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Due to her being a 'flight risk', her bail is set at an undisclosed, but high amount.

While Alice attempts to contact Helena's mother, Peggy, Helena is warned 'not to drop the soap'. in time to receive her ailing mother, who reinstates her heiress status.

At about this time, her wealthy mother cut her off financially.

After being cut off by her mother, and has a one-night stand with Papi.

Further into the season Helena gets involved with Dylan Moreland (played by Alexandra Hedison), and is eventually slapped with a sexual harassment lawsuit (as it turns out, Dylan was only using her to gain money).

Off-court meetings of this lawsuit presented in episode 3.10: Last Dance unveil Helena's past: In 1998, Helena was sued for sexual harassment; the claim was settled out of court.

Further on, Alice convinces Phyllis to hire Helena as a caterer for a party from which she ends up without profit after an incident in the kitchen.

Helena later joins Shane and Alice at the Roll the Dice movie premiere party.

She ends up winning the game, but still embarks on an affair with Catherine, as it is now theoretically on her own terms.

In 2002, Helena violated a restraining order filed against her by her psychiatrist. Helena helped Dana somewhat in her last days of her battle with Cancer and was at her funeral.

She also supported the fundraiser for Max's gender reassignment surgery, and paid for Shane's wedding during the third season finale (where she makes the disastrous decision of giving Gabriel Mc Cutcheon money which he used to run off leaving Carla, and which triggered Shane to also leave Carmen at the altar).

Later, after being romantically entangled with another butch inmate named "Dusty", her mother Peggy Peabody bails her daughter out of prison, only to have her escape out the back of "The Planet" with plans of finding her hidden money to set Dusty free and escape to a Polynesian island paradise with her, as is signified with the light fingering of a puzzle piece given to her by Dusty. She learns of changes that happened during her absence.

At her mother's encouragement, Helena takes over both She Bar and The Planet from Dawn Denbo.

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