You Probably Shouldn't Tell Me

There is a particular sentence I have learned to pay attention to.

“I probably shouldn’t tell you this.”

For most of my life, my instinctive response was probably the same as yours.

“No, tell me.”

Once someone has started a story, it is remarkably difficult to accept that you might not get to hear the ending.

I learned this lesson in a relatively harmless way at Woodhaven.

One day, I walked outside while some of the boys were sitting in the sunshine talking. I joined them just as someone was in the middle of saying something.

He stopped.

“Oh. I probably shouldn’t say that in front of Jill.”

Now I really wanted to know.

So I did what I used to do.

“No, no. Go ahead.”

He did.

It turned out to be exactly the kind of conversation that should have stayed among teenage boys sitting outside in the sunshine.

I blushed.

They laughed.

And I remember thinking, He was right.

His judgment had kicked in. Maybe thirty seconds later than it could have, but it had kicked in.

And I had talked him out of listening to it.

These days, when one of the boys starts to say something and then decides I am probably not the appropriate audience, I let him stop.

I have gotten pretty good at that with them.

I have not always been as good at it with the people closest to me.

When someone I love was in early recovery, he would sometimes start telling me something and then hesitate.

“I probably shouldn’t tell you this.”

I would push.

“No. Tell me.”

Sometimes it was another detail about his use. Sometimes it was something that had happened while he was high.

I thought I wanted to know.

Until I knew.

And then I was left holding a piece of information that changed absolutely nothing.

It did not change where he was that day.

It did not change his recovery.

It did not change what had already happened.

There was nothing for me to fix, prevent or even respond to.

It just gave me something new to picture.

Something new to worry about.

Something I could not unknow.

For a long time, I confused knowing with being prepared. I believed that if I understood everything, maybe I would not be caught off guard again. That somewhere in all those details was a way to keep the person I loved safe.

But there are details from the past that cannot make anyone safer.

They can only become yours to carry.

That was a difficult distinction for me to learn.

There are things I absolutely need to know. If someone is in danger, if information changes a decision I need to make, if knowing allows me to help or protect someone, I want the truth. All of it.

But there is another kind of knowing.

The detail that changes nothing.

The story that has already ended.

The information that does not ask anything of me except that I live with it once I have heard it.

I do not need all of that anymore.

Somewhere along the way, I also started hearing “I probably shouldn’t tell you this” differently.

I used to hear the unfinished part.

What were you going to say?

Now I notice something else.

The person stopped.

Maybe they realized the story was not theirs to tell. Maybe they realized I did not need to hear it. Maybe they simply recognized, a little late, that saying it out loud was not a good idea.

That pause is judgment.

I used to help people override it.

Now, more often than not, I try to respect it.

Not because I have stopped being curious.

I have not.

If you start a good story in front of me and then announce that you cannot finish it, some part of me is still going to want to know.

I just no longer believe that wanting to know means I need to know.

That has mattered most in loving someone in recovery.

There was a time when not knowing frightened me. I thought safety lived in having every piece of the story.

I know differently now.

Some information helps me understand what I need to do next.

Some information simply gives my fear more material to work with.

I am getting better at knowing the difference.

So when someone stops halfway through a story and says, “Actually, I probably shouldn’t tell you this,” I still wonder.

I just do not always ask anymore.

Dr. Jill DeRosa

Dr. Jill DeRosa is Co-Founder and Director of Education and Family Programs at Woodhaven Recovery. With more than three decades of experience as a teacher, principal, and Assistant Superintendent, she brings a rare combination of educational leadership, lifelong personal understanding of addiction and recovery, and deep commitment to her work with young people and families.

Her perspective is shaped by both professional expertise and lived experience. She co-founded Woodhaven Recovery to create a supportive environment where teen boys and their families can find healing, connection, and the foundation for lasting recovery.

At Woodhaven, Jill helps shape academic and family programming, contributes to the broader vision and daily life of the program, and works directly with residents across many aspects of their growth, including recovery, education, college and career planning, and transitions. She also works closely with parents, offering guidance and insight as they navigate their own role in the recovery process.

As a mother who has lived alongside addiction and recovery throughout her life, Jill writes from a place of genuine understanding. Her work reflects a deep belief in the capacity of young people and families to heal, grow, and build meaningful lives in recovery.

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Before I Knew What I Was Hearing