Kylie Minogue believed she'd finally found 'The One' in Joshua Sasse.
But after the 48-year-old called off their engagement on Friday amid claims she 'became suspicious of her fiancé's relationship with a Spanish actress', the British thespian became the latest in Kylie's long list of failed relationships, the Daily Mail reports.
The singer has been left heartbroken on several occasions since bursting into the public spotlight - including high-profile romances with Jason Donovan, Michael Hutchence, Oliver Martinez, Lenny Kravitz and Andres Velencoso all ending in tears.
And as she prepares for life without her 29-year-old toyboy fiancé, it would appear Kylie hasn't always been so 'lucky in love'.
Jason Donovan - 1986-1989
Kylie and Jason Donovan met and fell in love while playing Scott and Charlene in TV soap Neighbours. Their characters' on-screen wedding was an international event when it was broadcast in 1987, outrating Charles and Diana's in the UK.
Donovan later revealed they consummated their romance in a Travelodge and admitted he was 'devastated' when she moved on with Michael Hutchence.
He previously told The Mirror: "It was an extremely painful parting of the ways and, without doubt, I took a long time to recover from it.
"It was bad enough that she'd run off with anybody, but she happened to run into the arms of the greatest rock god of the period, the very guy who I secretly wanted to be."
He added that he and Kylie have never spoken about their heartbreaking split, claiming they simply "aren't close enough to get into that".
Michael Hutchence - 1989-1991
Kylie dated INXS rocker Michael Hutchence between 1989 and 1991 and the pair remained friends until his tragic death in 1997.
In December 2013, the singer was overcome with emotion as she discussed the late Australian singer during a radio interview.
Kylie fought back tears during her appearance on BBC Radio 4's Desert Island Discs as she opened up about her ex-boyfriend, picking the INXS hit Need You Tonight as one of her favourite songs and admitting: "It's getting me very emotional".
She continued: 'I met a new person and I fell in love. Yes, he was this wild guy, he was the rocker, he was all of that. But I'm always at pains to say he was Byron-esque, he was poetic, he was cultured and hilarious and tender, he was all of these other things.
"I guess, I was at the perfect age, I was 21 years old, to get the butterfly wings and go out into the world and we collided at that time and I guess he just fast-tracked some of it. Anyway, it was a glorious time. I loved it."
Kylie credited Hutchence, who died aged 37, with rebuilding her confidence as she learned how to perform live in front of audiences.
She explained: "Professionally, he was so supportive. Someone called me the singing budgie in Australia as a knock.
"So I did this warm-up gig and we said, 'It's the singing budgie, take that, own it and go out'.
"We did this little gig and I was so inexperienced at doing live performance. I feel my career is backwards. I started successful then I had to learn everything in front of everyone."
She continued: "I mean he was uber, uber famous. He's an icon already. And he was in the middle of the audience, just gazing up at me, and just willing me, willing me with all of his heart and his love to do well, and he believed in me. And it was at a time when so many people didn't."
James Gooding - 1999-2002
Kylie dated model James Gooding for three years but he later boasted of flying out to New York and cheating on her with model Sophie Dahl.
Kylie was said to be 'furious' when he did a tell-all interview about her.
Other stars who had romances with Gooding also slammed him, with former girlfriend Martine McCutcheon describing him as 'disgusting'.
Olivier Martinez - 2002-2007
Kylie dated French actor Olivier Martinez for five years before the couple called it quits in February 2007.
A joint statement released on behalf of the pair at the time read: "Olivier Martinez and Kylie Minogue have officially confirmed that they are no longer a couple.
"They have made it clear that the decision to go their separate ways was mutual and amicable. The media's false accusations of disloyalty have saddened them both. The two remain very close friends."
The separation came at the end of a tumultuous time for Kylie after she was diagnosed with breast cancer.
The singer was forced to abandon her Showgirl world tour in May 2005, and did not resume it until November 2006.
The singer spoke of how her "incredible" boyfriend of four years had helped her through the battle.
"On particular dark days, I'd be lying on the bathroom floor wailing and he'd say, 'OK, honey, you can cry for just five minutes, then I'm taking you on the bike for a ride around Paris'," she told Elle magazine in 2006.
"So I'd howl a bit more and then I'd find myself thinking, 'Hmm. Actually, a ride on the bike sounds pretty good'.
"Olli was there all the time, helping with the practical stuff and being protective."
At the time she denied reports the couple were planning to marry.
"I understand the excitement at the prospect of a wedding, but we're simply happy together and getting on with life," she said.
Andrés Velencoso - 2008-2013
The singer's most recent relationship before Sasse was with model Andrés Velencoso.
The songstress began dating Andrés after they met while filming an advert for her perfume range in 2008.
In 2013, Kylie ended their five-year relationship and cited the pressures of their conflicting work schedules as the reason for the split.
Her representative confirmed the break-up to The Sun On Sunday, insisting at the time they were still on good terms.
Friends later said her increased workload had led to them spending less time together over months leading up to the split.
"Kylie and Andrés haven't been spending much time together because she's been holed up in the studio in LA working on her new album," said a source. 'He's also been trying to carve out an acting career for himself.
"When she signed up for The Voice they knew they couldn't cope with the long distance pressures the job would put on them."
The news came only 12-months after Kylie said of her then-boyfriend: 'He's the one. Sound the alarm, four years. I think I'm pretty settled'.
Joshua Sasse - 2014-2017
In November 2014, Kylie revealed she was in a relationship with Joshua Sasse, who is 19 years her junior.
Joshua had reportedly confirmed their engagement after referring to Kylie as his 'fiancée' during an NME Awards after party.
According to The Sun, the couple announced the news at the event, with a source telling the newspaper: "Kylie may have been keeping tight-lipped, but Josh isn't as keen to keep it a secret."
They continued: "He was proudly calling her his fiancée to several guests and even joked that being with her meant he wouldn't have any trouble getting into parties."
Kylie was reportedly busy presenting an award during the show as Joshua made the candid remarks.
Kylie had showed off a diamond ring on her wedding finger earlier in the year, and Joshua is believed to have proposed in Switzerland during a skiing holiday.
The pair first met on the set of Joshua's TV series Galavant when Kylie filmed a guest role, and were inseparable ever since.
The Melbourne-born singer previously said: "I have a love of my life which is just a beautiful thing. I am kind of on cloud nine most of the time because of Mr Joshua Sasse, my beau."
And speaking to The Mail on Sunday's You magazine in 2014, Kylie insisted that despite their significant age gap, she and Joshua were the perfect match.
"I can't actually put into words how happy I am... We just completely fit together. He gets me, I get him," she said.