How to Have a Deep Conversation with Women | Build Real Connection
My name is Gary Gunn and I have been teaching communication skills for the past 17 years. If you go to standard training courses, they will teach you useful techniques such as active listening, demonstrating empathy, and reflective listening. Whilst these are good, I believe we can do better. We can build upon these principles to develop a real method for creating a deep conversation.
In your dating life, if you are not able to connect with your partner, or maybe with your colleagues at work, what I am about to teach you can be the building blocks for the deep conversation that you desire.
I personally think that if you do not have the ability to go deep in conversation, life often feels surface level. It can leave you feeling disconnected and isolated. That is why learning how to have a deep conversation is not only useful but essential.
Why I Decided To Explore Deep Conversation
To give you some context on why I am producing this piece, I am currently attending a five day acting course at the Royal Academy of Dramatic Art in London. Yesterday was day four of the training, and what I learned completely shifted my perception of deep conversations.
The discovery was simple yet profound. The use of metaphors is what is missing if you want to go deeper in conversation.
I will explain the exercises we did, how they built up, and why the final part of the training is not just useful in the acting world but can be applied across multiple areas of your life.
The Exercise That Changed My Perspective
We were working with something called the Meisner technique repetition. This is an exercise where you sit opposite a partner while the rest of the group watches. You start by simply noticing something about the other person. For example, you might say “You have short hair.”
Your partner then repeats back, “You have short hair.”
When you first begin the exercise you are constrained to say the exact same phrase back and forth. It can get frustrating. Tension builds in your body, and you can feel the desire to move, stand up, or escape. But the goal is to get out of your head and practice being fully present.
Once you can do this, more layers are added. Yesterday the exercise reached a new level when we were allowed to introduce metaphors. That was when the breakthrough happened.
The Moment Metaphors Entered the Room
Two people were at the front of the class. In the middle of their repetition one of them suddenly said, “You are a loaded gun.”
Her partner leaned forward and repeated back, “A loaded gun.”
Her face turned bright red and the intensity in the room changed instantly. Then she said, “You are a red tomato.” The exchange may sound playful when you read it, but in the moment it was incredibly powerful.
Why? Because metaphors bypass surface level communication. They allow truth to come out quickly and directly.
Why Metaphors Lead To Deeper Conversations
Most of us in daily life are not fully honest about what we want or what we feel. We think we are, but unless pressure is applied, most of the truth never leaves our lips.
During these metaphor exchanges, the truth came out without filters. That is the key to learning how to have a deep conversation.
Think about it like this. If I wanted to describe all the small details of your face and body language when you speak, I would need to use a huge amount of descriptive language. Even then it might not capture the full reality of what I was noticing. But if I said, “You are a block of ice” or “You are Medusa,” instantly you would understand.
Metaphors are a way of condensing complex information into a simple, powerful statement.
Overcoming The Fear Of Using Metaphors
A natural question is, what if the other person takes offense?
This is where intent matters. In the Meisner training, you are encouraged to speak the truth as you see it, but not to attack or harm. When metaphors are spoken with honesty rather than malice, they open up a deeper level of communication.
What I found fascinating was that the more truth you gave through a metaphor, the more truth you received back. This reciprocity is what creates a genuine deep conversation.
Real life is not the same as a studio exercise, but the principle still applies. You can use metaphors in your everyday conversations at a slower pace. You can observe someone, notice their energy or expression, and reflect it back as a metaphor.
This not only deepens the conversation but also gives tremendous value to the other person.
Applying This To Dating and Attraction
Now let’s look at how this works in the dating world.
When most guys go on a date, they stick to surface-level topics: where she’s from, what she does for work, her favorite hobbies. These are fine for warming up, but they don’t create emotional depth. And without depth, there is no lasting attraction.
If you want to know how to have a deep conversation on a date, you need to do something different. This is where metaphors become powerful.
Imagine she tells you she’s stressed about work. Most guys will say something like, “Yeah, work can be stressful.” That’s a surface-level reply.
But if you said instead, “It sounds like your boss is like a storm cloud that follows you home every night,” you’ve just given her a metaphor. Suddenly, she feels understood at a deeper level. She may even laugh or lean in because you’ve framed her experience in a way she hadn’t articulated herself.
That’s what creates connection. That’s what makes her feel like you truly get her.
Why Metaphors Make You Magnetic
Metaphors work because they bypass logic and speak directly to emotion. Human beings don’t remember facts as well as they remember images.
If you tell someone, “You’re confident,” that’s a flat statement. But if you say, “You’re like a lighthouse — steady, guiding, impossible to ignore,” it’s unforgettable.
In dating, this ability makes you magnetic. Most men try to impress women with achievements, stories, or rehearsed lines. But when you use metaphors authentically, you create a felt experience. She doesn’t just hear your words — she feels them.
This is why learning how to have a deep conversation is such an advantage in attraction. You’re no longer just another guy asking the same questions. You’re the one who makes her feel something different.
How To Practice Metaphors in Daily Life
The good news is you don’t need to be in a drama school class to practice this. You can start right now.
Here are a few simple ways:
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Notice body language – If someone is fidgeting, instead of saying “You look nervous,” you could say, “You’re like a kettle about to boil.”
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Reflect moods – If someone is upbeat, instead of “You seem happy,” you could say, “You’re like sunshine bursting through a window.”
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Play with imagery – If your date is passionate when talking about something, instead of “You really like that,” you could say, “You light up like fireworks when you talk about this.”
The key is to trust your instincts. Your first thought is often the most accurate and authentic metaphor.
Over time, you’ll get more fluent, and your ability to have deep conversations will grow naturally.
The Hidden Benefit: Vulnerability
One thing I noticed in the RADA training is that using metaphors requires vulnerability. When you tell someone, “You’re like a loaded gun,” you’re exposing your perception of them. That takes courage.
In dating, this vulnerability is attractive. It shows you’re willing to go beyond small talk and risk sharing what you actually notice.
Most people are starved for this kind of honesty. When you deliver it, you instantly stand out.
Conclusion: The Secret to Lasting Connection
When you learn how to have a deep conversation, you stop living in the shallow end of communication. You stop recycling the same boring small talk that everyone else uses, and instead, you create something alive, personal, and unforgettable.
Metaphors are the key. They allow you to bypass logic, access emotion, and reveal the truth that people rarely put into words. Whether you’re sitting opposite a stranger, your date, or even a colleague, the moment you use a metaphor, you invite the other person to meet you at a deeper level.
And here’s the truth: people crave depth. We are surrounded by endless noise, scrolling, swiping, and surface-level exchanges. When someone makes us feel seen, felt, and understood — we remember them.
That is why mastering deep conversation is not just a skill. It is a superpower.
Taking This Into Your Dating Life
If you are serious about improving your dating life, then practice using metaphors.
On your next date, instead of sticking to the usual interview-style questions, try reflecting back what you notice in a metaphor. Make it playful, make it bold, and watch what happens.
You’ll find that she leans in. She shares more. The conversation opens up. And most importantly, she feels a connection with you that she doesn’t feel with anyone else.
This is what builds chemistry. This is what builds attraction. And this is what creates the kind of relationships most men only dream about.
Final Thoughts
Learning how to have a deep conversation is not about memorizing scripts. It’s about cultivating presence, honesty, and the courage to speak what you really see and feel.
When you do this, you not only improve your dating life, you also transform every area of your communication. You’ll connect more powerfully with your friends, family, colleagues — and with yourself.
If you’ve ever felt like something is missing in your interactions, this is it. The missing piece is depth. And depth begins with metaphors.
Next Step: Work With Me
If you’re ready to go beyond surface-level dating and start building real attraction through authentic, deep connection, then I invite you to take the next step.
You can:
Explore my digital training courses where I break down step-by-step how to develop dating confidence.
Or, if you’re committed and ready for faster results, apply to work with me 1-to-1.
Both options are designed to help you master communication, build unstoppable confidence, and create the dating life you truly want.
The choice is yours. But remember this: if you don’t learn how to have a deep conversation, you’ll stay stuck in shallow waters. If you do, everything changes.
Written by Gary Gunn
I coach men to build real self-confidence so they can meet, attract and date the women they truly desire.
My coaching is practical, real-world and focused on lasting behavioural change.
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