1995: Growing up in rough-and-tumble Angel Square, Cristian (then-Yorlin Madera) was pressured to join one of Llanview's street gangs, but he resisted because that life put his older brother, Antonio, in jail. When Cristian found himself caught in the middle of a gang war anyway, the newly released Antonio helped him by restoring peace in Angel Square. Meanwhile, Cristian started dating Jessica, even though their parents did not approve because the two youngsters were from different worlds.

1996-97: Cristian and Jessica continued to date despite their parents' skepticism. Things came to a boil when Clint walked in on them as they were about to have sex. In time, Cristian was able to win over Jessica's parents, and they were allowed to attend the prom together. They grew closer when Cristian saved her from a warehouse fire, but distance came between them when they entered college.

1998: Things got even rockier when Jessica caught Cristian kissing his childhood friend Roseanne. To try to forget about it, Jess got drunk one night and lost her virginity to Will; she then discovered that she was pregnant.

1999: When Cris (David Fumero) found out about the baby, he claimed that he was the father and asked Jessica to marry him so they could raise the child together. Will argued that he should be allowed to raise the child, and one night during a fight between him and Cristian, Jessica ran off and was hit by a car (the driver turned out to be Dorian). Jess recovered, but lost the baby. When she woke up, she did not remember Cristian and instead got hot and heavy with Will. A heartbroken Cristian took solace in Roseanne's bed.

2000: Will and Roseanne schemed to keep Jessica and Cristian apart. When Jessica regained her memory and realized what was happening, she failed to get to Cristian in time to stop him from marrying Roseanne. But when Jess told him the truth about Roseanne's scheming and lies, Cristian left his new bride. Jessica and Cristian grew close again when they helped Will find proof that he had been framed for embezzling funds from the Megan Foundation, named in honor of his and Jessica's deceased daughter. Just when Cristian and Jessica seemed to be on the brink of a full reconciliation, she left him when Cris tried to keep her from seeing an important note from Will. Cristian tried to drink away his woes, and one drunken night he got in a car accident and hurt his hand, jeopardizing his career as an artist.