Sydney millionaire John Singleton, 81, splits from ‘carer’ girlfriend, 44

Sydney millionaire John Singleton has reportedly dumped his girlfriend after she became his “live-in carer” following his heart failure.

One of Sydney’s wealthiest men is back on the market after splitting from his latest girlfriend at 81.

Entrepreneur and investor John Singleton, who amassed his fortune in the advertising business in 70s and 80s, recently separated from Kim Dennis, 44.

The couple became an item in late 2021, with the pair going public after Singleton suffered heart failure, and Dennis moved in to care for him.

“Singo” has been married, and divorced, six times in his lifetime, including a short marriage to 60 Minutes reporter Liz Hayes in the early 90s, SMH reports.

He’s had a long string of girlfriends in the years since his last divorce, even controversially dating a “couple” of women at once, according to a report by TheDaily Telegraph in 2021.

His latest relationship breakdown with Dennis happened just before Christmas, with friends claiming he ended things over their “40-year age-gap”, a new report from TheDaily Telegraph states.

John Singleton, 81, has reportedly called time on his relationship with his much younger girlfriend.

Kim Dennis, 44, is said to have been ‘blindsided’.

Singleton and Dennis, a former ad rep who previously worked at Singo’s Macquarie Radio Network station 2GB, had bonded over their mutual love of horses.

Their romance became more serious when Singo had a serious cardiac episode that was said to have left him at “death’s door”.

Dennis, a divorced mother of two, moved into Singleton’s home at Mt White on the Central Coast to look after her much-older man.

She is said to have been “blindsided by the split” as the pair had been “busy making future plans for the couple including holidays abroad”.

Singleton is reportedly worth $768 million. Picture: Justin Lloyd

Before his relationship with Dennis, Singo enjoyed an on/off relationship with New York-based public relations expert Venessa Merrin.

The pair began dating in 2016 according to Daily Mail Australia, with the romance only coming to an end when Singo went official with Dennis in 2021.

Singleton is estimated to be worth $768 million.