In Derech Eretz Rabba (Ch.5), we find an expression that speaks to the conundrum you face as a parent of teenagers: kabdehu v'hashdehu, be respectful and be suspicious. You want to respect his privacy yet you wonder what he's doing in private. You want to trust his judgment and you worry that he doesn't always make the best decisions. He wants you to let go but you still want to know where he's going. You're ambivalent and quite sure about only one thing; that you mustn't reveal your ambivalence to your teenage child. And that's your only mistake. Because it leads you into doing the one thing you most wish he wouldn't do to you. It leads you to deceive him.

Your ambivalence is appropriate. You want to give your teen more independence, and you want to trust him with his privacy, but you don't entirely trust him and you want him to depend on you for guidance. What's the best way to address this puzzling situation? I think an example would be helpful.

Here are some excerpts from a conversation between a father and his teenage son.

Yossi, you got out of school at 6, and you should've been home by 6:30. Why didn't you get here until 7:15? Where were you?

At Eli's. We were working on a project together.

So you don't mind if I call Eli's parents to confirm that?

You don't trust me!

This isn't about trust!

Let's pause the conversation right here. At this point, dad has made it clear that he wants to confirm the veracity of Yossi's statement that he was at his friend's house. I would wonder, along with Yossi, why dad wants independent confirmation if dad does trust his son. If it really is not about trust, then what is it about? And where does this conversation go from here? If dad continues to insist that it's not about trust, the conversation devolves into a debate on why you would ask for confirmation of your child's statement if you do trust him.

There is an alternative. Here's how the conversation flows when dad responds to his son's statement more accurately.

Yossi: You don't trust me!

That's true, Yossi , sometimes I find it hard to trust you. Why are you reluctant for me to call Eli's parents to confirm that you were there? That would give you the opportunity to prove that you were telling the truth and that I was mistaken to think that you weren't.

Okay, fine, I wasn't at Eli's. I was at Public Library.

Doing what?

Why must you know everything that I do, why can't you just trust me?

Because you just lied, again.

Let's stop the conversation here. It's true that Yossi originally lied about where he had been after school, but then he told his father the truth, that he had been at the Public Library. Dad now heard the truth from his son who had the courage to admit that he had lied. Rather than thinking of Yossi as having no choice because his father "caught him," I would prefer for dad to see this as an opportunity to acknowledge something his son did well after having done something very poorly. I do not want dad to condone the lie. I want him to acknowledge the difficulty his son might have had in admitting the lie and telling the truth.

If dad were to say, "you see, Yossi, I was right, you were lying again, why should I ever trust you," Yossi would learn that the only thing worse than lying is getting caught. Next time he'll lie more carefully, and if he gets caught, he'll try to lie his way out of that, because his father taught him that admitting he lied just gets him criticized even more.

Here's an alternative. What does Yossi learn when his father says, "Yossi I really feel bad that you lied to me about where you had been. I appreciate your owning up to it now and telling me the truth. That took some humility and courage, and you did it well. Yossi, I would like to understand how to help you tell me the truth to begin with next time. What were you concerned would've happened had you told me the truth when I first asked you where you had been?"

What Yossi learns when his father speaks to him this way is that his father wants to trust him and that it's very hard for his father to trust him, sometimes. It's also hard for Yossi to be where his father expects him to be when he'd really like to be at the Public Library.

This is the conundrum of parenting teenagers. Dad has his concerns about Yossi being at the Public Library, and Yossi resents his father for not trusting him there. Yossi has no intention of looking at anything inappropriate at the Public Library. Dad is concerned that Yossi might be exposed to something inappropriate and have a hard time steering clear of it. Yossi wants his father to trust him to make appropriate choices when inappropriate choices are staring him in the face. Dad wants to shield his son from such temptations because he doesn't trust him to always withstand them.

So we are back where we started from. With one important difference. Dad still expresses appropriate and necessary suspicion. But he has added respect by being candid about it, and accepting the fact that his son resents him for it sometimes.

Nobody said parenting teens is easy. Check with your teen; he'll tell you being one isn't so simple, either.

Rabbi Yitzchak Shmuel Ackerman is a Licensed Mental Health Counselor with specialties in marriage, relationships, and parenting. He works with parents and educators, and conducts parenting groups for men and women. He can be reached at 718-344-6575.