This year will be the first time Jessica Condell has not spent Mother's Day with her mother.
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While her parents continue to isolate in Wagga, marking this weekend's special occasion has had to take some creativity.
"We're doing a Zoom trivia night with my mother, and my brother and sister in Wollongong instead of us all travelling," Ms Condell said.
"We've each prepared 10 questions in a theme, we'll dress in our own themes and we'll present them on Zoom."
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A mother herself, of two-year-old Alice and four-year-old Fletcher, Ms Condell said she will be missing the physical connection between the multiple generations on Mother's Day.
But given the COVID-19 situation, a technology-aided meeting would suffice.
"It is sad. My brother and sister usually come down and we'll spend the day really celebrating [mum]," Ms Condell said.
Ms Condell works as a case manager for the Mission Australia Youth on Track program in Wagga.
As part of her role with the charity organisation, she is using her creative mother's day venture to encourage others to connect virtually while staying in pyjamas to raise funds for those who are most affected by the COVID-19 downturn.
"As many isolate at home, so many of us can't truly understand what it's like to be homeless, particularly during this pandemic," said Mission Australia CEO James Toomey.
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Before the pandemic hit Australia, an estimated 116,000 people - including 44,000 children - were classified as homeless across the nation.
With limited housing resources and temporary accommodation options around the Riverina, caseworkers are concerned about the problem on a local level may be far more hidden than the official numbers suggest.
"To support people experiencing homelessness to stay well, reduce the spread of the virus and ultimately end homelessness, appropriate accommodation must be available, right across our country," Mr Toomey said.
Social distancing orders and restrictions on gatherings in Wagga have also forced challenges for those who would regularly feed those with no fixed address.
"We are very concerned about the impact of this public health crisis on people and families who are homeless or who are at risk of being pushed into homelessness," Mr Toomey said.
"More needs to be done to ensure that people are looked after, safely and appropriately housed and are able to receive support from the community services they need."
To build awareness for the issue on a national level, Mission Australia is encouraging the community to flood social media with #MothersInPyjamas photos at the weekend, calling for followers to donate through the charity's website.
"We'd love for as many children, mums, dads, carers, uncles, aunties, grandparents and friends as possible to partner with us in our ultimate goal of ending homelessness by participating in a virtual pyjama party for Mother's Day this year," Mr Toomey said.