We’ve all been there: sitting in a conversation that just isn’t clicking or walking away from an interaction feeling like we haven’t shown the best of ourselves.
Sometimes, our conversation habits can misrepresent how truly interesting, thoughtful, or fun we are. And ironically, the very habits we pick up to appear more engaging can backfire, making us seem less interesting than we really are.
Today, I want to highlight seven conversation habits that can hold you back—habits that many of my own clients and friends have struggled with. Let’s jump in.
1. Over-sharing personal stories
Have you ever caught yourself mid-conversation, about ten minutes into a monologue, wondering whether the other person has even spoken yet? It’s easy to do—especially when you’re excited or passionate about a topic.
But when we over-share personal stories, we risk turning what could be a great two-way exchange into a one-sided narrative.
In therapy sessions, I’ve seen this habit rooted in a desire to connect quickly. Sharing personal stories can break the ice and show vulnerability, which is wonderful. However, it’s a balance issue. When I first started my practice, I found myself sharing anecdotes with new clients, hoping to make them feel comfortable.
Then, I realized they often needed me to pause and really hear their side. Over-sharing tends to leave people feeling like they’re watching a performance rather than being part of an interaction.
If you notice yourself doing this, here’s a quick fix: ask questions. After you share something, pivot back with, “Does that ever happen to you?” or “What do you think?”
That small moment of turning it back to the other person can make the conversation more dynamic—and it can prevent you from sounding like you’re hogging the spotlight.
2. Not actively listening
We’ve probably all heard that listening is the key to great communication. But what does “actively listening” really mean? It’s more than just letting the other person talk.
It involves eye contact, nods, and verbal affirmations like “I hear you” or “That makes sense.” It means asking follow-up questions that show genuine curiosity.
Daniel Goleman, a leading expert on emotional intelligence, highlights that empathy is built on attuning ourselves to another person’s feelings and thoughts. That attunement can only happen when we truly listen.
If we’re planning our response or daydreaming about what to eat for lunch while someone else is talking, we’re missing the conversation’s core.
In my own life, I can think of times when friends have pointed out, “Hey, are you with me?” Usually, it’s right after I’ve drifted off into my internal to-do list.
Simply refocusing on their words—maybe by mentally summarizing what they’ve said—helps me come back into the moment. It’s a simple trick that genuinely enriches the conversation.
3. Constantly steering the conversation back to yourself
This one is a close cousin of over-sharing. You might have read my post on how to develop deeper connections, where I discussed how important it is to let others be the star of the show sometimes.
Well, constantly steering the conversation back to your own experiences is one surefire way to dim that star power for the other person.
Picture a friend saying, “I just got back from a trip to Italy—it was amazing!” and instead of asking questions like, “What was your favorite city?” or “Did you try authentic gelato?” you jump in with, “Oh, I went there once too! Let me tell you all about my trip…” Before you know it, the conversation is about you instead of them.
I’m a big fan of asking thoughtful questions in these moments. When someone shares good news or a unique experience, I try to imagine what they felt. Did they feel nervous, excited, or awestruck?
Asking about their emotional state keeps the focus on them. It’s a powerful way to remain interesting by showing genuine curiosity about their experience—rather than hijacking the topic for your own story.
4. Playing it too safe with small talk
We’ve all had those surface-level chats: the weather, the traffic, the polite “How’s work?” routine. Small talk isn’t inherently bad—it often opens the door to deeper discussions. But if we park our conversation there and never leave, we risk seeming unengaged and, frankly, a bit dull.
Susan Cain, author of Quiet, has noted how introverts often prefer meaningful discussions over small talk. Interestingly enough, a lot of extroverts do too. There’s a place for polite, quick conversation—like when you’re waiting for coffee—but if you really want to spark interest, experiment with more thoughtful questions.
For example, instead of asking “How’s work?” you could say, “What’s been the most challenging part of your job lately?” Or, “What’s something exciting that happened this week?”
As a psychologist, I love using open-ended questions. They invite people to share beyond the usual “I’m fine.” In my personal life, I’ve realized that asking, “What’s the best part of your day so far?” can lead to some surprisingly profound answers—and it instantly makes the conversation more engaging.
Don’t be afraid to dip your toes into deeper waters. You might be pleasantly surprised by how people respond.
5. Over-reliance on negative topics or complaining
We all need to vent sometimes, and there’s definitely value in processing tough emotions verbally. But if our conversational style consistently leans toward complaining or focusing on what’s wrong, we risk driving people away.
You know that friend who only talks about their bad day or the broken dishwasher? Yeah, it can get draining.
I remember a stage in my life when I was juggling two toddlers, a full-time job, and trying to master pottery in my free time. Stress was high, and I found myself complaining a lot to friends.
One day, a close friend gently mentioned that our catch-ups had become “Tara’s venting sessions.” It stung, but it was also the wake-up call I needed. I wanted to share more than just my frustrations—I wanted to connect in a way that felt uplifting, too.
This doesn’t mean avoiding difficult emotions. In fact, Carl Rogers emphasized the importance of genuine expression and empathy. If you’re feeling overwhelmed, share it—but remember to ask about the other person’s day or find something positive or reflective in your own experiences.
An honest conversation about challenges can be interesting and authentic, but a never-ending venting spree can leave people feeling drained.
6. Failing to read cues and interrupting
You’ve probably heard someone say, “Timing is everything.” This applies to conversations, too. Interrupting someone mid-sentence or ignoring signs they want to speak can give the impression you’re not really interested in a genuine exchange.
Conversations should feel like a dance—both partners need to find a rhythm. If you see someone leaning forward, inhaling to start speaking, or if their expression changes like they have something to say, that’s your cue to pause and let them in.
I’m the first to admit I’ve been excited and cut someone off. It’s something I still work on. But every time I succeed in letting that person finish, the dialogue flows better.
A practical approach to keep in mind is the “three-second rule”: after someone finishes speaking, silently count to three in your head before responding. This tiny pause can help you avoid unnecessary interruptions. It can also make your responses more thoughtful—and interesting.
7. Last but not least, avoiding self-disclosure altogether
Surprised by this one? We often talk about over-sharing, but the opposite extreme can be just as detrimental to how interesting you seem.
If you’re always deflecting questions about yourself—answering with “It’s fine” or giving generic “All good” replies—other people might interpret you as distant or aloof, rather than mysterious and intriguing.
I once worked with a client who wanted to improve her social life but told me she “didn’t have anything interesting to share.” Yet during our sessions, I discovered she had a deep love for painting landscapes at sunrise. This hobby wasn’t something she typically revealed to acquaintances.
When she started mentioning it in casual conversations—just a little detail here or there—people became instantly curious, asking questions about her art, the technique, and even if they could see photos. She realized her life was far more interesting than she gave herself credit for.
Carl Jung famously said, “Who looks outside, dreams; who looks inside, awakes.” We all have inner worlds brimming with insights, interests, and experiences. By sharing a slice of that with the people around us, we create richer, more engaging conversations. Being guarded can feel safe, but it often prevents genuine connections.
The bottom line
These seven habits aren’t permanent character flaws—they’re simply patterns we slip into. When left unexamined, they can make us come across as far less captivating than we actually are.
The good news is, each one can be unlearned with a bit of practice, whether it’s learning to pause before speaking, asking meaningful questions, or opening up just a little more.
Here at Blog Herald, our aim is to help people spark healthier, more rewarding connections—both with others and with themselves. One of the quickest ways to enrich those connections is to fine-tune how we communicate.
So the next time you catch yourself dominating the conversation or defaulting to stale small talk, pause and try something new. Share an insight, ask a deeper question, or show empathy by reflecting on what the other person said.
Small shifts in how we speak and listen can lead to big changes in how we’re perceived—and in how we ultimately feel about our relationships. Trust me, you’re already more interesting than you think you are. Let’s just make sure everyone else gets to see it, too.
