how to have deep conversations that motivate and inspire

Two people engage in conversation at sunset.

Share This Post

We live in a world of social media quick takes and politically charged debates about everything under the sun. Against this backdrop, authentic conversation seems like it’s in short supply.

But — there’s good news. Deep conversations are possible. And it’s easier to start a meaningful conversation than you might think.

Not only that, engaging someone in a thoughtful discussion will likely make both of you happier. That’s true even if the other person is a complete stranger.

Here’s how deep discussions motivate us, plus tips and sample questions to get you having compelling conversations in no time.

The surprising science behind deep conversations

If you feel reluctant to engage meaningfully with others, you’re not alone. Research shows that people typically expect harsh judgment if they reveal their weaknesses in conversation.

At the same time, we tend to underestimate how impactful a brief conversation can be on our own and other people’s well-being.

These dynamics lead us to avoid social interaction, even though it’s been proven to be a good idea in multiple ways. Meaningful conversations are a great way to build healthy relationships, facilitate shedding our psychological burdens, and develop deep connections.

If deep discussions are so great, though, why do we avoid them? It may be a case of our intuition leading us astray. Because our brains tend to favor being extra-cautious as a survival adaptation, sometimes the biggest challenge is combating our inclination to stay silent.

That’s why, when people are asked how they expected to feel after discussing questions like, “what are you most grateful for in your life?” they anticipate feeling awkward and only moderately happy. In truth, people report that having deep conversations isn’t very awkward at all — and leads to more happiness than they thought possible.

How to start a deep conversation with a stranger

Surprisingly, all of the above is true even when talking to strangers. In a series of experiments involving financial services executives, MBA students, online samples, and people in a public park, a team of researchers found some interesting commonalities among people with very different viewpoints.

All of the study subjects underestimated how positive they would feel in conversation with a stranger, overestimated how awkward the conversation would be, and underestimated how much their conversation partner would care about what was discussed.

In these experiments, the researchers provided the subjects with a list of deep conversation starters (as well as shallow ones to serve as an experimental control).

But in your own life, how can you devise thought-provoking questions of your own, without the help of a prompt from an academic expert?

Start shallow.

In the experiments involving executives, students, park visitors, and others, the researchers discovered that some of the people assigned to discuss shallow topics went on to talk about weightier ones completely unprompted.

“Some pairs assigned to discuss shallow questions eventually gravitated to deeper topics, suggesting there may be a natural drive to increasing intimacy over the course of a conversation,” the University of California-Berkeley says in a blog post on the research.

The lesson? If launching right in to personal questions isn’t your cup of tea, there’s nothing wrong with starting with small talk. Should you click with the other person, you may find yourself having a “real” conversation in no time.

Offer up something revealing about yourself first.

Nicolas Epley, a professor at the University of Chicago and a lead of this intimacy research, suggests that being the first to open up can pay major dividends.

None of the experiments measured the effectiveness of this approach; instead, it’s an opinion that was expressed by multiple study participants. Those who found themselves speaking first not only reported having a positive experience but gained more agency in the process.

“Cross the first imaginary line yourself and share something revealing. That will almost always elicit an equally open and sincere response,” Epley told Quartz.

Tap in to the “dead spots” in your day.

Another nugget of wisdom from Epley’s Quartz interview: the best way to find opportunities for a good conversation starter may be in the parts of your day that are brief and time-constrained. In other words, look to discuss deep topics in settings when you’d otherwise scroll through your social feeds or check your email.

This might be standing in line at the bank, heating up food in the office microwave, or waiting to be called at the deli.

In these situations, opening up with deep conversation questions probably isn’t the best strategy. Rather, look to these dead spots simply to say hello, introduce an interesting topic, and start to get to know the other person. It’s a great chance to practice cold opens and build your communication skills.

List of conversation starters and examples of deep conversation questions

Epley and his collaborators’ research points to some powerful deep questions that can get you more familiar with your conversation partner:

– What would constitute a “perfect” day for you?
– For what in your life do you feel most grateful?
– If a crystal ball could tell you the truth about yourself, your life, your future, or anything else, what would you want to know?
– Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?
– Can you describe a time you cried in front of another person?
– What is one of your most meaningful memories? Why is it meaningful for you?
– What is your biggest regret?

Conversely, shallow questions serve as great conversation starters and can be a jumping-off point to a deeper discussion, as described above. These types of questions included:

– What do you think about the weather today?
– How did you celebrate last Halloween?
– How often do you get your hair cut? Where do you go? Have you ever had a really bad haircut experience?

Consider getting creative with some of these. You can phrase them as more open-ended questions, or modify them so they are more important questions than just the surface stuff:

– What’s your favorite holiday and why? Do you have a favorite memory associated with this day?
– What element of personal care — clothes, hair, skincare — is most important to you? What piece of advice would you give about this thing?
– How do you cope when it’s too hot/cold? Do you have a favorite place to be in bad weather?

A cornerstone of this research into great conversations is the finding that we assume the worst of other people. That is, we let our biggest fears run rampant and expect people to be more indifferent and uncaring in conversation than they actually are. It turns out, though, that most people want to engage in deep conversation and discuss real topics on a deeper level. Sometimes it just takes a single action — or the right fun questions — to get the conversation flowing.

Photo by Rafael Garcin on Unsplash.

More To Explore

tech history

Internet Archive and the Wayback Machine

The “library of the internet.” What an amazing concept. To fully grasp the history of its creation we need to talk about Alexa. Yes that’s

tech history

The Legacy of Iomega Zip Drives

Ah, the Iomega Zip drive. It brings to mind the special memory of running back and forth between the university computer lab and the dorm

Congrats! You're now on our early access list.

We’ll send you an email when it’s your turn to sign up.

Calling Rates for

(+ )
i1 plan i2 plan i3 plan
[sc name="popup_total_minutes"][/sc]/min
i1 plan i2 plan i3 plan
illumy to illumy calling unlimited calling included unlimited calling included unlimited calling included
Landline n/a
Mobile n/a
Premium n/a
Details: Calls are rounded up to the nearest minute. A fair usage policy applies to unlimited calling capabilities. Some premium, special rate, or geographic numbers are not included. Restrictions apply.