Unveiling the Eastern Suburbs Bigwig Eyeing Young Buyer’s Agent Dating Ex-Sydney FC Chairman Scott Barlow

Unveiling the Eastern Suburbs Bigwig Eyeing Young Buyer’s Agent Dating Ex-Sydney FC Chairman Scott Barlow

When news broke in late 2024 that former Sydney FC chairman Scott Barlow had split from his Russian heiress wife Alina, it was like a bomb had dropped in the eastern suburbs.

So when Barlow was reportedly spied schmoozing with young Cohen Handler buyer’s agent Tara Brain on two separate date nights this month, the gossiping types certainly took interest.

Word is one of their dates was at Merivale‘s CBD hotspot The Press, and the other at Chris Lucas’ newly opened Grill Americano steakhouse.

‘All eyes were on the two of them,’ a source told The Daily Telegraph of one of their dates, while indicating it didn’t appear to be their first such meeting.

‘They looked extremely loved up.’

But now sources tell the Daily Mail that Barlow wasn’t the only wealthy eastern suburbs bachelor with his eye on Tara.

Former Sydney FC chairman Scott Barlow is dating Cohen Handler buyer's agent Tara Brain

Former Sydney FC chairman Scott Barlow is dating Cohen Handler buyer’s agent Tara Brain

Barlow split from his Russian heiress wife Alina in late 2024 (pictured together in May 2016)

Barlow split from his Russian heiress wife Alina in late 2024 (pictured together in May 2016)

Young-at-heart financier Tom Fennell is said to have taken interest in Tara before she was linked to funds manager Barlow.

Fennell, 52, is known for his lavish parties held at his multimillion-dollar Point Piper home, and it’s rumoured Tara was previously invited along.

Still, we can’t imagine Fennell is too heartbroken – his fabulous wealth and famous charm mean he’s rarely short of female company these days. 

The Barlows separated in November last year, after a decade of marriage.

Alina, who was previously said to be devastated over the break-up, is now believed to have moved on after she was recently spotted on a date in Double Bay.

It’s understood she is also staying in the former couple’s Queens Avenue trophy property in Vaucluse following their split.

Interestingly, one of Barlow’s date nights with Tara coincided with his ex-wife Alina’s birthday, which saw the ALINKA Fine Jewellery founder celebrate with 100 friends at new Double Bay hotspot Gran Torino. 

Barlow was the chairman of A-League club Sydney FC, which was formerly owned by Alina’s Russian businessman stepfather David Traktovenko.

Barlow wasn't the only eastern suburbs bachelor with his eye on Tara. We can reveal young-at-heart financier Tom Fennell (above, with ex-fiancée Annabelle Price) also invited her along to one of his famous parties at his Point Piper home

Barlow wasn’t the only eastern suburbs bachelor with his eye on Tara. We can reveal young-at-heart financier Tom Fennell (above, with ex-fiancée Annabelle Price) also invited her along to one of his famous parties at his Point Piper home

Fennell's insatiable lust for life is no secret. (He is seen, second from right, with a group of female friends celebrating the birthday of recruitment specialist Jacqui Paul at Bondi Icebergs)

Fennell’s insatiable lust for life is no secret. (He is seen, second from right, with a group of female friends celebrating the birthday of recruitment specialist Jacqui Paul at Bondi Icebergs)

He stepped down from the role in June after 13 years. 

Meanwhile, Fennell’s most recent confirmed romance was with glamorous single mother Annabelle Price.

Their ‘quickie engagement’ set tongues wagging in June 2023 when Fennell presented Price, who is in her thirties, with a five-carat diamond sparkler.

But just over a year after Price said yes, the pair quietly ended their engagement in August 2024 – though the split wasn’t reported until March this year.

Fennell – whose insatiable lust for life is no secret – was previously married to South African charity maven Vanessa Jacobs Fennell, who was once a shortlist candidate to appear on The Real Housewives of Sydney.

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