About AskForever

For people who want to truly know someone. Not just know about them.

Ask Questions That Matter

Most conversations stay on the surface.

"How was your day?"
"What do you want for dinner?"
"Did you see that thing online?"

These aren't bad questions. But they don't reveal anything. You could have the same conversation with a stranger.

Truly knowing someone requires different questions.

Questions where you have to dig into your soul to find the answer. Questions where the response isn't society's truth. It's their truth. Questions that reveal something transferable: not just what someone prefers, but who they are. How they think. How they'd respond to situations you haven't even encountered yet.

That's the difference between knowing about someone and knowing them.

When you know someone that deeply, you can predict what they're going to say, think, or be. That's real understanding. That's what AskForever is built around.

Two Stories

The New Couple

Three months in. Everything feels right. The chemistry is there. The conversations flow easily.

But here's the thing about easy conversations: they tend to stay easy. You talk about movies, weekend plans, mutual friends. You learn their coffee order and their sleep schedule.

You learn the logistics of their life.

But do you know their soul?

Do you know what they believe about money? About family? About what happens when things get hard?

There's a window early in relationships. A window of openness. Both people are willing to share, willing to go deep, willing to reveal themselves. But that window doesn't stay open forever. Life gets busy. Conversations get routine. And suddenly you're years in, realizing there are things you never talked about.

The couples who last aren't the ones who avoid hard topics. They're the ones who tackle them early. Before they're three years in, wondering if they missed something.

The Established Relationship

Five years in. Sitting at the same table, eating the same takeout.

The silence isn't awkward. It's comfortable. That's what they tell you to aim for, right?

But comfortable can become autopilot.

"How was work?"
"Fine. You?"
"Good. Tired."

These aren't questions. They're status reports. Data exchanged to keep the household running.

At some point, you stop meeting each other's souls.

Not because the love is gone. Because you stopped asking the questions that reveal who someone is becoming.

The Realization

I remember the moment it clicked.

I put my fork down and asked a question I'd read somewhere:

"If you could instantly master one skill, what would you choose, and why?"

She stopped. The autopilot look vanished.

"Violin," she said. "I've always wanted to make something beautiful that disappears as soon as you stop playing it."

We talked for two hours.

I learned she thinks about legacy. I learned she loves sad music. I learned something new about the person I thought I knew completely.

The answers were always there. I just stopped asking the right questions.

Why I Built This

Hi, I'm George.

I've always been the person who wants to skip small talk. The best moments of my life have come from deep, honest conversations, with partners, friends, even people I'd just met. The kind where you walk away thinking, "I didn't know we could talk like that."

Over time, I realized I had a skill for finding the right question at the right moment. The kind that opens people up. The kind that reveals who someone really is.

In my own relationships, I made it a point to truly know the other person. In and out. Their feelings, their desires, their trivialities. Where their future needed to go. And here's what I learned: even when those relationships ended, they ended well. Not because ending is easy. It never is. But because we both understood each other deeply enough to know why. There was no blindsiding. No wondering "what went wrong." Just the maturity that comes from actually knowing someone.

Most people don't have that. Not because they don't care, but because they don't know what to ask.

I wanted to give that skill to everyone.

So I spent a long time collecting questions, testing them, organizing them by depth and topic. Questions I would actually ask. Questions that reveal who someone is, not just what they prefer.

AskForever exists so you don't have to figure out what to ask. You just open it up and start.

What We Offer

For New Couples: 365 Daily Questions

One question a day for a year. Delivered by email.

Designed to progressively reveal what matters: values, dreams, fears, how they handle conflict, what they believe about family and money and the future.

By Day 30, you'll know their views on the things that matter.
By Day 365, you'll know them more deeply than couples who've been together for years.

Know if they're the one, before you're three years in.

Learn More About 365 Questions

For Anyone: Deep Conversation Starter Deck

250 questions for deeper connection with anyone: partners, friends, family, even someone you just met.

No daily commitment. Use it whenever you want more than small talk.

Great for date nights, road trips, or any moment when you want a real conversation.

The skill to connect with anyone.

Learn More About Starter Deck

What AskForever Is (And Isn't)

This is not therapy. We facilitate conversation, not treatment.

This is not a compatibility test. We don't score or judge your relationship.

This is not a guarantee of forever. We guarantee knowing. Truly knowing someone. What you do with that understanding is up to you.

This is for people who want to build intentionally. Whether that's a new relationship with the right foundation, or an existing one that deserves more than autopilot.

What's Required

AskForever works when both people are willing to be open.

If someone is stonewalled, defensive, or closed off to the point where even the best questions can't reach them, that's not a question problem. That's something deeper. That might require therapy, not a conversation tool.

We assume you want to connect. You just need help with what to ask and when to ask it.

"Questions are invitations. They only work if someone's willing to accept."

"The right question can start a conversation. It can't force one."

The Promise

AskForever doesn't promise that you'll stay together forever.

It promises that you'll know.

Know who they really are. Know what they believe. Know how they think. Know whether your paths are aligned. Or whether they're not.

The deepest form of love is truly understanding someone.

Understanding what you can give them. Understanding what they need. Understanding whether you're meant to walk the same path. Or whether you're not.

That understanding lets you love fully. Or leave gracefully. Either way, you'll know.

And when you know someone that deeply? You don't just understand one relationship. You gain a skill. The ability to connect with anyone: partner, stranger, coworker, family. You develop empathy. You learn to respect differences instead of fearing them.

Someone who uses AskForever doesn't just walk away with better conversations. They walk away saying:

"I understand them on a different level."

That's the promise.

Know them. Really know them.

If everything ended for you tonight, is there anything you'd seriously regret not saying to someone? Why haven't you said it yet?

If you could magically get the honest answer to absolutely anything about your life or future, what would you ask?

What is the absolute worst memory you have?

When was the last time you cried by yourself?

What was the very first thing you noticed about me, and what was your initial impression?

What do you value most in a friendship?

Ready to start?

Choose your path to deeper connection.

Get in Touch

Questions, feedback, or just want to say hi?

Email: hello@getaskforever.com

I typically respond within 24 hours.