Jackie O’s ciggie summit: New boyfriends, buried rifts – and why insiders at Pip Edwards’ party are convinced of her next move as she takes KIIS FM to court for $82million

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Pip Edwards celebrated her 46th birthday with a lot of Sydney’s most prominent socialites. However, it was the arrival of radio personality Jackie ‘O’ Henderson, not her new boyfriend, that really got people buzzing.

P.E Nation co-founder Pip Edwards, recently known for her work with the menopause supplement brand Biolae, celebrated her birthday on Sunday with a party at her favorite restaurant, Icebergs Dining Room and Bar.

Seeing Henderson with the radio star publicly for the first time in months fueled rumors that their close friendship had become strained during a difficult time in the star’s career.

After Henderson’s very public legal dispute with ARN, stemming from a falling-out with her former KIIS FM colleague Kyle Sandilands, rumors began circulating that she and Sandilands were no longer close.

Rumors really intensified earlier this month when Henderson didn’t attend Edwards’ event for Biolae.

Guests noticed someone was missing from the party, but the designer quickly addressed the gossip, telling the Mail that despite not being seen together much recently, they were still friends.

Okay, so everyone at the party definitely saw it too. I mean, I’ve been saying it for ages, but this weekend just confirmed everything! They were practically glued together, and honestly, it was amazing to witness. Any little doubt I had? Gone. Completely and utterly gone. They’re definitely a thing, and I knew it!

Edwards’ party attracted many of Sydney’s leading social figures, such as MCoBeauty’s founder, Shelley Sullivan, and DJ Milly Gattegno from The Faders.

Her new boyfriend, Nicholas Nogarotto, who leads the business consultancy Freshwater Strategy, was also seen in the audience.

Notably missing was Gemma O’Neill, Henderson’s manager, who has been a key figure in his legal case against ARN.

Although people at the party wouldn’t discuss what Henderson said about her legal issues, her attendance at the event – which was full of successful women entrepreneurs over the age of 40 – definitely turned heads.

According to a source familiar with the situation, people treated her with respect and didn’t aggressively question her about the case.

Seeing her there was fascinating, and it felt like a preview of her future.

According to a source, Henderson—already familiar with business through projects like Besties—is considering a career as an entrepreneur.

‘There’s a sense she’s thinking beyond radio,’ the insider continued. 

Spending time with successful women like Pip and Shelley could give her a lot of motivation. Once she’s finished with her legal issues, she might start her own business and really take off.

The photos capture Edwards arriving at the event location, looking stylish in a sparkly brown midi dress, a long grey coat, and high platform shoes.

She completed her look with trendy sunglasses and a burgundy velvet clutch bag. 

Henderson, looking noticeably thin, was smartly dressed in a beige linen vest and loose-fitting trousers.

She styled her blonde hair in big, flowing waves and completed her look with bold gold earrings, black pointed heels, and a woven gold bag.

After the party, a small group of guests continued to Sullivan’s house—a rented mansion in Point Piper—and took a group photo on the large balcony overlooking the water.

Henderson and Edwards became close friends in late 2024 after sharing photos and updates from their trip to Fiji on social media.

After that, they became inseparable and were often seen together around Sydney’s eastern suburbs.

Edwards reportedly provided encouragement to Henderson as she released her memoir and continued her path to recovery.

It’s unclear how involved Edwards will be in her friend’s current legal battle with her old company.

A legal battle continues in Federal Court, with Henderson suing ARN Media over the end of her estimated $100 million contract. This follows the breakdown of her popular radio duo partnership with Kyle Sandilands.

As a longtime listener of the Kyle and Jackie O Show, I’ve been following the drama closely, and it’s now coming out through court filings that things were really rocky behind the scenes for months before everything fell apart earlier this year. The documents detail a lot of internal struggles that led to the show’s breakdown – it wasn’t as sudden as it seemed!

Documents show Henderson voiced worries to KIIS network managers about Sandilands’ conduct on the radio months before their public falling-out during a live show in February.

According to the documents, Henderson started discussing ‘demeaning remarks’ made on the radio with KIIS executives around the middle of 2025.

The claim references a broadcast from August where Kyle Sandilands discussed Henderson’s private life and used language she considered offensive, causing her to temporarily leave the studio.

Court documents reveal text messages from September where Henderson told KIIS executives she was unhappy with how she was being treated and worried that listeners felt the on-air interactions were becoming abusive.

The tension between the two hosts reached its peak in February during their last show together. Sandilands publicly criticized Henderson’s passions and implied she was difficult to work with, which reportedly upset her so much she left the studio in tears.

According to the claim, ARN did not intervene during the segment.

The next day, Henderson reached out to ARN’s leaders, explaining that Sandilands’ behavior was unfair, inappropriate, and came without any reason. He also asked what measures would be taken to prevent similar issues in the future.

On February 26th, her legal team sent a formal letter to ARN’s Commonwealth Broadcasting Corporation claiming she was being bullied and couldn’t continue working with Kyle Sandilands. However, they indicated she would be open to staying with the network in a different position.

ARN claimed the letter meant her contract was cancelled, but Henderson disagrees with that interpretation.

She claims the broadcaster acted dishonestly and violated employment laws. She’s asking for at least $82.25 million in damages, along with additional penalties, interest, and legal fees.

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2026-04-28 05:51