You look forward to so many milestones with children: the first step, the first day of school, the first time your kid stays home alone, the first time he gets behind the wheel.

You don’t anticipate the first time you unintentionally tell a slightly off-color joke to your eleven-year-old son and his friends. And they get it. And they think it’s funny.

This happened last night at my house. Damn those Mad Libs.

The boys’ reaction to my Mad Libs gaffe confirmed for me something I’d already been planning for this summer: a renewed set of conversations with “Jack,” who will enter sixth grade in the fall, about tough topics I’ve addressed in the past: drugs, alcohol and sex. But while I’ve always been proud of the matter-of-fact attitude with which I’ve been able to approach these discussions, I realized that rather than getting easier to talk about these topics as Jack gets older, it will become harder because of one specific factor.

Now, on some level, Jack will actually understand what I’m talking about.

When Jack was younger, all of our conversations were theoretical. I’d like to think–indeed I hope–that they still are. But now Jack is at the age where he might actually be exposed to these things. I can pretend that none of the kids in his middle school do drugs or drink, but I know that’s not true. I can tell myself the kids don’t talk about sex, don’t experiment, but I know that’s not true, either.

The conversations Jack and I need to have now will be about real choices, about making good ones, even when faced with pressure from your friends. We need to talk about treating others with respect in the face of your own strong desires, and doing what you know to be right even when you really, really feel like you’d rather do something else. Knowing Jack, I suspect these will be mostly one-sided conversations. They’ll be uncomfortable for both of us, much more so than when he was a little kid who just wanted to know about the birds and the bees.

Because now he’s old enough to get the jokes about the birds and the bees. And if you can get the jokes, you need to have the real knowledge, too.

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