In 1994, an unhappy Jessica begins smoking and rebelling due to her parent's divorce. Marty Saybrooke catches her attempting to shoplift and tries to support her, telling parents that they should be worried about Jessica's unhappiness. In early 1995, as a teenager, Jessica meets Cristian Vega, and they are instantly attracted to each other. Jessica's father Clint and Cristian's mother Carlotta initially object to the relationship, forcing the teens to see each other in secret. The issues are eventually worked out. In 1998, Jessica later has a one-night stand with Will Rappaport and becomes pregnant; Cristian forgives her and the two decide to get married. In 1999, Dorian Lord accidentally hits Jessica with her car, and the baby (later named Megan) is stillborn. The miscarriage pushes Jessica and Cristian apart, and brings her closer to Will, but neither relationship survives.