Sit and TellSign in

For getting closer to the people who raised you

The real conversation with your dad
keeps not happening.

Once a week, Sit and Tell asks your dad or your mom one question worth sitting with, and gives them a week to think before they answer. You get the answers to the questions you don’t even know to ask yet: how they think, not just what they did. And the conversations you already have start going deeper.

Start with your dad See how it works

The thing nobody says out loud

You’re slowly forgetting how the people you love think.

Not the big stories. The small, true things. The way your dad reasons through a hard call. What your mom actually believes about money, or forgiveness, or staying when it gets hard. The things you half remember and can’t quite hear in their voice anymore.

They’re getting older. You keep reaching for the real conversation and it never quite lands. “How are you” is too small. And sitting them down to ask “so, what’s your wisdom” puts them on the spot and gets you a shrug. So the weeks go by, you talk about the weather, and the questions you actually carry stay unasked.

Why this exists

As I got older and had kids of my own, I started realizing that some of the things my dad told me when I was young, I just wasn’t ready to hear yet. Year after year I keep finding out how right he was. But I can’t remember exactly what he said, or how he said it.

Then my dad told me he’d called up his own father, my grandpa, who’s in his eighties, and asked him point blank if he had any wisdom to share from his life. And my grandpa didn’t really have anything to say. My dad was genuinely hurt by it. I felt for both of them. My dad came looking for something he didn’t get, and my grandpa got blindsided by a huge question out of nowhere and felt put on the spot.

Sit and Tell is the thing that would have saved that conversation, for both of them.

How it works

One question a week. A week to think about it.

1
A real question arrives
Once a week, one question lands for the person whose thinking you want to know. Just one. Never a pile of homework, never a thing to feel behind on.
2
They get a week to actually think
No being ambushed. They sit with it on their own time, over coffee or on a drive, and answer when the real answer shows up instead of the off-the-cuff one.
3
A gentle follow-up draws out the story underneath
When they answer, a kind follow-up asks the one more question you’d have asked if you were sitting right there, and the reasoning or the story underneath comes out.
4
Each of you on your own schedule
You both pick your own day. They answer on theirs, you read on yours. It’s built for two people whose weeks never line up. That’s the whole point.

The Sage

The one with the wisdom to share, usually a parent or grandparent. Signing in is a single tap from an email, the text is large, and one question takes five quiet minutes.

The Steward

The one who tends it, asks the questions, and keeps it for the family. Usually the son or daughter who started the whole thing.

One real answer

This is what you get to keep.

What a single question can pull loose. The kind of thing that never comes up at dinner.

Hard times

When things fell apart, what actually helped you get through it?

The winter I got let go from the plant, I didn’t tell your mother for nine days. I’d put on my coat every morning like I was headed in, drive to the library, and sit in the lot until it was a believable time to come home.

What got me through wasn’t a plan or a savings account. It was the morning she found out, and she didn’t say one word about the money. She made two cups of coffee and sat down next to me. I learned that the thing you’re most ashamed of is usually the thing that, the second you say it out loud, stops being so heavy. I just wish I’d made that second cup of coffee myself, a week sooner.

A gentle follow-up

You said you were trying to protect her. Looking back, what do you think you were really protecting?

Myself, mostly. The idea that I was the one who had it handled. Forty years old, and I thought being needed and being able to provide were the same thing. They’re not. She didn’t need me to have it handled. She needed me to let her in.

What it actually changes

You stop missing each other.

The answers are the obvious part. The real thing is quieter. Week by week, the person answering starts thinking a little differently, and that new thinking shows up in your normal calls and your normal visits, without either of you trying.

You get back the conversation you kept reaching for. The app isn’t the whole relationship. It’s the small weekly thing that reshapes all the rest of it, and pulls the two of you closer than a question on a screen has any right to.

Questions

Things people ask

What if my dad isn’t good with technology?+

That’s exactly who this is built for. He gets a plain email, taps one link to sign in with no password to remember, sees one question in large type, and types or even speaks his answer. If an 82 year old can’t do it in five minutes, we treat it as broken.

How often do questions come?+

One a week, and only one, on purpose. The weekly rhythm is the product. It keeps it from ever feeling like homework, and it’s what gives the week to think that makes the answers real.

Can I add my own questions?+

Yes. The Steward can send their own questions to the front of the line, so the things you’ve always wanted to ask get asked, in your own words.

Is it private?+

Completely. What your family writes is yours, walled off from every other family, and it’s never used for anything but the two of you. We will never share or sell your data. Ever. Period.

What does it cost?+

Forty nine dollars a year. One plan, no tiers. If it’s not right for your family, write us within 90 days and we’ll refund you in full, no questions asked.

Ask him this week, while it’s an easy question.

One question a week, a week for him to think, and the kind of answers you’ll be glad you have. Start the conversation you keep meaning to have.

Start with your dad

The real conversation with your dad keeps not happening.