1998: Shortly after arriving in Pine Valley, Ryan saved Dimitri's life by donating blood to the ailing count and soon went to work for Liza at WRCW. Ryan offered flirting lessons to Kelsey, who had a crush on Scott, and tried to help Kelsey incite Scott's jealousy by pretending to date her. But Scott's attention was fully fixed on Gillian Andrassy, whose charms did not escape Ryan's notice, either.

Liza and Erica caught on to Ryan's illegal financial wranglings and Liza offered Ryan a deal: either go to prison or tie the knot with Gillian, whom Scott had offered to wed to save her from deportation. Ryan took the bait and wooed Gillian all the way to matrimony -- unaware that the princess was completely destitute. When Gillian realized that Ryan had married her for her (nonexistent) money, she wanted to end the union, but decided to remain wed to avoid further immigration problems. Before long, the newlyweds began to develop real feelings for each other. But Ryan had a hard time showing his bride that he cared for her, so she fell into bed with David Hayward -- and Ryan caught them. Reeling from the shock of his wife's infidelity, Ryan got soused and did some intimate dance-floor moves with Kit Fisher, who later accused him of rape.

1999: Gillian and Hayley, Ryan's close pal, believed in his innocence and crafted a plan to help him elude the authorities. But Hayley was jailed for aiding a fugitive Ryan, so Gillian felt she had no choice but to turn to David for assistance. He agreed to help her out financially, provided that she sleep with him, which she did. But David betrayed her, leading the cops to Ryan's hideout and revealing to Ryan that his wife had betrayed him. Ryan was tossed in jail, where he was visited by his half brother, Braden. Ryan quickly realized that it was Braden who had raped Kit. Feeling indebted to Braden for shielding him during their difficult childhood, Ryan decided to take the fall for his sib. But before long, Tad and Dixie found proof of Braden's guilt and Ryan was released.

One of Ryan's first moves post-prison was to divorce Gillian. He grew closer to Hayley, and they eventually shared a kiss, which Gillian witnessed. Ryan also began a new company, the Internet-based wish-fulfilling service IncredibleDreams.com, and took a new lover: Greenlee Smythe. (Greenlee was genuinely smitten with Ryan, but for him, their relationship was strictly about sex.) Gillian, meanwhile, was left mute after a car accident that occurred after she learned that Adam, not Jake, was the biological father of Liza's baby girl, Colby.