was presented with a horrifying revelation – her true mother is none other than Katherine. Jill and Kay would go on to form a more familial – but still often volatile – relationship.

Jill was briefly reunited with her father, judge Arthur Hendricks, but he soon left town after suspicions about Arthur's past planted too many seeds of distrust. Single again, Jill begun dating district attorney William Bardwell but Gloria Abbott soon snagged him away. Newly appointed CEO of Jabot Cosmetics, Jill found herself madly attracted to Ji Min Kim. They grew close and soon became engaged which enraged Kay, who didn't approve of Ji Min. She thought he was after Jill's money. Adding fuel to the fire was the revelation that during her drinking days, Kay switched babies on Jill, giving the real Phillip Chancellor Jr. to another woman to raise. After much soul searching, a confession and some research, the real Phillip Chancellor Jr. was discovered tending bar right in Genoa City. Cane was shocked to find himself the Chancellor heir (although his wife Amber Moore was very pleased indeed!) but he soon found himself firmly entrenched in the Chancellor family, working with Kay and getting to know his real mother. Cane found out Amber tricked him into believing they were married but they were not legally wed. Stunned by her lies, Cane broke up with her.

Jill's happiness was short-lived when Ji Min was discovered dead. Detective Maggie Sullivan was trying to find out who murdered the handsome executive and just what secrets he had been hiding. Paul Williams and J.T. did some investigating and found out that Nikki's husband David Chow killed Jin Min before being killed himself in a mob hit. Meanwhile, Cane and Kay had a close call when a parking garage that Cane had been working on collapsed and trapped them underground. Eventually, they were freed but not before Katherine bonded briefly with Amber, who was also trapped. Later, Amber helped Katherine write her memoirs.

Jill had been noticing that Katherine had been acting strangely and keeping secrets. She didn't know that Katherine's look-a-like Marge had been in contact with Katherine and Jill's mother was trying to help her kick her addiction to alcohol. Katherine and Marge had an automobile accident and Marge was killed, while Katherine disappeared. Jill and Nikki found the car and thought that Marge was Katherine. Meanwhile, Marge's good friend Murphy found Katherine and nursed her back to help until her memory returned. Katherine returned to the Chancellor Mansion to tell Jill that she was alive but Jill thought Katherine was Marge and had her arrested!

Billy returned to Genoa City and met his half-brother Cane. He wasn't pleased to see Cane had seemingly taken his place in the family. He ran into an old flame, Chloe, who was pregnant and married to Cane. Billy set his sights on Cane's ex, Lily Winters, who had grown up to be a beautiful young woman. Jill was happy to have her family together but not too pleased that Chloe, Esther's daughter, was going to give birth to her granddaughter. Later, Billy and Chloe married and divorced. Jill's world was torn apart by the discovery that her mother, Katherine Chancellor (Jeanne Cooper), is not actually her mother, Cane (Daniel Goddard) is not actually her son and by her true son Phillip III's return from the dead.