Ultimate Guide to Conversation & Social Skills

Most of our fun, fulfillment, and connection in life occurs in social activity.

We are social creatures who have been designed to help each other out in life including meeting our goals, having fun as friends, experiencing life together, growing through painful and good times, and working to serve other people. 

The friends we meet with similar interests, the fun nights out on the town, the adventures, the romantic relationships, the business relationships, and the people we meet from day to day all make up our life’s meaning and fulfillment. 

This is why developing the ability to connect with people, having quality meaningful conversations, and creating a strong social network is important for living a good life. 

We are healthier and happier people with good relationships and social connections.

As someone who has struggled with social anxiety and maintaining relationships, I wanted to create a guide to the basics of social skills so that I and others can improve over time. 

Being Honestly You

The first thing I wanted to discuss before getting into the basics of social skills is the importance of being real and authentic above all else.

This is so critical because you want to connect with people who are genuinely interested in similar life goals and interests as you are in order for quality connection to take place.

If you put out a fake persona just to attract people it will lead to an inability to relate deeply to people and share authentically without pressure.

This starts with knowing what you want in life and being able to express those interests, passions, and desires to new people you meet in order to discover if they are a good fit in your life.

Above all else, try not to be fake or needy and develop the courage over time to be boldly and assertively yourself.

Essentially, the aim of improving your social skills is to develop the ability to express yourself fully so that you have the courage to meet the people you are meant to connect with in this life.

Part 1: Body Language, Vocal Tone, Attitude

Developing strong body language that shows confidence is an important part of being a good communicator.

Your body language, vocal tone, and attitude work directly with the way your body is presented and it gives a clear signal of the state of being you are in.

Despite what you say, your body language conveys how you hold yourself as a person.

The more open, clear, and strong your body language is, the more it will signal that you are confident, attractive, and command charisma. 

Key Tip: If you’re feeling anxious or not very confident the best thing to do is recognize it, accept it, and then see if you can practice changing your posture little by little over time working on sticking your neck out a bit and practicing holding eye contact a little longer than normal. Be sure to be kind to yourself as changes like this take time and courage.

Below are the main things to work on:

1. Establish Solid Eye Contact
   • When you can hold eye contact it shows confidence and trust. It also creates a deeper connection and shows the other person that you are present and interested in being with them.

2. Head Up Shoulders Back
   • Tendencies to slump the shoulders or look down at the ground will make you look insecure and unconfident. Work on holding your head high and keeping a straight spine. Practice sticking that neck out.

3. Smile
   • Smiling can show friendliness and put the other person and yourself at ease. That being said, don’t fake a smile and there are times not to smile as well.

4. Open Body Language- Take Up Some Space
   • Take up space and show that you belong and want to be heard, seen, and are confident in owning yourself. Try not to cross your legs or arms and stay open.

5. Speak Louder & Enunciate
   • Work on raising your voice just a bit louder than normal to project well. Let go of caring what other people in the environment think about your conversation and practice speaking from the diaphragm, not the mouth. Claim your right to be heard as a person.

6. Move Slower
   • Practice moving and talking a little slower. Like you are in a pool of honey.

Part 2: Approaching & Starting Conversations

After your body language and who you are as a person the first step in initiating any new conversation is being able to approach someone new (or someone you already know) and start a conversation from zero.

This step of being good socially is often one of the hardest for people to do because it usually causes some level of anxiety or nervousness about the possibility of rejection or judgment, especially when approaching someone new and putting yourself out there.

That being said it is also the most fun and rewarding aspect of social skills as it’s an opportunity to be able to meet new friends anywhere you go and expand your world.

Below are the main keys:

1. Choosing The Right Environment

In order to meet new friends or romantic partners that you actually want to build a relationship with it’s important to choose the right place, community, or environment where the people you like spend time hanging out.

For Example: If you are a health-conscious person who likes to workout, surf, do yoga, hike, and do business then the best way to meet people who you might really hit it off with is to put yourself in places such as a surf group, yoga studio, spiritual community, entrepreneur group, local gym, or any other place where those types of people may hang out.

It’s going to be a waste of time putting energy into trying to meet people in places where you don’t share any common interests.

The one exception is general social places like clubs, parties, or bars as most people who go to these places tend to go out for fun and go with the attitude of meeting new people. 

These environments are much more general so it may be harder to find someone you really connect with on a personal level but they are good social practice playgrounds.

In summary, demographics matter if you want to make quality connections so get clear on what you want for your life and what types of people you want to develop relationships with. Then put yourself in the right environment to strike up a conversation.

2. Having an Intention for The Conversation

After putting yourself in the right place it’s helpful that you have an idea of what you want out of the conversation before initiating it.

This is important because if you know that you’re serious about developing a long-term friendship with someone then you can spend the time to really get to know them and ask deeper open-ended questions to develop empathy.

On the other hand, if you’re just interested in a business relationship with someone or find a girl that is attractive but you don’t see long-term potential then you can steer your conversation in the right way for your intention.

Yes, you can also just be social and not have any intention for the conversation but when you want to steer your life in the right direction or have a limited amount of time (which is everyone) it can help to have clear intentions.

This saves your precious time and energy as you won’t waste it on people you don’t really want to dive deeper with.

3. Be Seen

Before you approach and strike up a conversation make sure to be seen and if possible make some eye contact with the other person. 

The worst thing you can do is startle someone approaching them from behind or sneaking up on them. The other person needs to feel that you are safe and friendly enough to want to chat.

It also helps if you are able to make eye contact or move into someone’s territory to sense if they are at all interested or not.

That being said, sometimes you just have to go for it even if you don’t get positive signals and see what happens.

4. Approaching & Opening Basics

Approaching and opening a conversation can be tricky. The goal is to keep it simple, open up the conversation, and get right into weaving (or conversation) with them.

There are a few ways to go about it.

Direct Approach

The first way to approach is to be direct and honestly tell someone why you wanted to say hi.

Then ask an open-ended question about them or the situation to get into a conversation.

The willingness to put yourself out there and be honest is often one of the best ways to approach someone new.

Here are a few examples:

• Hey, I saw you sitting there and I had to say hi, I thought you were cute. What’s your name?
• Hey, I saw you standing there and thought you looked (approachable, friendly, interesting, cute, badass, smart) and wanted to say hi. I’m Josh. What have you been up to today?
• Hey, I saw you guys laughing over here and thought you looked like the most fun group out here and I wanted to say hi.  I’m Josh. How do you all know each other?

The key with the direct approach is to be honest about why you wanted to say hi, ask a simple question, and then get into weaving (conversing on different topics) with the person to get to know them a little.

Indirect Approach

Indirect approaches are types of openers where you aren’t directly stating why you wanted to say hi but instead making a comment, asking a question about the situation, or saying something funny then getting into an open-ended question about them or the event.

Here Are a Few Different Types of Indirect Openers:

• Straight up Social: clinking someone’s glass with a cheers, or “hey how’s it going?”, it’s easy and shows confidence but doesn’t open up as well into deeper conversations.

• Situational Openers: you comment on or ask an opinion on something in the environment. Humor is great here or a fun interesting question about the situation.

Key Tip: When you arrive at the venue look around to come up with a few ideas.

1. What is there a lot of? 
2. What is out of place? 
3. What does something remind you of?

• Humor: making a funny statement or combining a situational opener with some humor is a great way to open up a conversation and show that you can be playful. There are a few main types of humor that are mentioned below.

1. Exaggeration– taking things to the absurd extreme is one way of showing that you are joking or messing around. 
2. Reversals– you simply say the opposite of what’s going on and exaggerate it a bit. If you’re at a really nice restaurant you could say “man, this place is a dump”.
3. Misinterpretation– this is when you purposely misjudge something in the environment that looks similar to something else and go with it to play around asking them how it’s been working for them.
4. Accusation– this is a simple way to play around by accusing someone of being up to no good or planning to steal something ridiculous.
5. Unreasonable Requests- this is where you ask for something ridiculous. When someone shows up at your house you can ask for their blood, urine, and stool samples to enter. Or you can ask to borrow someone’s car for the month.

Try keeping approaches simple and just going with them the moment you think of them and decide you’re interested in the person. 

If it doesn’t go well, who cares, move on. 

The more hesitation and overthinking of how you will do it, the harder and more anxious it will be. Focus on taking action and letting it happen with the following points.

• Slow Down
• Louder voice
• Interrupt smoothly
• Commit
• Expect success

Part 3: Maintaining a Quality Conversation (Weaving & Threading)

The next step in a quality conversation once you open it up is being able to maintain the flow and get to know the person you are talking to. This requires the ability to maintain and lead a conversation in a meaningful and fun way.

The key to starting a conversation that has some substance to it after you approach and open it up is to ask good questions (usually open-ended) that allow the other person to elaborate. 

Essentially good conversational skills consist of the following parts:

1. Asking great questions (open-ended for depth)
2. Active listening (or listening well)
3. Threading off of the free information given and expressing yourself on topics
4. Weaving (or directing the conversation in different ways with new questions)
5. Getting to depth and connection with core values, empathy, vulnerability
6. Closing a conversation and getting contact details to stay in touch  

1. Asking Great Open Ended Questions

Let’s simply go over what open-ended and close-ended questions are. 

Close Ended Questions: questions that call for a one or two word answer like true false or multiple choice questions.

• Where do you teach?
• Do you go jogging?
• Shall we have dinner at 5:30 or 6?
• Do you like that picture?
• Are you guys having fun?

The above questions all call for a one or two word answer. 

Close ended questions are not bad and are a part of any conversation as they allow people to disclose specific facts. You just have to realize that in order to really open up a conversation you will have to follow up with an open ended question for more depth. 

Some people who are naturally more talkative will elaborate from close ended questions but you can’t count on it especially if it’s someone you just met.

Open Ended Questions: questions that naturally promote longer answers which show your interest in the other person. They allow people to elaborate and express themselves.

• What are some tips you could give me about public speaking?
• What do you think that painting is trying to say?
• Tell me about why you made the decision to move.
• How’s the weather in Alabama different from here?
• Where do you want to be in 5 years from now with your life?
• Who do you think is the best pitcher in baseball?
• Why do you think you were able to achieve your goal?
• In what way do you think psychedelics can help the world?
• What is it about surfing that makes you feel good?
• Why do you like playing chess?

The above are all questions that allow your partner to elaborate and express themselves.

Close ended questions need to be followed up by open ended questions to allow the conversation to keep going and add depth and interest.

Key Tip: Keep in mind that it’s always critical to be genuine when asking questions as people can tell if you’re just asking them to get a response without actually caring. This means you have to actually care and be interested in the other person. If you’re not interested, move on, or don’t ask.

2. Active Listening

Active listening is just focused listening to your partner. 

Most people (myself included) tend to naturally get caught in their own internal dialogue.

It’s amazing to realize that people who actually sincerely listen to others are very rare.

This means that you need to practice dropping your own thoughts for a little bit and focus on trying to understand the other person before you respond. 

This is also a critical component of developing connections with others. Everyone wants to be heard and seen for who they are and in order to actually connect with someone on a deeper level your partner needs to feel that they are cared about and heard.

Paradoxically, if you focus your attention on really listening to the other person your brain will automatically generate topics to open up on based on the “free information” or details they discuss.

These can be considered portals or threads you can go down and allow you to determine where you want to steer the conversation next.

In summary, active listening is critical as it allows for connection and generates the threads or portals that you can steer the conversation down to keep an ongoing steady flow.

In order to listen well you have to let your own thoughts and worries go and focus on being present with the other person.

3. Threading & Weaving

Once you’ve approached, opened up, asked a good open ended question, and started to listen to your partner it’s time to lead and steer the conversation by threading and weaving.

Threading

Like discussed above threading is making comments, asking questions, and expressing yourself on the topics or information your partner brings up while they are talking.

Threads are like portals to deep dive down to discuss more. We all naturally do this even if we don’t realize it.

For example, let’s say you ask someone what they like to do for fun and they reply that they like to skate, go hiking, read, and work out. 

Skating, hiking, reading, and working out are all individual threads you can go down if you decide to. The cool thing is even if you go down one of them you can revisit the others at any time if you run out of things to talk about.

To open up one of these threads you simply would reply by saying “that’s awesome I used to skate a lot when I was a kid but I haven’t done it recently, where do you usually go?”

You can then decide how deep to dive into the topic and when it might be good to weave the conversation back in another direction to get to your intended goal.

In order to thread and weave well you have to listen to your partner :).

Weaving

Weaving is just a term that means to steer the conversation in a certain direction by asking a question that leads to another topic. 

For example, let’s say you opened up a conversation by asking someone what they were up to today and they replied that they have been working, took their dog for a walk, and went to the gym.

You would then decide which thread to open up (work, dog walking, gym) and comment on it while deciding how long you wanted to deep dive down that thread.

Next, in order to steer the conversation in a direction that allows you to hit your intended goal (could be to determine if they are a potential friend, romantic partner, or business connection) you will need to weave to another topic by asking a question that allows you to get to know that person based on what you are interested in.

For example, if you wanted to see if the person even lived in the same area and had any common interests you could make a comment about work and discuss how you work in a certain area of the city then ask them where they spend their time.

Next, in order to weave into learning about potential common interests you could thread on the area they live in and then ask them what they like to do for fun outside of work.

This structure of asking good questions, threading, and weaving in a conversation can basically go on forever if you listen, express yourself, and are interested in learning more about them.

Below is a Basic Weaving Conversation Structure:

• Partner 1: What have you been up to today?
• Partner 2: Answer
• Partner 1: Thread, then ”What part of the city are you from?”
• Partner 2: Answer
• Partner 1: Thread, then “What do you like to do for fun?”
• Partner 2: Answer 
• Partner 1: Keep going for as long or as short as want then if you connect and want to stay in touch with the person you can escalate to a contact exchange

One thing to keep in mind is that in order to get deeper with someone you will have to get into open ended questions that allow the person to express their core interests and values.

• Why do you like X?
• What do you like to do for fun?
• What are some goals you are working towards?
• What’s your view on work life balance?
• Is there anything you’ve struggled with in life?

If you are able to weave into those types of topics then this will enable you to determine if the person is a fit as a friend or partner you want to include in your life. It will also allow you to open up yourself on those topics and determine if there is a genuine connection.

If they reveal something to you about them and there is a genuine connection then you can express your empathy or excitement to them by saying something like “that’s awesome, it seems like you’re health conscious and I really like that because I am too”.

At this point in a conversation if you like the person, have some common interests, and want to stay in touch or escalate it’s the perfect time to exchange contact information.

4. Contact Exchange

Once you’ve opened up, asked an open ended question, and maintained a conversation to get to know someone you can either end it or ask for their contact information.

Contact exchange is always best when you have been able to establish some connection with the other person.

Without some connection, it is usually a bit awkward and less meaningful. With some connection, it is easy and smooth.

The key is to say something like “let me grab your number” or “let’s connect on Facebook” at the time when you both connect on something instead of waiting until the conversation is dull.

The chance of rejection dies down significantly if you genuinely get to know the person and connect on something.

If you just randomly ask the person for their number, it can work occasionally, but it’s a bit more shallow.

Remember, it’s all about the connection not just getting someone’s number.

Extra Tip: Rolling With Rejection

One of the keys to getting better at approaching people and overcoming anxiety and nervousness around meeting new people is to be ok getting rejected or looking stupid.

At the end of the day, it’s a numbers game and not everyone is going to like you or be a good fit in your life. 

What’s the best way to deal with rejection or social shaming when it occurs? 

To own it. To own who you are as a person and how they judged you even if you’re nervous or say something stupid. To deflect and flip something negative they said.

• “Well, I’m glad I said hi. Hope you have a good rest of your day.”
• “No worries, you’re missing out ;), have a good one.”
• “Ah, I love it, someone with a backbone to tell me the truth. I hope you have a wonderful night.”

Remember that the person who gets negative or defensive always loses.

Rejection can be a bit painful when it occurs but the pain is temporary and the courage to take action will lead to a much more amazing life than one without moving through any temporary pain. 

Own your mistakes, your rejections, your nervousness, your loss of words, and who you are as a person. And then try again next time.

Looking back you will be proud of yourself if you gave it your best shot.

Part 4: Working on Being More Assertive

As time goes on practicing social skills and improving your social life the ability to be assertive will grow as confidence grows.

Assertiveness is the ability to speak your mind, speak up when needed, tell people no, ask for what you want, be honest, and enter into conflict with a little more power and ease.

It’s a critical skill to master because if you don’t have some ability to be assertive, people will walk all over you and you won’t get your needs met. 

I see this skill with the analogy of how dogs bark at other dogs when they are encroaching on their territory. It’s the same with humans.

Examples of Saying No:

• Partner 1: Would it be cool if I borrowed $100?
• Partner 2: I’m sorry but I have a policy that I don’t loan money out to friends. I had some issues in the past.

• Partner 1: It’s been a long day. Do you want to go to the bar and drink after work?
• Partner 2: Thanks for the invite but I don’t want to drink so I’m gonna pass.

The key to telling people no is to be respectful, acknowledge their ask, then use “but” or “however” to explain why you cannot and state either no, no thanks, or I’m not interested. 

Think, make a decision, and stick to it firmly. Get rid of hesitation and too much wishy-washyness.

If someone continues to ask you, this is when you dial up your assertiveness level a notch and hold strong eye contact with the person as well as a firmer voice so they get the message.

The other types of assertiveness skills to practice are being able to tell people what you think honestly, give opinions, and disagree in a respectful manner.

Part 5: Expressing Yourself Through Senses, Storytelling, Intonation

One thing that all people who are attractive and charismatic have in common is the ability to use intonation in their voice, to tell good stories, and to express themselves and their experiences by using the senses.

Let’s dive a little bit into each of these skills.

1. Using the Senses in Speech and Stories

Below are the senses:

• Sight (I saw the bright sunrise out of my window)
• Hearing (I heard the sound of fans yelling)
• Touch (I hit my hand against the hardwood floor)
• Smell (I could smell the burnt popcorn in the air)
• Taste (The taste of the spice was bitter, pungent, and spicy)
• Feel (emotionally, I felt…) 

When you incorporate the senses into your storytelling or conversations to describe a situation it draws people into the visuals you create and allows for a deeper connection.

Using the senses also opens up greater depth and detail to your stories and statements which allows you to express yourself easier.

In order to put this into practice when someone asks you about an event or you are telling a story you can start by remembering to add a sense or two.

• I saw the bright green grass in the outfield
• I heard the loudspeaker and the fans yelling
• I felt my ass on the hard stadium seat
• I could smell the freshly brewed beer and nachos
• When I bit into my first Cardiff crack sandwich I could taste the smokey meat and tangy BBQ sauce
• I felt excited to be back at a baseball game

2. Using Vocal Intonation

Another important part of great communication is the ability to use intonation in your voice.

We naturally do this when we are relaxed and expressing ourselves but it’s important to remember that it plays a pivotal role in attractiveness, charisma, and fun.

Vocal intonation is the rise and fall of your voice when speaking.

It usually changes based on what you are speaking about and people who are great communicators are able to pick the right intonation and style of speech for each thing they are communicating.

Types of Vocal Tone Styles:

• Loose, deep, calm (usually when relating on an empathetic level)
• Firm and loud (when being assertive)
• Deep and accentuated with a higher spicy pitch (flirty)
• Loose, relaxed, whimsical, fun pitch (playful)
• Higher and faster (when excited about something)
• Relaxed and open (when chilling out)
• Energetic and commanding (when leading a talk or room to keep attention)
• Shallow, soft, and tense (when nervous or scared)

Those are just a few of the natural vocal tones that people use to express certain moods and situations.

The key to getting better at using vocal intonation is to practice raising and lowering your voice based on certain changes and allowing yourself to go for it instead of being monotone all the time.

3. Storytelling

Storytelling is one of the foundations of charisma and connection. When you open up it will help the other person open up as well and you will get to know each other on a deeper level.

Any good story will include both the senses and good vocal intonation to draw the listener in.

That being said, it’s also good to know a basic story structure so that you can practice telling stories and improving upon the way you can open up and express yourself to people.

When is a good time to tell a story?

• When someone asks you about something (an event, situation, or time when there are memories attached)
• When someone asks you what you did, why you like something, or how something was

Here is a simple storytelling structure to practice with in situations where it doesn’t call for a drawn-out story.

Present, Past, and Future Elaboration:

1. Someone asks you why you like to surf?
2. You respond by simply going into the present, past, and future to tell a simple story about why you love surfing

Example: “You know, whenever I put my wetsuit on, wax up my board, and cruise down to the beach on my bike I feel a sense of freedom, playfulness, and connection with nature. Not to mention I also love getting some good exercise in and swimming in the water. When I was a little kid I used to love going to the beach and playing in the sand and it always ignited in me a passion for being in the water as it made me feel alive and free. That made me realize that going forward in my life I want to keep surfing as something that I can always do as it brings so much joy and fun into my life especially when things get stale or I need to get out of my head and have some fun.”

Longer Storytelling Framework:

• The Introduction & Buildup
  • Tell them the goal or the outcome you were shooting for
  • Describe the plot and scene in detail and include senses/how you felt
  • Buildup the characters, environment, details
• The Problem
  • Describe the problem in detail and give some exaggeration/emphasis
  • Tell people the odds or roadblocks you realized you need to overcome
  • Describe the work you learned you had to do and how you were trying to overcome the roadblock
• The Resolution or Solution
  • Describe in detail how you overcame the problem
  • Tell of the relief and the details of how it felt to find the solution or answer

Mindset Shift: Developing Playfulness & Humor to See Social Activity as Fun

One of the most important mindset shifts that I’ve personally tested to help you have more fun socially, to be more enjoyable, and to make more friends is to develop a mindset and view of social activities as a playground.

Everyone is getting together or going out to have fun, to mess around, and to play.

Instead of approaching social situations to see how other people will respond to you or judge you (taking a defensive and reactive view towards new people), it helps tremendously if you can shift into a playful view where you are approaching people and messing around to see if they want to play or not.

For me when I can get into this mindset and attitude when doing social events it helps me to have a bit less anxiety and to loosen up a bit so that I can bring out a little humor or have the courage to be a little bit ridiculous.

Seeing the event as a playground where you can mess around and come up with fun games to play with people is something that I try to cultivate a little more in social interactions. It helps you get out of the perspective of needing other people’s approval and instead owning who you are and just seeing who is interested in having fun with you. 

Part 6: Tips to Work On for Social Anxiety

As someone who deals with some social anxiety, I know firsthand how it can be challenging to be smooth in social situations when you’re nervous.

Sometimes you literally freeze and it’s hard to think.

This is why it’s important to practice your social skills so that they become automatic and unconscious.

This way when you get nervous and your rational brain goes offline you have practiced enough to just operate on the structure you know like the back of your hand.

Anxiety is created by our own conditioned responses and internal beliefs to the situations (as well as being genetic) and not the situations themselves, so it’s possible to work on changing our response to these things over time with exposure and compassion for ourselves.

Here Are a Few Key Things That Can Help:

1. Defuse your anxious and catastrophic thoughts
   • An assertive defusion or just noting your anxious thoughts and labeling them as just thoughts or feelings instead of catastrophizing or predicting what could happen in the future
2. Accept and allow your anxiety to be present while taking action with it. Resistance will only make it stronger so own it and flow with it the best you can.
3. Apply paradoxical intention and see how awkward you can be
   • Make it a game to see how many rejections or bad looks you can get
   • Allow yourself the freedom to mess up or be awkward
4. Try to shift focus from your own thoughts to the people you are with and get more engaged in what’s going on in the present moment instead of your own worries. This is where consciously focusing on listening can help.
5. Work on facing your social fears and doing the things that make you nervous little by little to grow your courage

Obviously, these things are easier said than done because when the freeze or survival response kicks in it makes it very challenging, but practice and exposure over time can help.

At the end of the day sometimes it helps to remember that it’s better to be rejected and experience short-term pain than to live a life full of what-ifs. 

Also, keep in mind that not everyone is a fit for you so rejection is actually a good filter to help you find the right people.

Conclusion

There you have it. The basics of social conversation skills in one post.

Obviously, just reading a post about basic skills will not create a meaningful change. 

The most important thing you can do to improve your conversation ability is to practice talking to more people and allow yourself to mess up and test things out while you grow.

I like practicing on Jaunty (where I learned a lot of this), practicing in real-life social situations, and reading psychology books.

The path to improvement is not a straight line. It takes courage, practice, putting yourself out there, facing your fears, getting knocked down, and learning from your mistakes. 

It’s an up-and-down journey where you will fall down or be discouraged with yourself while then learning and making leaps forward. 

I wish you more social freedom, ease, and quality relationships in your life.