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“How can I have more interesting conversations? I get stuck in small talk and bore people and myself”
– Violette S.
1. Escape small talk by asking something personal about the topic
We need a few minutes of small talk to warm up. But to not get stuck in small talk, ask something personal related to the topic.
A good rule of thumb is to ask questions that contain the word “you”.
- If you have a boring conversation about unemployment rates, you can ask “What would you choose if you decided to completely change job?”
- If you talk about how it’s cold outside, you can ask “Where would you rather live if you could stay anywhere in the world?”
- If you get stuck talking about economics, ask “What would you do if you had an unlimited amount of money?”
2. Mention topics that interest you and see how they react
If it turns out that you have an interest in common, the conversation gets more interesting for both of you. If they don’t seem interested, you can try with another interest at a later point in your conversation. You might come across mutual interests more often than you think.
They: “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”
3. Make it your mission to learn 2-3 things about people you meet
It makes the meeting more interesting for both of you if you have a small mission.
It can be to learn what people do, where they are from, and what their future plans are.
Your mission can be to ask people about these things when it feels natural. You get a reason to talk to them and you might find common interests.
4. Share something slightly personal about yourself in between your questions
It’s not true that people ONLY want to talk about themselves. They also want to know who they are talking to. If they don’t, they might even feel interrogated and get uncomfortable.
When we share slightly personal things with each other, we bond faster. 
You: How long did you live in Denver?
They: 4 years.
You, sharing something slightly personal: Cool, I have relatives in Bouder so I have many nice childhood memories from Colorado. What was it like for you do live in Denver?
5. Force your attention back to the conversation whenever you get stuck in thoughts
A conversation gets more interesting the more focused you are on it. Bring the focus back to the conversation when you notice that you get self-conscious.
If someone says “I went to Paris last week.”, some start thinking: “Will they look down on me for not having been in Europe? What should I counter with? Is my posture weird?”
If you force your attention back to the conversation, it’s easier to be curious.
Your thoughts when you focus on the conversation: “Paris, I wonder what that’s like? How long did it take to go to Europe? What did they do there? How come they went?”
You: “That sounds exciting! What was it like?”
6. Refer back to something more interesting you talked about before when a topic dies out
Conversations don’t need to be linear. It’s completely natural to go back to an older topic if the current one feels done and there’s a bit of 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?
7. Ask “What do you like the most about X?” to lead the conversation into passions
Passions are often more interesting to talk about than facts about school or work. If it turns out that you have similar passions, those are great to delve into and form a friendship around.
If someone says that they’re a teacher, you can ask “What do you like the most about being a teacher?”
If they don’t like their job, you can ask “What do you like doing the most when you don’t work?”.
8. Ask open-ended questions
Open-ended questions are the ones you can’t respond to with a simple yes or no.
Closed-ended: Was the vacation good?
Open-ended: What did you do on your vacation?
If you often receive short yes or no answers to your questions, try asking open-ended ones instead.
9. Ask about their dreams
Learning about each other’s dreams makes the conversation more interesting, and you might find dreams you have in common.
You can ask younger people what they want to work with and their life goals. You can ask older people about their plans for the coming years.
They: “I study biology”
You: “Cool, what would be your dream job in biology?”
They: “I’ve been working in real estate the last 40 years”
You: “Wow. Do you ever think you’re going to retire or what’s your dream of doing the coming years?”
10. Ask questions containing “what, why, when, how”
Those questions help move the conversation from small talk to more interesting topics. They often inspire more in-depth answers.
They: I’m from Connecticut
What: What’s it like to live there? What do you like the most about it? What was it like to move?
Why: How come you moved?
When: Are there times you miss home? When did you move? Do you think you’ll move back?
How: How come you moved?
11. Ask about their personal opinion
It’s fun and engaging to get asked one’s opinion. The conversation that follows is usually more interesting than talking about facts.
I need to buy a new phone. Do you have a favorite?
I’m thinking of moving in with two friends. Do you have experience of co-living?
I look forward to my vacation. What’s your favorite way to wind down?
12. Show that you are interested to come off as more interesting
Use active listening to signal that you are interested in what they have to say. When you show that you are interested, conversations tend to become more in-depth and interesting.
- Keep eye contact whenever they talk
- Direct your body, feet, and head in their general direction
- Avoid looking around the room
- Humm when appropriate to show that you’ve heard them
- Summarize what they said. They: I didn’t know if physics was right for me so that’s why I started painting instead. You: Painting was more you. They: Yes, exactly!
13. Talk about FORD-topics: Family, Occupation, Recreation, Dreams
When a conversation gets boring, remember the FORD-topics and see if you can ask a related question to any of them.
They: Work is so stressing now because we are undermanned.
You: That sucks. Do you have any vacation plans you dream about?
14. Keep good eye contact to show that you are present
It can be hard to keep eye contact, especially if we feel uncomfortable. But lack of eye contact can make people think that we aren’t interesting, and they don’t dare to open up.
- Try to see the color of their iris and, if you’re close, the texture of the iris.
- Look in between their eyes or at their eye-brows 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 – like when they are having a few seconds break to formulate their thoughts, it can be a good idea to look away so they don’t feel pressured.
15. Figure out mutual interests
Let’s say that you meet this person and she tells you that she works in a bookstore. Just by using that tiny piece of information, what are some assumptions we can make about her interests?
- Culturally interested
- Prefers indie to mainstream music
- Likes to read
- Prefers to shop vintage
- Prefers going by bike 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.
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 I ask something to move the conversation in that direction:
“What’s your view on e-readers? I guess they have a lesser environmental impact 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” (Or whatever).
Judging by her answer, I will know if she seems to be concerned about environmental impact, and we can now segway into talking about that.
Or, if she seems indifferent, I try another topic.
(For example, talking about if she bikes to work and what bike she could 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 the girl above.
- Interested in career
- Reads management literature
- Lives in a house, maybe with her a family
- Drives to work
- Has an investment portfolio so 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, well, IT security
- Plays video games
- Interested in movies like Star Wars or other sci-fi or fantasy
As you notice, our brain is really good at coming up with assumptions about people.
Sometimes, that’s a bad thing, like when we’re being prejudiced.
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 the passions of our lives. Just something that you enjoy talking about is enough for an interesting conversation.
Making any conversation interesting, in summary:
- Ask yourself what the other person might be interested in
- Mutual interests – What might we have in common?
- Testing our assumptions – I move the conversation in that direction to see their reaction.
- Judging their reaction – If they are indifferent, I try their reaction to some other subject – If they respond positively, we can delve into that topic.
It’s when we find mutual interests that the magic happens.
16. Tell stories in a way that’s interesting
We, humans, love stories. Scientists believe that we are hardwired to like them: In experiments, they discovered that our eyes dilate as soon as someone starts telling a story.
By simply saying “So, a few years ago I was on my way to…” or “Have I told you about that time I…?”, something powerful happens in people’s brains.
You can use storytelling to connect with people and be seen as more outgoing. 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.
And as time passes, you will have more and more stories in stock.
Recipe of how to successfully tell a good story
- It needs to relate to the situation. Memorize your good stories to over time build up a stock. Stories are timeless, a good story can and should be told several times as long as there’s a new audience.
- Talking about how good you put people off. Therefore, avoid stories where you come off as being the hero. Instead, stories that show vulnerability prove to work better.
- Put people into a relevant context. Explain the setting so that everyone gets the story. More about this in the example below.
- Talk about things that others can relate to. Adjust your stories after the audience.
- Every story needs to end with a punch. It can be a small punch, but it has to be something. We’ll look at this at the example below as well.
It’s important to realize that people with a lot of stories don’t necessarily live more interesting 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’m waking up to an important day with exams and meetings. I’m waking up stressed because the alarm clock had apparently already gone off.
I feel totally exhausted and prepare myself for the day, taking a shower and getting shaved. However, my tiredness just won’t let go and I’m actually throwing up a little on my way out from the bathroom.
I become afraid of what’s happening but I’m preparing breakfast and I’m getting dressed. I’m staring at the porridge but can’t eat and want to throw up again.
I’m taking my phone up to cancel my meetings and realize that it’s 1:30 AM.
This wasn’t meant to be the story of the year – it’s just a great example of a nice story to pull of in a suitable 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.
Pay attention to the following:
- He doesn’t try to look like a hero. Instead, it tells the story of a struggle.
- It ends with a punch. The 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.
17. Learn a path from small talk to interesting conversation
When I start talking to someone, I obviously first present myself:
– Hi, I’m David. How are you doing?
Starting off from the first line, I’m keeping the conversation simple. The simpler you keep the initial conversation, the better it will flow, because it decreases the risk of pauses and awkward silence.
A common mistake people do is trying to come up with something clever to say already in the initial conversation. However, an interesting conversation is not created through smart comments; it’s created by talking about something you both enjoy discussing. And that is what these questions are designed to create. Let’s continue!
– How do you know people here?
This question can be used in most situations where you meet strangers. Let them explain how they know people and ask follow-up questions relevant to what they’re saying.
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 the first thing you do.
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 talk about. It’s useful even if the person is from the same town – you can talk about where in town and what it’s like living there. Perhaps you have something in common that you can both relate to about the area.
– 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. And 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.
If they are unemployed, just ask what they would like to work with or study. When you’re done talking about work, it’s time for the next question:
– Is it busy or will there be time for vacation/holiday?
When you’ve arrived at this question, you’re past the hard part. No matter what they reply, you can now ask my favorite question of all categories:
-Do you have any plans for your vacation/holiday?
Now you’re tapping into what they like to do the most. They think about positive things and it’s interesting for them to talk about. Even better, here’s where you might find mutual interests or similar places you’ve been to. Even if they don’t have any plans, it’s natural to talk about how they spend their free time. It’s often possible to find similar interests here.
- Swarat, S. (2008). What Makes a Topic Interesting? A Conceptual and Methodological Exploration of the Underlying Dimensions of Topic Interest. Retrieved from http://ejse.southwestern.edu/article/view/7773
- Aron, A., Melinat, E., Aron, E. N., Vallone, R. D., & Bator, R. J. (1997). The experimental generation of interpersonal closeness: A procedure and some preliminary findings. Personality and Social Psychology Bulletin, 23(4), 363-377. https://doi.org/10.1177/0146167297234003
- Glanzer, M. (1958). Curiosity, exploratory drive, and stimulus satiation. Psychological Bulletin, 55(5), 302-315. http://dx.doi.org/10.1037/h0044731
- Asking and Answering the 5 W’s and H Questions. Retrieved Aug 14, 2019. https://k12.thoughtfullearning.com/minilesson/asking-and-answering-5-ws-and-h-questions
- Olivia Kang, Thalia Wheatley. Pupil dilation patterns spontaneously synchronize across individuals during shared attention.. Journal of Experimental Psychology: General, 2017; 146 (4): 569 https://doi.org/10.1037/xge0000271