1996
Cris (then-Yorlin Madera) and Jessica continued to sneak around and got into trouble — like taking Joey's car out for a joyride and wrecking it. He pressured Jess into having sex, but she wasn't ready.

1997
Cristian finally won over Jessica's parents and they were allowed to attend the prom together. However, she dumped him when she caught him kissing her friend. They grew close again after he saved her from a warehouse blaze, but they began to drift apart when he entered college.

1998
Jessica felt threatened when Cristian's gorgeous childhood friend, Roseanne, came to town and occupied his time. Meanwhile, Jessica became a stepsister to Lindsay Rappaport's son, Will (Jason-Shane Scott), during Clint's brief marriage to Lindsay. One night, after seeing Cristian and Roseanne getting cozy, Jess got drunk and lost her virginity to Will; she then discovered that she was pregnant. When Cris learned about her condition, he claimed that he was the father.

1999
Will felt left out when Cristian (David Fumero) proposed to Jessica. At the engagement party, Cris and Will got into a huge fight. Jess stepped outside and was accidentally run down by Dorian, who was ironically heading to the party to make amends with Viki. Jessica survived the accident, but her baby girl (whom she and Will had intended to name Megan) didn't. Jess also suffered amnesia. While unconscious, Jess was visited by the spirits of both Megans — her late sister and late daughter. At first, it seemed as though Jessica was handling the tragedy well, but then it turned out that she'd been "haunting" Dorian — and had no recollection of doing so. A guilty Dorian intended to let Jess run her down with a car, but Jessica had second thoughts and couldn't do it. Throughout the drama, Will and Cris continued to battle it out for Jess, while Roseanne fought for Cristian.

2000
Will and Roseanne teamed up to keep Jessica and Cristian apart. Jess tried to prevent Cris from marrying Roseanne, but she locked Jessica in a closet before the ceremony. After, Jess told Cristian the truth about Ro's lies and he left his new bride. Jessica and Cris then helped Will elude the law when he was accused of embezzling funds from the Megan Foundation, named in honor of his and Jessica's deceased daughter. While on the lam, Jess hid out with musicians and posed as a rock star. Jessica eventually chose between the two guys and picked Cristian, but left him again when Will skipped town and Cris tried to keep her from seeing Will's note.

2001
When Will returned, Jessica tried to have a relationship with him, but she couldn't completely trust him. Jessica then fought with newcomer Natalie (Melissa Archer) over Seth, who was paired with Jessica in a film class. Nat vowed to destroy Jessica and did so by revealing that she, not Jess, was Clint and Viki's daughter.

2002
Jessica and Seth grew closer. Viki adopted Jessica, but Jess and Nat had a difficult time adjusting to the situation. Jessica tracked down Roxy Balsom, the woman who raised Natalie and who Jessica believed was her birth mother. Roxy tried to "bond" with Jess so she could get her fortune. Jessica later learned that Mitch Laurence, not Clint, was her biological father and that Clint and Viki are actually Natalie's birth parents. A shaken Jess dumped Seth when she found out he'd known about Mitch and didn't tell her. She left for London to be with Clint and figure things out.