When Vanessa Bennett arrived in Pine Valley, it quickly became obvious that her son, Dr. David Hayward, was none too thrilled to see her - she suffered a heart attack and he did nothing to help her.  David learned that his mother had lost her fortune to a succession of young lovers, and suspected that she was after money from him, despite her claim that it was out of love for him and a desire to get help for her heart condition.  He eventually lost his temper and accused he of being responsible for his father's suicide.  She countered that he was responsible for the accident that had disfigured Erica, and told Erica the truth about her face (before that, Erica had not realized the extent of the damage).

Still in need of cash, Vanessa teamed up with Donald Steele to write a nasty tell-all book about he friend Erica.  She manipulated Erica into letting Vanessa live with her; all the while Vanessa supplied Steele with bits for the book.  Janet and Trevor came to the rescue and pointed the scheme out to Erica, and when Vanessa claimed that David had killed his father himself, Erica ran out of patience and gave her the boot. Vanessa had intended to continue with the book, but David pretended to poison Steele and got him to admit on tape that she was behind the scheme. 

Vanessa next set her cap for Palmer Cortlandt, who had recently split with is wife, Opal.  Vanessa and Palmer shared several dinners, then she accompanied him on a trip to Brazil where Erica was recovering from plastic surgery.  When David returned, he discovered that his mother had checked out of her suite at the Valley Inn.  At first pleased, thinking she'd left town, he was disappointed to learn she was on a cruise with Palmer.

Palmer became suspicious that his new wife was cheating on him and hired a private investigator to keep tabs on her.  The investigator uncovered the "lover", Leo duPres, in NY and Palmer schemed to have Vanessa killed at a party, then frame Leo for the murder.  Palmer had Leo drugged and brought to Pine Valley, but Leo overheard enough to realize that Vanessa was in danger.  As the party reached the point where Vanessa was to have been shot, Leo stumbled into the room.  Vanessa cried out for someone to help her "son" and Palmer realized his mistake.  He took the bullet meant for his wife.

By April 2000, Vanessa had taken up with gigolo Paolo, who was also blackmailing Leo.  Vanessa accidentally gave Paolo a lethal drug overdose, but stood by silently when Leo was arrested for the murder, assuming Palmer's lawyers would get him off.  David and Erica were sure Leo was innocent, and with Palmer's help, led Vanessa to think that she was having a fatal heart attack.  She made a deathbed confession which freed her son, but he was devastated that she'd let him take the blame for the murder and cut all ties.  Palmer didn't want his wife to go to prison, and so devised his own punishment - he set her to work plucking chickens at the Chicken Shack, and cut her off without a cent!

Once again desperate for funds, Vanessa struck up a friendship of sorts with Arlene Chandler, and agreed to keep the secret that Stuart was alive - for a price.  She got some money from Arlene, although perhaps not as much as she had anticipated, but before too long the secret came out anyway when Arlene sprung Stuart from the attic in time to save his brother's life.  Vanessa stuck by Arlene, and was there for her when she suffered her miscarriage, devising a way to parlay the tragedy into gain for them both.  She advised Arlene to frame Liza for the miscarriage, thus ensuring that Arlene would remain Mrs. Adam Chandler and retain access to the money promised to Vanessa.   A friend indeed.