Jackie ‘O’ Henderson seen smoking a cigarette as she enjoys lunch date with best friend Gemma O’Neill followed by Pilates class in Sydney

Jackie 'O' Henderson seen smoking a cigarette as she enjoys lunch date with best friend Gemma O'Neill followed by Pilates class in Sydney

In my humble opinion, it seems that Jackie and Kyle are two individuals who have vastly different perspectives on life, and their conversation in this article is a testament to that. While Jackie appears to be a woman constantly striving for self-improvement and seeking knowledge about the universe, Kyle seems content with his current lifestyle and prefers discussing topics like Trump and TV.


Jackie O Henderson was having a girls’ lunch date with her good friend Gemma O’Neil’ on Tuesday. 

The KISS FM radio host headed out for the low-key meal in Sydney, followed by a Pilates class.

In a stylish outfit consisting of a sleek black tank top and relaxed pants both in the same shade, the 49-year-old confidently displayed her trim physique.

She strolled along while smoking a cigarette and wore a pair of designer sunglasses. 

Jackie seemed to be wearing only a small amount of makeup during her excursion, sporting a lightweight foundation and a subtle touch of pink lip color.

She accessorized her style by including a couple of white, layered sneakers, while keeping her long blonde hair tied in a ponytail.

She completed her casually chic ensemble with a leather tote bag slung over her shoulder. 

Jackie and Gemma chatted as they tucked into their meals with Jackie appearing to opt for a salad.

Jackie 'O' Henderson seen smoking a cigarette as she enjoys lunch date with best friend Gemma O'Neill followed by Pilates class in Sydney

Jackie 'O' Henderson seen smoking a cigarette as she enjoys lunch date with best friend Gemma O'Neill followed by Pilates class in Sydney

Following the incident, Jackie felt deeply embarrassed when she recognized she had been engaging in typical high-society dialogue during dinner.

On her KIIS FM broadcast, the affluent Australian radio personality (with a fortune exceeding $50 million) aired a popular TikTok video made by an American content creator, focusing on dialogue variations between different societal strata.

The TikTok creator remarked, “I have both affluent and financially struggling friends, and one obvious difference in their conversations during meals is the subjects they discuss.”

She shared that her friends who are less financially well-off typically discuss topics like reality TV, popular culture, current events, and politics, whereas her more affluent friends focus on personal aspirations, personal growth, and spiritual matters.

Jackie 'O' Henderson seen smoking a cigarette as she enjoys lunch date with best friend Gemma O'Neill followed by Pilates class in Sydney
Jackie 'O' Henderson seen smoking a cigarette as she enjoys lunch date with best friend Gemma O'Neill followed by Pilates class in Sydney
Jackie 'O' Henderson seen smoking a cigarette as she enjoys lunch date with best friend Gemma O'Neill followed by Pilates class in Sydney
Jackie 'O' Henderson seen smoking a cigarette as she enjoys lunch date with best friend Gemma O'Neill followed by Pilates class in Sydney

Following the video, Jackie expressed surprise by saying: ‘I hadn’t realized that spirituality was something affluent people tended toward.’

In response, her fellow host, Kyle Sandilands, aged 53, said, “I don’t think so,” and followed up with, “Who has the luxury of wasting time on that?”

He stated, “Typical individuals are too busy to ponder whether planetary alignment influences their mood today.”

Jackie expressed, “It seems like we’re constantly discussing this topic among our circle of friends, as we often ponder over profound questions regarding the cosmos.”

Jackie 'O' Henderson seen smoking a cigarette as she enjoys lunch date with best friend Gemma O'Neill followed by Pilates class in Sydney
Jackie 'O' Henderson seen smoking a cigarette as she enjoys lunch date with best friend Gemma O'Neill followed by Pilates class in Sydney

She then challenged Kyle and asked what he speaks about with his friends. 

“Trump and television. Being wealthy yet living among the economically struggling suits me just fine,” he replied.

Kyle then told Jackie to ‘keep [her] goals to herself’ and ‘don’t go showing off to your friends.’ 

‘We’re not showing off!’ Jackie said defensively. ‘We’re trying to better ourselves as humans.’ 

Kyle wondered, “Just how much more successful or content do you aim to be? At what point do you draw the line? You’ve shed pounds, left a less than ideal relationship behind, and excelled professionally. What else are you striving for?”

Jackie 'O' Henderson seen smoking a cigarette as she enjoys lunch date with best friend Gemma O'Neill followed by Pilates class in Sydney

Jackie: ‘You can always better yourself as a person!’

‘You’ve made yourself worse,’ Kyle laughed. 

Over the past few years, the radio host, who used to have a modest group of friends, has blossomed into a prominent social figure.

Jackie’s circle of friends used to consist of Kyle, radio personality Brooklyn Ross from KIIS, and her business partner at Besties, Gemma O’Neill.

Currently, the striking woman is mingling with Australia’s high-profile individuals and has also traveled to Europe to attend a wedding of one of her friends in July.

Jackie’s strong connection with Pip Edwards of P.E Nation has led her to mingle within the same social sphere as renowned Sydney stylist Jess Pecoraro, makeup artist Max May who works with celebrities, and Michael and Alexander Porter, the heirs of Four Seasons condoms.

Following a lavish vacation to Greece with Gemma, Jackie went on to attend the wedding of Alexander and his partner Chris Ledlin, which was held at Château de la Napoule in France.

2023 saw Jackie and Kyle penning a whopping $10 million, 10-year contract with their umbrella firm ARN, allowing them to broadcast the Kyle and Jackie O radio program nationwide throughout Australia.

Kyle shocked radio listeners recently by claiming that the pair ‘earn way more’ than the reported $10 million each annually. 

He mentioned that it’s significantly greater than the information given in the report, but Jackie prefers not to discuss this matter further. In actuality, it’s approximately three times as much, he explained.

In 2022, it was reported that Kyle’s fortune stood at approximately $40 million, while his young son, Otto, has been mentioned as having a millionaire status in the past.

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2024-08-27 10:50

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