How to Move Past Awkwardness and Have Better Conversations (That Actually Last)

Share this article

If you’ve ever laughed at sitcoms like The Office, Parks and Recreation, or Friends, you’ve likely noticed how much humor hinges on social interactions—sometimes painfully awkward ones. Michael Scott’s cringe-worthy attempts at small talk or Ross Geller’s over-explanations about paleontology may come to mind. But in real life, forming genuine connections doesn’t always come with a laugh track or a perfectly scripted moment.

We are familiar with awkward silences that stretch too long, fumbling for the “right” thing to say, or feeling like we’re talking at someone instead of with them. Conversations being the cornerstone of all relationships, are both art and skill. Whether it’s a first meeting at a party, casual chats to deeper connections, bonding with a coworker, sparking a romance, or even just chatting with a cashier, conversations are the foundation of human interaction. Knowing how to connect through words can elevate those moments from mundane to memorable.

The truth is, we struggle with this in ways we don’t openly admit. This isn’t exclusively about the stereotypical “nerds” on TV who trip over their words or overthink their social interactions. In reality, some people—regardless of personality type—have felt the sting of a stalled or awkward conversation.

Spilling the tea on how to  form connections and maybe even turn small talk into less awkward and genuinely enjoyable—for you and the other person. Read on. 

 

01

First and Foremost, Sometimes You’re the Problem and That Needs to Change

Brushing up your communication skills without the right attitude is like polishing a car with no engine—it might look good on the surface, but it won’t take you anywhere. Communication is more than words, it takes sincerity and willingness to attract the receiver. Without the right mindset, even the most polished communication techniques fall flat, no matter how hard we try to mask it, what’s inside the heart shapes how we connect (or fail to connect) with others.

Can you recall the last time you felt frustrated, tired, or distracted during a conversation. did it seep into your tone when someone asks you how your day was? Did your tone come across as dismissive? Did you find yourself mentally checking out or offering half-hearted responses? 

Because even the smallest irritation can influence how you respond to others. These little signs reflect the state of mind. When it comes to relationships, if you always show disinterest or  don’t place importance on them, it’s only a matter of time before they start feeling uncomfortable around you. 

One way this happens is finding out. One day you  wake up wondering why your close friends are gone or have no one to talk to after years of maintaining such an attitude. When we fail to address what we’re holding inside, it creates barriers between us and the people we care about.

Read:  7 Daily Choices That Make Up 95% of Your Success in Life

If you have an emotional baggage you’re hauling around, it’s time to pause, reflect, and take steps to heal. Whether you need to see a therapist or confide in someone you trust, sometimes it takes receiving help from others to heal from years of pain, resentment, and past mistakes. And that’s okay, you don’t have to carry it all alone.

 

02

The Art of Asking Questions

Ever notice how the most engaging conversations—on a first date, at a networking event, or catching up with an old friend—share one common thread? They’re filled with curiosity. 

Referencing a character in a TV show, one smooth conversationalist—the one who can effortlessly connect with anyone? Take Ted Lasso for example. One of Ted’s secrets to charming every character he meets? It’s not his witty one-liners (though they help), it’s his genuine curiosity about others. He asks questions. Lots of them.

In real life, though, many of us shy away from asking too much. It’s a skill that feels deceptively simple. Yet, in our everyday lives, we fall short. Too many conversations fall into a rhythm of shallow exchanges or fizzle out entirely because neither party asks the right questions—or worse, doesn’t ask any at all.

Why? Maybe we think we’ll come across as nosy or, sometimes it’s because we’re distracted. Other times, we’re simply not that interested. While it’s perfectly fine not to connect with every single person, this tendency to disengage can create a pattern that leaves conversations flat and relationships stagnant. When you stop asking, the conversation stops growing. 

So, how do you become someone people love talking to?

By learning how to ask the right questions, at the right time, for the right reasons. There are a number of ways to find out about someone you meet for the first time, asking about, what they do, what they’re interested in, what type of music they like, have they seen a good movie lately, what books they’re reading, or even what they did or do on weekends. 

Questions can transform even the most mundane chat into something meaningful. It’s a habit worth building, not just with new acquaintances but with people you’ve known forever. After all, everyone has layers, stories, and interests waiting to be uncovered. You just need to ask.

 

03

Be a Little More Real With Your Responses

There are way too many fleeting, forgettable hallway conversations that feel more like a reflex than an exchange.

“How’s it going?”

“Good, busy as always. You?”

“Same here. Crazy week.”

Read:  13 Tips and Guide to Cope and Hack Your Way into Adulthood

And just like that, the moment fizzles out, leaving you and the other person none the wiser about each other’s lives. It’s the conversational equivalent of treading water—safe, predictable, and completely unremarkable.

How many times have you asked someone about their day, only to hear the same vague answers—“busy,” “fine,” “same old, same old”? Or, worse yet, how often do you catch yourself giving those same bland replies? 

We churn out the same generic empty answers everyone else is giving because it’s easier, quicker, and feels “safe.” The problem? It keeps our conversations stuck in neutral and blocks any chance for meaningful connection. 

Genuine connection can’t happen when we’re only skimming the surface.

If you want to have conversations that matter—ones that leave both you and the other person feeling seen and heard—you have to do better than that, being a little more real with your responses goes a long way. Being real doesn’t mean oversharing, you just have to move a little beyond clichés and offer something authentic, even if it’s small. You may be surprised at how quickly a conversation can take flight when you give it a try. 

 

04

Finding Common Ground

When was the last time you truly connected with someone? Maybe it was over a shared love of music, a mutual hobby, loving the same childhood TV show, frequenting the same local coffee shop, or even something as simple as rooting for the same sports team. That “aha” moment of realizing you have something in common often feels like the key that unlocks a deeper connection.

Relationships, whether romantic, platonic, or professional, thrive on shared interests. While opposites might spark curiosity, it’s common ground that fosters lasting bonds, they give us a starting point—a bridge to cross the gap between two strangers or acquaintances. After all, we naturally gravitate toward people who understand us, who share pieces of our experiences or perspectives.

Building these connections doesn’t have to be a complicated process. It starts with curiosity, again, this points to asking the right questions, being attentive, and staying open to possibilities. 

Everyone has something in common with someone else, likes, dislikes, and memories, it’s just a matter of being open enough to uncover it. Take the time to dig a little deeper, and you might find that you have more in common with the people around you than you ever imagined. 

 

05

Maintain Subtle Eye Contacts

Have you ever tried talking to someone who never quite looks at you? Maybe their eyes dart around the room, focused on their phone, or seem fixated on some invisible point in the distance. How would you feel? Dismissed? Unimportant? It’s unsettling, isn’t it? It leaves you wondering

Read:  10 Habits That's Slowly Making You Ugly

 

Are they even listening to me?

Distracted conversations like this are all too common, and they can derail even the best intentions to connect.

Eye contact is one of the simplest yet most impactful tools in communication. It doesn’t require words, but it speaks volumes. A steady gaze shows that you’re present, engaged, and genuinely interested in what the other person has to say. It tells them, “You matter right now,” in a way that no casual remark or polite nod ever could.

A first meeting with a client, an introduction at a party, or even a catch-up with an old friend—each of these moments is shaped by whether or not you make eye contact. It’s a small, practical habit that can make all the difference in how others perceive you and, more importantly, how they feel when talking to you.

Of course, don’t overdo it, you don’t have to stare someone down. Too much eye contact can come across intense or even awkward. But a natural rhythm—meeting their gaze, breaking away briefly, but always return to the person you’re engaging with—creates a balance that feels comfortable and warm. It’s a small habit that can transform how people perceive your presence and the depth of your conversations.

 

06

Put Your Phone Away 

It wasn’t that long ago when the first centerpiece of social spaces began to shift from people to technology. The TV dominated households and demanded everyone’s attention. And today, we carry an even more captivating screen everywhere we go.

The smartphone.

It’s hard to deny how much our phones have become extensions of ourselves. They’re alarm clocks, calendars, cameras, and sources of endless entertainment. But, they’ve also become barriers, distractions that pull us away from the people sitting right in front of us.

How often do you catch yourself glancing at your phone mid-conversation only half-listening, with one eye on the person speaking and the  other on a glowing screen? Scrolling through notifications or emails that can wait? Each time you do, it sends a subtle but clear message:

This screen is more important than you right now.

It’s a habit that chips away at genuine connection and leaves both parties feeling undervalued. It’s not intentional rudeness, it’s just become a reflex. But the truth remains, no notification, meme, or viral post can replace the depth of human interaction.

Phones aren’t inherently bad. They’re incredible tools when used intentionally. If you’re serious about building meaningful relationships, it starts with a simple act. Putting your phone down—even for short bursts—signals that you’re invested in the moment and the person you’re with.

 

Share this article

Leave a Reply

Your email address will not be published. Required fields are marked *