1984: Hillary Wilson lead the perfect life until her mother, Betty Wilson, fell terminally ill. On her deathbed, Betty revealed that Hillary’s father was still very much alive. She was to seek a man named Professor Langley Wallingford who was now living in Pine Valley.
Hillary was shocked to see who exactly Langley was. He was married to Phoebe English, one of the richest women in Pine Valley. Phoebe was the closest thing the small town had to royalty. When she arrived at the Wallingford Estate with the news about her origins, the Wallingfords welcomed her with open arms. Phoebe and Hillary grew especially close.
At Pine Valley University, Hillary had to put up with flirtation from class nerd Alfred Vanderpoole. Hillary then met teen rebel Tad "the Cad" Martin. Their innocent flirtation grew into something much more. But, Hillary knew Tad was off limits as long as he was dating Dottie Thornton. Plus, Phoebe disapproved on Tad based on his reputation as a womanizer. Soon, none of this would matter, as Dottie was pregnant with Tad’s child. Hillary was content to dating Tad’s friend, Bob Georgia.

1985: Bob confided in Hillary that he was diagnosed with a terminal illness. Remembering her mother's last days, Hillary wanted to make Bob’s final days as happy as they could be. They married in a small ceremony at the Wallingford Estate.
Tad left Dottie after she miscarried. He proclaimed his love for Hillary, but she was trapped in a loveless marriage. Bob learned that his disease had went into remission. He tried to keep the diagnosis a secret, but Alfred told the truth to Tad. Hillary arranged for a quick divorce so that she and Tad could be together.
Phoebe voiced her disapproval for Tad. That Christmas, she asked Langley to take Hillary on an archeological trip to Arizona. Little did Hillary know, Phoebe mislead Tad into thinking they had left for Australia. Phoebe hoped that Tad would only be able to scrounge up a one way ticket out of town.

1986: Hillary and Tad were set to marry. But on the wedding day, Tad was missing. Phoebe was convinced that he was up to his old ways. Phoebe wanted Hillary to forget about Tad, but she loved him too much. She ran into the street in front of the church and was hit by a car. The driver was none other than Edna Thornton, Dottie's mom. Dottie confronted Hillary and helped her calm down. They returned to the Wallingford Estate while they waited for news on Tad. Tad revealed he had been held up at the Pine Valley Bank. He begged Hilary for forgiveness. That night, they married in a small ceremony at the Estate.
But married life proved to be its own hardship for the couple. Tad’s reputation kept Hillary on edge. She found herself fighting the many women who clung to Tad including Skye Chandler and Robin McCall. Tad had learned that Robin’s brother, Wade Mathews, planned to con a newly single Phoebe. When Hillary learned Wade almost killed Phoebe, and that Tad had known about his plot all along, she lashed out on him. Hillary asked for a divorce. After they settled their affairs, Tad left town.

1987: Hillary and Skye’s feud came to heads when both women fell in love with Mitch Beck. Mitch was dating Skye, but had feelings for Hillary. Hillary’s animosity with Skye stemmed from when she caught her with Tad together right before he left town. Mitch dumped Skye, and pursued Hillary.

1988: Mitch had left town for Boston after getting a new job. Hillary was at a cross road. She just graduated from Law School. As if the stars aligned, she received an offer from a firm in Boston. She decided to make a fresh start there, hopefully with Mitch.