Pip Edwards‘ relationship history reads like an almanac of the most famous men of Sydney’s eastern suburbs.
But after dating athletes, fashion designers and property developers, the P.E. Nation co-founder appears to have settled into a familiar archetype that many women will recognise: the charismatic hospitality entrepreneur.
Rumour has it her latest squeeze is Australian-born New York City bar owner and Scots College old boy Dylan Hales.
Daily Mail can reveal that Dylan, 41, has spent most of his life working in hospitality.
During his Sydney days, he worked the doors, curated events and was involved in cafés before he jetted off to pursue bigger and better things in the U.S. in 2007.
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Pip Edwards, 45, spent last weekend with Aussie bar tycoon Dylan Hales, 41, in New York
Given her track record of whirlwind romances, it remains to be seen whether Pip and Dylan will go the distance – or if this is just a fling for a New York minute
He started out in Georgetown, in Washington, D.C., but soon moved to New York to work with Lincoln Pilcher, whose mother Nancy was a long-time editor of Vogue Australia.
Lincoln, another Scots old boy, mentored Dylan, giving him a job as general manager at Ruby’s Cafe, an Aussie institution that was once the only place where you could get a decent flat white in the Big Apple.
In the following years, Dylan struck out on his own, founding a club called Baddies and starting the Randolph Hospitality Group.
His ventures proved so successful that he earned a coveted spot on restaurant guide Zagat’s ’30 Under 30′ list, recognised for excellence in the hospitality industry.
Two years later, Dylan reconnected with yet another old Scots College alum Ronnie Flynn, and developed the idea for The Flower Shop, a 1970s-inspired bar and restaurant which fast became a celebrity hotspot.
The pair set out to create a laid-back vibe – no hulking bouncers at the door, and definitely not a place you could buy your way into.
They teamed up with New York locals William Tisch and David Turner to make it happen, along with investors including pro skater Tony Hawk and fellow Sydneysider Paddy Coughlan, who was once the CEO of the now-closed Riversdale Group.
When it opened its doors in 2017, the Flower Shop quickly earned cult status among locals and celebrities alike, known for its vintage wallpaper, pink fireplace and Kama Sutra posters in the bathrooms.
From late 2024 to early 2025, Pip dated Joshua Clapp , the brains behind architecture firm Steel & Stitch, which specialises in high-end hospitality venues
Before that, she was linked to businessman Geoff Bainbridge, formerly the chief executive of ASX-listed alcohol company Lark Distilling and one of the early investors in burger chain Grill’d
Back in 2021, the streetwear designer dated Cameron Northway, co-owner of Rocker, a breezy, upscale restaurant on Campbell Parade in North Bondi
It was the first of a series of venues Dylan and Ronnie would open together in the following years, establishing them as leading Aussie figures in New York’s nightlife scene.
In 2020, they braved the hostile Covid landscape to open their second venue Little Ways, a SoHo supper club.
Intent on keeping the Australian flavour in their American ventures, Little Ways was designed by Sydney firm Akin Atelier, founded by A-list architect Kelvin Ho, known for his Merivale projects.
Two years later, Dylan and Ronnie teamed up with TAO Hospitality Group to open the subterranean nightclub Loosie’s, in Moxy Lower East Side.
It was followed by Silver Lining, a live music lounge in the same venue, which opened in October 2023 and has hosted Met Gala and fashion week after-parties.
When Dylan is not running the nightlife of New York’s Lower East Side, he spends his free time fishing, attending football games and rock concerts, and now hanging out with Pip Edwards.
The pair were most recently seen riding a motorcycle through the streets of NYC.
Dylan last appeared on Pip’s Instagram on Saturday, when she shared photos of herself on the back of his bike. Another snap showed Dylan sitting at an outdoor café table set for two.
Later on, the P.E Nation founder uploaded another picture of the two walking side-by-side in matching hats.
Dylan, a Scots College old boy, has spent most of his life working in hospitality
Dylan (pictured) founded a club called Baddies and started Randolph Hospitality Group
In 2015, Dylan opened The Flower Shop bar and restaurant with schoolmate Ronnie Flynn
Her latest relationship suggests Pip has a type when it comes to men: namely hospitality bigwigs.
From late 2024 to early 2025, she dated Joshua Clapp, the brains behind architecture firm Steel & Stitch, which specialises in high-end hospitality venues.
His designs include the trendy Mexican restaurant Chula and the 1970s Miami-inspired bar Flamingo Lounge, both in Potts Point.
Before getting together with Joshua, she was linked to high-profile businessman Geoff Bainbridge, formerly the chief executive of ASX-listed alcohol company Lark Distilling and one of the early investors in burger chain Grill’d.
And back in 2021, she dated Cameron Northway, co-owner of Rocker, a breezy, upscale restaurant on Campbell Parade in North Bondi. Northway is also a long-time friend of Pip’s ex-partner, Ksubi co-founder Dan Single.
What is it about hospo guys that keeps Pip coming back? Anyone who has watched The Bear will tell you the appeal is obvious – charisma, creativity, a touch of chaos.
But given her track record of whirlwind romances, it remains to be seen whether Pip and Dylan will go the distance – or if this is just a fling for a New York minute.
They were both contacted for comment.
