- Kindred
- Posts
- D...is for DEPTH
D...is for DEPTH
How to have deeper conversations
Eric Jeng
June 14, 2024
Did you know that, according to psychologists, having deeper conversations can lead to greater connectedness and happiness?
In this article, I’ll share some tips on deepening conversations, using a recent experience as an example.
The coffee culture in Europe is strong
Last week in Berlin, I met a follower for coffee. It was our first meeting, and at some point, I asked her what brought her to Berlin. She replied, “I moved here for my boyfriend.”
Interesting, I thought.
“How did you and your boyfriend meet?”
Tip #1: Let your curiosity lead you deeper.
People respond well to genuine inquiry and intrigue. Remember from the previous article that curiosity implies care.
“Well, we met many years ago on a dating app. We dated for a couple of years but were always long-distance. It was a magical relationship, but the timing wasn’t right. We eventually ended it but kept in touch.”
“Ok. And then what happened?”
She sheepishly smiled, “And then…”
Tip #2: Create a story arc.
Get more plot points. “And then…” in a conversation creates a story, and story creates depth. “This happened, and then this happened, and then this happened…”
“I was single for a while and then met another guy. We were together for four years. Everything was going well, but the night before we were to move out of the city and into the countryside together, I felt a knot in the pit of my stomach. Something didn’t feel right.”
“Why?”
Tip #3: Delve into a person’s motivations.
Understanding why someone does what they do allows you to steer the conversation more meaningfully.
“I wasn’t ready to settle down and live a simpler life. I wasn’t experiencing a flow in the relationship, maybe because there wasn’t a sense of challenge and growth. It didn’t have anything to do with him. His love was big, but I didn’t feel like I was experiencing the whole spectrum of life.”
“So you left the safe thing for the unknown.”
Tip #4: Understand the other person’s values and viewpoints.
Beyond understanding motivations, it's crucial to understand a person’s values and viewpoints. Empathy and perspective-taking lead to better moral reasoning and closer relationships.
“Yes, I tend to do that. I felt there were things I needed to overcome in myself, to learn about, and to grow. I’m always attracted to ideas and conversations and being more than myself.”
“Yeah. And then what happened?”
“I broke up with my boyfriend of four years. Sometime after, I got back in touch with my now-current boyfriend, the one that got away. I had to see things through with him, or I’d always wonder what if.”
“I see. So now you’re in Berlin with your old flame…is this what you were looking for?”
“There are good days and bad days. I see them as reflections of our deepest insecurities. Sometimes I react negatively, and that’s something I’m learning to overcome and grow in.”
“So it is what you’re looking for.”
“I think so.”
I took a moment to pause and reflect on our conversation.
“So, how do you feel about all of this?”
Tip #5: Pause and reflect.
When a conversation reaches a certain level of depth, take a step back and get meta, asking them to reflect on everything discussed. This adds another layer of depth.
“The thing I often ask myself is, if I knew it was going to end like this, would I have started it in the first place? With someone who loved me so much? What I regret most is hurting him.”
“Help me understand the regret part. What do you regret specifically?”
“That I couldn’t love him as much as he loved me.”
“I see. How do you think you will get over this?”
“I’ve accepted that I can’t be responsible for his hurt, though that’s easy for me to say since I broke his heart. I hope he eventually sees past this and finds some sort of acceptance, which I know he doesn’t have right now.”
Tip #6: Seek truth and understanding.
In any conversation, I aim to get to the heart of things. Whether it’s a self-realization, a lesson, or just acknowledging that the person is still in the thick of it, there’s always a nugget of wisdom to find. When the conversation becomes bigger than the people involved, the conversation starts to get really deep.
If we imagine a person’s inner life as a knot, a conversation is a way of slowly loosening that knot. By following the thread, peeking under the hood, and taking a step back every once in a while, we begin to untangle a person’s psyche and let their innermost being reveal itself.
A Few Final Thoughts:
Don’t force it. Let conversations naturally flow and get deeper. You cannot force someone to go deep with you. They have to be willing and able. A gentle nudge is okay; sometimes people need a little encouragement.
The more depth you have within yourself—through life experiences, self-awareness, understanding, wisdom—the deeper you can get with others and the sharper your intuition will be on what question to ask next. In the conversation above, I was able to intuit how she was feeling based on my past break-up experiences and thus ask more pertinent questions.
There is much more that can be said on having deep conversations, and in truth, I am still learning and reflecting, but this seems a good place as any to stop. Not to mention, we have 22 articles left in this A-Z series to explore the art of conversation and dialogue. Until next time, E is for…
With curiosity,
Eric
PS: Here’s a challenge for you. What potentially deep conversation have you been avoiding with someone recently? How can you use curiosity, story arcs, and empathy to create an opportunity for depth and connection?
If this article was helpful consider forwarding it to a friend. If you haven’t subscribed yet, click the button below to subscribe and never miss out on more articles: