Dina Broadhurst marks 50th with three-day Sydney birthday bash, Icebergs lunch and rave-cave after-party

Dina Broadhurst celebrated her 50th birthday with a three-day celebration in Sydney's eastern suburbs, capped by a lavish long lunch at Bondi Icebergs last Friday. After the lunch, she and guests returned to the home of her on‑again, off‑again boyfriend, John 'Herman' Winning Jr., for an after‑party described by attendees as a 'rave cave'.

The lunch was described by guests as a standout event, with Dina arriving in a skimpy black crop top paired with a $2,600 Miu Miu elasticated‑waist mini skirt, a navy blazer, sunglasses and white stilettos. She carried a pink Chanel 19 Flap Bag — a gift from Herman that can retail for up to $12,500 — and a smaller white Chanel clutch.

Herman Winning Jr. is the CEO of Winning Appliances, a family firm he took charge of in 2011. The couple’s romance has been characterized as on‑again, off‑again since they first linked in early 2024, with a split around the Scots College wedding at the end of that year. They began publicly reuniting in 2024, and Dina confirmed the renewed relationship in an interview with News Corp's Stellar magazine. An insider described Herman as “head over heels” for her and noted gestures such as the pink bag she carried at Icebergs.

During their time apart, Dina pursued other experiences, including a Paris escape in March with 23-year-old model Kengi Meert, a former Love Island Belgium star. She was also seen in Bondi in June with ex‑boyfriend Tony Benjamin. The timeline also tracks a series of public sightings and reunions that culminated in the latest celebration. Herman's family fortune is estimated at about $700 million, and Winning Appliances remains a powerhouse in the kitchen and laundry appliance sector, founded in 1906 by Herman's great‑grandfather Richard William Winning.