Killing Small Talk.

Meaningful Conversation Matters.

I find myself thinking all the time that I wish I had more meaningful conversations, especially over a meal or over coffee with someone.

It’s hard.

Getting to know people, and steering the conversation into substance is one of the most invaluable traits you can possess. There is, of course, the classic question you can resort to when you’re first getting to know someone:

What do you do? (or Where do you go to school?)

This makes people uncomfortable. To me, it doesn’t show that you really care about the conversation.

Next time you really want to discover something about the person sitting across the table from you at dinner, here’s what I’d ask of them:

Brag about something.

This catches people off guard, and tells you so much. Everyone has different priorities. Everyone is accomplished in their own rights. But what do they choose to tell you about when asked to brag? Oh, the things you’ll find.

Tell me about your last birthday.

Frame of mind is everything. How does this person highlight their day? Though most people react similarly in times of tragedy, celebrations are often where we’re most different. You’ll get to know their personality quirks, friend group, and even how thankful they are about milestones in their life.

What are you obsessed with?

Everyone has an obsession. Yet, this question isn’t just about the person’s priorities. It tells you how they perceive obsession. Do they see it as passion, or something negative? How personal do they get in their response? There’s a lot you can learn if someone answers chocolate vs someone who answers “my children”.

What keeps you up at night?

This touches at another end of the spectrum. Everyone worries — often for good reason. This will usually get either a really emotional response or a rather dismissive one — either way, it’s revealing.

Who holds you back?

The people in your life are most important. There’s good reason this question is negatively phrased. The positive phrasing — “Who motivates you?” — often lends itself to an easy answer (i.e. friends, family, idol). This one makes the person think more about who they’re afraid to disappoint. Who keeps them from achieving success?

When would you quit?

This is a purposely open-ended question. Quit what? What’s “when”? Most people are taught that quitting is wrong. That we should perservere. How does this person deal with difficulty? Where is the line for them when it’s not worth it?

What makes you tear up?

Some people genuinely don’t cry. Others are hugely emotional. This question gives you insight into how willing they are to open to you. More importantly, it pushes them to recount a situation in which they were vulnerable — certainly not easy for most.

How satisfied are you?

People will take this all sorts of different directions. That’s the magic of this question. Society attaches a lot of stigma to this — either you should always be full of passion and never content with your position, or maybe you should be happy with what you have and not be jealous. Where do they stand on this topic?

Describe the smallest form of happiness.

This “question” is powerful. Most people are scared of happiness because we’re led to believe it’s some intimidating, almost too-good-to-be-true goal in life. Downsizing that to “smallest form of happiness”, it really forces the person to take a step back to what puts a smile on their face.

Who cares most about you?

This question makes them step out of their own box. It makes them think about which people depend on them. It’ll give you a good sense of their perspective on relationships.


Don’t get me wrong — these questions are by no means conversation starters, especially with someone you’re just meeting for the first time.

Yet, if you’re really trying to dig deep, you can’t go wrong with these.


If you liked these questions, it would mean a lot to me if you hit recommend below! ☺