How to Have a Deep Conversation

Getting Down the Basics

Find the right person. Sometimes, chemistry plays into the depth of connection between two people. If you have been trying and failing at engaging in deep conversations, it could be because you are trying with the wrong people. Look for other people like you who thrive on deep conversations. A “deep” person may be very curious, thoughtful, open-minded and show excitement when discussing topics that go beyond the surface. One way to find a group of people who like in-depth discussions may be to search for a Meetup in your area for that purpose.

Assess the temperature. Even if you find most ideal person, you can still run into a wall if that person is not in the mood to talk or if the context and setting are not appropriate. Education level and knowledge base may also play into whether someone is willing to get deeper with you on certain topics. Feel out the person first and try to discuss topics that are relevant and interesting to your conversation to him or her. Bad times to engage in a deep conversation may be when running late for an event, when someone is angry or upset, in a noisy or crowded place or when it’s close to bedtime. Ultimately, it will depend on you and your conversation partner.

Start with small talk. You may dislike small talk, but it’s difficult to get to a deeper conversation without some sort of lead-in. You need to warm yourself and the other person to the idea of going deeper, which means starting at the surface and seeing how the two of you get along. Ways to engage in small talk might be to ask an easy, straight-forward question or to give the other person a compliment. For example, you might say “Oh, I really like your handbag. It’s so colorful,” and see how the other person responds. Reader Poll: We asked 372 wikiHow readers about the best topics to bring up when you’re getting to know someone better, and 75% agreed that it’s best to discuss the other person’s hobbies and interests. [Take Poll]

Listen to understand. A great method to getting another person to share more is to be an effective listener. When you actively listen to another person is saying, he or she feels affirmed and is more likely to open up. Many times, you may listen to prepare a response. Instead, try to listen to really understand what the other is trying to communicate. Active listening involves: Paying attention – Turn towards the other speaker. Clear your mind and environment of any distractions. Make occasional eye contact. Demonstrating that you’re engaged – Nod your head when you agree. Respond by smiling or laughing as appropriate. Maintain open body language with your legs and arms uncrossed and relaxed at your sides. Offering feedback – Paraphrase what was said like “It sounds like you’re saying…” and ask clarifying questions like “Is this what you mean?” Avoiding judgment – Refrain from interrupting the speaker to argue with a point. Allow the person to completely finish talking before saying anything. Responding – Share your own opinions while still showing respect to the speaker. Aim to be open and honest.

Focus on quality over quantity. You can't click with everyone no matter how hard you try. Sometimes, it seems a conversation is going nowhere—and it is. When having a conversation, the quality of it is more important than the quantity or length of time you spend talking. Refrain from trying to keep the other person engaged when it’s clear he or she does not want to participate. For example, you may talk to someone every day with a simple “Hi, how are you?” Yet, you may find you know more about someone else whom you only talk to once a week. It all depends on the quality of the conversation.

Asking the Right Questions

Avoid close-ended questions. When you’re trying to get someone to open up and go deeper in conversation with you, you want to avoid questions that close off the discussion. For instance, you might immediately start trying to learn the person’s likes and dislikes by asking “What’s your favorite color? Food? Season?” The problem with such a question is it doesn’t promote a detail-oriented answer because it can be answered with only one word (e.g. “Purple. Pizza. Summer.”). Aim for open-ended questions which allow for broad answers along a range of topics. These sorts of questions can lead anywhere. Ask open-ended questions as follow-up to close-ended questions like “What’s your favorite color/food/season? Why?” Or, you can ask such a question to learn more about another person, such as “What are doing over summer break?”

Query about the person’s passions or dreams. People are happy to talk when the conversation is circulating around their interests. To get another person talking in a deeper direction, try to learn about what drives the person each day. You can ask a questions as simple as “What are you most passionate about?” When the person responds, be sure that you demonstrate excitement and interest in the subject to keep him or her talking.

Figure out what makes that person feel fulfilled.Asking your conversation partner what makes him or her feel fulfilled is a way to uncover what makes the person happy. When you find out what makes him or her happy, you can modify your line of questioning to deeper, more emotional topics. For example, you might say “What makes you most fulfilled?” and the person responds “My family.” You can then follow-up and say “Tell me about them”. This can lead to an in-depth and rewarding discussion.

Show interest in the person’s quirks. Although people like to find commonalities between themselves and others, they also like to stand out. Question your conversation partner about what makes him or her different or unique to trigger a deeper discussion. You might ask “What do you think makes you special?” or “What’s something about you that people don’t often know?”

Ask “why” to get more information. As a rule-of-thumb, you can ask your conversation partner “Why?” after almost any statement to prompt the person to dive deeper. People don’t often go to the toughest or most detailed answer first. But, when you show more interest by asking “why” you invite the person to go deeper with you.

Being Vulnerable

Be ready to take a risk. If you want to enjoy heartfelt, philosophical talks with the people around you, you’ve got to be willing to strike out. If you’re afraid to risk starting a conversation with the wrong person at the wrong time or about the wrong topic, then you might not find the person with whom you have crazy chemistry. Anticipate that, sometimes, people will be uninterested in your conversation starters. Sometimes, they won’t. If you come across someone who is lackluster, simply move along to the next best candidate. Remember, nothing ventured, nothing gained.

Share personal stories. Self-disclosure shows vulnerability and opens the door to a deeper conversation. When you share a personal story with someone, you put yourself out there in a courageous way. Hopefully, the person will follow suit and be receptive to your sharing. Keep in mind that you should use discretion when sharing personal stories. For example, you might not feel bothered about sharing the story of your adoption with a casual acquaintance, but you may not want to discuss a romantic relationship. Share what you feel comfortable sharing and make sure that your disclosure is appropriate for the level of relationship you have with the other person.

Respond genuinely. If it’s an appropriate time for you to share or respond, do so honestly and sincerely. You don’t have to pretend you agree, if you don’t. In fact, you may not have that deep of a conversation if you and the other person share the exact same views on every topic. Don’t be afraid to disagree, as long as you’re not doing it offensively. The conversation can grow deeper when you have varying opinions that you are able to share respectfully and without trying to make the other person agree with your perspective.