Jackie O Henderson opens up about her relationships after two divorces: ‘Really dark times’

Radio star Jackie “O” Henderson has opened up about her past relationships, admitting there had been dark times after her two divorces.

In a promotional video launching the Red Flag Project, a relationships course as part of her Besties business with Gemma O’Neill, Henderson made some very frank admissions about the ups and downs of her love life.

WATCH THE VIDEO ABOVE: Jackie O opens up about relationships.

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“Introducing the Red Flag Project — your ultimate guide to transforming your love life and building healthier relationships!” the video was captioned.

“With over 30 insightful videos, detailed handouts, and reflective guides, this course is designed to help you break free from unhealthy patterns and find the love you deserve.”

In the accompanying video, Henderson talks with O’Neill and Red Flag Projects’ two relationship instructors, doctors Justine Corry and Gemma Gladstone, about her own rollercoaster ride through love.

“People often say to me, ‘You seem so great and happy after going through what are dark times, like a divorce or a massive change’,” she began.

Henderson was only 19 when she married radio co-host Phil O’Neill, who was 10 years her senior.

They were married for five years before calling it quits.

In a No Filter podcast last year, Henderson described the relationship as “like a high school romance”.

Henderson said her second divorce, from Lee Henderson, was more painful because there were children involved.

The Hendersons were married for 15 years and had a daughter, Kitty, before separating in 2018.

Since then, the Kyle & Jackie O Show star has been navigating the dating scene — which is where the Red Flag Project came in.

“I wish so much that I had known this earlier on, like, I envy girls who are watching this now at 20,” she said of some of the relationship advice from Corry and Gladstone.

“We used to see love bombing as, ‘Oh my god, he loves me, this is everything I’ve ever wanted’,” Henderson said in one segment.

She also made a candid admission in the video about her sex life, telling Corry and Gladstone: “I’ve had some experiences in the bedroom that really haven’t been great at all. There’s really no way to sugar-coat it.”

Henderson said the course was “designed by women for women” to give them the building blocks for approaching dating and relationships “quite differently”.

The concept seemed to hit a note with many of Henderson’s followers.

The video was “liked” by several celebrity followers, including Schapelle Corby, musician Bonnie Anderson, TV personality Sophie Monk, celebrity trainer Michelle Bridges and influencers Nadia Bartel and Ellie Gonsalves.

“This is a wonderful idea,” one follower wrote.

“So needed! Well done,” wrote another.

“Great idea ladies, love that you’re making a positive difference for women.”

Henderson’s high profile means her romantic life has been the subject of much speculation and gossip since her split from her second husband.

Recently, the 49-year-old was romantically linked with tradie-turned-model Jack Tyerman after the pair was spotted at Justin Hemmes’ new restaurant Good Luck in Sydney’s CBD.

Rumours of a relationship first surfaced in August 2023 when Tyerman was spotted on the balcony of Henderson’s home in Sydney’s eastern suburbs.

But Henderson has hosed down rumours she was dating Tyerman.

“He is cute, but no, there is nothing going on. We went out with his sister and her husband. We were just catching up,” she said.

“Jack is a good friend of mine.

“I know him through a friend of ours.

“We didn’t meet on a dating app or anything like that.”

Henderson has also been open about how some potential suitors are intimidated by an independently wealthy woman, admitting some men found it challenging that she earned more than they did.

“I should be proud of the money I earn,” she told Mia Freedman on the No Filter podcast last year.

“Maybe it’s just the way I was brought up. I don’t want to gloat.

“Money is so great on the one hand because it gives you this beautiful, comfortable life, and you don’t have those worries or pressures.

“And on the other hand, sometimes you just want to be rid of it as well, because it changes dynamics.

“I think some men can be comfortable with it, but I think that can be hard to find.”

Henderson said she had to be “wary” about dating because of her wealth, adding many men believed they needed to be the breadwinner in a relationship.

“I feel that men still have it ingrained in them,” she said.

“They could say, ‘Oh, I don’t care. I’m comfortable. I’m OK with the woman earning the money’.

“But there is something innately within them that they have to be the provider and, if they don’t, there’s some sort of inadequacy they have as a result of it internally.

“It’s tricky because you sometimes feel you don’t want to live the life that you’re used to living because you’re trying to downplay it, to equalise it.”

The radio star added younger men were more likely to be OK with her earning more money.

“I do think younger men are definitely more comfortable with it,” she said.

“They’ve grown up around women and mothers who work for a living, and it’s very different now.

“And I think they’re a lot more comfortable and confident with that.

“But I think that for the older generation — ones probably in my age group — it’s more difficult.”

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