I did some things at school that I'm really not proud of and caused me great pain.
Don't get me wrong, I was a good student who captained the school rugby league and cricket teams but when it came to the wider world I was more clueless than Alicia Silverstone could ever be.
If there was a class in Social Conventions and How Women Work it would have taken me 11 years to finish Year 12.
It's not like I grew up in a secluded commune with no access to television (although to be fair for most of my childhood our TV only received two channels, NRTV and ABC).
I was simply the eldest of three boys to hard working parents who didn't have a girlfriend until I got to uni and alcohol got involved.
Actually, that's not completely true.
I went steady with Alanna Harrigan in Year Five but had no idea what that meant so never spoke to her again; Katrina Brown and I went out for two months over the Christmas school holidays between primary school and high school during which time we saw each other exactly zero times.
I was George Costanza a decade before Seinfeld existed; if Katrina couldn't find me she couldn't break up with me.
That stood as my longest relationship for more years than I'd care to admit.
These next two stories are horrifying and so ingrained in my psyche that they can't not be true: In Year Seven I became so besotted with a girl by the name of Debbie Riley that I wrote a knock-off version of New Kids on the Block's breakout hit 'You Got It (The Right Stuff)'.
And I gave it to her.
Well I didn't, but one of my mates who was confident enough to talk to attractive girls did. Whoever it was must have been giddy at the humiliation I had just willingly inflicted upon myself.
For 30 years whenever I see mates from school that's the first thing they mention. Grinning like idiots.
The other incident also occurred in Year Seven only this time during Mr Murphy's Science class.
I liked Craig McLachlan and Check 1-2. Believe it or not but in 1989 lots of people did. So I put a photo of Craig McLachlan on the cover of my science book.
Did I mention I was clueless?
Mr Murphy hammered me and as I scanned the room at all the sniggering faces I realised the other 12-year-old boys were now covering their books with bikini girls cut out of the latest issue of Waves magazine.
They'd moved into a stage of maturity of which I was still blissfully unaware, which brings me to my son.
He's ten and this chain of thought was sparked by simply washing up his lunchbox one Monday night.
This one in particular is a Mambo lunchbox so it's cool for a kid in Year Four. No one really understands why Mambo is cool but plenty of people think it is so the rest of us just nod and go along with it.
Dogs farting musical notes and misshapen heads; never not funny.
He's also got a Pokemon school bag and I'm wondering whether it's time to move him up into something that cruel pre-teen boys won't tease him about.
Like a Mambo bag. Because Mambo bags are cool. Everyone knows that.
But I like the essence of innocence that he still carries. We haven't let him watch Deadpool even though almost every other kid in his class has seen it. We carry on the tradition around gift giving at Christmas even though I suspect he knows the truth.
I don't want my boy to grow up too fast but I also want to protect him from the excruciating embarrassment that I put myself through as a kid through sheer naivety.
You see my predicament.
I still don't know what to tell him if he ever asks about the best way to impress a girl but I can thankfully point to his mother and show him that there is hope for everyone.
Even a shy hopeless romantic kid from Coffs who still can't figure out how he got so lucky.
Perhaps it's best I let him figure it out for himself after all.