Pip Edwards' New Love Interest Echoes a Familiar Pattern

Pip Edwards, 45, was seen in New York last weekend with Dylan Hales, 41, an Australian-born bar owner who operates several nightlife ventures in the city. The sighting underscores a continuing pattern in Edwards's personal life, where a particular type of partner—charismatic hospitality entrepreneurs—keeps returning.

Edwards, the co-founder of P.E. Nation, has long dated figures connected to Sydney's high-profile social and business circles. Her dating history reads like an almanac of the eastern suburbs' most famous names, spanning athletes, fashion designers and property developers. The latest pairing with Hales aligns with a trend of hospitality-power men in her orbit.

Dylan Hales grew up in Australia and built a career in hospitality in both Australia and the United States. He started in Georgetown, in the Washington, D.C., area, before moving to New York in 2007 to work with Lincoln Pilcher, whose mother Nancy was a longtime Vogue Australia editor. Pilcher mentored him and gave him a job as general manager at Ruby's Cafe, an Australian institution in the Big Apple known for its flat white.

Two years later, Hales founded a club called Baddies and started the Randolph Hospitality Group. His ventures earned him a place on Zagat's '30 Under 30' list, recognized for hospitality excellence. Two years after that, he reconnected with Scots College alum Ronnie Flynn and developed The Flower Shop, a 1970s-inspired bar and restaurant that quickly became a celebrity hotspot. 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 Paddy Coughlan, the former Riversdale Group CEO, to launch the venue.

When The Flower Shop opened in 2017, its vintage wallpaper, pink fireplace and Kama Sutra posters in the bathrooms helped it cultivate a cult following among locals and visiting stars alike.

From late 2024 to early 2025, Edwards was linked to Joshua Clapp, founder of Steel & Stitch, a firm that specializes in high-end hospitality venues. Clapp's designs include Chula, a trendy Mexican restaurant, and Flamingo Lounge in Potts Point. Prior to Clapp, Edwards was linked to Geoff Bainbridge, the former chief executive of ASX-listed Lark Distilling and an early investor in Grill'd. 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 Edwards's ex-partner, Dan Single, co-founder of Ksubi.

What connects Pip Edwards to this cohort, observers say, is a blend of charisma, creativity and a certain appetite for nightlife chaos. The Bear may have nudged that image into cultural shorthand, but the appeal, for Edwards, appears to lie in partnerships with people who run immersive hospitality ventures rather than traditional fashion or media circles. Whether this latest romance will endure remains unclear, especially given Edwards's history of whirlwind relationships.

They were both contacted for comment.