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Welcome to The Group Chat with Lucy Manly, where Australia's most trusted society insider shares the hottest gossip before it makes the news
Bachelorhood beckons
When I first heard that Tom Fennell was dating busty 21-year-old Mackenzie Bridgewood, I thought the legendary Sydney tomcat had finally found Mrs Right.
As it turns out, I was wrong.
I can reveal the colourful eastern suburbs financier is officially back on the market and taking his search for love online.
Fennell, the 54-year-old founder of Tama Capital, has joined dating app Hinge after his brief romance with blonde student Ms Bridgewood came to an end.
When I first heard financier Tom Fennell was dating busty 21-year-old Mackenzie Bridgewood, I thought the legendary Sydney tomcat had finally found Mrs Right. Alas, I was wrong
Ms Bridgewood was seen entering a taxi after leaving Fennell's eastern Sydney home in May
The father of two says on his verified dating profile that the hallmark of a good relationship is 'connection and trust'.
Fennell and Ms Bridgewood's romance began late last year and quickly accelerated.
The young mother was soon spending time at Fennell's famous Bellevue Hill party pad before the pair jetted off to Paris and Switzerland during December and January.
Bridgewood was later spotted aboard Fennell's boat over Easter, suggesting the relationship was still in full swing.
And in May, the lovebirds are said to have lent a livelier tone to the typically serene cocoon of first class while on an Emirates flight from Zürich to Dubai.
According to the eyewitness, a lengthy retreat to the bathroom was followed by claims that Ms Bridgewood was suffering a panic attack.
Before you jump to any conclusions, I spoke to Fennell himself at the time, who confirmed that Ms Bridgewood, whose parents both died in January, was suffering a grief-induced panic attack and was also feeling unwell.
Fennell was assisting her, which he made clear to the crew at the time. The Group Chat does not suggest otherwise.
A source claims Fennell ultimately ended things with Ms Bridgewood in June over 'commitment issues' on her part - hardly surprising given her age
He was previously engaged to late socialite Annabelle Price (right), who died in March aged 32
My source also told me that when the crew decided it was time to close the bar for first-class flyers, Fennell was allegedly among those voicing objections.
There was nothing formally noted on their travel record, I was told, though the next crew was apparently given a 'heads-up' before the Dubai-to-Sydney leg.
In an amusing postscript, I hear curiosity got the better of the on-flight staff, who looked up the couple - only to discover this very column.
But behind the five-star holidays and harbour jaunts, all was apparently not smooth sailing for the May-December couple.
A source claims Fennell ultimately ended things with Ms Bridgewood in June over 'commitment issues' on her part - hardly surprising given her age.
His latest romance inevitably attracted attention, given Ms Bridgewood's striking resemblance to his late former fiancée, socialite Annabelle Price.
Price died in March aged 32, a year after she and Fennell called off their engagement.
NSW Police said there were no suspicious circumstances surrounding her death.
Fennell's love life has never lacked drama.
He previously endured a notoriously bitter split from charity maven ex-wife Vanessa Jacobs Fennell, who made headlines last year after crashing her Range Rover into a parked Tesla before assaulting a police officer.
She later pleaded guilty to negligent driving, assaulting police, refusing a breath test and failing to provide her particulars to the owner of the damaged property.
The 55-year-old formally entered the pleas at Waverley Local Court in May last year, but is still seeking to have the matters addressed under mental health provisions.
Money meets money
His romance with socialite Emma Steel may be ancient history, but commercial property mogul and Prezzee entrepreneur Shaun Bonétt has now found himself a new companion whose bank balance is firmly in his league.
Sources tell me Bonétt, who was recently spotted basking in the glamour of the Monaco Grand Prix, has been introduced to the family of jewellery tycoon and Sydney FC co-owner Alina Barlow on the French Riviera.
It's unclear when the pair's romance began, but one thing is certain: this was no ordinary 'meet the parents' moment.
Barlow comes from serious Russian money: her mother Tonya is a former banker and her stepfather is prominent billionaire David Traktovenko.
Rich Lister Bonétt's latest romance follows a puzzling semi-retraction by a Sydney tabloid in July concerning him and heiress Barlow.
Prezzee entrepreneur Shaun Bonétt (left) has now found himself a new companion whose bank balance is firmly in his league: Sydney FC co-owner Alina Barlow (right)
Scott and Alina Barlow separated in late 2024 after more than 18 years of marriage. (They are pictured here at the Sydney FC Foundation Dinner in May 2021)
The outlet removed an image from its website, ostensibly showing Bonétt and Barlow holidaying in Saint-Tropez, because an unnamed 'friend' of Barlow - who did not respond to requests for comment before publication - alleged it was AI-generated.
Why anyone would go to the trouble of faking a holiday snap of two otherwise unattached people, absent any hint of scandal, is unclear.
What I can say is that 'take it down, it's AI' is fast becoming a go-to line for people keen to keep their private lives out of the press - and with the technology now capable of producing remarkably convincing images, it can be difficult for editors to prove otherwise.
Barlow and her ex-husband, former Sydney FC chairman Scott Barlow, separated in late 2024 after more than 18 years of marriage.
The couple had spent months denying rumours about the state of their relationship, at one point even laughing off suggestions their marriage was on the rocks.
But Scott, the managing director of property funds management company STRADA Group, has wasted little time returning to the dating scene since his split.
Bonétt previously dated 'femme fatale' socialite Emma Steel, who is now back in the saddle... horse riding, that is
After being spotted around CBD hotspots last November with glamorous buyer's agent Tara Brain, sources say he's now seeing someone new.
I'm told he was spotted last Saturday at Merivale cocktail joint Charlie Parker's with another striking woman on his arm.
Meanwhile, Bonétt's ex Emma Steel, whose acrimonious split from neurosurgeon Dr Timothy Steel in 2020 earned her a reputation as a 'femme fatale', is back in the saddle... horse riding, that is.
As for whom she'll be riding alongside next, only time will tell.
Trouble finds Tom
The drama in the sporting Fairfax family - not to be confused with the publishing dynasty - has taken another turn after I first broke the story in June.
Tom Fairfax is now facing a different kind of legal headache, just two months after police obtained an AVO to protect his father, former rugby star Russell Fairfax.
The 30-year-old, whose sister is Sydney 'It' girl Nadia Fairfax-Wayne, has landed in hot water again, this time over an alleged offence of possessing a prohibited drug.
Tom Fairfax is seen on the right at his influencer sister Nadia's 2021 wedding to Michael Wayne
Nadia Fairfax-Wayne is seen with her father, former dual-code footballer Russell Fairfax. Police have taken out an AVO to protect him from Thomas Fairfax. Nadia is not involved
The latest charge adds another layer to a troubled period for the family, with Tom already facing allegations of destroying or damaging property and common assault.
Police secured an AVO for Russell in March after an alleged incident involving his son.
According to court documents, between March 1 and March 4, Tom allegedly recklessly destroyed property, including a glass window and a lounge, at his father's Little Bay home.
It was not the first time authorities had stepped in, with officers previously obtaining AVOs to protect the former Sydney Roosters great in 2024.
The Fairfax name is hardly unfamiliar to Sydney's social set.
Russell is a former rugby union and rugby league player, while daughter Nadia rose to prominence as one of Sydney's original fashion influencers before marrying financier Michael Wayne.
Her brother, by contrast, has largely stayed out of the spotlight - until now.
Tom was listed to front Waverley Court on Wednesday in relation to the drug possession charge, but is now scheduled to appear next week.
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