1996
Roger's son Hart, who harbored a grudge against his father, turned his eye on Dinah to get back at Dad, but Hart's feelings for Dinah soon became real. When Dinah discovered that Roger had stolen from her inheritance, she and Hart conspired to get her money back: They would trick Roger into thinking that he was crazy, and then Dinah would gain control of the Cayman Island bank account where the money was hidden. Roger, meanwhile, was doing some plotting of his own and was drugging Dinah with a psychoactive substance. Hart realized what Roger was up to in time to stop a drugged up Dinah from leaping off her penthouse roof. Roger and Hart faced off, and Roger shot and killed his son — or so he thought. Hart's "death" was actually part of the plan. Roger started to believe he was crazy when he began seeing his "dead" son. After Roger was hospitalized and Dinah got her money back, Dinah and Hart got engaged. Roger, who was pretending to be cured, scammed his way back into the couple's lives and threw a wrench into their relationship by bringing Dinah's old French lover Jean-Luc to town.

1997
When Dinah started mixing with her jetsetting friends from Europe, Hart was forced to see that Dinah preferred the fast life to the quiet life, and the couple called it quits. They later reunited when Matt locked them together in a shed. Much to Dinah's happiness, her mother returned alive and well to Springfield. (Vanessa was suffering from a disease and had faked her death to protect her family.) Dinah expressed fear that her mother's disease would pass onto a child she had with Hart, but she was just using Vanessa's disease as an excuse and was secretly taking birth control pills. When Hart found Dinah's pills, he ended their relationship. To win Hart back, Dinah conned Hart into thinking that she was finally embracing her maternal instinct. Dinah surprised Hart with a wedding on his birthday, but he broke up with her instead of saying "I do."

1998
Desperate to get Hart back and away from Cassie, Dinah bribed Cassie's ex-hubby Rob for help. To Dinah's great fortune, Hart showed up at her penthouse upset and drunk over Cassie. After Dinah convinced Hart that they had sex, she slept with Rob to get pregnant. Dinah miscarried the baby she claimed was Hart's, but her plans to keep Hart did not end there. Dinah took Vanessa's meds to make it look like she was dying, and then she convinced Hart to marry her despite his feelings for Cassie, who he did not know was pregnant with his child. When Hart found out that he was the father of Cassie's baby and Dinah knew, he left Dinah. Dinah went after Cassie and tricked Cassie into getting into her car, where Cassie went into labor. Hart arrived after Dinah delivered the baby, leaving Dinah to watch the proud parents with their newborn son.

1999
Vanessa, concerned about Dinah's unhealthy obsession with Hart, urged Dinah to seek help, but Dinah refused. Once Cassie learned that Hart wasn't the father of the baby Dinah lost, Dinah confronted Cassie. Hart arrived just as Dinah shot a gun at Cassie, and he jumped in front of the bullet. Later, Dinah fled from Hart's hospital room, after sending him into cardiac arrest, but was caught by Matt, who ended up letting her go for Vanessa's sake. Dinah escaped to Switzerland.

2004
Dinah is living the high life in Europe masquerading as Princess Cassie.