Sydney millionaire John Singleton dumps girlfriend Kim Dennis

Sydney multi-millionaire John Singleton, 81, has ended his relationship with his 44-year-old ‘carer’ girlfriend as it was speculated she was preparing for a proposal.

Singleton – worth an estimated $768 million – broke up with his former employee Kim Dennis shortly before Christmas.

The pair began dating in 2021 after bonding over a shared love of horses and moved in together after Singleton suffered heart failure and fluid on the lungs in November of that year, Daily Telegraph reports.

Dennis lived with Singleton in his Mt White home on NSW’s Central Coast and helped nurse him back to health.

Sydney multi-millionaire John Singleton (left) and his 44-year-old former carer and girlfriend Kim Dennis (right) have broken up

Singleton reportedly split with Dennis (pictured in 2019 with her former partner, 2GB radio host Steve Price) over concerns about their nearly 40-year age gap

Singleton reportedly ended the relationship over concerns about their almost 40-year age difference. They were together for some 18 months. 

Dennis – a divorced mother of two from western Sydney – worked for ‘Singo’ at his Macquarie Radio Network station 2GB and knew him for several years before they started dating. 

However, her position was made redundant by 2GB’s new owner, Nine.

She has since started a new job with an American skincare company. 

Sources close to the former couple told the Telegraph Dennis was ‘blindsided’ by the break-up and had been busy making plans for future overseas holidays.

They also said Singleton ‘will likely have been generous to Dennis’ after their sudden split. 

Singleton (pictured left in 2022) is worth an estimated $768million and invited Dennis to live with him in his Mt White home after he suffered heart failure in 2021

Dennis was also reportedly holding out hopes of a proposal from Singleton that would see her become his seventh wife. 

She formerly dated 2GB radio host Steve Price with the couple pictured together in October, 2019.

Price had separated from his then-second wife Wendy Black that same year but had denied the break-up in June.

Singleton also boasts an impressive list of ex-girlfriends and wives – having been divorced six times, including once to 60 Minutes reporter Liz Hayes in the early 1990s.

Before Dennis, Singleton dated New York-based public relations expert Venessa Merrin, as reported by Daily Mail Australia.

Their relationship began in 2016 and reportedly only ended once Singleton went official with Dennis in 2021.  

Singleton made his fortune in the advertising business in the 1970s and ’80s.