“Others will be bored with what I have to say”

What do we do when it feels like we aren’t interesting or that people get bored talking to us?

Look at these comments from two members of the SocialSelf community:

“I am doing an exchange semester abroad. Recently, I have been feeling very insecure and like I was the most boring person in the world to talk to, mainly because of lack of genuine interest and affection from the people I talk to.

I did not know what to talk about and people did not seem interested in me. Also, someone I got to know a bit better, mentioned that I ask a lot of questions (that’s how I get when I am trying to be extroverted), without providing anything about myself (again, because I feel like I have nothing to add and that I am boring).” 

– Aida

“My biggest social life challenge currently is talking to my peers without being boring. The conversation starts off with a lot of energy but begins to fizzle out after 5-10 minutes. After the conversation hits the 10-minute mark, I find it hard to find what topics or things to discuss. I want the conversation (especially with girls) to continue on and be fun for a very long time.

– Nathan

Things are made worse by the advice you find online on how to be more interesting.

Here’s some actual advice from the top results on Google…

Terrible advice 1: Memorizing questions to make the conversation interesting


“Working on any passion projects at the moment?”

“Besides work, what gets you up in the morning?”

You can’t just fire off canned questions. If someone out of the blue asked me what “passion projects” I work on, it would probably just feel weird.

Terrible advice 2: Crack jokes


“For example, when someone asks how he’s doing, he responds, ‘My lawyer says I don’t have to answer that question.’

It’s always fun to see a new person’s reaction. It just sets up the rest of the time together, true human connection and a good time, and isn’t that what it’s all about?”

Obviously, cracking jokes like this gets old fast. Plus, it misses the core of the problem. We don’t feel uninteresting because we crack too few jokes.

We need to go deeper.

What actually DOES work to have interesting conversations?

The advice above is trivializing the issue. Often, when it feels like someone loses interest in what we’re saying, our self-esteem takes a punch.

One time, I had a conversation with a girl I liked at a meetup. Then, she got eye contact with a guy behind me that she knew. It was like she forgot that we were talking, and she walked right over to him. I was gutted.

As you can guess, I was pretty quiet the rest of that night. Naturally, that also made me more boring to talk to. My fear of being boring became a self-fulfilling prophecy.

It takes more than cracking a few jokes to get past that.

Examining WHY we feel boring

Sometimes, we end up just listening to others. Then, when it’s our turn to speak, we just don’t know what could possibly be interesting enough to say.

Or, we get stuck in small talk. After 5-10 minutes of small talk, the conversation fizzles out.

Here’s a third cause: Our mind goes blank, and we can’t come up with anything to say.

Luckily, there’s a single solution to all of these problems. The trick I use is to ask about people’s relationship to the current subject.

So for example, if we make boring small talk about work, I ask about the person’s RELATIONSHIP to their work. So maybe I say:

“Do you like your job or do you dream of working with something else?”

As opposed to the bad advice above, this isn’t a canned line or a cheap joke.

Asking about someone’s relationship with the subject turns boring small talk into a deep conversation about dreams and thoughts.

The reason we think small talk is boring is that it’s often about facts and not what people think and feel. Since we can google facts anyway, they aren’t that interesting to talk about. (Unless both of you happen to be highly interested in the topic. I talk about that in this article on making interesting conversations.

But this method still won’t help us out of the “listeners trap” of feeling uncomfortable talking about ourselves.

This is where the thoughts and feelings method come in…

Whenever you’re making small talk and want to connect, share personal thoughts or feelings about the subject.

“But David, are you telling me that I have to share my thoughts on child labor and feelings about my grandmother’s death!?”

No! This isn’t about becoming an open book. It’s about opening up enough to not be a walking black box. What you actually do open up about can be very mundane. We can learn to do this, even if we feel uncomfortable talking about ourselves. Let me show you how.

You see, conversations get boring when they are only factual and shallow; we break out of that by sharing feelings and opinions.

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Here are the steps:

  1. Share a personal thought or feeling about the topic you’re on.
  2. Ask about their thoughts and feelings on the subject.
  3. If they give you a long response, share more of your original thoughts and feelings to match the other person’s reply in length.

This helps you out of the listener’s trap and creates a balanced conversation.

Here’s an example:

Say that you have a boring and factual small talk about how apartments are expensive.

“Apparently there’s been a 15% rent increase the last year, so it’s not like it’s going to be cheaper any time soon.”

Instead of talking more about rent increases, you share a personal thought or feeling. In other words, something that shows a little bit of who you are:

I get stressed living in the city.


I would love to buy my own place one day.

And then, you ask them about their thoughts or feelings.

Do you get stressed living here?


Where would you like to live if you could choose any place?

If they give you a long response, you can now talk more about where you would rather live or in what way the city stresses you.

As you see, you don’t have to open up in a way that’s uncomfortable. You just need to share a little bit of yourself, without having to be vulnerable.

Another example, say that you have boring and factual small talk about the weather.

“They say it will get cooler soon.”

Here, you can say something like:

“Warm weather makes me drowsy so I’m actually looking forward to that.”


I was thinking last year of moving somewhere with more sun.”

You don’t have to travel the world or have an amazing life to be able to have these kinds of conversations.

You don’t have to share anything provocative and it’s not about finding differences between you. Notice in the examples how the conversation is simple, easy-going, and still interesting.

“But David, my head goes blank. How can I come up with all these thoughts and feelings?”

Your head is already full of thoughts and feelings. As proof of that statement, just think about how many thoughts and feelings come up when you talk with someone you’re truly comfortable with.

If you can’t access your thoughts and feelings, it’s because you are in your own head, chasing things to say, rather than being focused on the conversation, letting your thoughts and feelings come to you.

Did you know that you can learn to better at focusing on a conversation? The trick is to continuously re-focus on it when you blank out. After a while, your brain becomes really good at staying focused on the topic.

You can practice this in conversations with anyone, preferably around people you already feel at ease with.

After some weeks of practice, you will notice how it’s easier to stay present in the conversation. As a result, your thoughts and feelings naturally pop up.

I talk more about this in this article about how to focus and be more present in a conversation

So, whenever you make small talk, share your personal thoughts and feelings about the subject. Ask about theirs. Let your conversation move to thoughts and feelings, rather than grinding facts.

This is the recipe for an interesting conversation.

You also might like this article on how to not be boring.

What do you think? Leave a comment below!

David Morin is the founder of SocialSelf. He's been writing about social skills since 2012. Follow on Twitter or read more.

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  1. This is great advice, David. Thanks. I just have one question: what do you do if you open up about a personal experience that could end up being uncomfortable for the other person you want to tell them?


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