Sydney Real Estate Love Twist: Developer Caught with Agent’s Ex After $8.4M Sale, Plus Surprise Couple Swap

There’s a saying about people in the eastern suburbs: they won’t date anyone west of Edgecliff Station.

Yes, those coastal elites are an incestuous bunch, with the beachside enclaves full of recycled flings, overlapping love triangles and exes playing musical chairs.

Now, property developer Max Shepherd is the latest to hop on the merry-go-round.

The 30-something former toyboy of ‘nude artist’ Dina Broadhurst, 48, was spotted out and about on Sunday with Hannah Waites, a DJ and executive business manager at technology investment management firm Future Now Capital.

Last we heard, Max was dating model Simone Holtznagel, the older sister of Justin Hemmes‘ baby mama Madeline, but it looks like the wheels came off that romance.

From A-list scandals and red carpet mishaps to exclusive pictures and viral moments, subscribe to the DailyMail’s new showbiz newsletter to stay in the loop.

Property developer Max Shepherd was spotted on Sunday with Hannah Waites, a DJ and executive business manager at technology investment management firm Future Now Capital

Hannah, a former executive assistant for The Rubinstein Group, was seen cuddling up to Max and holding his hand as the pair went for a stroll through the ‘burbs 

Hannah, who used to be in the real estate game as an executive assistant for The Rubinstein Group made famous by Luxe Listings Sydney, was seen cuddling up to Max and holding his hand as the pair went for a stroll through the ‘burbs.

A new eastern suburbs glamour couple – big deal, right? Well, it gets interesting when you take a deep dive into Hannah’s dating history and find not one, but two rather interesting exes.

Let’s start with the most recent one.

Back in November, Hannah, a Kambala old girl, was spotted cuddling up on the beach with a handsome, tatted-up fella by the name of Dale. It’s unclear when they split. 

However, our society spies tell us that around the time Hannah began seeing Max, Dale was spending time with (drumroll, please)… Max’s ex, 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.

Last we heard, Max was dating model Simone Holtznagel, the older sister of Justin Hemmes’ baby mama Madeline, but it looks like the wheels came off that romance 

A new eastern suburbs glamour couple – big deal, right? Well, it gets interesting when you take a deep dive into Hannah’s dating history and find not one, but two rather interesting exes 

They were every inch the matching pair in their black athleisure wear and monochrome caps

As readers of The Group Chat will know, David is the hotshot real estate agent who handled the recent sale of Max and Dina’s Darling Point apartment.

He secured a buyer for the newly renovated unit just hours before it was set to go under the hammer on June 5.

David told us at the time it had sold ‘for around the price guide’ of $8.4million, meaning the friendly exes made a tidy profit, having bought the harbourside property for $5.2million 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.

Back in November, Hannah, a Kambala old girl, was spotted cuddling up on the beach with a handsome, tatted-up fella by the name of Dale

It’s unclear when Hannah and Dale (pictured together at the beach) split up

However, our society spies tell us that around the time Hannah began seeing Max, Dale was spending time with (drumroll, please)… Max’s ex, Dina Broadhurst – pictured here on Sunday

Another of Hannah’s old flames is Highland Double Bay director David Malouf (seen together)

In a bizarre twist, David is the same hotshot real estate agent who handled the recent sale of Max and Dina’s (pictured together) $8.4million Darling Point apartment. Fancy that!

Earlier this week, we called David to ask what he thought of Max being seen with his ex-girlfriend only weeks after he helped sell the guy’s apartment for a small fortune.

He had plenty of answers (and laughs) about it – though nothing he wanted to put on the record.

In yet another coincidence, Hannah once worked for real estate company JT Allen Agency, which facilitated the purchase of Max and Dina’s Darling Point pad in 2022.

Hannah seems to have left the agency in January that year, while Max and Dina finalised their purchase a few months later in April, so she may not have been involved in the transaction.

Now, if that tangled web of romances and coincidences was exhausting to read, imagine what it was like to write!

David secured a buyer for the unit hours before it was set to go under the hammer on June 5

In yet another coincidence, Hannah once worked for real estate company JT Allen Agency, which facilitated the purchase of Max and Dina’s Darling Point pad in 2022 

Hannah is now out of the real estate game and works as the executive business manager for Future Now Capital, a specialised technology investment manager

Long seen as one of the eastern suburbs’ most eligible suitors, Max dated socialite Dina – who is about 15 years his senior – from 2018 until mid-2023.

They apparently hit it off when he bought one of her artworks.

After they ended their four-year romance, Max jetted off to Europe to nurse his broken heart on several luxury superyachts.

He later moved on with American actress and former Vanderpump Rules star Vail Bloom, and they dated for about a year.

But that relationship faltered in late 2024 when Max and Dina were pictured reuniting at the beach.

As for Dina’s recent dating history, after splitting from Max, she hooked up with multimillionaire refrigerator heir John Winning Jr. at the start of 2024 

Dina was also spotted out and about on Sunday, enjoying brunch in Double Bay with friends while elsewhere Max cuddled up with Hannah

Despite the winter weather, she couldn’t resist putting on a leggy display in a beige skirt

As for Dina’s recent dating history, after splitting from Max, she hooked up with multimillionaire refrigerator heir John Winning Jr. at the start of 2024.

They dated for about eight months before Dina announced the end of their romance by rocking up solo to Pilates queen Bernadette Fahey‘s wedding to Jordan Sukkar.

A few months ago, she jetted to Paris for a steamy hook-up with Belgian toyboy Kengi Meert, a former Love Island star who, at 23, is less than half her age.

She was seen with another ex-boyfriend, Tony Benjamin, in Bondi earlier this month.