Ahead of her stint on the boot camp reality show, New Idea takes a look back at Roxy and Oliver’s relationship, to answer the pivotal question: who is the man behind the woman?
According to an extract of Annette Sharp’s biography, Blonde Ambition: Roxy Jacenko Unfiltered, which was published on The New Daily, Oliver was 24 when he met Roxy, then 29.
At the time, the investment banker was engaged to his “childhood sweetheart” of five years, Hermione Underwood, who befriended Roxy through Oliver’s sister Sophie.
The two blondes were only a few months into their friendship when Hermione invited Roxy to a charity event in 2010, which she later claimed ended her relationship with Oliver.
Hermione headed home after dinner, leaving Roxy and Oliver to party with friends, but within 24 hours she allegedly confided to friends that Oliver had moved on.
“It devastated Hermione. Oli had been her first love. They had moved in together one week after she finished high school,” a family friend claimed in Sharp’s biography.
“The wedding was called off and the whole Curtis family was kind of in shock. They loved Hermione. They still do.”
Within months of hooking up, Oliver and Roxy were engaged and by February 2011, the couple revealed they were expecting their first child, a daughter named Pixie, now nine.
Dubbed Sydney’s “wedding of the year”, the couple later tied the knot in March 2012, before splurging on a $6.6 million Woollahra house in Sydney’s Eastern suburbs.
Oliver and Roxy then welcomed their second child, a son called Hunter, now six, in May 2014, before Oliver was sentenced to one year in jail for insider trading in 2016.
In June 2017, the former stockbroker was released from Cooma Correctional Centre and greeted by Roxy and his children, who were waiting for him in a private jet.
Roxy has since opened up about a short-lived affair she had with ex-boyfriend Nabil Gazal, while Oliver was in prison, stating that the fling “wasn’t my fault”.
Since his release, the couple have chosen to move on from the incident, with Oliver vowing to forgive the infidelity if Roxy forgave him for the jail sentence.
Speaking to WHO magazine in 2019, Roxy seemingly joked about how she and Oliver hooked up, saying: “It was his sister's fault and he was engaged!
“But then he saw me and knew he was making a dreadful mistake. If only I'd had hindsight on my side. I thought I was marrying Richie Rich. Richie Rich ended up in jail,” she said.