How To Become More Interesting

Why the Answer Has Nothing to Do With Being Impressive and Everything to Do With Trying

There is a question I get asked more than people probably realize.

It sounds simple on the surface, but it hits deeper than most guys expect.

How do I become more interesting?

Most people ask it thinking about dates, conversations, first impressions. That moment where someone across the table decides whether they want to lean in or mentally check out.

But when I sat with this question, it cracked open something bigger.

“I think this question applies to every facet of your life. Dating, your job, your career, your friendships, work, your relationships, your mindset, your confidence, your life. Really everything.”

Because this is not just about sounding cooler. It is about how you see yourself when you wake up. How you talk about your life. How much energy you bring into rooms without forcing it.

And the uncomfortable truth is this.

Most people are not boring. They are just not doing anything that excites them.

Why Feeling Uninteresting Is a Confidence Problem, Not a Personality One

When someone says they feel uninteresting, what they usually mean is this.

They do not feel engaged with their own life right now.

They do not have anything they are actively pursuing, exploring, or figuring out that feels alive. So conversations start to feel flat. Dates feel repetitive. Work feels stale. Even friendships can feel harder to show up fully in.

And the problem compounds.

Because the less interested you feel in yourself, the harder it is to be curious about other people.

“It affects how you think about yourself, how you talk about yourself, how you walk, how you interact, how you perceive yourself.”

Psychologists back this up. Research summarized by the American Psychological Association shows that curiosity and engagement are tightly linked to confidence and well-being. When people stop learning or exploring, self-perception quietly declines, even if nothing looks “wrong” on the surface.

This is the same confidence erosion I talked about in How To Stop Overthinking Everything, where your inner narrative quietly shapes how you show up long before you say a word.

Becoming more interesting is not about becoming someone else. It is about becoming more engaged with being you.

The Thing Nobody Wants to Admit About Interesting People

Interesting people are not born interesting.

They are just willing to be bad at things in public and private.

“I think the easiest way to start answering this question of how do I become more interesting lies within experimentation, in trying new things, in allowing yourself to kind of make a fool of yourself.”

This is where most guys get stuck.

Trying something new means being a beginner. Being a beginner means being uncomfortable. And being uncomfortable means risking embarrassment, judgment, or feeling stupid.

So we stay safe.

We scroll. We talk about what we want to do someday. We fantasize about becoming someone without ever stepping into the messy middle required to get there.

But interesting lives are built in the messy middle.

A study published in Psychological Science found that people consistently underestimate how much others appreciate effort and curiosity, and overestimate how harshly they’ll be judged for being new at something. Most of the fear is imagined.

Why Talking About What You Want to Do Is Not Enough

There is a huge difference between someone who says they want to do things and someone who actually does them.

“It’s not nearly as interesting to talk about wanting to do the thing as it is to share what you’ve learned while doing it.”

That line matters.

Because most first dates, interviews, and conversations fall flat for the same reason. People talk in hypotheticals instead of experiences.

I want to travel.
I want to write.
I want to get in shape.
I want to start something.

But when you never move past wanting, there is nothing to build momentum around.

People are drawn to motion.

Not certainty.
Not perfection.
Movement.

This is the same reason How to Sound More Confident Instead of Insecure: Guide to Building Self-Assurance resonates so deeply. Confidence grows when you are doing, not when you are planning.

This is why behavioral researchers like BJ Fogg at Stanford emphasize that action precedes motivation. You do not wait to feel interested. Interest follows doing.

The Simple Exercise That Changes Everything

At one point in the episode, I ask a question that quietly reframes the whole idea of being interesting.

Pause and think of three things you would love to try but stop yourself before you do.

Not ten.
Not a bucket list.
Three.

“I want you to think to yourself, what are those things? What are the things I could potentially be interested in or potentially want to try?”

For me, they were simple.

Learning how to cook.
Writing a book.
Watching more movies intentionally.

None of those require permission. None require talent to start. None require you to reinvent your life.

But each one gives you something real to engage with.

And that is where interest starts to build.

Why Experimentation Is the Whole Point

One of the biggest mindset shifts in this episode came from advice by Will Shortz, the longtime editor of The New York Times Crossword.

“Trial and error is inherent in the process of interest discovery.”

That sentence removes so much pressure.

You do not need to find your thing forever.
You do not need to commit in Sharpie.
You are allowed to start in pencil.

Shortz has talked publicly about how curiosity and play are core to mastery, not seriousness or perfection. That mindset applies to far more than puzzles.

If something does not stick, that does not mean you failed. It means you learned.

And learning builds confidence faster than getting it right on the first try ever could.

Why Ambition Is Quietly Attractive

This episode started with dating, but it does not end there.

People are drawn to ambition, whether they say it out loud or not.

Not hustle ambition.
Not performative ambition.
Real ambition.

“I think people are much more attracted to ambitious people and ambition.”

Someone who is curious.
Someone who is exploring.
Someone who is trying.

This is the same dynamic behind How To Act More Confident. Confidence is not bravado. It is momentum.

The Difference Between Not Knowing and Not Trying

Not knowing what you want is normal.

Refusing to try anything is the problem.

“There is a big difference between somebody who doesn’t know what they want to do and somebody who doesn’t know what they want to do but never tries to figure it out.”

Trying is interesting.

Exploring is interesting.

Even being unsure, while actively experimenting, is interesting.

Apathy is what drains conversations, not confusion.

How to Actually Start Becoming More Interesting

The answer is almost annoyingly simple.

Follow what interests you right now.

Not forever.
Not perfectly.
Right now.

“What is interesting to you right now? That is the answer to this question.”

That thing might seem ordinary.
That thing might seem uncool.
That thing might feel random.

Good.

The less impressive it sounds on paper, the more likely it is to actually change how you feel.

The Real Outcome Nobody Talks About

You do not become more interesting for other people first.

You become more interesting to yourself.

While that happens, everything else follows.

Confidence rises.
Conversations get easier.
Dates feel more natural.
Life feels fuller.

“Finding your passion or your hobby may lead you to feel more confident, or to stand up taller, or to think about yourself better.”

That is the real win.

Not being impressive.
Being engaged.

FAQ: How to Become More Interesting

Do I need a unique hobby to be interesting?
No. Genuine interest matters more than novelty.

What if I try something and quit?
That is part of experimentation. Learning what does not fit still builds momentum.

Is this really about dating?
Dating is one outcome. This is about confidence, curiosity, and engagement with your life.

How many hobbies should I have?
As many or as few as you want. There is no correct number.

What if nothing excites me right now?
Start anyway. Interest usually shows up after action, not before.

If you’re willing to try, you’re already on the path to becoming more interesting.