At 30, he's the third oldest player at Richmond behind Shane Tuck and Chris Newman.
It's a leap from where he sat at Geelong last year, where seven players exceeded him in age.
He's also a husband to his high school sweetheart Whitney, and a father to three children.
While there aren't many other Tigers with kids – Tuck being one – it's the age of Stephenson's that sets him apart from the majority of AFL players.
His eldest daughter, Emilie, will soon turn 14, his son Patrick will soon be 12. Sophie, the youngest, turned 10 earlier this year.
Now in his second AFL season, Stephenson can reflect on the fact he's been able to share his journey with his wife and kids, who are rarely absent on game day.
The "hoops" are gone and the yellow and black guernseys have rolled into the family home, with the Stephensons now barracking passionately for a larger breed of feline.
"It's been fantastic and a massive bonus. For my wife and the kids, it's something they'll never forget so I'm pretty blessed to be able to share it with them," Stephenson told AFL.com.au.
"Patrick last year was rolling around the rooms with the Geelong Cats and this year he's rolling around with the Richmond Tiger boys.
"He wouldn't pass it up for quids. He loves it and the girls have had a lot of fun with it as well. It's a massive bonus that we can share these pretty good times in our lives with our kids."
The Stephensons have lived in Ballarat since 2002 after moving from the Riverina in New South Wales.
They're still there, with Stephenson boarding four nights a week with Whitney's cousin in Malvern East for ease in getting to Punt Road.
He goes home the night before the players' day off and stays there until the morning he's due back, and likes to occasionally "sleep in his own bed" before games.
Stephenson's entry into the AFL is notably different. He was the oldest first-time recruit in draft history when picked up at 29, becoming a Cat after winning three VFL premierships with North Ballarat.
He'd trained with AFL clubs over the years but never made it onto a list until the Cats came knocking in 2011.
He played eight senior games and won a fourth premiership in 2012 with the Cats' VFL side but the off-season acquisition of Hamish McIntosh saw his AFL dream end there – briefly.
He was disappointed, naturally, but understanding that these things happened.
So, he revisited his working life – he holds two trades, one as an electrician and the other as a telecommunications technician – and waited to see what would happen next.
"I knew there were discussions going on [with clubs] but there wasn't anything concrete until around the rookie draft," Stephenson said.
"I had a training run with the Richmond boys for a week or two and they went away to Cairns for their pre-season camp and I just had to sit around and wait.
"It was difficult being in the unknown. It was not dissimilar to the period where I've been training with clubs and they were a chance to take me but this time, it worked out the right way."
The Tigers used selection No.33 in the NAB AFL Rookie Draft to throw him a lifeline. The dream was alive again.
On the eve of the 2013 home-and-away season, after showing promise in the NAB Cup, Stephenson and ex-Demon Ricky Petterd were elevated to the senior list.
Last week against Port Adelaide the ruckman made his club debut at AAMI Stadium, with Whitney and his kids there cheering him on.
"It was really good to be out there. I've really enjoyed my time at Richmond; it's been fantastic and it was really good to get a win as well," he said.
Stephenson might be older than his teammates, have a different living situation and be raising a daughter who is just five years junior of his youngest teammate.
But none of that has affected his ability to fit in.
"We're really pleased for Orren. He's just one of those guys you certainly love having around your footy club," coach Damien Hardwick said.
"He's a great character, he fitted straight into our football club and it great to get a result for him, and for him to play as well as he did [against Port Adelaide]."
Jennifer Phelan is a reporter for AFL Media. Follow her on Twitter @AFL_JenPhelan.
