Property Scene SHOCKED by Real Estate Love Swap That No One Saw Coming

PHOTO: So Who’s Dating Who Now? Hannah Waites, former executive assistant at The Rubinstein Group and now a rising corporate star. Asad Photo Maldives.

🏠💋 When Real Estate Gets Personal

The exclusive enclaves of Sydney’s eastern suburbs are known for their sky-high property prices—but now, it’s the tangled web of romantic crossovers causing the real drama.

Property developer Max Shepherd, best known for his luxe listings and relationships with Sydney’s elite, was recently seen hand-in-hand with Hannah Waites, former executive assistant at The Rubinstein Group and now a rising corporate star.

If the name rings a bell, it should. Hannah is the ex of David Malouf, the same agent who just sold Max’s $8.4 million Darling Point pad. Let that sink in.

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!

🔁 Love Triangle—or Full Love Square?

Let’s break this down:

Max used to date Dina Broadhurst, 48-year-old socialite and artist.
Max’s $8.4m apartment was recently sold by David Malouf of Highland Double Bay.
David also happens to be the ex-boyfriend of Hannah, Max’s current flame.
Meanwhile, Dina has now been linked to Dale, who was dating—wait for it—Hannah.

💥 That’s two romantic swaps in one social circle. You couldn’t script it better.

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

👀 So Who’s Dating Who Now?

Here’s the current status—at least as far as Sunday’s paparazzi shots show:

Max and Hannah were spotted looking cozy and coordinated in black athleisure wear.
Dina was seen brunching in Double Bay with friends on the same day.
Dale, Hannah’s previous beau, has reportedly been seen spending time with Dina.
David Malouf, who sealed Max and Dina’s recent $8.4m deal, reportedly laughed off the new pairing—politely declining to comment on the record.

This goes beyond romantic chaos. It’s a full-circle real estate soap opera.

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

🛏️ The House Where It All Began

The Darling Point apartment that started it all?

Purchased in 2022 for $5.2 million by Max and Dina.
Recently renovated and prepped for auction.
Sold hours before hammer time by David Malouf for around the $8.4 million guide.
And now? The seller and agent are dating each other’s exes.

This isn’t just a case of “I’ll take the commission, you take my ex”—it’s a new version of Monopoly.

💃 Past Flings, Paris Affairs & Pilates Weddings

This is far from Max’s first high-profile relationship. Let’s rewind:

After splitting from Dina, Max had a Euro-luxury rebound with American actress Vail Bloom.
Then he dated model Simone Holtznagel, sister of Madeline Holtznagel (Justin Hemmes’ partner).
Dina, meanwhile, briefly dated John Winning Jr., heir to the Winning Appliances empire.
She’s also been linked to Belgian Love Island star Kengi Meert, 23.
Her exes include Tony Benjamin—last spotted together in Bondi.

Who needs reality TV when Sydney’s social set keeps the drama this spicy?

🧠 Did We Mention the Work Connection Too?

Adding another layer: Hannah previously worked at JT Allen Agency—the firm that facilitated Max and Dina’s 2022 property purchase. While she reportedly left a few months prior, the crossover is uncanny.