It was splitsville for Avril Lavigne and her billionaire boyfriend this week, with the pair calling it quits on their relationship after two years.
Lavigne, 35, was first linked to Phillip Sarofim, the son of Texas billionaire investor Fayez Sarofim, after the two were spotted on a dinner date in Los Angeles in March 2018.
They reportedly met through mutual friends and had already been an item for a few months at the time, per People magazine.
They were last seen together in June when the former couple stepped out for a day of shopping in West Hollywood.
The news followed a long line of failed high-profile relationships for the Canadian punk star.
In 2006, she married Sum 41 rocker Deryck Whibley, 39. But the pair called it quits in 2009.
She then had a brief romance with Brody Jenner from 2010 to 2012 until The Hills star broke things off, according to Us Weekly.
Her second marriage to Nickelback crooner Chad Kroeger, 45, began in 2013, but the pair divorced two years later.
It's been a rocky few years for the songstress, who at one stage was considered the biggest music star on the planet.
HER RAPID RISE TO STARDOM
Avril's first ever record deal, with Arista Records, was worth more than $US2 million, an astronomical amount considering she was unheard of and only 16 at the time.
In 2002, one year after signing her debut deal, she released her first album Let Go – with hits such as Complicated, Sk8er Boi and I'm With You.
It climbed to number two on the Billboard 200 chat, peaking at number one in Australia, Canada and the UK.
Her rise was rapid. She became the best-selling female artist of 2002, and the youngest ever female soloist to have a number-one album in the UK at the time.
She was quick to put out a second studio album, Under My Skin, which was released in 2004 and debuted at number one in Australia, Canada, Japan, the UK and the US.
But it wasn't just her music that made Avril so popular.
Her skate punk persona was a breath of fresh air in an era where Britney Spears and Christina Aguilera were the dominant forces among young girls.
Avril carved out her own unique style, and was considered a pioneer for female-driven punk music.
After years on top, releasing music and touring the world, Avril fell sick in 2014 and took a break.
This is when things turned weird.
BIZARRE THEORY AVRIL DIED, HAD BODY DOUBLE
In 2015, a strange theory went viral that Avril had killed herself in 2003 and was replaced by a clone, Melissa.
The original theory said that because Avril rose to fame when she was just 18 years old, her record label employed lookalike and "best friend" Melissa Vandella to impersonate her for the paparazzi as the "real Avril" struggled to deal with attention.
Then when Avril "died" in 2003 at the height of her career, label bosses decided to cover up her death and continue to release songs by Avril, but using Melissa instead.
As the suggestion gained some serious movement, theorists then analysed the shape of Avril's nose, her autograph and her voice — which they claimed had a different tone and grew increasingly out of tune since 2003.
Avril's second album Under My Skin was thought to be a "subliminal message" from the fake Avril — who even once posed with the name Melissa written on her hand.
A blogger said: "Launched in 2004, it is completely different to the first CD! It's an album full of subliminal messages apparently left by the 'New Avril'.
"The CD is called 'Avril Under My Skin', this is very suggestive! From here it was no longer true Avril, but 'Avril Lavigne' under the skin of another singer!
"The 'New Avril' poses for photos always sad and morbid expression, sometimes dropped to the ground as if to say something."
As the rumours continued to flood the internet, one fan echoed many by announcing: "This is a case for the FBI."
Even when the singer tweeted her mum to wish her "Happy mother's day," the responses from fans included: ""Happy Mother's Day, Melissa" and "Melissa, it's OK. We're here for you."
And it's not just physical features that users believed changed — others were suspicious when Avril promoted a slimming bar as a "yummy and healthy snack".
One user pointed out: "Avril Lavigne would never promote a Slim Secret bar. The jig is up Melissa."
Just last year Avril addressed the rumours she was a clone, talking to Aussie radio duo Kyle and Jackie O.
"Yeah, some people think that I'm not the real me which is so weird!" she told KIIS 106.5. "Like why would they even think that?"
Of course the singer is very much alive, but battled Lyme disease since 2015 and also went through a painful divorce from Nickelback frontman Chad Kroeger.
WHY SHE WENT OFF THE RADAR
Avril practically vanished after her tour ended in late 2014.
It was strange from someone who had been so prominent for the better part of a decade.
No wonder people started thinking she was dead.
In a tearful interview with Good Morning America in June 2015, Avril detailed her struggle with the disease, as well as doctors misdiagnosing her.
"Why don't you try to get out of bed Avril, and just play the piano? Are you depressed?", a tearful Lavigne told Good Morning America during her first on-camera interview discussing her battle with a severe case of Lyme disease.
"I was in Los Angeles, literally, like the worst time in my life and I was seeing, like, every specialist and literally, the top doctors, and they were so stupid, and they would pull up their computer and be like, "chronic fatigue syndrome," the singer recalled.
"This is what they do to a lot of people who have Lyme disease. They don't have an answer for them so they tell them, like: 'You're crazy.'"
At the time Avril said she was in recovery and was almost clear of the disease. It was only last year she wrote an open letter to fans revealing her battle didn't end there.
"I spent the last few years at home sick fighting Lyme disease. Those were the worst years of my life as I went through both physical and emotional battles," she wrote in a post on her website in September last year, while announcing the imminent release of her new album, Head Above Water.
"Thank you for waiting so patiently as I fought through and still continue to fight, the battle of my lifetime. The first song I am choosing to release is called Head Above Water. It is also the first song I wrote from my bed during one of the scariest moments of my life.
"I had accepted death and could feel my body shutting down. I felt like I was drowning. Like I was going under water and I just needed to come up for air. Like I was in a river being pulled in a current. Unable to breathe. Praying to God for Him to help me just keep my head above the water. To help me see through the stormy weather."
It wasn't the only trauma Avril was going through. In September 2015 it was announced Avril had split from her husband, Kroeger, after two years of marriage.
She said at the time, "It is with heavy heart that Chad and I announce our separation today. "Through not only the marriage, but the music as well, we've created many unforgettable moments. We are still, and forever will be, the best of friends, and will always care deeply for each other. To all our family, friends and fans, thank you sincerely for the support."
Her announcement came one day after her ex-husband Deryck Whibley tied the knot.
HER BIG COMEBACK
Having finally overcome the worst of her disease, Avril is set to embark on a world tour with her Head Above Water album next year.
It will kick off in Switzerland in March, travelling throughout Europe before finishing off in Japan in May.
In her blog post, Avril was determined to get back to doing what she loves, despite setbacks.
"I now have a very strong, triumphant, powerful and true record to me and my experiences over the last few years," she said of Head Above Water.
"I'm so excited to be returning with new music and to have you on this journey with me. Let's do this! New era!"