It seems the dating pool in Sydney's eastern suburbs is getting smaller and smaller.
After news broke over the weekend that Dina Broadhurst's ex, appliance heir John 'Herman' Winning Jr, had moved on and was now seeing Big Brother star Holly Young, Daily Mail can reveal that the personality was once friends with the nude artist.
Back in May 2025, Holly and Dina, 50, were spotted looking very chuffed to be in each other's company at the Silver Party – a fundraising soirée for the Sydney Children's Hospital.
In fact, Holly, 31, took to Instagram to document the occasion, sharing a carousel of images that featured Dina prominently.
Wearing a very revealing silver gown, Dina was seen smiling broadly as she cuddled up to Holly.
Curiously, the pair still follow each other on Instagram, despite Holly now dating Dina's ex.
There is a wild twist in the ongoing relationship saga between Dina Broadhurst and her ex-partner, appliance heir John Winning Jr
After news broke over the weekend that Dina Broadhurst's ex, appliance heir John 'Herman' Winning Jr, had moved on and was now seeing Big Brother star Holly Young (pictured left), Daily Mail can reveal that the reality TV personality was once friends with the nude artist (pictured right)
However, there may be some frostiness developing between the duo following John and Holly's reported new relationship.
Up until January, they were regularly liking each other's posts on Instagram.
But the last post of Holly's that Dina liked was back on January 17 – a carousel of images showing Holly trying on outfits at Sydney label Juliana Lilly.
Holly's romance with multimillionaire John means that she has possibly broken the strict 'girl code' of not dating your friends' exes.
Daily Mail has reached out to both Dina and Holly for comment.
News first emerged that John was dating Holly, who starred in the 2025 season of Big Brother, over the weekend.
Sources close to the reality star told The Daily Telegraph the pair had been spending a lot of time together and were recently spotted around 's eastern suburbs.
Meanwhile, Dina is believed to have moved on herself and is reportedly dating another local figure, although his identity has not been confirmed.
Back in May 2025, Holly and Dina were spotted looking very chuffed to be in each other's company at the Silver Party – a fundraising soirée for the Sydney Children's Hospital
In fact, Holly took to Instagram to document the occasion, sharing a carousel of images that featured Dina prominently
Curiously, the pair still follow each other on Instagram despite Holly now dating Dina's ex and up until January were regularly liking each other's posts. Pictured: Holly Young
However, there may be some frostiness developing between the duo following John and Holly's reported new romance
The last post of Holly's that Dina liked was back on January 17 – a carousel of images showing Holly trying on outfits at Sydney label Juliana Lilly
Dina's two-year relationship with John was punctuated by multiple breakups after they began dating in March 2024
'[Dina] doesn't know what went wrong. They were going so strong, then he broke it off,' a source said at the time.
