Deep Conversationalists Who Are Endlessly Fascinating Usually Say 8 Phrases When Talking To You
Andrii Nekrasov | ShutterstockTruly great conversationalists have the ability to leave you thinking long after your chat is over. Their fascinating opinions encourage you to reflect not only on what they shared but also on your own life.
Deep conversations leave you feeling fulfilled even if you don’t know someone that well. A study found that people not only benefit from meaningful conversations, but they also prefer them to surface-level interactions. Connecting with people beyond small talk makes us feel happier. There are so many reasons to let your guard down and be challenged by someone who is both interesting and thoughtful.
Great conversationalists who are interesting and aren't afraid to dig deep in a conversation usually say these things:
1. 'Tell me more about that'
viviana loza | Shutterstock
Great conversationalists want to challenge you. Not in a negative way, but to encourage you to look at the topic beyond the surface. It’s easy for people to nod and go along with whatever you’re saying, but not for someone interesting. They want to hear your true perspective because they care.
They also know that to get to the meat of a conversation, they have to keep the other person talking, and asking for more details is the best way to do that.
A study found that people are often afraid to have deep conversations, underestimating how much someone else cares about what’s going on in their life. As it turns out, people are more invested in our feelings than we think. Someone like this sees the value in engaging in deep conversations. They may push further to learn your perspective and weigh in on the situation from their perspective in hopes of having a meaningful discussion.
2. ‘Let’s take a closer look at that’
I’m guilty of trying to wiggle my way out of deep conversations. I’ll say something vague to avoid talking about something difficult, even if I know the person comes from a good place. When someone is a deep thinker, they may challenge you to be vulnerable with them, strengthening the connection.
Having a deep conversation requires us to move past barriers and take a good look at the topic. When someone is interesting, they likely have strong opinions. This makes them want to understand you, and by asking to dig deeper on something, they’re having a more fulfilling conversation while allowing you the opportunity to discover more about yourself and how certain things impact you.
3. ‘How does that make you feel?’
People often don’t talk about what they need to. They hold their feelings close to their chests because they don’t feel comfortable sharing or think the people around them wouldn’t want to be burdened by them. What we don’t understand when we’re in that place is that there are genuine, deep people who want to help you through this. They’re not only interested in you, but they’re interesting people who want to take a conversation to the next level.
This type of person doesn’t only want deep conversations about the hard stuff. They may ask how something like the current state of the world makes you feel. In that way, they can have an intellectually complex conversation that often leaves you thinking about it long after it ends. They’ll share their thoughts, too, which allows you to see another perspective.
4. ‘That’s interesting because…’
Zamrznuti tonovi | Shutterstock
Fascinating people view things from a different perspective, but rarely will they make you feel inferior for your thoughts. Instead, they’ll open up the conversation to understand your point of view, then circle back to share their own. They may say something is interesting, but that’s not where the conversation ends.
Research has shown that more engaging conversations boost dopamine. There is more to gain when speaking with a deep, interesting person. They will make the environment a comfortable space to share what both people think. And you'll have fun doing it.
5. ‘How are you actually doing?’
How many times has someone asked you how you were doing and you replied, "I’m good!" Keeping things on the surface can feel safer than being honest. If someone is truly interested, they’ll want to have a deep conversation about your feelings to get to know you better and possibly help you by giving advice.
Fascinating people can help you process your emotions. They may see things from a different perspective. When they ask how you are doing, they genuinely care. It allows you to feel comfortable with them and have a deep conversation.
6. ‘What made you change your mind?’
Our perspectives can easily change. We are always evolving as people, and our thoughts and feelings reflect that. Interesting people want to know how your brain works. If they notice you changed recently, they may want to dig deep to understand why. Some people may want to change your mind with their words, but this type of person wants to hear your perspective, not shift it.
After talking with them, you might feel like you have a better understanding of yourself. Digging deep and working through complex thoughts with someone who has a fascinating outlook on life might leave you thinking about the conversation long after it's over.
7. ‘Would you do it differently if you could try again?’
Stock Rocket | Shutterstock
We can be hard on ourselves when something doesn’t go as planned. While disappointment is part of life, some people encourage us to work through it rather than run from it. Those who prefer deep conversations to surface-level ones challenge us to look at what we would do differently.
We can’t live in regret forever. Complex thinkers want to help you grow from that point. Reflecting on what you would do differently allows us to make better decisions in the future. This type of conversation is deep, but often needed when you may be doubting your decisions.
8. ‘Do you want my opinion or just listen?’
Interesting people don’t feel like they need to give their opinions unsolicited. When someone thinks they’re better than others, it’s natural for them to weigh in even when it’s not asked of them. This doesn’t further a conversation, though.
Asking if you actually want their opinion sets fascinating conversationalists apart. While they have a unique perspective to share, they want to approach things with caution. It takes depth to do this, as many people can struggle to hold their tongue in certain situations. With an open mind, they may be able to get others to open up without feeling stressed or pressured. It will feel natural to have a meaningful discussion.
Haley Van Horn is a freelance writer with a master’s degree in Humanities, living in Los Angeles. Her focus includes entertainment and lifestyle stories.

