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The year was 1998 and a 19-year-old Ai'i registered a lone national provincial championship appearance for Auckland in a 33-22 win over Southland in Invercargill on October 10.
Since then Ai'i has gone on to play for Northland and gain another 47 caps for Auckland. He has also represented the Hurricanes and Blues in Super Rugby and spent time in France and Japan - plus don't forget his exploits on the sevens circuit.
The better part of 15 seasons on and Ai'i, 33, will slip in to the No 10 jersey for Auckland at Waikato Stadium today with 19-year-old first-choice pivot Simon Hickey hobbled by a groin problem.
In today's starting XV, Auckland fullback Lolagi Visinia is 20, centre Malakai Fekitoa is 21 and wings Saleaula Silipa and George Moala are both 22. Outside back Vince Aso, who is in the reserves, is only 18 and all these tyros were more worried about picking up a ball in the playground when Ai'i first laced up his boots for Auckland all those years ago.
Ai'i, who played for club side College Rifles this year and turns 34 in nine days, said the new boys gave him a dose of enthusiasm.
"They keep me young at heart as well," Ai'i said. "It's good to see these young blokes coming through and it's an opportunity for me to help them with my experience and enjoy their company on the field."
Those young blokes are also happy to remind Ai'i he is one of the elder statesmen in this year's ITM Cup.
"A lot of the young boys give me a bit of crap saying 'old man' or 'I was just a thought in my parents' mind [when you first played]'," Ai'i laughed.
"But for me it's quite humbling because I've seen a lot of great players, younger than me, retire at an early age and for me to keep playing, it's a good thing."
Ai'i played from the bench for Auckland in last weekend' 51-15 rout against Taranaki in New Plymouth, which marked his first appearance in the blue and white hoops since 2005.
The 1.70m utility wasn't required by Auckland last year and spent time with Northland but his veteran experience is gold this season in an exciting Auckland squad.
Wayne Pivac's side have won their first five games and only a diehard Waikato fan would bet against them making it six from six today.
Considering halfback Piri Weepu blew out 30 candles last Saturday, Ai'i and the former All Black will make up the oldest inside back pairing in the competition this weekend.
"He's excited actually, I think he feels a lot more mature now," Ai'i said of Weepu. "Being 30 there's only three of us in the 30-club but we just mix it up with these young boys."
Injured No 9 Junior Poluleuligaga is the other member of the older brigade at 32.
Ai'i said he still had a couple of good years left in him and wouldn't rule out another stint offshore if the offer was right. He spent most of this year setting up a gym with some friends in South Auckland where he is based, while his prowess as a sevens player has taken him to Sri Lanka and England.
Kick-off in Hamilton is at 2.35pm
Auckland: Lolagi Visinia, George Moala, Malakai Fekitoa, Hadleigh Parkes (captain), Saleaula Silipa, Orene Ai'i, Piri Weepu, Peter Saili, Sean Polwart, Joe Edwards, Patrick Tuipulotu, Liaki Moli, Angus Ta'avao, Tom McCartney, Pauliasi Manu. Reserves: Gafatasi Su'a, Sam Prattley, Jack Whetton, David Whitecliffe-Davies, Wayne Ngaluafe, Vince Aso, Tenina Sauileoge.
Waikato: Trent Renata, Tim Mikkelson, Save Tokula, Jackson Willison (captain), Semisi Masirewa, Wharenui Hawera, Brad Weber, Adam Burn, Jack Lam, Rory Grice, Sam Kilgour, Brian Alainu'uese, Paul Alo-Emile, Brayden Mitchell, Toby Smith. Reserves: Vance Elliott, Latu Talakai, Chris Middleton, Jono Armstrong, Mick Snowden, Sam Christie, Dylan Collier.