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Eyebrow-raising new romance for Montarna McDonald’s ex – one detail has Sydney society hooked. Plus, a dramatic twist in Chief Justice’s love life and the North Shore is rocked by a bitter divorce: THE GROUP CHAT

Welcome to The Group Chat with Lucy Manly, where Australia’s most trusted society insider shares the hottest gossip before it makes the news.

It’s a small world in the east…

The lawyer ex-husband of Sydney socialite Montarna McDonald has debuted his new girlfriend – and there’s one rather awkward detail that hasn’t gone unnoticed.

Nick Pitt‘s leading lady shares the same last name as his ex-wife. Yes, really.

His latest squeeze is Ashleigh McDonald, the founder and CEO of exclusive advisory and membership collective 42 Private.

And because this is Sydney high society – where somehow everyone is connected by marriage, money or mutual friends – there’s an even more eyebrow-raising twist.

Nick Pitt’s new flame Ashleigh McDonald shares the same surname as his ex-wife Montarna

McDonald is the younger sister of Amber Keating, formerly Mrs Aussie John Symond

The Pitts split in late 2024 but were rumoured to have tried couples therapy last year

Ashleigh (left) is the younger sister of Amber Keating, formerly Mrs Aussie John Symond. The Pitts (right) split in late 2024 but were rumoured to have tried couples therapy last year

Publicity powerhouse Montarna (left), founder of The Audience Agency, is pictured with Pilates instructor Bernadette Fahey (right), arriving at Mimi's in Coogee in September last year

Publicity powerhouse Montarna (left), founder of The Audience Agency, is pictured with Pilates instructor Bernadette Fahey (right), arriving at Mimi’s in Coogee in September last year

Ashleigh is the younger sister of Amber Symond… who was the stepmother of one of Montarna’s closest friends, Deborah Symond O’Neil… when Amber was married to Deb’s father, ‘Aussie John’ Symond, from 2016 to 2023.

Following that separation, Amber reverted to the surname of her ex-husband, Patrick Keating, the father of her two children and son of former prime minister Paul Keating.

Did you get all that? My head hurt writing it. But back to the former Pitts… 

Nick and Montarna, who share two daughters, quietly called time on their marriage in late 2024.

Montarna later made headlines by throwing a ‘divorce party’ on the eve of what would have been their six-year wedding anniversary, which was attended by several big names in the eastern suburbs, including Caroline Tran and heiress Louise O’Neil.

Insiders say the former couple attended therapy last year in a last-ditch attempt to repair the relationship, but ultimately decided they were better off focusing on co-parenting than rekindling their romance.

Soirée to sunrise 

It was the sort of soirée Sydney’s eastern suburbs does best – a no-expense-spared affair with free-flowing champagne and a glittering guest list. By Sunday morning, there were no doubt more than a few sore heads after Poppy Tzaneros (née O’Neil) celebrated her 40th in lavish style.

By Sunday morning, there were no doubt more than a few sore heads after Poppy Tzaneros (left) celebrated her 40th birthday in lavish style

By Sunday morning, there were no doubt more than a few sore heads after Poppy Tzaneros (left) celebrated her 40th birthday in lavish style

Sisters-in-law Deborah Symond O'Neil, Lou O'Neil and Poppy Tzaneros are pictured

Sisters-in-law Deborah Symond O’Neil, Lou O’Neil and Poppy Tzaneros are pictured

Condom heir Michael Porter is seen alongside birthday girl Poppy and Gigi Penna (right)

Condom heir Michael Porter is seen alongside birthday girl Poppy and Gigi Penna (right)

The birthday belle is the only sister of eastern suburbs brothers Ned, Jake and Toby O’Neil, – who together run property development company Addenbrooke, whose projects include residential, commercial, hotel and marina developments – and is married to Anthony Tzaneros, the son of freight magnate Terry Tzaneros.

It’s an impressive pedigree, I’m sure you’d agree. 

Her in-laws are no less well-heeled: Anthony’s sisters include socialite Barbara Coombes, wife of property heavyweight Michael Coombes, and Maree Andrews, married to Peter Andrews, chief executive of Haverick Meats. There’s also the estranged sister, Natasha Abrams, wife of nightclub impresario Adam Abrams.

Among the guests were condom heir Michael Porter and his husband Billy Mitchell, along with Lou O’Neil and Sydney socialite Montarna McDonald.

Chambers Cellars heir Joshua Chambers and his wife Catherine may have enjoyed festivities a little too enthusiastically, as Merivale staff reportedly asked him to make an early exit from Charlie Parker’s, the dimly lit bar beneath Fred’s on Oxford Street in Paddington.

If whispers from the night are to be believed, the party was as lively as expected from such esteemed company. At least two notable guests reportedly didn’t make it home until 9am – and that’s just the ones I’ve heard about.

North Shore divorce

Sad news from the North Shore society set: Charlie Graham and his wife Wallis ‘Wally’ Graham are said to be in the midst of an acrimonious divorce.

Friends close to the pair have been left stunned by the split, describing them as ‘two of the nicest people you will ever meet’.

The news comes just two years after the Grahams celebrated their joint 50th birthday with a three-day extravaganza in Aspen, Colorado, featuring a string of themed events that gave every impression their marriage was firmly on track.

Among the well-heeled guests were Barbara and Michael Coombes, Maree and Peter Andrews, and Harriet and Mitchell Waugh.

North Shore couple Wally and Charlie Graham are rumoured to have split

Charlie Graham is the son of Gresham Partners managing director James Graham

North Shore couple Wally and Charlie Graham are rumoured to have split

Wally, who works in private equity, attended Ivy League Dartmouth College in Hanover, New Hampshire, while Charlie is the son of Gresham Partners managing director James Graham.

The former couple tied the knot in New York in 2003 after being introduced by mutual friends in Boston – making the reported breakdown of their 23-year marriage all the more surprising to those in their tight-knit circle.

It remains unclear what will happen to the waterfront Mosman home they snapped up in 2008 for $8.5million. Of course, it would be worth double that now.

Legal lovers split talk 

If Melbourne’s legal circles thought Chief Justice Will Alstergren‘s romance reveal had settled the chatter once and for all, they may be in for another surprise.

Barely had whispers about Justice Alstergren and fellow judge Amanda Mansini begun ricocheting around chambers before a fresh rumour started doing the rounds.

I hear that, after all the fanfare of disclosing the relationship internally, Alstergren and Mansini have quietly parted ways. Say it isn’t so!

Back in February, Chief Justice Will Alstergren emailed his fellow judges to formally confirm his romance with Justice Mansini following his marital separation. (Pictured together)

Back in February, Chief Justice Will Alstergren emailed his fellow judges to formally confirm his romance with Justice Mansini following his marital separation. (Pictured together)

A new rumour - which I have not yet been able to confirm - is that Alstergren may be finding his way back to his estranged wife, Kate. (The former couple is pictured together)

A new rumour – which I have not yet been able to confirm – is that Alstergren may be finding his way back to his estranged wife, Kate. (The former couple is pictured together)

While that was relayed to me by a reliable source, another rumour – which I have not yet been able to confirm, but which would be delicious if true – is that Alstergren may be finding his way back to his estranged wife, Kate.

‘He’d be mad not to be trying,’ said a spy.

Back in February, the Federal Court boss emailed his fellow judges to formally confirm the romance with Justice Mansini following his marital separation.

He did so after questions began swirling following a society soirée at the National Gallery of Victoria.

A court spokeswoman said at the time: ‘Chief Justice Alstergren confirms that he separated from his wife almost six months ago and is in a consensual relationship with another judge.’

While it initially appeared to be a straightforward case of a middle-aged man separating from his wife and moving on, sources in the legal fraternity’s ever-reliable grapevine suggest enduring ties between Alstergren and Kate – and a belief that, despite his relationship with Mansini becoming public, the former couple could yet reconcile.

In happier times, the Alstergrens spent years cultivating a public image as the glamorous custodians of Satellite Island, their windswept private Tasmanian retreat once showcased across the glossy pages of Vogue Living and House & Garden.

If ever there were a place for a discreet reset away from the whispers of Melbourne chambers, one can imagine the secluded island sanctuary would fit the bill rather nicely.

Whether this latest round of murmurs is wishful thinking from mutual friends or something more substantial remains to be seen.

The Group Chat has contacted the Federal Court for comment.

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