He’d been divorced twice, dated a celebrity escort and was once engaged to a Young Australian of the Year whose AFL star husband was swept away in a tsunami.
But despite these relationships with high-profile women, TV personality Ryan Phelan, 45, always managed to enjoy a high degree of privacy.
On Monday evening, he was charged with assault following an alleged domestic violence incident with his newest partner, ballet instructor Chelsea Franklin.
The Channel Seven presenter began dating Ms Franklin in April 2018, just months after his whirlwind relationship with former escort Samantha X deteriorated.
A month into their romance – which was reportedly frowned upon by some of his colleagues – Phelan claimed he was in love with the escort. He had only separated from his second wife earlier in the year.
After learning of the charges, Phelan’s employers said on air that he would not be returning to his regular job as a host on The Daily Edition.
The program only has four episodes left. After a seven year run it was axed last week.
Here Daily Mail Australia takes a look at Phelan’s troubled love life.
The 45-year-old was charged with assault following an alleged domestic violence incident with his partner, Chelsea Franklin (pictured together) in their northern beaches home on Saturday night
Married to his childhood sweetheart
Phelan grew up in Ayr, northeast Queensland, where he met and married his childhood sweetheart.
They were only 18 when they married, with Phelan was an aspiring journalist.
The couple went on to welcome two children – both of whom are now adults and largely stay out of the public eye.
In 2001, when Phelan was 26, the couple separated after eight years of marriage.
Phelan had not yet become a household name, and the identity of his first wife was never publicly revealed.
Ryan Phelan ahead of the Cleo Bachelor of the year awards
Cleo Bachelor of the Year 2005
By 2005, the divorced father-of-two was hosting Channel 10’s Sports Tonight every weeknight.
He became a familiar face for many Australian families and was voted Cleo’s Bachelor of the Year for 2005.
At the time, he said he was shocked to receive the honour over fellow nominees Chris Hemsworth, Ian Thorpe and Guy Sebastian.
‘I don’t have rock hard abs like some of these guys,’ he told the now-defunct magazine.
‘I married young but I am very grateful for that because it has sort of put me where I am with my career and where I am with my life.’
‘I have just been in relationships my whole life. I think I need to allow myself a little time just to enjoy life.’
The then-30-year-old was up against 50 other eligible bachelors.
Pictured: Phelan’s Cleo Bachelor of the Year question and answers sheet
Engaged to a widow
Phelan was briefly engaged to widow Trisha Broadbridge, whose AFL star husband Troy died when he was swept away in the 2004 Boxing Day tsunami in Thailand.
They were on their honeymoon at the time, and had only married eight days earlier.
She was later named the 2006 Young Australian of the Year.
Ms Broadbridge met Phelan at the Australian Grand Prix in April 2006 and the pair immediately hit it off.
They called time on their engagement in 2006 a month before Phelan was due to move to the United States for a two-year contracted role with ESPN.
It was reported at the time his imminent departure contributed to the separation.
He was briefly engaged to widow Trisha Broadbridge, whose AFL star husband Troy (pictured together on their wedding day) died in the 2004 Boxing Day tsunami in Thailand. They were on their honeymoon at the time, and had only married eight days earlier
Trisha Broadbridge being comforted by friends and family at the funeral of her husband, tsunami victim and AFL footballer Troy Broadbridge
In March 2015, Phelan shared a photo of himself and a woman in a white wedding dress kissing on a pier.
The picture was posted to his Twitter account along with the caption: ‘Married the most amazing person on the planet today.
‘Sharing this for our friends abroad and friends in general.’
It is not clear how long the couple were together prior to their wedding, but he had not been romantically linked with anybody since his 2006 separation from Ms Broadbridge.
Her identity was never revealed, but just two years later they quietly parted ways.
In March 2015, Phelan shared a photo of himself and a woman in a white wedding dress kissing on a pier. The picture was posted to his Twitter account along with the caption: ‘Married the most amazing person on the planet today
Dating Australia’s most high profile escort
Phelan enjoyed a whirlwind two-month romance with high-end escort Samantha X from November 2017 to the end of January 2018.
The couple fell for one another while on the job, when Samantha (real name Amanda), a former journalist herself, appeared in the studio to promote her second book.
‘We met when Amanda came in [to Channel 7] to promote her second book, Back On Top, and I asked her out on a lunch date,’ he said after they went public with the relationship.
Back On Top was released on August 28 that year, while Samantha announced she was ‘hanging up the heels,’ and retiring as an escort on October 24.
Phelan previously enjoyed a whirlwind two-month romance with former escort Samantha X (right)
‘We have pretty much spent every day together since [we met],’ Phelan said at the time.
When pressed about her career, Phelan said: ‘I fell in love with Amanda, no one else.’
‘And that is who she is to me, Amanda, an outstanding mother and an outstanding woman.’
‘If anything she has achieved a lot in her career and given an industry a voice it didn’t have before,’ he concluded.
The couple announced their separation in January 2018, when Samantha confessed she had ‘IKEA furniture which lasted longer than that relationship’.
On Tuesday, Samantha told Daily Mail Australia she was blindsided by the separation
On Tuesday, Samantha told Daily Mail Australia she was blindsided by the separation, but feels like she ‘dodged a bullet’ in hindsight.
‘I went to a very dark place after Ryan ended our relationship,’ she said.
‘While I never spoke publicly about what happened, I will say I am thankful to have dodged a bullet.’
She said she was constantly made to feel as though she had dragged Phelan’s reputation down, but ignored potential red flags because she ‘fell for his charm.’
‘I wanted to believe the dream could come true,’ she said. ‘It was intense and emotional, driven by Ryan.’
Just three months after his relationship with Samantha X deteriorated, Phelan revealed he had started dating ballet teacher Chelsea Franklin, 44.
From April 2018, the couple were inseparable and often were spotted at public events together, including Derby Day and Stakes Day during the Flemington Spring Carnival in Melbourne, before making it official on Instagram with a series of loved-up snaps.
Earlier this year Phelan and Ms Franklin purchased their home in Frenchs Forest, on Sydney’s north shore, home after being outbid on several other properties.
‘We BOUGHT a house! Blessed beyond measure,’ Ms Franklin wrote on social media after the couple purchased the $2.16million house.
Phelan, 45, allegedly assaulted his girlfriend Chelsea Franklin on Saturday night at their $2.16 million home in Frenchs Forest, in Sydney’s northern beaches
Other than that, their relationship remained primarily out of the spotlight until Monday night, when it was revealed Phelan had been charged over an alleged domestic violence dispute in the home they’d only recently bought.
He presented himself at Manly Police Station just after 8pm on Monday and was interviewed by detectives, and then charged with assault occasioning bodily harm and was granted bail to appear before a court on June 30.
When approached by Daily Mail Australia on Tuesday, Ms Franklin said she was ‘gutted’ by the assault charges.
‘I’m devastated, I’m shattered. I’ve lost my lover, I’ve lost my boyfriend – I love him,’ Ms Franklin said.
‘It was just a horrible mistake really, we’ve had a wonderful two-and-a-half years together, nothing like that has ever happened before.
‘Obviously with what’s going on with him being made redundant and there’s a couple of other personal issues I had and he had, and I think it just took its toll.
‘I love Ryan, he’s an amazing person… its been a tough, tough week, but he’s been an amazing person to me and I love him. It’s just a horrible mistake.’
Phelan has since moved out of the home, while his daughter is understood to now be living with her mother.
Chelsea Franklin (pictured) leaves Ryan Phelan’s house in a black Mercedes-Benz SUV on Tuesday morning