That message also reveals a new piece of the puzzle - another name: Leah Marshall.
Pitkethley told the Herald that he's now happily married with two children and his wife has given the search her blessing.
He revealed that he wants "closure" from his quest to find Leah Spicer, with whom he shared a strong, fully platonic friendship at high school in the 1980s.
Pitkethley said although he harboured romantic feelings when the pair first met in 1982, when Pitkethley was in fourth form, he believed that Leah didn't share those feelings and didn't reveal his crush for fear of ruining their friendship.
The pair suffered constant jibes from friends who told them what a great couple they would make
They lost contact in 1994, when Pitkethley became engaged.
She visited him at home in Whanganui where he shared the happy news and Leah told him about her current, happy relationship.
The pair then embraced and Leah drove off into the distance. When she left Pitkethley told the Herald there was "a hole in my heart".
When Pitkethley's brother died from cancer two years ago he left Gene with a message: "Don't leave with any regrets," spurring him to search for Leah and deal with his "biggest regret".
If Gene Pitkethley finds Leah Spicer he says he just wants to catch up, but he knows it's a "two-way street" and she needs to want to make contact too.
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A photo of the ad was shared to Facebook, where opinion on Gene's quest for love was divided.
One woman said the ad was "so so cool and so so romantic" while another said that the plea was "potentially very creepy".
A man commenting noted that there must be a reason that Gene was reaching out after such a long time: "You know she's hot if a dude is reaching out on the classifieds," he wrote.
It's not the first time that newspaper classified ads have been a forum for romance, with an American man taking out an ad in the Herald last year to try to find love for his three sons.
Neil, from Oregon, placed a classified ad in the Herald looking to set his sons up on blind dates with Kiwi women during their holiday in New Zealand.
"We are from the States [Oregon], visiting your beautiful country. My wife and I have three wonderful, successful, handsome, alas unmarried, sons between the ages of 28-32," the ad read.
"We are not expecting, just hoping, to introduce our sons to nice NZ daughters. At the very least we'll embarrass our sons and the truth is, we do find some enjoyment in that."
Following the family's two-week holiday, youngest son Benjamin revealed they were left red-faced by the ad - but also confirmed they all went on a few dates.
"Between my brothers and I, we went on a few one-on-one dates," Benjamin told the Daily Mail.
"[New Zealand women] are very intelligent, kind, friendly people. We love their accents. They were a lot of fun, everyone we met seemed nice.
"I think we will continue to stay in touch with the people we met. We really want to come back - it was a beautiful country."