1997: Gillian Andrassy lived a life of worldly adventure as she gallivanted freely through Europe on her trusty royal expense account, fueling her lavish taste. But after being caught in bed with a much older man, her father sent the young princess to live with her cousin, Dimitri Marick, in Pine Valley. Adjusting to the small town proved difficult for the international party girl. But her life was going to change even more when Dimitri revealed her father had squandered their family fortune. Gillian needed money, desperately. She set out to find the richest, and youngest bachelor Pine Valley had to offer. By New Year’s 1998, that man would be 18 year old Scott Chandler.

1998: Gillian knew she could win Scott over with her good looks and passion for sex. But Kelsey Jefferson had her own plans for Scott. She teamed up with Ryan Lavery to break them up. Kelsey and Liza Colby led Gillian to believe that Ryan was a millionaire to lure Gillian away from Scott. Kelsey did not think her plan was working fast enough, so she called immigration on Gillian. Gillian was in the states on a visitor’s visa. If she did not want to be deported, she needed to marry a man. Scott volunteered himself, but Gillian chose Ryan.
Gillian was shocked to learn that Ryan’s wealth was all a ruse. The young couple moved into Wildwind, where the bickering never seemed to end. But, Gillian did not want to admit that she was growing very smitten with her new husband.
Gillian thought Ryan was sticking around because immigration was still investigating them. She found herself jealous over Ryan’s relationship with Hayley Vaughan, another Wildwind resident. Gillian warned Hayley to keep her distance.
Ryan was accused of the rape of Kit Fisher Montgomery. Hayley helped Gillian and Ryan escape the authorities. Hayley was to drop off money for the couple, but she never arrived at their meeting place. Gillian turned to Dr. David Hayward for help. He promised to give Gillian money if she slept with him. For Ryan’s sake, she gave in to David’s demands.

1999: When Ryan learned about David and Gillian’s one-night-stand, he filed for divorce. Gillian began volunteering at Pine Valley Hospital. There, she met Dr. Jake Martin. She found herself confiding in Jake about her troubled life. Gillian was attracted to Jake’s honesty and simplicity. Their friendship turned into romance.
Dimitri’s new wife, Dr. Alex Marick, came to Pine Valley with devastating news. Dimitri had died of a brain aneurism. Gillian was one of the few people who accepted Alex. Gillian knew how it felt to be shunned by the tight-knit citizens of Pine Valley, and did not want Alex to go through the same ordeal. Luckily, Dimitri turned up alive and in David's care.
David let it slip to Gillian that Adam Chandler was Colby Chandler’s biological father, not Jake. Gillian rushed to tell Jake, got in a car accident. When she awoke, she realized she could not speak because of complications from aphasia. Jake treated Gillian. It pained Gillian to not be able to tell Jake the truth.
Gillian was released in time for the Crystal Ball. At the event, Jake proposed to Gillian, and she accepted

2000: Gillian married Jake but still kept the truth about Colby from him. At the trial, it was clear that Jake was going to win custody of Colby. Liza broke her silence and admitted Adam was Colby’s father. When Jake found out everyone was lying to him, including his wife, he enlisted in Doctors without Borders in Chechnya.
Gillian found comfort back in Ryan’s arms. Gillian realized she never stopped loving her first husband. But Gillian wanted to remain faithful to her current husband. Ryan used money from his new company, IncredibleDreams.com, to rescue Jake. Gillian stowed away in the cargo plane to confront her husband. When Jake saw her, he pushed her out of the way of armed militants. Jake was shot and transported back to Pine Valley to recover.
Jake learned the injury he sustained had left him impotent. Gillian blamed herself and told Ryan she needed to stand by her husband.
Under the influence of the drug Libidizone, Jake and Gillian made love. Gillian confessed to Jake that she was no longer in love with him. She left Jake for Ryan.

2001: Gillian and Ryan were determined to marry again. But before she could divorce Jake, Gillian learned she was pregnant with his child. Ryan promised to love the child as if it was his own. Before it could come to that, Gillian got in another car accident and miscarried.
Gillian had to learn to pinch pennies if she was going to be Ryan’s wife again. They were resolved to have a simple wedding with the justice of the peace. Dimitri surprised Gillian with a lavish Hungarian wedding at Wildwind.
A documentary producer named Illene Pringle approached Gillian. Illene convinced Gillian she wanted to make a documentary about the fallen princess. Gillian saw it as easy money. Really, Illene was an assassin hired by Charlotte Devane to finally eliminate Anna Devane, Alex’s sister. Illene mistook Gillian for Anna, and shot her in the head.
Gillian’s spirit was welcomed to heaven by a slue of Pine Valley’s past residents. Gillian refused to believe she was dead. Natalie Marlowe caught Gillian trying to escape back to earth. She agreed to allow Gillian to tie up loose strings with the help of Jesse Hubbard. She was to return to earth on a special task. When the task was complete, she was to return to heaven.
Gillian knew that her mission involved Ryan. She tried to make contact with Ryan through Opal Cortlandt. Jesse kept Gillian in check. Gillian found out that Federal Agent Chris Stamp was Ryan’s biological father. Gillian struggled to convey the news to Ryan. She found her opportunity when Ryan nearly died in a fire on Fidelity. With her task complete, Gillian's spirit was at peace.