Friends of a Sydney woman who used to date Jackie ‘O’ Henderson‘s new boyfriend Richie Ryan say she is heartbroken over his relationship with the KIIS FM star.
After we published photos of the radio host, 50, kissing Richie on the balcony of her Clovelly home last Sunday, his ex on the other side of the world was reeling.
According to a friend, the woman – a cardiologist in her 30s – dated Richie earlier this year after he ended his engagement to a vegan chef named Emma.
Their relationship ended amicably before Richie began seeing Jackie, but the woman had held out hope they might reconcile.
But those hopes were dashed when she saw photos of pilot and DJ Richie canoodling with Jackie O splashed across the tabloids.
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A former girlfriend of Jackie O’s new squeeze, Richie Ryan, was ‘absolutely devastated’ to see them together on the radio presenter’s balcony on September 21. ‘She hoped things weren’t finished between them,’ a friend told the Daily Mail
Their relationship ended amicably before Richie began seeing Jackie (pictured here on February 18), but the woman had held out hope they might reconcile
‘She was absolutely devastated,’ a friend told Daily Mail.
‘She hoped things weren’t finished between them. Seeing him with Jackie killed any chance of that.’
When he ended things, Richie told the woman he needed space to deal with a personal matter.
He had texted her that he was finding it hard to give her what she deserved while trying to manage the situation.
When our photos were published last week, the woman was ‘really crushed’ to see Richie had moved on.
She was in Paris at the time, having flown overseas to mend her broken heart.
‘She burst into tears,’ said a friend. ‘Right now she’s just trying to heal overseas.’
Jackie and Richie declined to comment.
Richie was previously engaged to a vegan chef named Emma (right), proposing to her while kayaking around Sydney Harbour in 2021. Emma is not the ex mentioned in this story
Emma had been dress shopping before the wedding was called off. She appears to have selected a $6,500 gown, which was later listed for sale online as never worn (pictured: the listing)
This isn’t the first time Richie’s love life before Jackie has made headlines.
He was previously engaged to a vegan chef named Emma, proposing to her while kayaking around Sydney Harbour in 2021.
Emma – whose surname we’ve withheld for privacy reasons – had even been dress shopping for their wedding.
She looks to have selected a $6,500 couture gown, which was later listed for sale online as never worn.
As recently as January, Emma was updating a Pinterest board brimming with wedding inspiration. It’s unclear when exactly they split.
It comes after Jackie denied rumours in June that she was dating former NRL star Adam Muir, following the pair being spotted on a stroll in the eastern suburbs.
She had earlier revealed on her podcast Her Best Life that she was ‘very happy’ and in ‘such a good place’ after previously allowing her marriages to become stale.
‘In all my relationships, I have allowed it to get to a brother and sister dynamic,’ she told her co-host and manager Gemma O’Neill.
This complacency would lead to a lack of intimacy that left Jackie feeling ‘undesirable’ and the partnership ‘unfixable’.
She acknowledged that her experience was not unique, with many of her friends having gone through similar situations in their marriages.
‘The more I spoke to women, the more I realised this is actually really common in a lot of marriages. Like there’s just no sex anymore,’ she said.
In another episode of the same podcast, Jackie admitted she was struggling to let go of an ex.
Despite being ‘over’ that relationship, she said that in her weaker moments she would think to herself, ‘That’s my person.’
She said that the man, whom she did not name, ‘didn’t show up’ for her when she needed him.
Jackie O’s last romantic entanglement was with tradesman Jack Tyerman (right), who is now engaged to another woman and expecting a child
Jackie split from her second husband, Lee Henderson, in 2018. The pair share a daughter, Kitty
Her last romantic entanglement was with tradesman Jack Tyerman – who is now engaged to another woman and expecting a child.
She stated on air that Jack was not her boyfriend, even though she confirmed she was ‘dating’ at the time and they were pictured together on several occasions.
‘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,’ she said in August 2023.
After telling Daily Mail at the Logies that she was dating someone, Jackie later blamed herself for the media running with the story.
If she eventually makes things official with Richie, he’ll be her first confirmed relationship since her 2018 split from second husband Lee Henderson, with whom she shares her 15-year-old daughter, Kitty.
Before meeting Lee, she was married to the radio presenter ‘Ugly’ Phil O’Neil.
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