In the eastern suburbs, there’s an old belief that folks refuse to date anyone who resides to the west of Edgecliff Station.
Indeed, it seems that the social circles among the coastal elite often overlap significantly. Their communities along the coastline frequently host revolving relationships, former flames reconnecting, and love situations reminiscent of tangled webs – like old acquaintances dancing a continuous round of musical chairs.
Now, property developer Max Shepherd is the latest to hop on the merry-go-round.
38-year-old ex-companion of art model Dina Broadhurst, aged 48, was seen in public on Sunday with Hannah Waites, a disc jockey and business manager at the tech investment company Future Now Capital.
It seems Max’s relationship with model Simone Holtznagel, who is the elder sister of Madeline, Justin Hemmes’ child’s mother, has ended.
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Previously working as an executive assistant for the renowned Rubinstein Group in the real estate field, Hannah, famously known from Luxe Listings Sydney, was spotted walking hand-in-hand with Max, enjoying a leisurely stroll through suburban neighborhoods together.
Intriguingly, the latest high-profile pair from the eastern suburbs isn’t just any ordinary duo. Upon closer examination of Hannah’s romantic past, it turns out she has had quite a few intriguing former partners. Specifically, not one but two of her exes stand out as particularly notable.
Let’s start with the most recent one.
In November, Hannah, an alumna of Kambala, was seen cozied up on the beach with a good-looking, tattooed man named Dale. The timeline of their separation remains uncertain.
Meanwhile, it appears that as Hannah got acquainted with Max, Dale was found associating with Max’s former partner, Dina.
You couldn’t make it up!
It looks like we have a bona fide swap on our hands. But wait – there’s more.
Another of Hannah’s former flames is Highland Double Bay director David Malouf.
Readers of The Group Chat are familiar with the fact that it was David, the accomplished real estate professional, who managed the recent transaction of Max and Dina’s Darling Point apartment.
He found a buyer for the recently refurbished apartment mere hours before its scheduled auction on June 5.
David shared with us that it was sold approximately at its estimated value of $8.4 million back then, implying his former partners pocketed a substantial return on investment, as they had purchased the waterfront property for $5.2 million in 2022.
I’ll take the commission, you take my ex!
We understand there’s no bad blood, with Hannah and David’s relationship now ancient history.
Still, these people really could do with branching out.
Just the other day, I reached out to David to gauge his thoughts on the intriguing situation unfolding between Max and his former girlfriend. This comes hot on the heels of Max’s significant role in selling the latter’s apartment for a substantial sum of money. Quite an interesting turn of events, wouldn’t you agree?
He had plenty of answers (and laughs) about it – though nothing he wanted to put on the record.
It turns out that Hannah had previously been employed by the JT Allen Real Estate Agency, a company that handled the sale of Max and Dina’s apartment at Darling Point in 2022.
It appears that Hannah might not have participated in the deal since she had already departed from the agency by January, and Max and Dina completed their acquisition in April instead.
Indeed, if the intricate tapestry of romances and coincidences proved tiring to read, just imagine how taxing it must have been to weave!
For a number of years, Max was widely regarded as one of the most attractive bachelors living in the eastern suburbs. From 2018 to mid-2023, he was in a relationship with socialite Dina, who is approximately 15 years older than him.
They apparently hit it off when he bought one of her artworks.
Following the conclusion of our four-year relationship, I found myself embarking on a journey across Europe, seeking solace and healing on some opulent superyachts.
In this rephrased version, the subject “Max” has been replaced with “I” to make it a first-person account, while maintaining the original meaning and flow of the sentence.
Subsequently, he continued his relationship with the American actress Vail Bloom, who is also known for her time on Vanderpump Rules, and they were together for approximately one year.
But that relationship faltered in late 2024 when Max and Dina were pictured reuniting at the beach.
Regarding Dina’s recent love life, following her separation from Max, she began dating John Winning Jr., a wealthy scion of the refrigerator empire, around early 2024.
I was head-over-heels smitten with this guy for around eight blissful months, and then, out of nowhere, Dina showed up all alone at the grand wedding of Pilates guru Bernadette Fahey and Jordan Sukkar – a clear signal that our love story had reached its bitter end.
A couple of months back, she traveled to Paris for a passionate rendezvous with Kengi Meert, a young Belgian celebrity from Love Island, who is more than two decades younger than her.
She was seen with another ex-boyfriend, Tony Benjamin, in Bondi earlier this month.
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2025-06-25 18:09