Why Do I Struggle to Trust People When They're Being Kind or When They Seem Afraid?

The insecure mind has trouble understanding generosity.
The secure mind has trouble understanding fear.
Both wonder, what are you hiding?

I had dinner with an old friend a few years ago.

We hadn't seen each other in a while. We had a nice long conversation.

When the check came, he offered to pay, but I insisted, and quickly made the waiter take the card and charge it.

After that moment, he seemed odd the whole afternoon.

He was avoiding eye contact, and seemed to not want to talk anymore.

I got a little upset too. I couldn't understand why his mood suddenly had suddenly changed.


I decided to bring up his disconnect and asked him, “Are you alright man? What happened? I felt like I lost you.”


“You lost me? Why did you have to pay for the food? I wanted to pay. Nevermind, you won’t get it.”


And I was feeling the same thing from the other side - “What’s wrong with paying for the food? Why can’t you accept my generosity?”

I understood what happened years later.


He took my generosity as a judgment about him —  that perhaps he couldn't afford to pay, or wanted me to pay.

His resentment after I paid for it, was causing me to mistrust whether he indeed saw me as a close friend he could trust.

We can call this the Trust Paradox — A phenomenon I have never seen anyone talk about.

The Trust Paradox

An insecure mind lives in a constant state of protection.


It has been hurt before. It is carrying memories of disappointment and betrayal.

When someone offers genuine kindness, this wounded mind cannot accept it at face value. It searches for hidden motives, expecting some request or pressure.

The secure mind, having found its footing, operates from a different place entirely. It has learned to trust its own judgment and feels safe in the world.

But here's a surprising fact. Even a secure mind is not always fully secure. It's past insecurity can be triggered by an insecure person.


When a secure mind encounters fear in others, it can become suspicious too.

It thinks,
"If you have nothing to hide, why are you so afraid?"
“If you are afraid, that means you don’t trust me.” or

(in a work setting)
“If you got such a simple thing wrong, it must’ve been intentional.”

Both minds, from opposite ends of the spectrum, arrive at the same destination - mistrust.


The insecure mind suspects generosity. The secure mind suspects fear.

Why This Happens

Think about a time when someone was unusually generous with you. Did a small voice whisper, "What do they really want?"

This reaction comes from old wounds. As children, many of us learned that kindness sometimes came with strings attached. A parent's hug might have been followed by a lecture. A teacher's praise might have set us up for harder expectations.

Our mind, trying to protect us, created a simple rule. "If someone is being too nice, watch out."

The secure mind falls into a different trap. Having worked hard to overcome its own fears, it sometimes forgets how frightening the world can feel to others.

When it sees someone acting nervous or withdrawn, it assumes deception rather than recognizing pain.

It thinks, "Confident people are honest. Fearful people must be hiding something."

The Path Forward

Here are some practices to move past these patterns in your own life.

Notice Your First Reaction: When someone is generous with you, pause before your mind creates a story about their motives. Ask yourself, "Am I looking for problems that might not exist?"

Be Generous in Your Trust: When you encounter someone who appears fearful or anxious, try assuming they're in pain rather than being dishonest or deceitful. Fear often masks hurt, not deception.

Examine Your Own Security: Notice whether you tend to be suspicious of kindness, or suspicious of fear. Both reactions point to areas where your own trust needs healing.