Humans Bold Enough To Ask These 8 Questions Often Are The Most Interesting People In The Room

Captivating people's interest is more about them than it is you

My roommate's father is probably the best listener in the world.

Or at least my world.

I see him periodically — once every couple of years. What's crazy is I actually met my roommate's father, Bruce, before I met my roommate — but that's another story.

Bruce has a way of being the most interesting man in the room, regardless of the other people, the decor, the energy, or the context.

He tells me a story about when he was at a cocktail party with his first wife.

He was in his early thirties and he was brought to this party to network with some of his wife's colleagues.

When the two arrived at the party, they were quickly pulled in different directions and Bruce had to "fend for himself" in regards to carrying on conversations with strangers.

A few hours elapsed.

  • People started drinking.
  • People started sharing more.
  • The party got louder.

And shortly thereafter — it was time to go home.

Before Bruce and his wife left, however, they were stopped at the door by numerous couples,

"Honey — this is the man I was telling you about. His name is Bruce and we chatted for hours." The lady in question looked at Bruce's wife, "I'm sure you probably hear this all the time but your husband had the most interesting things to say at this party!"

Bruce's wife thanked the couple and soon they were in their card heading back to their house.

While starting up the car, Bruce's wife turned to him and asked,

"What the hell did you talk about that made you so interesting? What did you tell him that you haven't told me?"

Bruce chuckled to himself, "Sweetheart — I didn't talk about myself at all! All I did was ask him questions about himself!"

Bruce was able to get people to think he was interesting by showing others interest in them and asking "interesting" questions.

You can be like Bruce — the smartest and most interesting person in the room, if you're asking these questions.

1. "What are you passionate about?"

Don't have anything other than small talk to pass the time with a stranger or acquaintance?

Use this simple 5-word question and watch the Universe burst wide open…

“Talk to someone about themselves and they’ll listen for hours.”

Dale Carnegie, How to Win Friends and Influence People

People love talking about themselves. Scientific American notes that on average people spend 60% of the time talking about themselves.

Sometimes this can be a mind-numbing drag. We've all heard the stories,

"And then, when I was 14 I had my first kiss with my crush — Daniel. It was amazing. I mean, we had no idea what we were doing but…"

It makes it hard to feel engaged in a conversation when it's about someone else and a historical event of that person (the way most of the conversations go).

However, when you choose to ask about someone and their passions — the doors spring open.

People's passions vary ad infinitum.

Generally speaking, when someone talks about their passion, you'll find it interesting as well.

  • It either connects with you.
  • Or it's a topic you know nothing about but are interested in.

This causes more questions, thus making you more interesting to the other person.

2. "What's your favorite thing in the world?"

This is a question I have a personal relationship with (even though all the questions in this piece I've used and seen extraordinary results from).

I remember when I had a crush on my now girlfriend.

I thought about this question one night and realized I had never consciously asked it before.

It was one day at work (we used to work with one another). We were setting up for our shift and without any qualifier I asked her,

"Hey — what's your favorite thing in the world?"

For her, it was her family and the relationship she had with them.

It made me know that I really wanted to be with this woman.

After her, I started asking others. The responses I got back ranged considerably:

  • "My children are my favorite things in the world."
  • "Mint chocolate chip ice cream is my favorite thing in the world."
  • "My pitbull is my favorite thing in the world."
  • "That feeling of making others feel awkward with non-PC jokes is my favorite thing in the world."

The follow-up question (unless the conversation is already traveling in a positive direction) is always:


Asking “why” digs one level deeper and you get an understanding of someone's values.

I promise you — you will never not get someone to answer this question!


Well, we already noted people love talking about themselves and this is their favorite thing.

3. "How did you end up achieving [fill in achievement]?"

This question is one of my personal favorites — especially within the professional context.

Being an entrepreneur, I'm always looking for people and mentors who have already accomplished what I want to accomplish.

This could include a number of different things:

  • Accomplished income goals.
  • Accomplished certain trait or skill goals.
  • Accomplished mindset changes or growth.

Whenever I get to a place in conversation where I feel we've gotten to a notable achievement, accomplishment, or goal; I am compelled to ask,

"How did you end up achieving…?"

What this question does (among getting the person to of course talk about themselves) is allow them to talk about the way their mind thinks.

There are many ways to "skin a cat."

There are thousands of millionaires, for instance. Each one of them has their own way of achieving that pursuit and you can make them feel interested enough to talk about that.

If you're looking to expand your knowledge and skillsets within a particular professional context (long way of saying you want to get better at your career) and have the opportunity of meeting someone who has done something you want to do — don't skimp on asking this question!

You'll also seem like an interesting person to them when you get them to talk.

4. "What do you feel you learned too late in life?"

This is a hugely popular question for the internet as well.

Plain and simple — you can't have it all in this life.

There are too many things to know and too many directions to head.

With that in mind, everyone has a gift they can share with you.

When you ask someone this question, it shows that you're looking for someone's help and advice (thus noting interest in them) while also opening the door to the person showing their status of overcoming their own personal obstacles.

Every human has a story that can be a gift — if you're willing to ask about it.

One might think at first glance that this is a question that should be completely reserved for "older folks" however, even younger generations are still learning things as they get older.

5. "What fact amazes you every time you think about it?"

Like, dude…

Want to get your mind blown?

Ask this question to someone and see where it takes you.

I've heard so many different things from people after asking this question:

And more.

You'll notice that even from my short list the interpretation of the word "fact" is loosely defined when you ask this question.

I personally enjoy that.

As soon as you respond with something along the lines of,

"Oh yeah, I heard about [fact in question"

You'll see the recipient of the question becomes more interested in you (when really they're interested in the topic, you're just the receiver).

It allows you another access to discovering what someone is passionate about because generally the facts shared relate to the person's interests.

This question always forms a crowd. People love talking about the obscure things they know that others don't.


Just kidding.

Imagine if you're the person who is facilitating a group of individuals sharing facts they think are cool.

You just became the cool one.

6. "What ridiculous goals do you have for yourself?"

Why is it so hard for two (or more) humans to sit back and dream the grandest dreams with one another?

Well, when you ask someone this question, you allow for a person's imagination to run wild.

Generally, I've found that you can't really start with this question.


Because the word "ridiculous" can be a little off-putting before you've established rapport with the person you're talking with.

If you can sense the conversation is in a fluid and flowing state — put the car in a higher gear and start asking questions that get you both to use your imagination.

That isn't to say that everyone is always going to talk about "unachievable" goals — it's really just opening the door for the person to talk about things that maybe he or she is embarrassed to talk about.

When you're the one asking them (with genuine interest) you're going to come off as an interesting person yourself.

7. "What makes you feel young?"

If you want people to feel like you're fun in conversation, get them to remember the "good old days."

People love reminiscing about their "prime."

Heck — people love remembering when they were young, even if they're still young!

That's what cool about both you and the person you're talking to by asking this question.

  • You can learn something about what the world was like at a specific moment in time.
  • You can learn about how much a person has changed.

8. "Which of your personality traits have been least useful?"

Again, this is a question that probably shouldn't be asked straight from the start.

This is after you've built some type relationship.

This gets the person to talk about something that they've perhaps changed in their life or want to change.

Questions like this help you get more vulnerable with the person which builds trust and intimacy.

Now I'm not saying you need to marry or date the person, but it's always nice when two or more individuals can get past all the surface-level B.S. that plagues social gatherings.

Allow the person you're talking to to open up and get honest.

Perhaps this will open the door to the person talking about past mistakes they've made and what they've done to reconcile them.

9. "Creed or Nickleback?"

Maybe this one is just for me…

I find this question absolutely hysterical.

It's funny because the question can take many different forms:

  • Sometimes people answer one of the bands immediately with a favorite.
  • Sometimes the people give you a confused glance.
  • Sometimes people beg you to not have to answer.

If you don't understand this question, you might have to do an internet search for the bands "Creed" and "Nickleback".

They are two polarizing bands from the late 90’s and early 2000’s that draw mixed opinions.

There are many levels to the question if you understand it and it's funny to see how people react.

The people that get it will understand your sense of humor and thus bring the conversation to a more playful and engaging state.

You can be the most interesting person in the room — if you show interest in everyone else

People think that in order to be the most interesting person in the room, they have to have traveled the world, tasted the most exotic cuisine, and conquered the most feared beasts.

Sure — that can work for a little bit.

It might be a good attention grabber at first.

However, we all know of a person who talks too much about themselves (if you can't think of anyone — it's probably you).


We like ourselves (some more than others). We want to be interesting so we constantly go off thinking we need to impress people.

It's funny, however, when we realize that we can be the most interesting person in the room by simply showing interest in others.

How do you do this?

By asking the right questions. Some of those questions are:

  • "What are you passionate about?"
  • "What's your favorite thing in the world?"
  • "How did you end up achieving [fill in achievement]?"
  • "What do you feel you learned too late in life?"
  • "What fact amazes you everytime you think about it?"
  • "What ridiculous goals do you have for yourself?"
  • "What makes you feel young?"
  • "Which of your personality traits have been the least useful for you?"
  • "Creed or Nickleback?"

When you can show a genuine interest in others, you show you care.

When you care, the world opens up to you.

And perhaps that's why you become so interesting to others. Being a person of care and integrity is such a rarity in the world today.

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