No more boring conversations: How to connect deeply with others

We all long to connect more deeply with others. Human connections are what we truly seek in our social interactions, yet we can all remember being trapped into meaningless exchanges and social waist of time, when nobody is satisfied.

It can be the case with strangers or relatives at social gathering, but even with friends, partners and family. Even with our close ones we can experience a difficulty to connect. The time might not be right, or we might have slowly drifted apart, forgot what made us tick. It can sometime be hard to find again this sense of connection if you start to feel alienated from the people you love.

Why do we want to connect with other people?
The objective of interactions is to learn about each others, connect and have fun. Depending on the setting, an interaction focuses more on the exchange of information and facts or more on building report.

In either case, a positive bond and an emotional connection between participants will always make interactions more successful and meaningful.

On a deeper level, we need to connect deeply because it is vital for our very sanity and happiness. Beyond simple words, we need and seek:
-Attention and validation, maybe empathy
-Fun and distraction
-A feeling of belonging
-A feel of being supported and safe.

Why do people stick to small talk even though everyone hates it?

Small talks is a necessary part of human interaction but we tend to get stuck in it. Small talk is like an introduction or a social lubricant. We show that we are not agressive and reasonable people. Yet, past that point, apart from a minimum of attention, nothing is truly gained.

We still stick to small talk because it has become a default mode. It the easiest non-creative way to interact. It requires little cognitive efforts and emotional investment.

On top of that, surface level interaction are safe. There is no social risks with small talk. We are not seen as being weak or vulnerable and are unlikely to be judged. The conversation is unlikely to influence social status or upset the balance of perceived power. Essentially, it is staying in the confort zone.

So How do we go about shortening and/or skipping small talk?

Going beyond small talk is what allows us to connect as human beings. Getting past small talk is not difficult, it mainly requires to get out of the habit of shallow interactions and be present for each others. Here are some tips on how you can connect  more deeply through conversations:

Be genuinely curious

Try to Develop your curiosity. Genuinely aim to discover others. We often get stuck in boring small talks because we do not take the initiative of asking meaningful and personal questions.

Asking personal questions is difficult because it requires of us to be vulnerable and possibly rejected, but it is an important step in creating important connections.

Try to develop the mindset that you can learn something from anybody. Imagine that others are like a goldmine, and that conversation are the way to dig for wisdom and knowledge. The deeper the connection with someone, the more you can venture into the cave.

Show curiosity by asking people for information about themselves. Don’t make it about you, make it about them as much as possible and you are more likely to learn something new. Learn and engage in what they like. People will surprise you if you do not take them at face value and you will soon find yourself in passionate discussions.

Ask good questions

Questions are the structure of conversations, and the bread and butter of quality communication. Good questions mean good conversations and poor questions mean poor communication, it’s as simple as that.
Learn to ask better questions and you will be amazed at the increase in quality of your interactions.

Here are a few tips to improve your questioning game:
-Learn to ask ‘open’ questions: Questions can be open, or closed, unspecific or specific.
When you ask closed questions, that can be answered by a yes or no, or very specific questions, you are decreasing the other possibility for self-expression.

-Asking open questions let them decide where they want the conversation to go more easily, and you can find out what interests them more rapidly.
-A great open question which can be answered in anyway the person likes is:
Whats your story? A question like that is open enough that the person you are talking to choose to talk about their work, hobbies, reason for being here, whatever they want.

-It’s fine if the questions you ask are vague. If the person has difficulty answering, you can always ask something more specific, but remain as open as possible.
For exemple: What are the elements that lead you to be here now?

-Remember that you do not want to zero in two much on facts and details of what others say and conduct an interview. Only keep digging if you can see that the person enjoys the topic and feel comfortable. Try to look for feelings not facts.

-Try to build an emotional connection by relating to their answer with personal comment, or better similarities, which are shortcuts for connections.

-You can also use randomly surprising questions that break expected social patterns, and logical precedents. This will surprise, amuse and create an opportunity for instant connections or keeping relationships fresh.

It can be anything fun, engaging and meaningful. It is more powerful if it is out of context. It doesn’t really matter what it is. Random questions are so unexpected that it forces you to think for a second and be present.

For example: Would you find me more engaging if I came up to you and say “so, what do you do for work?” or “hey, do you like chocolate?”
-Bonus point if the random question leads up to a meaningful conversation. For example: “hey nice to meet you, what was one of your dream as a child?”

Here is a short list of great connection starter questions:
.If you had a superpower what would it be?… Why?
.What does your perfect day look like?
.What the best thing you’ve ever bought under 100 dollars?
.If you’d die tomorrow and had an unlimited cash today, what would you do?
.Whats one thing you want to do before you die?
.Do you believe in karma?
.What scars of yours as the most interesting story to tell?
.What the quality your admire the most about your …mom, dad, whoever?
.If you could listen to one song, read one book, what one movie for the next year, what would it be?

However, don’t tern questions into pickup lines and ask the same thing every time you meet new people. Stay natural, tell what’s on your mind at the moment, you’ll be surprised how well people respond, compare to making a comment about the weather.

-Make your questions personal: Ask question about things you notice about them or what they told you about themselves. You can frame a question as personal with statements such as:
-I have a question for you…then your question
-Since you are…comment…then your question

-Turn question into guessing games to make conversations more fun. After asking a question, say something like: Wait a minute let me guess and then go on guessing… People will find it entertaining, and some of your guesses can take the conversation to some unexpected places.

-You’ll know if your question hit the spot when it leads to a profusion of words. If the person becomes very talkative, they are glad you asked and are likely passionate/touched by the topic, stay on track.

-Remember that when asking questions you should look for whys not whats, look for stories instead of answers, this is were the human dimension lies.

Once you’ve build a bit or report, use questions to dig deeper and enter the zone of intimacy, it is easier if your share things about yourself first. You can ask things about:
-Important personal values
-Sense of identity, who they believe themselves to be
-Their family, children, past, history, how they grew up
-Current important relationships
-Past time and passions
-Causes and opinions they feel strongly about (but be careful as it can be divisive)
-Hops and Dreams
-Biggest experiences and accomplishments
-If you are very confident and develop enough intimacy: you can share and ask about vulnerabilities, challenges, life difficulties, fears and worries
-what brings them happiness and fulfillment, political and spiritual beliefs, hope for the world

Learn to listen

Often, we fail to connect with other on a deeper level because we fail to listen to them properly. We are to busy focusing on our next point, our own problems, or distracted with various fantaisies to pay proper attention to them.

The thing is, there are varying degrees of listening. The idea that you either listen or you don’t is false. You can listen a little, not being very focused, to being mildy engaged, to giving the other persons your full attention.

Listening requires presence, and presence requires focus or attention.
This is partly a conscious choice, partly a habit, and partly physiological, having the mental and cognitive space to be able to engage.

When you really listen, you increase your opportunities to rebound on interesting information and follow up with questions and comments. You are also more likely to connect intuitively with the other persons. To be a better listener, try to:
-Practice meditation, presence and grounding
-If you find yourself distracted in social situation try to come back in the now
-Try to stop seeking validation but seek connection instead

In order to truly listen, it is important to be able to temporally forget what you know, suspend disbelief and be as open minded as possible. Before jumping in to conclusions, allow others to share their reasoning with you, they likely didn’t come to their opinions randomly.

If you find what they say offensive, try to seek out the experiences and reasoning that lead them to these claims, before asserting your ideas and values.

When you are able to listen and relate to the thinking process of others not only can you connect with them more deeply, but you will be more effective at finding truth as well as sway others to your own opinions.

Develop your intuition

Communication happens on may different levels. When you start to be more present and really listen, you start noticing more that meet the ear, so to speak.There is a big gap between what people say and what they are trying to convey, because we’re not perfect at communicating, and not always self aware or honest either.

The speaker might be unsure, confused, in a state of inner-conflict, distracted, bothered, so many thing can disturb the flow of good clear communication.

When you learn to read between the line, you can go straight for meaning behind the words and burst through small talk quickly by connecting on an emotional level.

-Learn to develop your intuition by asking yourself; how does this person feel? How do I make them feel? How does…the topic… make them feel, influences them?

-Try to establish a conversation about emotions rather that fact as quickly as possible.

-Use empathy statements to connect with them once you have identify what the person is feeling or seeking. Your assumptions can be a risk if you get it wrong but it a chance at establishing a strong connection.

-Take educated guess or interpretations of what they say, lead the conversation with comments, you must have felt…, or if you don’t know simply ask, how did you feel? Don’t just take what people say at face value.

-Learn to watch and interpret body language, physiological signs, mannerism, tonality and speed of speech. All that will give you information about the other person and will give you a feel for them. You can’t keep track of all that informations consciously, but once you’ve learn cues and practice, it can become intuitive and automatic, and you’ll know how people feel without the need to voice it in your mind.

-You can go even deeper by learning to notice the hidden needs, motives and coverts behind what people says, the information behind the information. What is it that they are truly saying?
Notice what people bring up. What people talk about is not random, try to decipher the real intention behind statements, the hidden need, where are they going with this? What do they want? How do they feel and want to feel?

Developing this social intuition often goes hand in hand with developing your own emotional intelligence and be in tune to how you and other people feels at given moments, as well as your ability to deal with your and other people emotions.

-Ultimately, when you are very intuitive, you’re able to make people feel what you want, connecting with them deeply. Becoming proficient with humor, empathy, vulnerability, motivational speech, banter, quizzical conversation as well as your very way of being will help you get there.

Becoming a better communicateur:
If you’re an authentic, curious, intuitive listener, most of your interactions are already sorted.

However in the rare cases that conversation still go stale, when you can’t seam to connect, or if you are after something in particular, you need to learn how to lead conversations and clarify communication.

Here are some general tips on becoming a better communicator:

-Repeat and reserve what they say: this will clarify the discussion and show them that you are really listening. It also give you the opportunity to redirect the conversation with a question of your choice.

-Mimic body language will naturally increase bonds with people. Find commonalities and give unique compliments, to make the person feel special and increase connection.

-Lead topic of conversations with leading questions and by contributing actively to the shared pool of knowledge. If you are bored, just bring something new to the table.

-Talking about family is very likely to bring people close together when all else fails.

-Be honest and vulnerable but also Learn to express you boundaries when you don’t want to talk about something. You don’t have to connect at all costs.

-Become proficient at changing topics and ending conversations. Learn to be candid and honest, putting people down gently when the conversation is not going the way you want it to.

-When connecting through technical subjects, if you know what you are talking about connect on technical details and opinions. If you don’t know, connect with eagerness to learn and enthusiasm by asking questions, but don’t pretend to know more than you do.

Make interaction more fun and engaging:
when both parties are having fun and feel good, bonding happens automatically. Try not to take things to seriously and turn conversations into games. Using humor, suppositions, guessing games and banter can let you be playful and make an interaction more organic. Everybody is socially awkward on some level and everybody wants to have fun.

There are a few ways to make conversation more fun and engaging:
-get them to use imagination
-create scenarios and would you rather game
-come up with guessing games
-learn banter and witty come back
-learn improvisation and situational humor

Ask for opinions and advices

Everybody has opinions, and don’t we love to share it. Asking for people’s opinion not only make them feel important, but also let you set the frame for a discussion topic that interests you.

Maybe you can have prepared subjects that are important to you at the moment and plan on connecting with others on that level. Besides, you never know, you could always come across good advices:
-Ask for people opinions and advices
-Start with something honest and personal but not to big. Don’t ask, what’s the best way to get a divorce, ask something along the line of, “I am looking to change my hair style, any ideas ?”

-You can ask opinion and advice from anything like clothing and style, activities, to more serious matter, career, life missions, relationships. Intimacy and connection can happen very quickly through this process

-There is a chance people will share with you things about themselves and maybe reciprocate by asking your opinion, and then the game is on.

-Bonus point if you ask advice after giving a compliment, or something that is relevant to what the person said. To keep the example from earlier, if your interlocutor just mention he/she is a hairdresser, all the better to ask for haircut tips. People don’t always want to talk about their work, however everybody likes to be admired on their expertise.

-Start a debate but be very careful at mediating different opinions. If you’re good and effective at communication and can talk about controversial matters without being confrontational, debates are a great way to have a good time.

Remember that debates aiming to create connections are very different from debates you are trying to win. In this instance, you want to favorise, validate, ask for others opinion, seek mutual agreements, and stay open minded even if you don’t agree.

Keep the mental mind-frame “that’s interesting that you think that, tell me more”, instead of “you’re wrong and I’m right”. If you disagree, let them finish their point before you ask if they are willing to hear yours.

Keep it balanced

Conversations are not lectures, if you want the conversation to be engaging, real, and natural for both parties, you have to strive to keep it balanced. In some interactions, you can notice that some people take up more room and speak most of the time. The pourcentage of time you speak is often an good indicator of how well the interaction is going.

Obviously it varies between circumstances, personalities and needs: some people are more talkative that others, some prefer to listen. In this fashion and “extrovert and introvert can be complementary.

Some people might have certain knowledge the other don’t and could be untitled to speak more about a certain topic. Even if that’s the case, one should not alienate others, and should always focus his/her attention on the audience, because it is the point of an interaction after all.

If you are to focused on listening to your own voices, you might have a good time for a while but you won’t be building connections, and it is likely that you’ll soon find nobody to talk to you and or sit through your lectures.

If you notice you are talking to much, chances are you are boring people. It is difficult when you are passionate about something that other do not resonate with, but you just have to accept it and move on, or find someone else who shares your passion. 

Pay attention to conversation efforts:

Conversational efforts are the ways people provide information and give cues for the communication to keep going by contributing to the shared pull of knowledge. This is done through statement, questions, follow up, listening cues (approval, nods, etc)

It’s important to notice who is putting more effort into the conversation. Often the person who puts to much effort in a conversation can be categorized as needy, or seeking validation, if there is no reciprocity. 

It’s OK at the start to invest more effort into the conversation in order to be engaging, curious and spark a conversation. However if after a while, you are the only one showing conversational effort and showing interest, the interlocutor is likely not interested in you.

In this case:
-Either leave the conversation
-If you stay, have a good reason, not out of seeking approval. Find a way to communicate better in order to engage them.
-Dont be desperate, you cant connect deeply if you dont allow others the space to choose to engage with you or not. 
-At some point for report to be created, both parties need to put in the work. If you do all the work, you actually decrease the connection with the other person.

You can make the other person do some work to keep the conversation going. If you find your interlocutor disengaged and uninterested, it’s OK to disqualify them.
People will also like you more because they try to connect to you, and seek from you as well. If you are the only one seeking, you appear needy, it needs to be mutual.

If the other person is not very engaging, you can use silence to your advantage. People will often diffuse social awkwardness by being more active.

In the same way, if they talk to much and become boring start showing less approval and validation, they will often adjust and let your space to speak and change the subject, or even do it themselves.

-If they are completely disengaged, silence gives your space to leave:
Remember that you can’t be a good match with everyone. Socializing is partly a selection process, when you identify who you can connect deeper with and establish relationships.

Be Candidly honest

Remember that connecting deeply with someone does not equate with pleasing them. We often get stuck in shallow conversation because we avoid social risks and offending people. This also what keeps us from keeping it real and fulfilling.

Just be yourself and learn to say what you think, feel, like. It’s acceptable to put forth your opinions, by validating or be oppositional if you don’t agree.
You’re entitle to say “I like that, I don’t like that.”

Even when you seek the best in people, when you are open minded and kind, sometime its just not the right fit. It doesn’t make any of you a bad person, it might just be the circumstances.

By being honest, you take some of the guessing game out of the equation and make connecting easier, or lack of possibilities appear faster.

If all else fail and you can’t connect with someone just leave:
-You dont even have to be nice, just be honest, your being dishonest by staying, and doing your self and the other a disservice by waisting time and air.

-Excuse yourself to the bathroom, go get a drink, or find any excuse you want. You’re not likely to see that person again.

-Most of the time, it is possible to connected even with “boring” or asocial people through kindness , talk on an emotional level can often let this kind of people out of their shell, and you might find that they are pretty interesting. 

-If you get stuck in a conversation, say that you need a break, it’s absolutely fine if you are honest and polite about it. Don’t go for the mean spirited move of switching with someone else that has to endure the painful conversation in turn.

Don’t take the other for granted:

One of the reason we might have difficulty to keep connecting with the people we love is that we start taking them for granted.
The more time we spend we them, the more natural their presence feels to us. They start to become like the furniture, and are hardly noticeable anymore.

In such instances, conversations stays factual and become shallow. These conversations feel like news update, and are often redondent.

Keeping facts about each others and small talk are still a way to start connecting and it help show people that you care, if on a regular basis. However, when we become trapped in this kind of interactions, our passion for the other can take a hit.
To not take others for granted try to:
-talk about your feelings for the other person
-share vulnerability
-talk about your current passion
-ask and connect with their current passion
-plan shared activity
-Make an effort to show interest and take responsibility in the relationship.
-Be honest and cut through the uninteresting if you feel like your conversation is routine.
-Bring back the conversation to something meaningful. If you are bored, chances are the other person is bored to.
-it can be difficult for long distance relationships as talking is often the only possible medium for connection. The ability to connect through conversation is all the more important. 

Be in the right place:

Ultimately you have to be in the right frame of mind to interact with others. If you feel like being alone, socializing will feel like a drag and a burden. You don’t have to socialize if it isn’t what you want to do.

When you need to be alone, find a way to find space. To be good at connecting with people you need the ability to be present and take risks by breaking mundane social settings. Having the right attitude will make interactions seamless and effortless.

These trait will help you connect with people effortlessly:
-Don’t be to invested in the outcome, learn not to care to much and just have fun.
-Project and expect excitement: be like a child discovering something new, turning on your curiosity and honesty. Treat socializing like a game, a treasure hunt, or even role-playing. (but be yourself)
-Be empathetic and kind with others, keep in mind that everybody want to have fun and be appreciated. We all suffer and have problems
-Be in a state of feeling good about yourself. Allow yourself to be real and vulnerable but not needy, give others space to interact or not. Don’t be afraid to share about yourself.

-If you are going through a hard time, be honest about you’re pain and hurts but don’t put it on other people’s shoulder. If you are sad and depressed people will not want to interact with you. To be good with others you have to be good with yourself first.

-Learn to love yourself and stop seeking validation. Make it about others, elicit advices, opinions, and personal details. Keep the conversation focus on their passion and interests. Find commonalities quickly, and notice how good you feel.

-Greet new people as like a long time friend that you’ve havent seen in a long time, or that you’ve forgotten. A stranger is a friend that you haven’t met yet. Literally say to yourself in your head “this person is my friend”, and imagine that you already know them, before talking to someone, and see what happens.

Recommended reading:
If you want further advice and really delve in the complexity of communication, I would recommend these books: 
-Nonviolent communication by Marshall Rosenberg
-The psychology of persuasion by Robert Cialdini
-How to meet friends and influence people by Dale Carnegie

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