His divorce made it into the pages of the AFR - every finance bigwig's nightmare - but rumour has it Barrenjoey banker Dyson Bowditch's latest romance may be on borrowed time.
A well-placed society source tells me that Bowditch and girlfriend Chloe Hayes, a 27-year-old account director in the investor relations sector, are re-evaluating their relationship after first getting together in early 2025.
According to one version of events, Hayes and Bowditch recently ended things amicably because they 'are at different stages of their lives', which sounds entirely plausible given that Bowditch is a 46-year-old father of two.
But when I contacted Hayes on Friday, she was quick to hose down the suggestion, telling me in fierce yet oddly robotic correspondence that she continued 'to reside at my home shared with my partner and you are welcome to contact Dyson directly to verify this'.
While I'm happy to make clear that Hayes and Bowditch's relationship is intact at the time of writing, I will be keeping tabs on them given the reliability of my sources.
Of course, Bowditch's love life has already generated plenty of headlines.
His previous marriage to second wife Jessica Bowditch, a prominent socialite and former morning TV producer, officially unravelled in 2024, though not before the pair became entangled in one of Sydney's messiest society friendship breakdowns.
The former couple were once close with Tama Capital boss Tom Fennell and his late ex-fiancée Annabelle Price, who tragically died in March.
His divorce made it into the pages of the AFR - every finance bigwig's nightmare - but rumour has it Barrenjoey banker Dyson Bowditch's latest romance may be on borrowed time
Dyson and his ex-wife Jessica (pictured together), a prominent socialite and former morning TV producer, were accused of engaging in 'childish behaviour' by a Magistrate
I was first to report that Bowditch, Barrenjoey's co-head of equity markets, was dating Hayes
But by 2024, the glamorous foursome had spectacularly fallen out, with insiders saying loyalties split firmly down the middle: Jessica to Fennell, while Dyson maintained ties to Price.
Jessica had notably stood by Price years earlier during her highly publicised legal battle with ex-husband and fellow financier Fredrik 'Freddie' Blencke.
Back in 2021, Blencke faced a charge of common assault after allegedly attacking Price. He later fought the allegations in court and, that October, was cleared of assaulting his wife and breaching an AVO taken out for her protection.
Then came the Bowditches' own spectacular implosion.
During the couple's split in 2024, Jessica was alleged to have entered Dyson's bedroom during an argument over a recent purchase and struck him with a pillow, before calling the police.
However, it was Jessica who was subsequently arrested, taken to Waverley Police Station and charged with assault, while police also secured an AVO against her.
In court, Deputy Chief Magistrate Theo Tsavdaridis reportedly accused both parties of engaging in 'childish behaviour'.
Thankfully, cooler heads prevailed and the 'pillow fight' was recognised for what it was: nothing.
The Bowditches' Darling Point family home was sold in 2025
Jessica Bowditch (who recently returned to work at Network Ten) dated Texan financier Denham Schiff after splitting from her husband, but they are no longer together
Schiff (left) had previously split from his ex-wife Juliet Anderson (right) at the start of Covid
No conviction for Jessica was recorded, on the understanding she kept to a regular mental health program and complied with the AVO for two years.
As for Jessica's love life since the separation, she later fell into the arms of strapping Texan financier Denham Schiff.
Denham's own marriage had broken down at the start of Covid when his wife Juliet Anderson, a Double Bay boutique owner, left him and began dating a colleague, Rowan Rundle.
Sadly, their romance wasn't to last. They called it quits after almost a year of dating, which I exclusively reported in July last year.
Now single and living in a boutique Bellevue Hill apartment, Jessica recently returned to the workforce as a producer for Ten News.
This is a preview of the upcoming subscribers-only gossip column The Group Chat with Lucy Manly, published every Friday. Read the latest edition here.