Even if your teenager feels like he hasn’t learned much at all during the school year, one of his classes has probably taught him more than the others. Find out which one it is. And if this first question goes well, you can naturally follow up with: “Which class are you learning the least in?” But it’s best to start with the positive version first. If asked first (or alone) the negative version of this question sounds like you’re teeing up a pep talk or something judge-y. Continue reading Which class are you learning the most in so far? →

Arrested. Haha. That’s what caught my eye about this series of questions. It’s edgy enough perhaps to get a response! You know? Throw ’em a curveball! Follow up with these other career categories and if it goes well, try out: “What future would your friends say is most likely for you?” Continue reading Who at school is most likely to be arrested? A standup comedian? A millionaire? →

(Online technology) + (Asking your teenager for help) = (Recipe for a good interaction)

Plus you can always expand the conversation by asking your teenager where he found the videos he’s recommending, what he thinks grandma will say, and if he has any video recommendations that YOU might like. Continue reading Grandma was asking about Youtube. What would be a good, funny Youtube video we could send her so she can see how it works? →

There’s a higher chance of your teenager answering this question if only because he gets to call you old. I’ve seen this question lead to some very interesting discussions. I think it’s because you as a parent are being intentionally vulnerable in asking it. And from your teenager’s perspective, if the adults in the world are growing old, then that means the teenagers are growing up. Grown up is how he wants to feel. Continue reading How old is “old”? →

I’ve gotta come clean – I’ve got about as much insight as the next random person about what will or won’t work with a teenager. I can see this question working with some of the teenagers in my life but it all depends on the relationship you have with them. (And it depends on the day you ask…) Give this one a try, though. It’s hypothetical enough to be fun and allows people to reinvent themselves a little bit which is what adolescence is all about. Let us know how it goes! Continue reading If [name] wasn’t your name, what would you want your name to be? →

Take a trip down memory lane. There are less hormones on that lane. This question gets your teenager thinking about the good old days. And saying “when you were a kid” helps solidify that you are starting to see your teenager not as a child anymore. He’ll dig that. Continue reading If we could repeat one of the vacations we took when you were a kid, which one would you want to repeat? Why? →

This question is solid because it implies that you understand how weird and tumultuous the teenage years can be. You’re not telling your kid to be different in any way. You’re just asking how the landscape is different (and how she’s different). Continue reading What’s the biggest difference for you between this year and last year? →

Asking your teenager for “advice” (no matter how small the issue) can lead to a conversation that will leave you both feeling valued. Your teenager will welcome the role-reversal and you’ll actually get to talk to him. He’ll probably have opinions about what’s fun/impressive to share with guests. Continue reading We’re having guests stay with us from out of town. What do you think we should show them? →

Just kidding.  That’s not actually a good question.  But if you clicked to this section, then you probably have a teenager in your life.  You need all the humor you can get.  Hang in there! Continue reading Will you just listen to me?! For once in your freakin life will you listen?! →