How to Truly Understand A Person

To truly understand another person, and to be understood, is a magical experience, and might be the most important step toward real connection.

But how do we actually do it? How do we begin to truly understand a person?

1. Look for Clues in Childhood

One of the best places to start is someone’s past.

What was their childhood like? Did they grow up with abundance or with lack?

What were their relationships with their parents? Did they feel freely loved, or did they learn to earn love through grades, good behavior, or constant striving?

What role did they play in the family— the peacemaker, the troublemaker, the overlooked middle child?

I recently had a long-overdue catch-up with a good friend from high school. I’ll admit, for years I had quietly judged him as stingy — he always vetoed trips, cheaped out on restaurants, and avoided spending money.

As our conversation deepened, he shared that as the middle child, he often felt his siblings received more attention and love — in both time and money. Since they always seemed to get a bigger allowance, he learned early to pinch pennies, never knowing when more would come.

The moment he told me this, my understanding of him shifted.

After 20 years of friendship, I saw him differently. His frugality wasn’t a flaw but a survival strategy. Once I understood that, my judgment softened, our connection deepened, and we both opened up more.

2. Suspend Judgement

That conversation with my friend reminded me that understanding someone requires giving them space — space free of your own judgments and attachments.

There’s a kind of surrender in it: putting aside your hopes, expectations, and assumptions about who you think they are, and allowing them to reveal themselves.

Recently, I interviewed a woman with multiple personalities. I asked if dating was difficult, since each personality had different tastes and preferences. She said no — in fact, honoring all her personalities made finding love easier.

I didn’t believe her. I kept pressing until finally she stopped me: “Where is your questioning coming from?” (as a therapist she had the awareness to ask that question)

I paused and realized — oh, I was projecting my own dating experiences onto her. “My bad,” I said. She smiled knowingly: “It happens.”

Understanding someone requires loosening your grip on your own narrative. The more mental attachments you bring into a conversation, the less space the other person has to be who they truly are.

3. Make Sure Their Story Makes Sense

Sometimes, people don’t even fully understand themselves. With honest and curious questions, you can help them get there.

I was interviewing a woman who told me she had only recently accepted that she wanted to date exclusively Christian men.

“Why would it not be okay?” I asked.

She said, “Because I want to be able to pray with my partner, to talk about faith openly. I want those conversations inside my relationship, not outside of it.”

I thought about what she said and realized she didn’t answer the question, so I pressed a little and clarified my question.

“I still think it’s interesting,” I said. “You said it’s okay to date Christians — like you needed permission. Why would it not be okay?”

She thought for a moment, then said: “Because we’re told to be so open-minded, to not lock in. And I think that’s true in many ways. But there are some things you shouldn’t compromise. For me, being with someone Christian is one of them.”

Her answer pointed to something broader — not just personal preference, but societal pressure. So I followed that thread. “Did you feel guilt around that? Shame?” I asked.

It was a leading question, which I sometimes get called out for, but I’ve learned that sometimes it helps to step into the vulnerable place first. To signal: it’s okay to go there with me.

She hesitated. “Yeah… I guess I was afraid of putting myself in a box. Of looking like a stereotype — that girl who only wants a Christian partner. I was judging myself.”

That was the moment. Together we named it: she wasn’t ashamed of her desire — she was ashamed of how she would be perceived by others and herself for owning that desire.

Later she went on: “I’m in a season of life where I’m trying to break away from thinking I need permission for everything — not just in dating, but even at work or with friends. Permission to speak up, to say what doesn’t sit right with me.”

Her story wasn’t just about dating anymore. It was about voice, agency, and learning to trust her own desires.

By pressing gently, by clarifying, we uncovered something deeper: the hidden permission slips she thought she needed, and her desire to live without them.

Why It Matters

Understanding someone means:

• Looking at their past and how it shaped them.

• Giving them space, free of your own projections.

• Seeking their deeper truth, making sure their answers really get to the heart of what you’re seeking to understand. Clarify. Satisfy your curiosity.

For me, it’s deeply fulfilling to know a person truthfully. It makes me feel more connected — not only to them, but also to myself and the wider world.

The more I understand others, the more I understand myself. The more I understand myself, the more I understand the world.

And in that exchange, I catch glimpses of what is, and what could be — and to me, that feels nothing short of magical.

With curiosity,
Eric

P.S. 

If you need help working through your story or creating a new one, I’m here to help. Email me “CURIOUS” to connect for 1:1 coaching.

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