2000: Jake helped nurse Gillian back to health and the two tied the knot, but he walked out on his wife (and Pine Valley) after learning she'd kept the truth about Colby from him. Ryan and Gillian renewed their romance, but when Jake returned to town badly injured, Gillian felt unable to request a divorce. Ryan and Gillian broke up again. But they hadn't fallen out of love; Gillian and Ryan became lovers once more. Gillian learned she was with child, but she wasn't sure who had impregnated her: her current husband or her former one. After Gillian miscarried, Jake granted her a divorce.

2001: Once she was no longer Mrs. Martin, Gillian and Ryan were remarried in a lavish ceremony paid for by Dimitri. But the couple's bliss would not last long. A henchwoman working for the nefarious Charlotte mistook Gillian for Anna and shot her. A devastated Ryan made the difficult decision to remove Gillian from life support, and her heart was donated to an ailing Laura du Pres, whose life was saved by the transplant. Ryan had a rough time recovering from his wife's death and sought physical comfort from Liza (who had just discovered her husband Adam's infidelity) and her half sister, Mia.

2002: Ryan learned that his biological father was law enforcement agent Chris Stamp -- who had fatally wounded the man Ryan had believed to be his father, the abusive Patrick, during a drug bust. Ryan fell for Kendall Hart, who had just returned to Pine Valley. Ryan took a bullet for Chris when a sniper attempted to end Stamp's investigation into the drug lord Proteus by ending his life. As he healed from the injury, Ryan began to bond with Chris. Ryan proposed to Kendall, who had been wrongfully accused of arson. The two planned to begin a new life away from Pine Valley once her name was cleared. But when Ryan discovered Kendall trying to seduce Aidan as part of an ill-advised scheme to prove her innocence, Ryan dumped his fiancée and roared out of town on his motorcycle.