“How can I have more interesting conversations? I don’t know how to spark up a conversation, and it feels like I bore everyone, even myself.”
– Violette S.
I can relate to Violette. After years of studying social skills and reading books on making conversation, I want to share what I’ve learned about having interesting conversations.
We need a few minutes of small talk to warm up. But to make sure you don’t get stuck in trivial chitchat, ask something personal related to the topic.
A rule of thumb is to ask questions that contain the word “you.”
- If you’re stuck in a boring conversation about unemployment figures, you can ask, “What would you do if you decided to follow a new career path?”
- If you’re talking about how cold and unpleasant the weather has been recently, you can ask, “If you could live anywhere in the world, where would you pick?”
- If you get stuck talking about economics, you could ask, “What would you do if you had an unlimited amount of money?”
If you give yourself a mission when meeting someone new, you’ll enjoy the conversation more. Here are 3 examples of things you can try to learn about someone:
- What they do for a living
- Where they are from
- What their future plans are
You can challenge yourself to ask people about these things when it feels natural. A mission gives you a reason to talk to someone and helps you uncover things you have in common.
One of the most popular conversation tips is to let the other person do most of the talking, but it’s not true that people ONLY want to talk about themselves.
They also want to know something about who they are talking to. If they don’t, they might feel interrogated and uncomfortable. When we share slightly personal things with each other, we bond faster.
Here’s an example of how to make interesting conversation by sharing something about yourself:
You: “How long did you live in Denver?”
Them: “Four years.”
You, sharing something slightly personal: “Cool, I have relatives in Boulder, so I have many nice childhood memories from Colorado. What was it like for you to live in Denver?”
“How can I improve my conversation skills? I tend to get stuck inside my own head and freeze up when it’s my turn to say something.”
If someone says, “I went to Paris last week,” some of us might start worrying and start thinking things like, “Will they look down on me for not having been to Europe? What should I say in response?”
When you notice yourself getting self-conscious, bring your focus back to the conversation. This makes it easier to be curious.
To continue with the example above, you might start thinking, “Paris, that’s cool! I wonder what it’s like? How long was their journey to Europe? What did they do there? Why did they go?”
Do you see how much easier it is to make interesting conversation when you focus on what the other person is saying instead of yourself?
Good conversation doesn’t have to be linear. It’s completely natural to revisit something you’ve already talked about if you reach a dead-end and there’s a bit of a silence.
They: “So, that’s why I prefer oranges over apples.”
You: “Oh, I see…”
You: “By the way, you mentioned that you were going to a psychology seminar last week. How was it?”
It’s more fun to talk about passions instead of swapping facts about school or work. If it turns out that you have similar passions, delve into those. They can be a strong basis for a friendship.
If someone tells you they are a teacher, you can ask, “What do you like most about being a teacher?”
If they don’t like their job, you can ask, “What’s your favorite thing to do when you aren’t at work?”
Closed-ended questions can be answered with a “Yes” or “No,” whereas open-ended questions invite longer answers. Use open-ended questions when possible.
Closed-ended: “Did you have a good vacation?”
Open-ended: “How was your vacation?”
It’s a simple adjustment, but it will go a long way in learning how to have better conversations.
Learning about each other’s dreams makes the conversation more engaging, and you might find you have some dreams in common. You can ask younger people what kind of work they want to do and what their life goals are. You can ask older people about their general plans for the future.
Them: “I study biology.”
You: “Cool, what would be your dream job in biology?”
Them: “I’ve been working in real estate for the last 40 years.”
You: “Wow. That’s a long time! Do you ever fantasize about retiring?”
“I don’t know how to make a conversation interesting for the other person. What kind of questions should I ask?”
These questions shift the conversation away from small talk toward deeper topics. They encourage the other person to give you more meaningful answers.
Them: “I’m from Connecticut.”
“What” Questions: “What’s it like to live there?” “What do you like the most about it?” “What was it like to move away?”
“Why” Questions: “Why did you move?”
“When” Questions: “When did you move? Do you think you’ll ever move back?”
“How” Questions: “How come you moved?”
It’s fun and engaging to get asked about one’s opinion. It’s more stimulating to talk about opinions than facts.
“I need to buy a new phone. Do you have a favorite model you could recommend?”
“I’m thinking of moving in with two friends. Do you have any experience of co-living?”
“I’m looking forward to my vacation. What’s your favorite way to wind down?”
Use active listening to signal that you care about what the other person has to say. When you show that you are interested, conversations tend to become deeper and richer.
- Keep eye contact whenever the other person is talking to you.
- Make sure your body, feet, and head are pointing in their general direction.
- Avoid looking around the room.
- Say “Hmm” when appropriate to show that you’ve heard them.
- Summarize what they said. For example:
Them: “I didn’t know if physics was right for me, so that’s why I started painting instead.”
You: “Painting was more ‘you,’ right?”
Them: “Yes, exactly!”
“How can I not be boring? I never know what questions to ask or how to make a conversation fun. I don’t think people like talking to me.”
When a conversation gets boring, remember the FORD topics.
Them: “Work is so stressful now. We are so understaffed.”
You: “That sucks. Do you have a dream job you’d love to do?”
Here are some other topics to talk about:
- Role models, e.g., “Who inspires you?”
- Food and drink, e.g., “Have you been to any good restaurants lately?”
- Fashion and style, e.g., “I love your bag! Where did you get it?”
- Sport and exercise, e.g., “I’ve been thinking about joining the local gym. Do you know if it’s any good?”
- Current affairs, e.g., “What did you think of the most recent presidential debate?”
- Local news, e.g., “What do you think of the new landscaping they’ve done in the local park?”
- Hidden skills and talents, e.g., “Is there something you’re really good at that surprises people when they find out?”
- Education, e.g., “What was your favorite class at college?”
- Your surroundings, e.g., “I love that painting over there! What do you think of it?”
- The situation, e.g., “Do you think this exam is going to be tough?”
If you’d like some more ideas, use this list of 222 questions to ask to get to know somebody to help you start an engaging conversation. Asking insightful questions will make you come across as an interesting person. Here’s a guide that explains how to not be boring.
“I can’t hold a conversation and make eye contact at the same time. What should I do?”
It can be hard to keep eye contact, especially if we feel uncomfortable around someone. But lack of eye contact can make people think that we don’t care what they have to say. This will make them reluctant to open up.
- Try to see the color of their iris and, if you’re close enough, its texture.
- Look in between their eyes or at their eyebrows if direct eye contact feels too intense. They won’t notice the difference.
- Make it a habit to keep eye contact whenever someone’s talking.
When people aren’t talking — for example, when they are taking a quick break to formulate their thoughts — it can be a good idea to look away so they don’t feel pressured.
If you think you might have something in common with someone, such as an interest or a similar background, mention it and see how they react.
If it turns out that you have something in common, the conversation will be more engaging for both of you.
If they don’t share your interest, you can try mentioning something else later in the conversation. You might come across mutual interests more often than you think.
Them: “How was your weekend?”
You: “Good. I’m taking a weekend course in Japanese, which is very engaging”/“I just finished reading a book about the Second World War”/“I started playing the new Mass Effect”/“I went to a seminar about edible plants.”
Let’s say that you meet this person and she tells you that she works in a bookstore. From that piece of information alone, what are some assumptions we can make about her interests?
- Interested in culture
- Prefers indie to mainstream music
- Likes to read
- Prefers to shop for vintage items instead of buying new things
- Prefers cycling over driving
- Environmentally conscious
- Lives in an apartment in a city, maybe with friends
These assumptions might be dead wrong, but that’s OK because we can put them to the test and engage in conversations.
I don’t know that much about books, at least when it comes to non-fiction. But I do enjoy talking about environmental issues, and I hypothesize that she might too. So after she’s talked about working in a book store, I can ask something to move the conversation in that direction:
“What’s your view on e-readers? I guess they have less of an impact on the environment than books, even though I prefer the feeling of a real book.”
Maybe she says, “Yeah, I don’t like e-readers either, but it’s sad that you need to cut down trees to make books.”
Her answer will tell me whether she’s concerned about environmental issues. If she is, we can now segway into talking about that.
Or, if she seems indifferent, I can try another topic.
For example, I could talk about cycling, ask if she bikes to work, and what bike she would recommend. I’m looking at bikes right now, so that’s something I would be interested in talking about.
Here’s another person you can try with:
You meet this woman, and she tells you that she works as a manager at a capital management firm. What assumptions can we make about her?
Obviously, these assumptions will be very different from those I’d make about the girl above:
- Interested in her career
- Reads management literature
- Lives in a house, maybe with her family
- Drives to work
- Has an investment portfolio and is concerned about the market
Here’s another one:
This guy tells you that he works in IT security. What would you say about him?
- Computer savvy
- Interested in technology
- Interested in (obviously) IT security
- Plays video games
- Interested in movies like Star Wars or other sci-fi or fantasy
As you can see, our brains are really good at coming up with assumptions about people. Sometimes, that’s a bad thing, like when we make judgments rooted in prejudice. But here, we’re using this extraordinary ability to connect faster and make interesting conversation. What is interesting to us that we also might have in common with them? It doesn’t have to be our top passion in life. It just needs to be something that you enjoy talking about. That’s how to make a chat interesting.
- Ask yourself what the other person might be interested in.
- Discover mutual interests. Ask yourself, “What might we have in common?”
- Test your assumptions. Move the conversation in that direction to see their reaction.
- Judge their reaction. If they are indifferent, I try another subject and see what they say. If they respond positively, we can delve into that topic.
It’s when we find mutual interests that the magic happens. Once you have established that you have at least one thing in common, you have a reason to follow up with them later and ask them to hang out. Here’s a guide on how to make friends that will tell you how to do that. When you know how to make conversation with anyone, you’ll come across as more likable, and people will be more likely to spend time with you.
Humans love stories. We might even be hardwired to like them; our eyes dilate as soon as someone starts telling a story.
Just by saying, “So, a few years ago I was on my way to…” or “Have I told you about that time I…?”, you are tapping into the part of someone’s brain that wants to hear the rest of the tale.
You can use storytelling to connect with people and be seen as more social. People who are good at telling stories are often admired by others. Other studies show that stories also will make people feel closer to you by being able to relate to you.
- The story needs to relate to the situation. Memorize your good stories. Stockpile them over time. Stories are timeless, and a good one can and should be told several times to different audiences.
- Talking about how good or capable you are will put people off. Therefore, avoid stories where you come off as the hero. Stories that show your vulnerable side work better.
- Give your audience enough context. Explain the setting so that everyone can get into the story. We’ll look at this in the example below.
- Talk about things that others can relate to. Tailor your stories to fit your audience.
- Every story needs to end with a punch. It can be a small punch, but it has to be there. We’ll come back to this in a moment.
It’s important to realize that people with a lot of stories don’t necessarily live more fascinating lives. They just present their lives in an interesting way.
I have a friend who’s an awesome storyteller. When he starts telling a story, people give him their full attention.
Here’s a story that he told me recently:
So a few days ago, I woke up with a day of important exams and meetings ahead of me. I’m waking up feeling stressed because the alarm clock has apparently already gone off.
I feel totally exhausted and prepare myself for the day, taking a shower and shaving. However, my tiredness just won’t let go, and I’m actually throwing up a little on my way out of the bathroom.
I become afraid of what’s happening but I’m preparing breakfast, and I’m getting dressed. I’m staring at my porridge but can’t eat and want to throw up again.
I’m picking my phone up to cancel my meetings and realize that it’s 1:30 AM.
This isn’t Story Of The Year, but it’s a great example of an engaging story you can tell in a social situation.
What I like about this story, in particular, is that it’s not an exceptional event; you’ve probably been through several similar things in your life. However, this guy succeeds in turning it into an interesting story.
Also, notice how you probably felt motivated to read that story more than anything else you’ve read in the guide so far – that’s how hardwired we are to like stories.
- He doesn’t try to look like a hero. Instead, he tells the story of a struggle.
- It ends with a punch. A punch is often the difference between awkward silence and laughter.
- Notice the pattern: Relatable -> Context -> Struggle -> Punch
Whenever he’s telling these stories, he gets everyone’s full attention. Through these stories, he makes people feel good and makes them want to be around him. Storytelling is why people see him as an outgoing person.
Read this guide on how to tell a good story.
“I’d love to know how to be better at conversation beyond small talk. How can I move from superficial stuff to something more exciting?”
When I start talking to someone, I begin by introducing myself:
“Hi, I’m David. How are you doing?”
This opening starts the conversation on a simple note. This is how to make a conversation flow from the outset. There are fewer pauses and awkward silences.
A common mistake people make is to try and come with something clever and interesting to say at the beginning of the conversation. However, an interesting conversation doesn’t happen when you make smart comments; it happens when you start talking about something you both enjoy discussing.
That’s where these questions come in. For example:
“How do you know the other people here?”
This question can be used in most situations where you meet strangers. Let them explain how they know people and ask relevant follow-up questions.
This question is designed to help gradually transition into a more personal conversation, as it obviously would feel weird to start talking about personal stuff immediately after you’ve met.
Read more: How to start a conversation.
In between these questions, share a little bit about yourself once in a while.
“Where are you from?”
This is a good question because it’s easy for the other person to answer, and it opens up many avenues of conversation. It’s useful even if the person is from the same town; you can talk about which part of town they live in, and what it’s like living there. Perhaps you’ll find a commonality. For example, maybe you’ve both visited similar local attractions or like the same coffee shops.
“Do you work/study?”
I ask about either work or studies, depending on how old the person is.
Some say that you shouldn’t talk about work with people you just met. I agree that it’s boring to get stuck in job talk. But knowing what someone is studying or working with is important for getting to know him or her, and it’s often easy for them to expand on the topic.
If they are unemployed, just ask what work they would like to do or what they want to study.
When you’re done talking about work, it’s time for the next question:
“Are you very busy at work, or will you have time for a vacation/holiday soon?”
When you’ve arrived at this question, you’re past the hardest part of the conversation. Whatever they say, you can now ask my favorite question of all:
“Do you have any plans for your vacation/holiday?”
Now you’re tapping into what they like to do in their own time, which is interesting for them to talk about. You may discover mutual interests or discover that you’ve visited similar places. Even if they don’t have any plans, it’s natural to talk about how they spend their free time.
One common piece of advice is to avoid sensitive topics when you haven’t known someone for very long. These include:
- Political beliefs
- Religious beliefs
- Personal finance
- Intimate relationship topics, e.g., sex
- Ethics and lifestyle choices, e.g., veganism
However, these subjects are interesting and affect most of us. As you get to know someone better, they can inspire good conversations. So when is it OK to talk about them?
In general, it’s OK when:
- Both of you are already comfortable sharing opinions about less controversial topics because this suggests you feel safe opening up to each other.
- You are prepared to deal with the possibility that their views might offend you.
- You are willing to listen, learn, and respect their opinions.
- You are in a one-on-one conversation or in a group where everyone is comfortable with one another. Asking someone their opinions in front of other people can make them feel awkward.
- You can give them your full attention. Look for signs that it might be time to change the subject, such as an inability to look you in the eye or shuffling from side to side.
When you follow these guidelines, you’ll learn how to make a conversation interesting and personal without causing offense.
Memorize a useful phrase to redirect a conversation that has become tense or difficult. For example, “It’s interesting to meet someone who holds such different views! Maybe we should talk about something a bit more neutral, like [insert uncontroversial topic here].”