The co-host of the Kyle & Jackie O Show, whose real name is Jacqueline Henderson, was inundated with direct messages from a stranger on Instagram over five months.
She did not respond and instead recorded the messages in approximately 700 screenshots, each of which captured up to five missives.
The man at the other end of the phone was David Gourlay, an unemployed 38-year-old who graphically detailed his sexual fantasies involving the radio host.
Many of the messages were sent consecutively and reflected personal details about Henderson, including information about her family.
Despite having never met the radio presenter, her stalker wrote as if they had a pre-existing relationship and a child together.
"I am not giving up on us," he wrote in one message sent on the morning of July 3.
Later that day, Gourlay sent a bouquet of flowers to Henderson's home.
The broadcaster was afraid for her family's safety given her stalker knew where she lived, according to the facts.
Police traced the flower order - which was mistakenly addressed to 'Jackie Anderson' - to Gourlay, who had listed his mobile number.
They found him sitting on a bench opposite Henderson's house and took him into custody before he was taken to Prince of Wales Hospital for a mental health assessment.
Gourlay faced Downing Centre Local Court on Wednesday to plead guilty to stalking the broadcaster and using Instagram in a menacing, harassing or offensive way.
Five other charges - including being armed with the intention of committing an indictable offence - were withdrawn by prosecutors.
Gourlay will be sentenced when he returns to court in December.
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 him from assaulting, threatening, stalking or harassing the radio presenter or anyone with whom she had a domestic relationship.
It comes as Henderson and her co-host Kyle Sandilands face criticism over mounting breaches of the Commercial Radio Code of Practice decency rules.
Their KIIS FM breakfast show was found to have breached the rules seven times between August to December 2024, prompting accusations of systemic issues.
The breaches included broadcasting audio clips of male and female staff members urinating and a game where a contestant provided an offensive description of a sexual position.
The Kyle & Jackie O Show has been a regular ratings juggernaut in Sydney, but has struggled to capture the Melbourne market since launching there in April 2024.
Its hosts signed a 10-year contract extension in 2023 that was said to be worth more than $200 million.
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