This week, the 31-year-old uploaded a throwback snap from her highschool formal and mused: "My prom pic with my first boyfriend @shwayze how cute!"
"He's now a very talented rapper! We bonded over music. I had my dress made to [look] like Britney Spears dress at the MTV Music Awards! Remember that dress? OMG I looked so skanky!"
Fans were quick to point out just how much the only child of Olivia Newton-John has changed over the years and even Chloe herself admits to undergoing several procedures.
Setting the record straight earlier this year with Woman's Day, Chloe explained she'd undergone two breast augmentations in order to correct a botched job when she was 18, as well as having fillers from her lips and face removed.
“All those things were a disaster. Not only did the lip implants look ridiculous, the first boob op I had in Australia when I was 18 left me looking mutilated," she told us.
In 2013 she was treated for alcohol and cocaine addiction: "I was using most days and nights. And not only was I doing coke, I was drinking vodka heavily also. I had to combine the two," however nowadays the aspiring singer seems much happier and healthier.
Chloe is determined to stay sober. "For anyone out there struggling with addiction. I feel you. Keep your sobriety. You never regret not drinking"
But perhaps her biggest battle yet is supporting her beloved mum ONJ after she was diagnosed with breast cancer for a second time.
"My mum is so powerful she will beat this in no time. My mum and best friend is going to be fine," Chloe assured fans.
Scroll through the gallery to see Chloe's transformation!