#18 TRENDING IN Relationships 🔥

Advice: How to Have a Genuine and Deep Conversation


December 25, 2023

My face stiffens, and my breath trembles. The water in my mouth absconds, leaving it parched like a desert. Sweat streams down my ashen face, racing down my body.

Clamminess subdues my tense hands as they concoct the perfect potion to rizz my crush up. Eureka! An idea strikes, and I implement my master plan. My heart thumps as I type it out - "Hru?"

The pandemic impaired our conversational abilities, forcing us to shift entirely to virtual communication during school, with little communication left. On average, the brains of teens who went through 10 months of lockdown aged around three years. This premature aging correlates with depression and isolation.

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Having deep conversations creates stronger connections. Through these connections, we learn how to express our feelings and thoughts. Deep conversations teach us a lot about ourselves, Whether with a teacher, your best friend, a crush, or your sibling. So, how do you have a deep conversation?

Keep it Interesting

"Hey, how are you man?"

"I'm great, how are you?"

"Doing good. Catch you later."

Nothing worthwhile results from small talk like that. Instead, keep it concise and dive straight into a topic that interests both of you. To initiate a conversation, pose an open-ended question, allowing them to ponder while taking the lead in thinking.

Deep Questions

Here's a brief list of deep conversation starters.

  • What is one thing you'll never change about yourself?
  • If you were a book, which one would you be?
  • What does success mean to you?
  • If you redesigned society, what would you change?
  • What does a perfect day look like to you?
  • What is your favorite color...and why? (The "why" part is crucial)
  • If you could change something about your childhood, what would you change?
  • How did we build our friendship/relationship?
  • What does emotional balance look like to you?
  • How do you handle mood swings and negative emotions?
  • Do you experience empathy, and if so, what does it look like?

Subsequently, actively listen and share your opinions. Steer clear of redundancy, and resist the urge to unveil your life story all at once, especially during dates. Maintaining an air of mystery enhances your charisma and keeps the conversation captivating.

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When recounting a story, focus on the moral; what message are you conveying? Don't get derailed by fluff, such as names and dates. Frankly, no one cares, and interrupting your train of thought to recall your second cousin's dog's name does nothing. Just improvise on the spot.

Another aspect of conversation involves compliments. No, I'm not talking about generic remarks like "I love your skirt" or "I love your bracelet." Compliments like those may come across as insincere, even if genuine. Instead, compliment things you know the other person worked hard on.

This makes their efforts feel appreciated. For instance, saying, "I love how your energy radiates when you smile. It makes me want to smile as well," carries more weight than a generic comment about their hair. However, the occasional compliment of that nature is alright, so use your compliments judiciously.

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This doesn't just mean putting your phone down; it means genuinely paying attention. I won't dictate how this should look, as it should be natural. If the conversation revolves around something you're passionate about, you should already want to pay attention.

Sometimes, we don't listen because we simply don't care or perhaps have something "urgent" to share. However, it's not always about you. Listening and being emotionally present make a person feel seen, heard, and loved, fostering healthier conversations.

A key component of healthy conversations is going with the flow, as they never stick to one topic. For instance, you could start discussing plans for the weekend, shift to the Drake concert next month, and finally, the funny movie you saw a week ago.

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To go with the flow, avoid fixating on the one thing you didn't get to share. When that thought occupies your mind, you're not fully listening to the other person, and at the worst possible moment, you might go off on a tangent, making the conversation awkward and choppy.


Everyone has something to teach, and conversations reveal those lessons. So, concentrate on the perspective of a conversation by embracing open-mindedness. This involves listening – a vital aspect of any conversation.

It also means embracing silence. Silence is a crucial component of a conversation. Try replacing filler words with moments of silence to gather your thoughts. This promotes a more productive conversation.

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One form of a productive conversation is debate. People often shy away from heated debates, but these debates establish connections between ideas and individuals. As teenagers, we have become polarized, often befriending only those with similar opinions. Look beyond the opinions and focus on the person.

Additional Tips

Speaking is a skill, so here are a few tips to help you practice.

Let's be honest – nobody appreciates a Pollyanna or a goody two shoes. So, highlight your flaws! This will make you appear relatable and vulnerable, two crucial components of any conversation. Ditch the belief that you must be perfect and embrace vulnerability and imperfection.

Also, go for depth. Having five strong links is preferable instead of a hundred weak ones. To fortify these connections, delve into the person!

Move beyond "wyd" and "hru." Remember to pose open-ended questions to guide the conversation. Learning about others aids in self-discovery, so break out of your bubble! Don't confine yourself to the same people at a party or event; go and introduce yourself. It may be nerve-wracking, but after the first word, it'll flow like word vomit.

In conclusion, engaging in a profound conversation lays the groundwork for self-discovery. It's crucial to seek perspective in any conversation and genuinely listen to achieve that. Deep conversations shouldn't be dull.

Frankly, tips like "pay attention" and "maintain eye contact" are tedious. These tips should come naturally. So, step out of your comfort zone and explore!

Dev Shah
50k+ pageviews

Writer since Sep, 2023 · 30 published articles

I am a high school sophomore living in Largo, Florida. My goal as a journalist and interviewer is to help our generation of teenagers by providing inspirational writing and exploring complex topics. I focus on mental health, self-love, entertainment reviews, and narrative experiences. My work has been published in The Washington Post, Tampa Bay Times, Fortune Magazine, Education Week, and more local papers. I use my experiences as the 2023 Scripps National Spelling Bee Champion to guide my writing and pieces, and my vast verbal knowledge to best articulate my thoughts.