2000
Phyllis returned, still harboring feelings for Jack. After turning down an offer to work as Jabot's Web site producer, she signed on with the competition, Newman Enterprises.

2001
Jack and Phyllis got engaged and started talking parenthood. Phyllis lost their baby, undergoing emergency surgery for a tubular pregnancy that left her infertile. Jack convinced her that they still belonged together and they married right after Christmas.

2002
Intent on giving Jack a child, Phyllis almost died from her fertility drugs. The Phyllis/Diane battle kicked off when Jack found out he was the father of Diane's son, Kyle. Diane became committed to stealing Jack from Phyllis, even if she had to use her son to do it. Needless to say, the confrontations between Jack's scheming ladies were fierce. Not only did Diane throw herself under Phyllis' car, but she lit the pool house on fire to frame her nemesis for attempted murder — and was almost successful!

2003
After being fired from Newman Enterprises for being married to Jack, Phyllis helped the company steal Jabot's target cosmetic line, Satine, to prove her loyalty to and earn her job back. This set in motion the newest feud between both the couple and their respective companies. By year's end, Phyllis had shared passionate kisses with Jabot's new hot chemist Damon, but she still refused to give up on her marriage.

2004
Phyllis finally agreed to work for Jabot so that she and Jack could be reunited, but then Jack wouldn't agree to fire Diane in turn. Furious, Phyllis sealed the fate of their relationship by refuting Jack's testimony against Victor. Meanwhile, little Daniel returned to town, all grown up and with no interest in a relationship with his mother. With Jack's ring still on her finger, she found solace in Damon's arms.