Jackie ‘O’ Henderson and Braith Anasta were spotted flirting while sailing in Sydney Harbor earlier this month, among a host of other stars.
The 49-year-old radio host and 42-year-old former NRL star celebrated SailGP’s fifth visit to Sydney ahead of the KPMG Australia Sail Grand Prix.
The blonde Kyle & Jackie O show co-host wore a bright yellow flared mini dress from Alexis, which costs around $900, and kept her hair tied in a ponytail for the windy weather.
She laughed and chatted with Braith between sips of what appeared to be a bottle of non-alcoholic Peroni Nastro Azzurro beer.
Footy player and television presenter Braith dressed casually in a black T-shirt and white shorts and was also spotted chatting to Jackie’s best friend Gemma O’Neill.
Jackie ‘O’ Henderson and Braith Anasta were spotted flirting while sailing in Sydney Harbor earlier this month, among a slew of other stars
He and Jackie had a very animated conversation with the other attendees.
On Tuesday, the day before Valentine’s Day, Jackie looked delighted when a bouquet of flowers was delivered to her home.
The radio titan, who is currently single, smiled hugely as she picked up the luscious flowers sent by a mystery person.
The next day, Jackie talked about the surprise romantic gesture from a “secret admirer” on the Kyle and Jackie O Show.
The 49-year-old radio host and 42-year-old former NRL star celebrated SailGP’s fifth visit to Sydney ahead of the KPMG Australia Sail Grand Prix
He and Jackie had a very animated conversation with the other attendees, including her best friend Gemma O’Neil
While the identity of the sender remained a mystery, she revealed that the accompanying card provided a clue.
“It said, ‘Meeting you last week was like fate, darling X,'” she told listeners.
“Last week I ran into a guy I knew but had never met,” Jackie added, describing them as “mutual friends.”
She said she then received a text from the man that read: “It was a coincidence that I met you like this.”
Jackie said she sent a flirty response: “Oh, I love that you used the word ‘coincidental.’
She laughed and chatted with Braith between sips of what appeared to be a bottle of non-alcoholic Peroni Nastro Azzurro beer.
The blonde Kyle & Jackie O Show co-host rocked a bright yellow flared mini dress by Alexis, which retails for around $900
However, Kyle said the mystery man sounded like “a loser.”
“Sounds like Alan Jones is trying to romance you,” the shock jock joked.
Jackie has also been photographed several times entertaining younger men at her home in Sydney’s eastern suburbs.
One of the men has been identified as 29-year-old male model Jack Tyerman, represented by top modeling agency IMG Models.
Jackie was spotted spending time with the part-time tradie in August last year.
Footy player and television presenter Braith, dressed casually in a black T-shirt and white shorts
Jackie had her hair tied in a ponytail because of the windy weather
Later in 2023, she was seen entertaining another handsome young man on her balcony.
Earlier this month, Jackie opened up about her struggles with loneliness since splitting from Lee Henderson in 2018.
Speaking to fans at the launch of Luke McLeod’s book Everyday Enlightenment, the radio titan admitted she is ‘desperate’ for love and companionship.
She explained that she was having lunch with Luke last year when they brought up the subject of her love life and she felt like she was “missing something.”
‘I just really want to find someone. I can’t find it and I’m a little lost right now,” she recalled telling Luke.
When Luke asked why she was so desperate to be in a relationship, Jackie said she couldn’t put her finger on it, but it felt like “a piece of her was missing.”
Jackie is pictured arriving at the event, which was held in early February
The pair later posed for their own solo photos, including holding the SailGP trophy
Braith later chatted with Gemma and journalist Melissa Hoyer
‘I have a lot of love to give, or I want that affection, that company. It just feels like something is missing in my life,” she added.
Jackie went on to tell her fans that Luke gave her some advice that “changed my life.”
He said she gave off too much “desperate energy,” and if she really wanted to attract love into her life, she needed to be grateful for what she already has.
“I said to him, ‘How do I change what I want and need?’ I feel like I need that in my life and I really want that. “I can’t just turn that off,” she said.
Still, Jackie said she tried Luke’s method and began spending 15 minutes a day thinking about the things she was already grateful for in life.
‘NNow I’m in a place where I’ve almost gone the other way. I“I’m so happy that I’m single and not looking for someone because I’m genuinely happy with my life,” she said.
She revealed that after a year of meditating on what makes her happy now, she finds it much easier to “be present” rather than “think about what’s missing in my life.”
Jackie has been married twice. She divorced her first husband, DJ ‘Ugly’ Phil O’Neil, in 1999.
She was married to Lee from 2003 to 2018. The couple co-parents their only daughter, Kitty.