How to Take a Conversation Deep

Here are some of the things I’ve noticed that help take a conversation deeper. These are my observations from conversing with a good friend of mine in which we constantly delve into deeper conversation.

1. As with most conversations, begin with small talk to get a feel of their current feelings and catch up to see if there are any major events in their life. Begin to probe for areas in the conversation that have more emotional substance. By listening actively and being genuinely curious in what they are saying, begin to ask questions that will yield more emotions, feelings, and thoughts. The real meat of the conversation begins here. To take it even deeper, delve appropriately based on the flow of the conversation for more personal and private thoughts and feelings. These thoughts and feelings are ones that have an element of vulnerability in them. These are personal thoughts and feelings that will make us seem less than perfect. These private feelings we reveal will express pain in areas of our lives. It is these intimate thoughts and feelings that others can connect with so well that allow connection to be built easily and deeply. Revealing something that has been bothering us, something that we are afraid of, something that made us feel embarrassed, angry, or hurt can all count as being vulnerable in a relationship.

2. The environment needs to be one that is quiet with no visual, auditory, or physical distraction. So for example, conversing with a friend one on one while shooting hoops presents a source of distraction for both people. Deep level conversation requires concentrating on talking and listening to each other. If we are in a loud place, this destroys all chance of going deep. We can’t talk and learn about the other person if we are having trouble hearing each other. Also, if we are having a conversation in a car in a nice quiet place but there are flashing lights outside, we are going to be distracted as well. Having a comfortable, quiet place with no distractions except having a conversation is absolutely essential to take a conversation deep. This is all the more true because when conversations delve into personal thoughts, feelings, and emotions, there may be some anxiety going on. I have noticed this to be true for myself. Many times when I reveal something more personal or vulnerable about myself, I become a bit anxious. This doesn’t mean I do not want to take the conversation deeper. However this may not be true for all people though. So just remember that nervousness in a conversation from going deep does not mean the other person does not want to go deeper. Nor does it necessarily indicate the person does want to. They may be a little bit too scared at times, which can be observed through their body language and voice tone, so the thing to do then is the bring the conversation slightly lighter by laughing a bit. Laughing releases the social tension that may be there. It does not need to be something funny for the both of you to smile and laugh when conversations go deep and anxiety is present. When there is anxiety, even statements not meant to be funny can induce laughter.

3. I may have briefly mentioned this one in a previous bullet point, but this one is quite important. For me, one on one interaction is absolutely necessary to take a conversation deeper. My twin and I have a friend who we delve into deep conversation with, and although on the surface my brother and I may seem similar, deeper down we both have our own independent thoughts and feelings. However, many times I feel we are viewed as one, that, what I say and feel is assumed to be true for my brother and vice versa. When we talk, we aren’t so much three people conversing, but more two people conversing. If I did not know the third person as well, going deep would be more difficult. It is the trust factor playing here. If I do not know the third person comfortably, I would feel quite hesitant to share my more personal thoughts and feelings. We would all need to feel that we can trust each other when sharing our thoughts in order for deeper level conversation to be achieved. Also, all three people need to desire taking the conversation deeper. With three people, it can be harder to direct the conversation especially if the third person continuously cracks jokes, changes the topic, and thereby influencing the conversation to be lighter. With one on one interaction, I can direct the conversation without having another person redirecting. Even if the third person enjoys deeper conversation, they may ask more fact based questions than emotion filled questions. They might not know they are unintentionally redirecting the conversation away from as much potential depth. One on one conversations are easier to direct and have less chance for misdirection.

4. Asking the right questions is a must to bring the conversation deeper. Asking questions that will elicit personal thoughts, feelings, emotions, and stories are necessary while asking questions to get the facts are not as important. Girls tend to do this naturally whereas guys tend to care more about the facts of the story. This is a reason girls tend to have more close friendships than that of guys. Keeping in mind a few power questions is always handy. Power questions are questions that require more thinking. They require the person to spend a certain amount of time in introspection, which is another reason why introverts are better able to go deep, and they are questions that elicit personal thoughts and feelings. I have a list and a few books that are filled with terrific power questions that will elicit interesting, deep conversation; I may post that list onto my blog soon.


5. Vulnerability. It is a must to develop intimacy. Lack of vulnerability can stem from fear of intimacy. Intimacy is a deep emotional connection formed by taking the time to share our personal thoughts and feelings, the areas of pain in our lives and understanding and empathizing with the feelings of others when they express emotional hurt. Courtesy to http://powertochange.com/sex-love/menintimacy/ for my definition. My definition of intimacy matches the definition women tend to have for intimacy. I feel a certain amount of embarrassment for how much I love intimacy. I guess I’m afraid people won’t understand and I would be subject to ridicule. While imparting something in your life that is painful, you must, must convey with your voice tone and body language that you are telling them something personal about yourself because you like and trust them. You are not looking for their help, nor do you want their help. You want to tell them something about yourself that not many people know because you feel you guys have something special going here. You must convey with your voice tone and body language that you are not going to suffocate them with neediness and insecure behavior when you tell them something about your past that may have caused you lots of pain. This is absolutely essential. If we act like we desperately NEED their help or are trying to get them to do something for us, they will run and do as much as they can to avoid us. Clingy and neediness will drive people away. Use a calm, quieter, softer tone of voice and speak slower when expressing your more inner feelings and thoughts. Open body language is best to show others that you want to talk about what’s at hand. Feel those more vulnerable feelings and let your voice tone and body language flow naturally.

6. Look for more introverted individuals to talk deeply with. Introverts tend to prefer and enjoy small, intimate get-togethers rather than parties. Introverts generally spend lots of time thinking and reflecting over their own lives, making intimate, deep discussions more likely. More introverted individuals also prefer depth to variety, so more introverted individuals love thinking deeply about things. All these reasons and more make introverted individuals the preference for having deep conversations with. However, here's the catch 22. The more introverted the person is, the more time they need to fully express themselves. My communication style often times revolves around listening and asking questions that will allow them to reveal their personal thoughts and feelings. However, I know for myself, who is an introvert, that I need time to warm up to get to the point where I can find the right words, become fully invested in the conversation topic, and fully express my thoughts and feelings. I believe this to be true for more introverted individuals. There is actually a scientific basis to support my belief. In “The Introvert Advantage”, the author delves into the differences in the brain between more introverted and extroverted individuals. Introverts require time to think over questions and come to terms with what they want to express and how they want to express it. This explains why introverts tend to be good writers. Writing gives us time to completely formulate how we want to word things and express ourselves. The main lesson here is that the more introverted individuals usually need time to warm up to be able to fully express what they want to express. Since I have not met a person who asks deeper level questions for me to the extent I feel I do for others, I know from my experience that when asked a relatively personal question, I’m thinking how to word it in the way I want it to sound and have my message be communicated in the most concise and eloquent manner. For me to feel like I’ve fully expressed my thoughts and feelings, it definitely takes the patience and time of someone who will ask deeper level questions without going back to talk about themselves right after asking. When a question is posed my way and I begin to answer the question (deeper level questions), I’m beginning to work to find the right way to express myself, and I often feel frustrated when someone asks me a deeper level question and resorts to talking about themselves after I give my initial and incompletely expressed answer.


It’s helpful to remember that when asking deeper level questions about other people, start simple. Weeks ago, I felt my friend made this mistake. I believe we shouldn’t ask, "What was your biggest challenge in high school?" right off the bat, especially if they were taking part as the listener and questioner for a while- remember that introverts need time to warm up to get their train of thought going. I think we should help them remember by leading their memory back. Ask instead, "which year of high school was toughest for you?" "How would you describe yourself?" and slowly probe deeper and deeper from there.

The way I see it, part of not being able to fully express myself is an inherited flaw in my communication style. Again, when I meet a friend one on one and we begin to delve into deeper topics, I listen, ask deeper questions that elicit more personal thoughts and emotions, and allow them to fully express what they want to say. The flaw is that now they are fully engaged and invested in the conversation. They feel the urge to express themselves and have the other person understand them. This means that occasionally they will pose a question your way out of genuine curiosity and perhaps also because they don’t want to seem like they are only invested in talking about themselves in the conversation. I want to show them that I enjoy and desire deeper conversation, so I reciprocate by being interested and curious about them. This usually results in the other person talking a lot about themselves, and I completely understand why that is. This is not to say that I don’t want them to fully express themselves. I love one on one conversations and delving into the mind of others. I want the other person to be able to fully express himself and for me to be able to empathize with what they are feeling. At the same time though, I desire to express myself, who I am, how I feel and think about things. I desire to have others understand and accept the more personal and intimate sides of me, but partly due to my own lack of initiative to talk about myself and communication style, many times I end up feeling frustrated. I need to find a balance.

There have been a few occasions where I’ve felt satisfied with what and how much I got to express of myself, and l know in hindsight that I also failed to ask the other person their thoughts and feelings on the topic. In those moments when I was completely expressing myself, I felt a powerful urge to be heard and understood. This is another reason I feel compelled to express myself in my blog. My blog allows me to think and fully express what I feel with complete focus. I require lots of focus when expressing myself and distractions throw my focus off course. This is another tendency of introverts according to “The Introvert Advantage”. It takes us a lot of energy to refocus back to our thoughts after being interrupted and brought to the surface from deep conversation. That is the flaw in my conversation style, but I think this style may be necessary to show the other person that I want to take the relationship and conversation deeper. If I don’t take the initiative to take the conversation deeper, with most people, they won’t bring it deeper themselves. I have a friend who freely shares his more personal thoughts and feelings. Our desire to have deeper level conversations allows us to transition into meaningful conversation without too much effort. I need to work on expressing my own personal thoughts and feelings more freely. To do that, I have found that I need to adopt a mindset of being curious, listen actively, ask questions that elicit emotions, personal details and stories about themselves, connect with what they are feeling, and reveal my own more personal thoughts and feelings related to the topic. The great thing about having this blog where I express my personal thoughts is that if a familiar topic arises, I can express how I feel and think about the topic through reading out loud the post I have already written. Many times my mindset is geared towards asking deeper questions and allowing them to express themselves. And while this is good when they are really expressing how they feel deeply about something, I may have to be a little more self interested. A good way to ensure this is to reveal your own personal thoughts and feelings about the topic every two or three questions that you pose. If you don’t do this, your mindset will be conditioned to keep asking and very little disclosure. It’s all conditioning. The more you ask and the less you talk about yourself, the more this style of communication will continue throughout the conversation. “An object in motion tends to stay in motion, while an object at rest tends to stay at rest.” Be interested in their life, make the topic something about them, but gradually reveal your personal thoughts on their thoughts and feelings and reveal your own personal thoughts and feelings of a time when you felt like that. I know that the revealing part is more difficult when they are talking a lot about themselves, so reading a post from your blog that relates to their situation will allow you to express your inner feelings deeply and without much interruption. I am currently thinking, when I read a post that relates to their situation, I should allow them to talk every so often about what they think and feel about what I’m reading to them, without having them wait all the way to the end of the article, since my articles tend to be quite long and they may forget their thoughts or insight that spontaneously comes into their mind. Perhaps every few paragraphs or wherever appropriate, I should let them talk about what they think and allow them to fully express what they think and feel about what I read. This way I don’t make the same mistake of talking all about myself until I feel done expressing myself completely and forget to address what they fully think about the topic.

If I haven’t previously blogged about their situation, and I have some things I want to express, reveal them and slowly up the ante. It does require making an effort to express yourself when you’ve made them to be the center of the conversation. You need to get that ball of vulnerability and expressiveness rolling into motion. You can ask a question to get their thoughts and express your side of the situation as well. For example, “what do you think about…because for myself, I feel that…”. It doesn’t have to be a huge insight, but talk about yourself as well. Don’t hide how you feel about something just because they didn’t ask. Take the initiative and assume that they want to know the same about you. They probably do but remember how we tend to forget to ask other’s opinions when we feel that urge to completely express ourselves? Remember again that the exception to this is when they are really expressing how they feel about something deep down that is/ was important to them and you want to help elicit the most emotions as possible. Then it would be a great idea to listen actively, ask deeper and deeper questions without butting in and talking about yourself.

I have noticed that when both sides really desire to express themselves, and there isn't that one person who will ask deeper questions, it tends to become an “Oh, I really have something to say about that!” conversation where depth is lost because both sides are trying to express how they feel deeply about something, at the same time. Neither side is fully listening to the other as both are in their heads. They are feeling a lot about the topic, they are lost in their heads both trying to express themselves fully, and they both feel that powerful urge to be understood. This almost always results in both sides feeling not completely expressed and understood. In my opinion, this type of relationship will begin to breed a certain amount of hidden resentment, as both sides feel the other person is only in the conversation for themselves. As both sides talk about themselves, the other person butts in and talks about themselves, thereby interrupting the train of thought of each other. It’s also funny to watch two people trying to talk louder than the other. This is why it is essential to be that person who will listen, ask deep questions, be patient and give time to allow the other person to completely express themselves, and then go on to express who you are and your own more intimate thoughts and feelings. I believe this method will work better for getting into deeper conversation because we need to allow each other to fully express themselves uninterrupted. This will allow them to feel understood and they will love you for it. Remember the last time when someone showed a genuine interest in who you are and you felt like they really got to understand you? Treating that person like they are the most important person in the room is the quickest way I know to make a friend. This is my own take on it and I can’t say if this is true for everybody.

I’m glad I’ve found what I want for myself at age 19. I’ve been searching for what I want to do with my life since junior year in high school. This is another step to getting me closer to developing the deeper relationships I desire in my life.