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The Complete Guide on How to Keep a Conversation Going

By David Morin and Viktor Sander

The Complete Guide on How to Make Conversation


CHAPTER 1:

How to Start a Conversation With Anyone

WHAT YOU'LL LEARN IN THIS CHAPTER:

  • What goals to set for your conversations (And what goals NOT to set!)
  • How to always know what to say next to someone you just met.
  • What NOT to do when you start talking to someone (But most people do anyway).
  • 7 universal questions that you can always use to get a conversation going.

THE TRUTH ABOUT STARTING A CONVERSATION WITH SOMEONE:

bubbles

A team of scientists from Boston wanted to understand what really happens when two strangers meet, and they made a surprising discovery about the initial conversation between two people.

Their discovery can help us become better at starting conversations with people we just met. Small talk, which I used to see as something quite pointless, turned out to be more important than they first thought.

While we make small talk about things that in themselves don’t really mean much, some really important things happen subconsciously. We need to make seemingly random conversation while we subconsciously create a “mental picture” of the other person. And we need that mental picture to become comfortable moving on to deeper, more interesting conversation.

The scientists said that the best way to describe small talk is like a “bonding ritual.”

The scientists said that the best way to describe small talk is like a “bonding ritual.”

They also found that exactly what we talk about isn’t that important. And here’s where most people make their first mistake - they are too picky with what they should say. That causes them to censor themselves too much, and then they become self-conscious and can’t come up with anything to say at all.

So - trying to come up with a good opener or something smart to say will mess up your conversations. Instead, start off with really simple small talk subjects. That will make both of you more relaxed and you'll be able to get a good start to your conversation. As a result, you’ll also begin to feel more confident when talking to people.

(Read the chapter on how to be more self confident when making conversation here.)

WHAT GOALS TO SET FOR YOUR CONVERSATIONS (AND WHAT GOALS NOT TO SET!)

The first thing to know about conversational goal-setting comes from therapist Emily Roberts, who recommends setting positive goals instead of negative ones. “Think of something positive you want out of this conversation. . . Don’t start with a negative goal, like ‘I don’t want to look like a dork.’ Then you’ll already be focusing on seeming like a dork!”1

When setting positive goals, think of something quantitative you’d like to accomplish. This means choosing goals that you can count your progress towards. For example, your positive, quantitative goals could include:

  • “I will have at least one conversation with a stranger every day this week.”
  • “I will ask three ‘getting to know you’ questions during a conversation with a new person every day.”
  • “I will meet three new people during my commute every week.”

If you are serious about improving your conversation skills, it will require intentional practice. Setting goals is a great way to hold yourself accountable for practicing as well as tracking your progress as you improve.

You can find free goal-setting worksheets here.

Some questions to ask yourself when setting conversational goals include:

  • What type of conversations do I want to have/improve upon? (Small talk, “getting to know you,” deeper conversations, etc.).
  • What type of people do I want to have these conversations with? (Strangers, acquaintances, co-workers, classmates, etc.).
  • Where do I want to have these conversations? (School, work, via text, via Facebook message, over the phone, on the bus/train to work, etc.).
  • How many conversations do I want to have/how often do I want to have conversations? (# per day, # per week, etc.).
  • What do my conversations need to include in order to be successful? (# of questions asked, # of personal details shared, etc.).

Once you’ve set your goals for improving your conversational abilities, it’s time to keep reading so you can learn everything you need to know for accomplishing them!

THE TRUTH ABOUT SMALL TALK

Small talk is one of the most universally hated aspects of social interaction. This is because of two things:

  1. Small talk is surface-level, and research shows that people who spend more of their time in deeper conversation than they do in small talk are generally happier2; this is more than likely because they are spending time with closer friends and not strangers, which leads us to…
  2. Small talk typically occurs between two people who have recently met or who have not yet developed a deeper relationship. This means that small talk occurs between people who are less comfortable around one another, which is naturally less enjoyable than talking to your closer friends who put you at ease.

But take a moment to think about your close friends and acquaintances with whom you’re comfortable having deeper conversation (talk other than small talk).

Even with these people, you had to start somewhere, right?

Small talk is what allows us to get to know someone well enough to begin opening up to them about more personal things, and this is what leads to bonding, the result of which is deeper conversation.

For this reason, small talk is an absolutely necessary part of making conversation, and skipping it is a fast track to social sabotage.

You wouldn’t walk up to someone you hardly know and ask, “So how are your parents doing after their divorce?” (unless you want a Slurpee in your face).

That’s because it’s much too personal of a question to ask someone you haven’t developed a close relationship with.

That’s where small talk comes in. Like we mentioned earlier, what you talk about doesn’t matter that much—it’s about having the opportunity to get comfortable talking to this person at all.

It’s also a great chance to learn about things you have in common, which can help you bond and promote further discussion.

So let’s get started with 7 small talk questions you can use any time.

7 SENTENCES THAT YOU CAN USE TO GET ANY CONVERSATION GOING

I want to show you 7 questions that I almost always use when I've just met someone. They apply to any situation, so I can always rely on them to get a conversation going. And since I know them by heart, I never have to worry that I won’t know what to say when I meet someone.

And now I can look back and think…

...Why didn’t I memorize these questions ten years earlier?

Then I would have been so much more comfortable meeting people, because my biggest fear in making conversation has always been that I might run out of things to say.

The trick to using my 7 universal questions is this:

  1. I keep the questions simple.
  2. I try to genuinely get to know more about the person I'm talking to by asking follow-up questions.
  3. Throughout the conversation, I share similar bits and pieces about myself, related to what the person is saying (so it’s not like I’m conducting an interview; it’s more give-and-take).

Later, I'll talk about how to start a conversation at places where you’re not explicitly meant to socialize (say, if you end up next to someone on the train or in a lunch queue). But first, I'll cover what I do when I’m somewhere I’m expected to socialize, like at a party or when I meet friends of friends.

BALANCING YOUR CONVERSATIONS

Before we get into the seven universal questions you can ask to anyone at any time to start a conversation, let’s look at the balance involved in a good conversation. Like we mentioned before, conversations should be give-and-take instead of a game of 20 Questions.

If someone gets the feeling that you know a lot more about them than they know about you, they will start feeling uncomfortable. Balancing your conversations is a good way to prevent this.

One way to do this is by answering your own questions. This means that once the other person has provided a response to the question you asked, if they don’t automatically ask a reciprocating question, you should take the initiative to share the same information about yourself that they just shared. This allows the other person to get to know you at the same rate you are getting to know them, even if they are too nervous, shy, etc. to ask their own questions.

Here’s an example:

example

You: “So what do you do for a living?”

Jared: “I work for a car insurance company.”

You: “Nice! How long have you been doing that?”

Jared: “About 5 years.”

You: “Cool! I work for a travel agency. I’ve been there about three years. Before that I waited tables at a few different restaurants around town.”

Notice that in the example, you are still asking follow-up questions to express an interest in what Jared is telling you. You don’t want to appear too eager to turn the conversation back to yourself; this is intended to balance the conversation, not make it only about you.

A willingness to share information about yourself causes other people to instinctively find you trustworthy, while exclusively asking questions (and not offering any information about yourself) can come across as ingenuine and put the other person under a lot of pressure.

People cannot bond with you if they don’t know anything about you, and if you don’t build any rapport during your initial conversation it is unlikely that they will ever approach you for future conversations.

MY SEVEN UNIVERSAL QUESTIONS

Now we’re getting to the good stuff: Here I’m going to share with the seven universal questions that you can keep in the back of your head to use when you’re having trouble starting a conversation or when an existing conversation comes to a pause.

You aren't supposed to fire all these questions off at once (this isn’t an interrogation). Make sure to spend roughly the same amount of time talking as you do asking questions. That means that you will spend a lot of time answering the other person's questions (or answering your own questions, like we explained above) and sharing bits and pieces about yourself.

When beginning a conversation with someone you’re meeting for the first time, you always want to offer an introduction and ask the other person how they’re doing. Many times, your introduction will come after you break the ice with the person by asking a question or making a comment related to the current situation (which we’ll explain later). The introduction doesn’t necessarily have to be the first thing you say, but it should definitely occur at some point in your conversation.

example

I start off by saying:

- Hi, I'm David. How are you doing?

And they typically reply, “Good,” and introduce themselves in return. (Remember: Only use the name "David" if your name is in fact "David").

Introductions can be different depending on where you are and to whom you’re introducing yourself. If you’re introducing yourself to a co-worker, you may want to add what job you do and where you’re located in the building. Example: “Hi, I’m Amanda. I work in customer service and I’m in cubicle 4. How are you?”

Doing this gives the other person a little more information about you, which makes you more memorable, and it also lets them know where they can find you if they ever need your help or want to socialize further.

If you’re in college and introducing yourself to classmates, include your major or area of study and what year/class you’re in. Example, “Hi, I’m Amanda. I’m a sophomore Communications major. How are you?”

If you’re at a networking event where multiple employers/employees of different companies are in attendance, include the name of the company you work for to help distinguish yourself from any other David’s they might meet. Example, “Hi, I’m Amanda Haworth from Social Pro. How are you?”

*Note: In work and business situations, it’s much more professional to include your first and last name. This will also make you more memorable and easier to find should the other person ever need to contact you. In small groups or casual social events, it’s more acceptable to present only your first name, although adding your last name can never hurt.

- How do you know people here?

This question helps you determine if you have any mutual friends. Even if you don’t, finding out someone’s connection to the host or event is a great conversation starter. However, to turn a simple question into a full-blown conversation you must be able to ask follow-up questions that elaborate on the response the person gives. Here are some examples:

If they met through work or school, it's a perfect opportunity to ask more about where they work or what they are studying. Some follow-up ideas include asking if they like it, how long they have been doing it, if they have any free time, what they do in their free time, and so on.

Perhaps they know each other through a group or met at an event. I ask them about what type of group it is. What do they do there? Is it fun? Is it hard to learn? Who's best at it, the person I'm talking to or the friend?

If they are childhood friends with someone, I might ask where they grew up.

If they don’t know anyone, you can build on that too by asking them what brought them to the party/event.

- Are you having a good time?

Asking how the person is liking the social event expresses that you care whether they are enjoying themselves.

Even though you may have just met the person, expressing an appropriate amount of care and concern is a great way to bond with someone and pave the way for future conversations and rapport-building.

There are several different types of responses you may receive when you ask this question.

“Yeah!” If you get this simple response, don’t let it surprise you; this likely means the person is either not comfortable enough with you (yet) to elaborate on their true feelings about the event, or they are nervous and unsure of how to respond.

If you get this response, you can say, “Good! So am I. I really like the ______________. What’s your favorite part?”

Offering an opinion and asking for their opinion will keep the conversation going instead of allowing their one-word answer to cause the conversation to hit a dead-end.

“Yeah, I love the ___________!” Some people may respond affirmatively and provide an opinion that explains why they’re having a good time.

This is easier for you to respond to, as the door is now open for you to share the things you are enjoying at the event.

“Actually, I’m having a hard time meeting people and I’m pretty nervous.” There are many ways that someone might imply they aren’t having the best time.

You can respond by saying, “I’m sorry to hear that. Let me introduce you to my friend _________!”

Helping the person meet people will not only help solve their problem, but it will also help you expand your social circle by introducing someone new to your existing friends.

If you don’t know anyone at the event to introduce them to (or for some reason you don’t want to) you can relate to them by saying, “Yeah I feel the same way.

These types of events always make me nervous. Good thing we met, huh? We can stick together!” Empathizing with someone is a powerful way to make them feel better, and it will go a long way towards bonding with them.

- Where are you from?

If the person is from the same town as me, I ask them what area they live in and how they like it there.

Being from the same place can also lead to a discussion about favorite local amenities, such as restaurants, shopping malls, and/or new businesses that have recently opened.

(Example: “Oh, did you ever go to the Central BBQ on Summer Avenue? The whole building is Memphis Tiger-themed! It was one of my favorite spots in college.”)

If they are from somewhere else, you can follow up on that by asking how they liked it there, why they moved and if they plan on moving back. You can also ask what their favorite things to do in that area are in case you ever visit. There's enough stuff for an entire conversation here!

When discussing hometowns, you can also ask if they have family there. Some follow-up questions include:

- “Do you get to visit them often?”

- “Have they always lived there?”

- “Do they ever come visit you in your new city?”

- “Are you able to go home for holidays?”

- “Was it difficult to move away?”

As the person answers your follow-up questions, remember to share any similar experiences you have had related to the question you asked.

This can quickly and easily create bonding experiences that may lead to deeper conversation.

People tend to be more comfortable talking about things they are familiar with, such as their hometowns, so this a great topic to “camp out in,” so to speak, when making conversation.

- Do you work/study?

Some say that you shouldn’t talk about work when you're at a social event, and that's partially true: It sucks to get stuck in job talk.

But it can be helpful to know what someone is working with, as it will help you find mutual interests. And as I said before, it’s often easy for people to talk about because they are familiar with the subject.

If it turns out that they are unemployed, be ready to say something so they don’t have to feel bad, like this:

“So I guess that means you can enjoy sleep-ins every morning?”

And then I ask if they spend their time on any hobbies or interests, and we’ll continue the conversation talking about that.

Job talk is okay for a while, but you don’t want your job to become the only thing you can talk about.

Not everyone may find your job as interesting as you do, and no matter what the topic is, if you talk about the same thing for too long it will inevitably become boring.

To avoid this, just change the subject by asking:

- Is it a super busy job or will you have any time off this summer/winter for a vacation?

This question allows you to change the subject without being random or “off the wall.”

The question still relates to what you were just talking about, but it opens the door for an entirely new topic of conversation that will naturally lead into many other new topics.

For example, someone may reply “Yes, I have two weeks off that I’m planning to use for a Caribbean cruise!” You can then ask if they’ve ever been on a cruise before, what they’re most looking forward to, and share any of your own vacation-related stories and plans.

- What’s your favorite way to spend your vacation / time off / weekends?

This is my favorite question! Here you’ll discover their favorite interests and hobbies or places they want to go.

No matter what they reply, you can now begin sharing your own passions and dreams. In my opinion, passions and dreams are the most rewarding subjects you can bring up with someone.

They’ll love to talk about this and you'll have a great opportunity to find mutual interests. Remember to find opportunities to share your interests/hobbies as well so that they can continue getting to know you as you are getting to know them.

If they mention an interest/hobby that you don’t know about, begin asking follow-up questions that will help you learn more about it, such as:

  • “How does that work?”
  • “How do you do that?”
  • “Who taught you to do that?”
  • “How often do you do that?”
  • “How long have you been doing that?”
  • “Do you have many friends who do that too?”

If you find any common ground (for example, if you’ve both been to the same place or share any interest) you can merge into that conversation just like you talk to any close friend.

You’re off the shaky launch and into a conversation you'll both find entertaining.

These questions should help you to avoid any awkward silences that may otherwise come up, but make sure to also read this chapter on how to avoid awkward silence.

And that’s it! These seven questions have helped me start great conversations with so many people.

If you want a flying start, memorize them and practice them whenever you get the chance.

Just be sure you always ask them in a genuine way (meaning don’t ask them if you don’t really want to know the answer, and be sure to pay attention to the person’s responses and ask follow-up questions).

You don’t need to learn them in a specific order, and you don't need to phrase them exactly like I did. Ask them in the way that feels most natural to you, and keep them in mind for use when your conversations begin to lull.

3 things most people don't know about bonding and making friends

whiteboard

There are 3 specific things when it comes to making close friends that surprisingly few people know about.

You'll learn:

  • What to say next in any conversation
  • Two proven self confidence quick-fixes
  • How to avoid awkward silence forever
  • Secrets of "socially successful" people
  • Why you don't have to "go out of comfort zone"
  • How to turn the video into real results


A FEW MORE TIPS ON SMALL TALK

A good formula for making small talk is this:

Situation + Surroundings = Small Talk

This is simply a summary of what we discussed earlier; use the current situation to break the ice by asking a question or stating an observation. Then you can begin using the 7 universal questions for making conversation.

Another good tool for coming up with ideas is “the 4 W’s” of making conversation. These are:

  1. Who: Who are you talking to? What are their interests, hobbies, career aspirations, hometowns, etc.? “Who” questions allow you to get to know the person you’re talking to.
  2. What: What is the current situation? What’s happening right now? Is it the cake-cutting ceremony at a wedding, or is it a business meeting? What’s happening during your conversation can provide you with plenty to talk about.
  3. When: What time is the social interaction taking place? Is it after morning rush hour, or is it ate at night? Is it New Year’s Eve, or is it Labor Day Weekend? The “when” of your conversation can help you come up with small talk topics.
  4. Where: Where are you? Comment on the décor, the architecture of the building, the drive/ride to the venue, etc. Use the location of your social interaction to fuel your small talk.

You may have noticed that the fifth “W” is missing. This is because asking “Why” questions can be dangerous territory, particularly when you’re speaking to a relative stranger.

“Why” questions can easily become too personal and too invasive, so for the purposes of small talk it’s best to leave the fifth “W” at home.

STARTING A CONVERSATION WHEN YOU'RE NOT NECESSARILY EXPECTED TO:

Sometimes you want to start a conversation even when you’re not explicitly meant to socialize.

In other words, there are times when it would be perfectly acceptable for you to remain silent and not socialize with the people around you (as opposed to events where it would not be acceptable for you to remain silent).

However, situations where you don’t have to socialize can turn out to be some of the most fun situation for socializing! In these settings, it’s too direct to start asking people stuff out of nowhere. Instead, you first need to say something related to the situation.

My advice here is to not try to fake questions about the situation. You don't have to. Your brain has a constant inner conversation, so just let some of that conversation out by saying something that’s on your mind. Let's say that you end up next to someone on a train:

example

“Excuse me, do you know when we will arrive?”

or

“Do you know what the next stop is?”

or

In addition to asking questions related to the situation, you can also state an observation you’ve made and ask the other person’s opinion on the same thing. Let’s use the example of waiting in line to order a at a restaurant:

“Something smells wonderful. Do you like the food here?”

or

“They always play the most random music here, don’t you think?”

As soon as you've initiated a conversation using a situation-related question, it's more natural to ask something about the person you're talking to.

“Where are you heading?”

or

“How long of a lunch break do you get”

And after this warm-up you can go over to the universal questions above, like:

“Where are you from?”

Asking a question or stating an observation related to the current situation is the most natural way to break the ice with someone. You can then begin getting to know them using the seven universal questions or any other “getting to know you” questions in you repertoire.

THE 4 MOST COMMON MISTAKES WHEN STARTING A CONVERSATION:

There are many things people do in conversation that unknowingly sabotage their conversational success. Learning what these mistakes are (and how to avoid them) will go a long way towards improving your conversation skills.

  1. Being too linear in the conversation.

Don't be afraid to jump around among the subjects and go back to what you were previously talking about. Or, you can relate to a new subject. You don’t want to be too random, but if you’re afraid to veer from the current course of conversation you will have a hard time as soon as that topic has been exhausted.

If I can’t come up with anything on the current subject, I just fire off any of my other questions or relate back to something we were previously talking about. For example:

“So you mentioned earlier that you were headed to your aunt’s house. How often do you visit?”

  1. Asking too few or too many questions in relation to how much you share about yourself.

I make sure to share bits and pieces about myself, so it’s a give and take throughout the conversation.

I make sure to keep a balance in how much I share, meaning if someone tells me a longer story about where they work or what they do, I share a story of the same length and depth with them so they don’t feel like they open up without getting to know me. If they give me a shorter reply, I don’t give them the long story back in return. This balance helps me quickly connect with anyone I meet.

  1. Not being genuine when asking something.

Ask questions like you genuinely want to get to know the person you're talking to. This means paying attention to the person’s response after you’ve asked a question.

If you ask someone how they’re doing, then immediately start looking at your phone or staring into space as they answer, they’re going to know that you were asking out of obligation and not out of a genuine desire to get to know them.

  1. Trying to follow the rules of conversation and being afraid to do something wrong

Break the rules! Just because I use these questions doesn't mean that other questions are wrong. Use these questions as lifelines if you lose track, but don’t let them confine you.

It’s better to experiment and allow yourself to make mistakes than to 1) make boring conversation or 2) not make conversation at all. It's impossible to truly become good at something without making some mistakes along the way.

TOOLS AND TIMING FOR ENDING A CONVERSATION

So you’ve successfully started and maintained a conversation, but things are starting to lull and now you’re desperately searching for a way out before an awkward silence can occur (or, because we’re all human and will experience this at some point, the conversation sucked and you need to escape). What do you do?

Knowing the signs of a dying conversation is the first step in preventing awkwardness and ending the discussion before things become uncomfortable.

It’s important to note that brief pauses and silences are normal parts of human interaction and don’t necessarily indicate the end of the interaction. But sometimes conversations lapse into silence and just never pick back up again—if this happens, let it be; don’t jump in with a well-intentioned “It was nice talking to you!” if you’ve both been staring out your respective windows in silence for the last fifteen minutes.

Here are some signs that the conversation has reached its natural “ending point”:

  • The other person stops talking and begins looking at their phone, a book or magazine, or out the window
  • The person stops making eye contact with you and instead looks in another direction or at the floor
  • The person begins gathering their things as though they’re going to leave
  • The person makes a “closing comment” (like the ones we’re about to discuss)

When these things happen, it’s time to take the hint and end the conversation.

Here are some closing comments you can make to end the conversation:

“It was nice meeting you!”

“It was good talking with you!”

“I’m glad we got a chance to catch up!”

“It was so good to see you!”

These can be followed by a well-wish stemming from the conversation you had:

“Have fun _______!”

“Enjoy _________!”

“Good luck with __________!”

“Have a good day/morning/afternoon/night/week!”

If the conversation went well, it’s appropriate, and you want to, you can ask for a time to talk to or meet up with the person again in the future. For example:

“Do you want to grab coffee/drinks/lunch/dinner with me tomorrow?”

“I really enjoyed talking with you. We should chat again soon!”

“We should hang out sometime!”

Not knowing when or how to end a conversation can turn a perfectly good social interaction into a cringe-worthy moment of regret. Learning when it’s time to say goodbye and how to part ways with someone is an important part of being a good conversationalist.

For more, read The Best Strategies for (Politely) Ending a Conversation.

Great work!

You're already done with chapter 1. You now know how to hit up an interesting conversation with someone. Now - how do you keep that conversation going? And how do you actually start bonding?

It's time for Chapter 2: How to keep an interesting conversation going.

References:

  1. Bartz, Andrea. 2017. How to talk to anyone. Scholastic Choices, 33(3). 6-9.
  2. Hayes, Stephanie. 2016. Nice day, eh? Atlantic, 318(3). 22-22.
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