By Abby West
August 12, 2012 at 06:00 PM EDT

I happen to think that Dave Chappelle was/is a comedy genius. Chappelle’s Show (2003-2006) was a master stroke in adult comedy. I miss it so much that when I do stumble upon a repeat on Comedy Central, I am incapable of flipping away. And that’s what happened the other night when I caught that classic Dave Chappelle/Wayne Brady episode from the beginning. Except that this time my kids were in the room.

I’ve been a pretty middle-of-the-road parent when it comes to my son and daughter’s media consumption — not too permissive and not too strict, I think. The biggest problem area has always been the video games my son got into, mostly first-person shooters, an experience he shared with his dad. (That’s for another post.) For the most part though, when they were younger their father and I tried to keep them separate from our primetime TV or movie viewings. I’m all about trying to keep things age-appropriate. But somehow when you go by your memory of a favorite thing, you can go astray. And as the kids have gotten older, the line’s gotten fuzzier.

Since they are 11 and 14 now, we are constantly bumping up against a lot of teen issues and having to adjust the boundaries of what they can and cannot see. But excessive cursing, violence, or racy sexual content are still pretty much no-go issues. And this skit had all of that. A year or so ago I wouldn’t have even entertained the idea of letting them see it. Yet somehow I rationalized that now it could be okay, and heck, might even be sort of “educational.” It’s a major contemporary comedy reference point, right? And we’re kind of connoisseurs of comedy in our house, so surely they should know the source material.

Yeah. Not buying it are you? Well, my daughter, the youngest, didn’t even pay attention. She was busy playing Temple Run on her iPod Touch. My son, the oldest, looked up from the computer long enough to watch, and then laughed at all the right things. Which I found bothered me because, I’d decided by the end, that was some pretty grownup stuff.

I again tried to rationalize that in order to find it funny he had to have that basic understanding that none of the shenanigans in it (shooting, drugs, prostitution–Lord, what did I do?) were normal, acceptable behavior. That it was the extremeness that made it funny in context of the setup. Score one for me, right?

And yet…that didn’t make me feel any better. All I wanted to do was revel in the shared experience. But the very fact that in between guffaws I spent most of the time thinking of what parts warranted a parental interjection, mentally cursing my flawed memory of the routine, meant that I knew on some level that I shouldn’t have indulged. We’ve had moments before when we’ve misjudged a movie we’d settled in to watch together and had to turn it off because I was uncomfortable with some aspect of it for the kids, but that was often when I hadn’t done my homework to get a good enough sense about it going in. I couldn’t say that about this time.

The skit is still funny, and I don’t think seeing it has scarred them for life or anything.  But it turns out that exposing them to it now was way past my comfort zone. I don’t know what the right age would actually be for them to watch it (even hindsight isn’t 20/20 on this) but for me,this wasn’t it. Well, there you have it. Parenting mistake No. 2,624.

What is the worst thing you’ve ever let your kid watch? Or at least the thing you regretted the most? And how did it happen for you?

Follow Abby @EWAbbyWest