A man struggling with mental illness developed an obsessive belief that he was romantically involved with radio personality Jackie O, leading him to send her an overwhelming number of messages and eventually appear at her residence.

David Gourlay bombarded the well-known broadcaster with approximately 2,000 messages on Instagram over a span of five months. Many of these messages were sent in rapid succession and contained references to her personal life.

Despite never having met Jackie O, whose full name is Jacqueline Henderson, the 38-year-old communicated as though they shared a history and even a child.

In one message sent on July 3, he declared, “I am not giving up on us.”

Throughout this deluge of messages, the co-host of the Kyle and Jackie O Show chose not to engage, even as some messages detailed Gourlay’s explicit fantasies involving her.

The situation escalated further when Gourlay attempted to send her flowers, mistakenly addressing them to “Jackie Anderson,” and had them delivered to her home.

Police found him sitting on a bench outside the radio host’s home in Sydney’s east and took him into custody before arranging a mental health assessment.

Gourlay – who has been diagnosed with schizoaffective disorder with bipolar – had delusions of being in a relationship with Henderson, his lawyer told Sydney’s Downing Centre Local Court today.

“He is battling quite a significant mental health issue,” Trudie Cameron explained during her client’s sentencing.

He had not been compliant with his medication and had reported suffering paranoia and hallucinations before sending the barrage of messages to Henderson, she said.

An expert report drew a direct correlation between his mental health and the offending because Gourlay’s actions arose out of his delusion, the court was told.

“When he’s medicated, when he’s well, he is a productive member of the community,” Cameron told the court.

She pushed for Gourlay to serve his sentence in the community, citing his genuine remorse for the offences and his insight into the fear it would have caused Henderson.

But the prosecutor pushed for the 38-year-old to be jailed over the “abhorrent” sexual messages in order to send a message to the community.

The facts didn’t make for pleasant reading, Deputy Chief Magistrate Theo Tsavdaridis agreed, pointing to the overly sexualised nature of some missives.

“The messages were targeted, unwanted and incessant,” he said.

He said Henderson had rightfully feared for her family’s safety when a stranger had showed up near her house after flooding her with messages.

Gourlay had an extensive criminal record and had been serving two community sentences at the time, Tsavdaridis noted.

He sentenced Gourlay to 16 months’ imprisonment, with at least eight months to be served behind bars.

With time served, the 38-year-old will be eligible for parole in March.

A five-year apprehended violence order prohibits him from approaching Henderson or contacting her except through a lawyer.

The order, which expires in 2030, bars Gourlay from assaulting, threatening, stalking or harassing the radio presenter or anyone with whom she had a domestic relationship.

1800 RESPECT (1800 737 732)

National Sexual Abuse and Redress Support Service 1800 211 028