Pip Edwards ushered in her 46th birthday surrounded by the cream of Sydney’s social crop – but it was the arrival of star guest Jackie ‘O’ Henderson, rather than the appearance of her new boyfriend, that had the gossips talking.

The P.E Nation co-founder, who has been making headlines of late for her work with menopause supplement brand Biolae, celebrated her big day on Sunday with a party at her favourite high-class haunt, Icebergs Dining Room and Bar.

Henderson’s appearance marked the first time the pair have been publicly spotted together in months, after whispers that their once-tight friendship had cooled during a turbulent period in the radio star’s professional life.

As Henderson became embroiled in her high-profile legal battle with ARN following her catastrophic falling-out with former KIIS FM co-host Kyle Sandilands, there were whispers the longtime friends had drifted apart.

Earlier this month, those rumours reached fever pitch when Henderson was a notable no-show at Edwards’ event promoting Biolae.

Partygoers were quick to raise eyebrows at the absence, but the designer swiftly shut down the chatter, insisting to the Mail that despite their sparse public appearances lately, their friendship remained intact.

Pip Edwards (left) ushered in her 46th birthday surrounded by the cream of Sydney’s social crop – but it was the appearance of bestie Jackie ‘O’ Henderson (right) that had gossips talking

The P.E Nation co-founder celebrated her big day on Sunday with a party at her favourite high-class haunt, Icebergs Dining Room and Bar

It’s the first time the pair have been publicly spotted together in months, after whispers their once-tight friendship had cooled during a turbulent period in Henderson’s professional life

Any lingering doubt appeared to be put to rest at the birthday gathering this weekend, where onlookers say the pair looked closer than ever.

Edwards’ guest list was, as always, studded with some of Sydney’s most influential socialites, including MCoBeauty founder Shelley Sullivan and The Faders DJ Milly Gattegno.

Her new boyfriend Nicholas Nogarotto, director of the business consultancy firm Freshwater Strategy, was also spotted in the crowd.

Seemingly absent, however, was Henderson’s manager Gemma O’Neill, who has been playing a central role in the star’s ongoing civil proceedings against ARN.

While guests remained tight-lipped about what Henderson said – or didn’t say – at the party regarding her court case, her presence at an event packed with influential, over-40 female founders did not go unnoticed.

‘Everyone was very respectful – there was no grilling her about the case,’ one well-placed insider said.

‘But it was interesting to see her in that environment. It felt like a glimpse of what could come next.’

The source added that Henderson, who has already dipped her toe into the business world with ventures like Besties, may have her eyes on becoming an entrepreneur.

As Henderson became embroiled in her high-profile legal battle with ARN following her falling-out with former co-host Kyle Sandilands, there were whispers the friends had drifted apart

Earlier this month, rift rumours reached fever pitch when Henderson was a no-show at Edwards’ event promoting Biolae. (Guests Milly Gattegno and Georgia Gorman are pictured arriving with Edwards on Sunday)

Partygoers raised eyebrows at the absence, but Edwards shut down the chatter, insisting to the Mail that despite their sparse public appearances lately, their friendship remained intact

Edwards’ new boyfriend Nicholas Nogarotto (right) arrived in style

Edwards’ guest list was, as always, studded with some of Sydney’s most influential socialites, including MCoBeauty founder Shelley Sullivan (pictured) and The Faders DJ Milly Gattegno

Edwards’ new boyfriend Nicholas Nogarotto (left), director of the business consultancy firm Freshwater Strategy, was also spotted in the crowd

Seemingly absent from the evening, however, was Henderson’s manager Gemma O’Neill, who has been playing a central role in the star’s ongoing civil proceedings against ARN

Sullivan showed off her slimmed-down frame in a mauve turtleneck skivvy and pink mini skirt

While guests remained tight-lipped about what Henderson said at the party about her case, her presence at an event packed with influential, over-40 female founders did not go unnoticed

‘Everyone was very respectful – there was no grilling her,’ one well-placed insider said

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

‘Being around women like Pip and Shelley, who’ve built serious brands, could be really inspiring. Once the legal situation is behind her, don’t be surprised if she makes a bigger move into business on her own.’

Our photos show Edwards arriving at the waterfront venue, dressed to the nines in a shimmery brown midi dress paired with a long grey coat and platform heels.

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

Meanwhile, a very slim Henderson looked stylish in a beige linen waistcoat top and matching loose trousers.

Wearing her blonde hair in voluminous waves, the former breakfast host accessorised with gold statement earrings, black pointy-toe pumps and a woven gold handbag.

Following the party, a select group of guests went back to Sullivan’s rented Point Piper mansion, posing for a group photo on the expansive waterfront balcony.

Henderson and Edwards’ close friendship began in late 2024, when the pair began sharing glimpses of their getaway to Fiji on social media.

‘It felt like a glimpse of what could come next,’ a source said of Henderson

Some wonder whether Henderson, who has already dipped her toe into the business world with ventures like Besties and My Best Life, may have her eyes on becoming an entrepreneur

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

‘Being around women like Pip and Shelley, who’ve built serious brands, could be really inspiring. Once the legal situation is behind her, don’t be surprised if she makes a bigger move into business on her own’

Our exclusive photos show Pip arriving at the waterfront venue, dressed to the nines in a shimmery brown midi dress paired with a long grey coat and platform heels

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

Henderson looked stylish in a beige linen waistcoat top and matching loose trousers

From then on, the pair were attached at the hip, frequently stepping out together in Sydney’s eastern suburbs.

Edwards was also said to be a source of support for Henderson during the rollout of her memoir and her sobriety journey.

As for how present Edwards will be during her friend’s ongoing legal matter with her former employer remains to be seen.

Henderson remains at the centre of a high-stakes Federal Court case against ARN Media over the termination of her reported $100 million contract, following the collapse of her long-running radio partnership with Sandilands.

Court documents, filed as part of Henderson’s statement of claim, outline months of internal tension leading up to the dramatic breakdown of the Kyle and Jackie O Show earlier this year.

According to the filings, Henderson raised concerns about Sandilands’ on-air behaviour with KIIS network management months before the relationship publicly deteriorated during a live broadcast in February.

The documents allege Henderson began speaking with senior KIIS executives in mid-2025 about what she described as ‘degrading comments’ made on air.

One August broadcast is cited in the claim, during which Sandilands made remarks about Henderson’s personal life and used language she found offensive, prompting her to briefly leave the studio at the time.

Following the party, a select group of guests went back to Shelley Sullivan’s rented Point Piper mansion, posing for this group photo on the expansive waterfront balcony

Milly Gattegno dared to bare in an open-front beige cardigan paired with denim jeans and a matching jacket

Guests mingled on the balcony as the festivities continued

Edwards sipped wine and smoked a cigarette as she spoke to Henderson on the balcony

Henderson and Edwards’ close friendship began in late 2024, when the pair began sharing glimpses of their getaway to Fiji on social media

From then on, the pair were attached at the hip, frequently stepping out together in Sydney’s eastern suburbs

Edwards was also said to be a source of support for Henderson during the rollout of her memoir and her sobriety journey

As for how present Edwards will be during her friend’s ongoing legal matter with her former employer remains to be seen

The court material also outlines text exchanges between Henderson and KIIS executives in September, where she reportedly said she would not accept the way she was being spoken to, and raised concerns that listeners were describing the on-air dynamic as ‘abusive’.

The breakdown escalated in February during what would become the duo’s final broadcast, when Sandilands criticised Henderson’s interests on air and suggested she had become ‘almost unworkable’, comments that allegedly left her in tears and prompted her to leave the studio.

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

The following day, Henderson contacted senior ARN executives, describing Sandilands’ conduct as ‘unfair, inappropriate and completely unprovoked’, and questioning what safeguards were in place going forward.

On 26 February, her lawyers formally wrote to ARN subsidiary Commonwealth Broadcasting Corporation alleging bullying and stating she could not continue working alongside Sandilands, while leaving open the possibility of remaining within the network in a different role.

ARN later responded that her letter amounted to termination of her contract, a position Henderson disputes.

She is now alleging the broadcaster engaged in misleading and deceptive conduct and breached the Fair Work Act, and is seeking compensation of at least $82.25million, plus penalties, interest and costs.