People who crave deep connections but struggle to initiate conversation usually display these behaviors, according to psychology

It’s not easy to form meaningful relationships in a world that often rewards quick interactions and fleeting digital exchanges.

If you’re anything like me, you might sometimes feel stuck in that weird in-between where you genuinely want deeper connections, yet find yourself hesitating or stumbling when it comes to breaking the ice.

I’ve lost count of how many times I’ve replayed a conversation in my head after the fact, thinking, “Why didn’t I say something more interesting?” or “Why didn’t I just ask that question?” And I know I’m not alone in this.

Psychology tells us that there’s a common set of behaviors many people exhibit when they’re longing for deeper bonds but struggling to reach out. Let’s explore those behaviors, one by one.

1) They overthink every interaction

Ever sit there and meticulously rehearse your lines in your head before saying “Hello”? I certainly have. This tendency to overthink is practically the hallmark of someone who craves a deeper connection yet isn’t confident about how to get there.

Why do we do it? Often it’s anxiety talking. We worry about rejection or coming across as awkward. We might even wonder if our conversation topic is “interesting enough” to hold someone’s attention. The fear of judgment can be paralyzing.

As Brene Brown has famously said, “Vulnerability is the birthplace of connection.” But stepping into vulnerability is scary—it means taking a risk. Overthinking, in many ways, becomes our safety blanket, even as it holds us back from actually forming those connections.

I try to remember that most people are too busy thinking about their own stuff to overanalyze what I’m saying. Everyone has their own mental monologue. So, keep it simple. Ask how they’re doing, comment on something happening around you, or share a genuine compliment.

2) They rely on surface-level banter

You know how you sometimes meet someone new, and the conversation never gets past the weather, what you do for work, or your favorite Netflix show? That’s a classic pattern for those who crave depth but hesitate to lead the conversation somewhere more meaningful.

At times, it might stem from a fear of being “too much” too soon. Other times, we’re simply uncertain about whether the other person wants to go deeper, so we stay in safe territory.

Simon Sinek, known for his work on leadership and connection, once noted, “Dialogue is about connecting, not proving a point.” If you’re constantly juggling superficial topics, you might be missing the chance to spark a real exchange.

I like to break the cycle by asking open-ended questions: “What’s inspiring you lately?” or “What do you love about what you do?” These questions can encourage deeper reflections and steer the chat away from shallow small talk.

3) They wait for others to initiate

I’ve noticed that some of my most introspective friends—those who yearn for profound connections—will rarely start the conversation. Instead, they hang back, waiting for the other person to approach them. Why? Because initiating is inherently vulnerable.

But letting others always take the first step can create a missed opportunity. It’s like waiting at a dance party for someone to ask you to move to the dance floor, when in reality, you might have the best moves in the room.

Cal Newport, who dives deep into the intersection of focus and meaningful work, said something along the lines of how important it is to “structure” your attention for what matters. If forging deep human connections is important to you, then consider structuring your approach so you’re not perpetually sidelined by fear.

Give yourself small challenges. For example, the next time you’re in a social or professional setting, say hi first. Or if you’re in a Zoom meeting, be the first to ask a question when the facilitator opens it up for discussion. Baby steps can build momentum.

4) They hide behind technology

Here at Small Biz Technology, we know technology can be a powerful tool. But for those who struggle to initiate face-to-face conversations, technology sometimes becomes a crutch—or even a shield. It’s tempting to just text or DM someone rather than chat in person or call them up.

This behavior might feel safer because you get to edit your words, avoid immediate rejection, and take your time to respond. But in the long run, relying too heavily on digital communication can limit the real-time spontaneity that fosters closeness.

James Clear, author of Atomic Habits, has observed that building a connection is a daily practice of small steps—like building any habit. Messaging might be part of the puzzle, but face-to-face or voice-to-voice contact is often where genuine empathy and trust grow more quickly.

Set intentional “offline” or “real-time” conversation goals. If you meet someone interesting in an online forum or email thread, try suggesting a quick call or in-person meetup. Technology should enhance our ability to connect, not replace it.

5) They seldom share personal stories

I have a friend who’s always been a great listener. She’ll ask me questions about my life and really pay attention. But whenever I try to flip the script, she smiles politely, answers minimally, and changes the subject. Turns out, she’s deeply afraid of being judged.

People who crave depth but shy away from initiating often struggle to reveal themselves because they fear their experiences won’t be well-received. But the irony is, sharing personal stories is often the quickest way to deepen a bond.

Research from the American Psychological Association has shown that self-disclosure fosters trust and intimacy. When we share who we are—our real stories, not just the highlight reel—we invite others to do the same. That’s how two people get past the surface level and build something that lasts.

You don’t have to reveal your deepest secrets immediately. Start with a small anecdote—something that made you laugh or something that was a bit of a challenge. See how the conversation unfolds. Once you see it’s safe, you might feel braver about sharing more next time.

6) They self-criticize (a lot)

Have you ever noticed that the harshest critiques of your social performance often come from inside your own head? This is especially true when you’re eager for meaningful bonds but fear messing up. You might replay every little thing you said, blowing small slip-ups out of proportion.

In my own journey, I’ve found that excessive self-criticism actually hinders growth. It becomes this loop of negative thinking that can leave you feeling like you’re just “bad” at conversation.

Charlie Munger, who’s famously partnered with Warren Buffett, once warned about the dangers of “unconstructive negativity”—if you see everything through a lens of self-reproach, you stop learning and improving.

Next time you catch yourself going down the rabbit hole of self-blame, pause and reframe. Instead of “I’m awful at this,” try, “That moment was awkward, but at least I’m showing up.” Compassion towards yourself can make it easier to practice new conversation skills without the weight of excessive judgment.

7) They’re excellent listeners but rarely open up

In my corporate days, I worked with someone who was universally liked because he was the person you could go to and just vent. He’d nod, empathize, and genuinely seem to understand your perspective. Yet, he never talked much about his own life. Years later, I learned he felt deeply lonely.

Sound paradoxical? It’s a classic dynamic: People who hunger for genuine connections often excel at letting others talk—this is the “deep soul” trait.

But the bond remains one-sided because they rarely share their own thoughts and experiences. The result is feeling unseen or misunderstood, even if everyone else appreciates their listening ear.

Great listening is a gift, but two-way vulnerability is what anchors real relationships. Try balancing the scales. If someone you’re close with is opening up about a personal challenge, consider offering a bit of your own story in return. This reciprocity can deepen the connection for both parties.

8) They fear they’re “too sensitive” or “too intense”

Some people have so many layers of emotion and depth that they fear “overwhelming” the person they’re talking to. Maybe you’ve been told you’re “too sensitive” or you ask too many “heavy” questions.

As a result, you keep your desire for deeper connection under wraps, worried you’ll push others away if you go full-throttle.

But here’s what I’ve learned: the right people won’t be put off by your depth. In fact, they’ll appreciate it. Viktor Frankl, in Man’s Search for Meaning, pointed out that our quest for purpose and understanding is universal. If that search makes you more curious or introspective, that’s not a flaw—it’s part of your essence.

Aim for emotional pacing. You can choose when and how to unveil your deeper thoughts. Gauge the other person’s comfort level, but never apologize for having depth. Over time, you’ll naturally attract those who resonate with your wavelength.

Final words

That’s it for this one folks. I hope these insights shed some light on why it’s totally normal to crave depth yet hesitate to kick off conversations. The gap between wanting closeness and knowing how to build it can feel frustrating, but remember: all it takes is one small shift at a time.

If you recognize yourself in any of these behaviors, know that you’re not alone. I’ve mentioned this before, but real connection begins the moment you decide to be a bit braver, a bit more vulnerable, and a bit kinder to yourself.

As always, I hope you found some value in this post. Until next time—and here’s to more meaningful, soul-enriching conversations ahead.