Everyone starts a virgin and sex won't blow your mind: the things I wish I had known as a boy

Piece of pie: sex isn't the be all and end all, even if that's hard to comprehend while in your teens - Film stills

Boyhood, for many, is toxic. It's a time when we are taught to beat down our feelings and to see success in purely macho terms. Sporting prowess is everything; academic ability is something to be ashamed of; and members of the opposite sex are something to be used and abused. Boyhood, for many, is toxic beyond belief.

This isn't a new hypothesis, of course, it's just that we have only begun to talk about it relatively recently; and last month, comedy actor Robert Webb's book How Not To Be A Boy shed more discussion on the issue. It tells of Webb's difficult adolescence with his emotionally distant father; and how his Lincolnshire schooldays only further stunted his emotional life.

All men will recognise some of Webb's experiences, no matter how loving their family backgrounds or forward-thinking their schools were. And we can wonder about how different we would have been, had our formative years been otherwise. With just an extra dollop of information or insight, how might we have turned out?

I, for one, wish that I had known a thing or eight about navigating male life when I was a teenager at an all-boys' grammar school...

Hugh Grant imparts life lessons in About A Boy Credit: Film Stills

1. Everyone is a virgin for a while...

When I was 16 I had an evening job selling double glazing on the phone (yes, I know). The other canvassers were all a few years older than me and one night when the conversation turned that way I insisted – subtly, a gentle nod of the head, a knowing look in my eye – that I had, in fact, been naked with a chick at least once. For a few seconds, I felt the respect blossoming. And then the sceptical glances flashed between them. They too had been 16-year-old liars once.

When I think back now to how it did happen for me – after my university freshers' ball, in black tie, rather than ten minutes in the local park like more than one of my schoolmates – I'm glad it was that way. It's more of a story to tell and stories are important as we reach adulthood; usually much more important than being the first to achieve something.

2. ...And sex won't blow your mind

It will run the gamut from a waste of an hour to an evening you want to repeat every night for a month. But, contrary to what Matt Parker told me during PE, having done it doesn't change everything and there really is more to life.

3. You don't need to be a sports star

Scoring the winning goal on a football field – or in my case, a very rare try on a rugby pitch – is a great feeling, but it doesn't last. Moments like those are easy to understand and that's why teenagers, always looking to the next hour rather than the next year, focus on them.

For most of us, success at slower pursuits – writing, political engagement, scientific discovery, or just being a good egg last longer and count for more in the long run.

4. Wearing all black isn't that cool

OK, it is from time to time, but if you spend the first year of university entirely monochrome, you will eventually be told to stop it.

Stop it: Marilyn Manson has never taken the hint Credit: Getty

5. Girls aren't just for kissing

They're pretty good for having lunch with and shooting the breeze with. Also for very specific advice on seducing their friends.

6. Everybody hurts

The REM song may have been on repeat at the sixth-form disco, but even if we listened to the words, we never really believed them. It hardly made sense when Arnold Schwarzenegger was the most famous man in the world. Now friends who I always saw as tougher or happier or more satisfied than myself are paying £65 per hour for therapy and I'm sure that it stems, at least in part, from a refusal to accept and address the sadnesses and conflicts we felt when we were moulding our adult selves, and the fact that talking about our emotions was something to be roundly and brutally mocked.

7. And they're all busking it

There were guys I was at school with who just seemed to have the sunlight shine on them. They seemed destined for greatness like the son of Caesar and I just accepted that I wasn't going to be the same. But of course they were making it up as they went along and letting everyone fall in around them.

8. Beer will taste awful at any age

Aged 17 I couldn't work out why anyone drank it. I still can't. So that was quite a lot of money wasted in the pubs of Canterbury.