Millionaire businessman, Tim Guest sits across the table from transgender homeless woman Bellatrix. She's been sleeping rough "off and on for years" but things "went downhill" over the course of the last decade as she deteriorated from drug use which, she tells Tim, made homelessness bearable.
Tim asks Bellatrix how old she was when she first used drugs and her answer is shocking. She was two. And the introduction came via her mother.
It's part two of the SBS three-part-series Filthy Rich and Homeless and unlike the first episode which aired on Australian television on Tuesday night, the second installment adjusts the lens on the experience, as the five wealthy participants meet some of the people trying to survive on the street.
More than 105,000 people are homeless in Australia on any given night, according to Mission Australia.
Fifty-six percent of homeless people are male, but the number of women experiencing homelessness has risen significantly. In 2010, half of the people who sought help from a specialist homelessness services were under 25, and a third were under 17.
At the start of the experiment, millionaire Tim Guest, boxing champion Jeff Fenech's daughter, Kayla Fenech, beauty entrepreneur Jellaine Dee, pub baron Stu Laundy and Richard Wilkins' son, Christian Wilkins all confessed to a disconnection when it came to Australia's homeless.
"If I'm walking through the city and someone approaches me, asking for change or for money, [I act] like they don't even exist. I could walk past them," Tim said at the beginning.
Kayla Fenech believes homelessness is almost a life-style choice, and that she if she ever found herself in that situation, she would "buy some nice clothes" so she could get a job to get herself out.
For part two of the documentary the five are individually buddied-up with a homeless person.
21-year-old Christian is paired with Nigel who has been homeless for 16 years and has suffered from depression most of his life, and four years previously, tried to kill himself.
"If you become homeless and you haven't got any mental issues, you soon will have," he tells Christian. It's a sentiment echoed among others doing it tough that the group encounters.
Leading the social experiment homelessness expert, Dr Catherine Robinson assists the wealthy Australians to comprehend the complexity of homelessness.
"One of the key things [the participants have] been learning in the last few days is just how many layers there are to the homeless experience," she said.
"Giving people long-term affordable housing is the core of addressing homelessness. [But] it is not the magic bullet.
"Safe housing is a human right, and so the ability to extend that to everybody, in my view, is such an important starting point."
Part three and the final installment of Filthy Rich and Homeless airs Thursday on SBS at 8.30pm.
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