MomLogic discusses Maternal Truths, and how much should we tell our kids about our pasts.
I have often thought about this very question. Without going into detail, I have had more than a few evenings (and mornings) that one could call learning experiences. However, I didn't always learn from them the first (or third) time. No one really ever talked to me about sex or drugs or interpersonal dynamics as a kid (besides the health teacher, and who listens to her?). I am still waiting for my mother to have the "sex talk" with me, but I guess she realized I figured it out on my own. I did have a Catholic upbringing, so Sister Janine hammered into my head that all the fun stuff was a sin, and probably a Cardinal sin at that; so she kept me in line till about 16. But then I met some people, tried some things, and started to realize that certain forbidden fruits were kind of fun and really not as dangerous as advertised in PSAs and filmstrips.
And college was a wonderland of freedom and experiments - positive, fun, scary, amazing, mind-altering, soul-crushing, heart-breaking, life-changing and just plain new experiences. But I think the most learning-intensive time of my life was the early 20's. I lived and partied and made some questionable choices. But I did it my own way (well, with a splash of peer pressure). And boy, do I have some stories!
So now I sit here as a mother in her early 30's thinking ahead to when my son is closing in on the teen years: what am I going to tell him about my own adolescence? (And now I have to add that his father has also had some fun and broken a couple of rules (and laws), but I think that Dads and Sons can have their stories and it is just different. A guy thing, maybe.) And I've come to this: I am going to be honest when he asks me questions about my own experiences, but I'm not volunteering stories or details. I'm not going to volunteer the story of how I lost my virginity, for instance, but I will answer his questions about how old I was, who it was with, etc. Same goes for drugs and drinking and any other topic.
My son is going to know me well enough to know that I was no goody-goody and he'll also be able to tell I'm lying if I try "never touched the stuff". I want him to be honest with me about his questions and experiences. I may not like what he tells me, but together maybe we can help him avoid some of the learning experiences that I regret or that could get him killed or in jail or guilt-ridden. I don't want my kid to be perfect or never take a risk. I want him to relish life, even the darker sides. Because honestly, that's where they hide a lot of the fun.