Financier Tom Fennell has reportedly rejoined the dating app Hinge following the end of his relationship with 21-year-old Mackenzie Bridgewood. Fennell, 54, founder of Tama Capital, met Bridgewood late last year, and their relationship quickly progressed. Bridgewood, a mother of one whose parents both died in January, spent time at Fennell's Bellevue Hill residence before they traveled to Paris and Switzerland in December and January.
Turbulent Flight and Relationship End
In May, the couple was reportedly on an Emirates flight from Zurich to Dubai. Eyewitnesses told the publication that Bridgewood claimed to be suffering a panic attack after a lengthy period in the aircraft's bathroom. Fennell stated that Bridgewood was experiencing grief-induced panic and feeling unwell, and he was assisting her. A source indicated that Fennell ended the relationship in June due to Bridgewood's perceived commitment issues, which the source attributed to her age.
Fennell was previously engaged to socialite Annabelle Price, who died in March at age 32. NSW Police stated there were no suspicious circumstances surrounding her death. Fennell's past relationships have also drawn public attention, including a contentious split from his ex-wife, Vanessa Jacobs Fennell, who faced legal issues after a car crash and assaulting a police officer.
New Romance for Tech Entrepreneur
Meanwhile, commercial property mogul and Prezzee entrepreneur Shaun Bonétt has reportedly been introduced to the family of jewellery tycoon and Sydney FC co-owner Alina Barlow. Bonétt was recently seen at the Monaco Grand Prix. Barlow's mother, Tonya, is a former banker, and her stepfather is billionaire David Traktovenko.
A Sydney tabloid reportedly removed an image that appeared to show Bonétt and Barlow holidaying in Saint-Tropez, after an unnamed friend of Barlow claimed the image was AI-generated. Barlow and her ex-husband, former Sydney FC chairman Scott Barlow, separated in late 2024 after more than 18 years of marriage. Scott Barlow has reportedly been seen with a new companion.
Legal Troubles for Tom Fairfax
Separately, Tom Fairfax is facing a new legal charge of possessing a prohibited drug. This development follows an earlier incident in which police obtained an apprehended violence order (AVO) to protect his father, former rugby star Russell Fairfax. Fairfax is also facing allegations of destroying property and common assault. Court documents indicate that between March 1 and March 4, Fairfax allegedly destroyed property, including a glass window and a lounge, at his father's home. AVOs had previously been obtained to protect Russell Fairfax in 2024.
Russell Fairfax is a former rugby union and rugby league player. His daughter, Nadia Fairfax-Wayne, is a prominent Sydney influencer who married financier Michael Wayne. Tom Fairfax has largely remained out of the public eye until recent events. He was scheduled to appear in Waverley Court on Wednesday regarding the drug possession charge but is now set to appear next week.