Last fall, I sat with my teenaged daughters and watched Juno, the much-talked-about movie depicting a teen’s emotional and physical journey through an unplanned pregnancy. There was much discussion afterward about what it’s like to be a pregnant teen — and my kids were all too willing to make the political personal.

My kids can do the math; I had my first daughter two months after my 18th birthday, and my second daughter before I turned 21. Sometimes they figure this makes me an expert on teen pregnancy and other choices that I made along the way. Discussions about their academic paths also tend to be dicey. After all, they were both present when I graduated from high school at the age of 23, and have vague recollections of mommy studying for university finals while they watched YTV in the living room.

The teenage years are full of change and challenge for kids, and the opportunities for making good and bad choices seem to multiply at an alarming rate. For parents, it can seem like having a ringside seat to an encore performance of their own formative years. So how much, and when, and how, should we share with our kids about our own teenage experiences?

truthiness with your teen

“I volunteer a lot less information than I used to,” says Kim Wilson, a Windsor, Ont., mother of two, Iain, 13 and Riley, 7. “We used to talk a lot about “when I was a kid,’ but as Iain gets older, the last thing I want him to do, in some cases, is use my experience as a guidebook.”

That’s fine, says Sarah Chana Radcliffe, a psychological associate in Toronto and the author of Raise Your Kids Without Raising Your Voice (HarperCollins Canada). “There’s no obligation to share something you’re more comfortable keeping private.” However, if things are common knowledge, “It’s probably better to share,” she says. Hearing it from you may be better than hearing others’ versions of the story. And your experience, or the experiences of those you know, may serve as a cautionary tale, especially if it is something you are not so proud of. In that case, “Be as straightforward as possible,” says Radcliffe. “Yes, I did it. I regret it. I understand you might feel differently, and I can’t stop you from doing it, but I have confidence in your ability to make the right decisions.”

If you can communicate the feelings and emotions that came into play during your teen years, your child may also feel empowered to make different decisions. “I’d like to think that I can help him see consequences or alternative choices he may not have thought about,” says Wilson.

but you did it too

When it comes to risky behaviour like experimenting with drugs, drinking or sex, teens are likely to defend their actions with a well-aimed, “You did it and you turned out okay.” This can be the starting point for a conversation that reinforces the difficulties encountered, or an opportunity for you to illustrate that many others weren’t as lucky. But don’t be surprised if you don’t get the result you were looking for. “If your purpose in sharing is trying to save your teen from learning the hard way, it’s probably not going to work,” says Radcliffe, who encourages parents to acknowledge out loud that their child needs to make his own decisions. “Give your kids the power to own their choices by showing that you own yours. It’s okay to stress that you regret some things, if you do.”

good timing

These conversations should never take place when you or your child are upset. Instead, look for the teachable moments when they often take the lead — like watching Juno — and being faced with questions you knew would come eventually.

In my case, having children as a teen was not the end of the world, but it wasn’t easy either. My daughters have literally lived the consequences of their parents’ early actions, things like financial hurdles and emotional struggles. Has this stopped them from making poor choices, or caused them to make different ones? Sometimes, yes. And sometimes, there’s no counsel in the world that will make a teen believe he is not infallible. “Do as I say, not as I’ve done” may fall on deaf ears. “A better message is that you have confidence in their good judgment,” says Radcliffe.

Shelley Divnich Haggert realizes that her teenagers might not learn from her experiences, but that doesn’t stop her from hoping!