The Surprising Upside of Awkward Moments (Yes, Really!)

📖 Read time: 7 minutes

Objectives 🎯

1. Understand why avoiding awkwardness keeps you stuck.
2. Learn why messy experiences build real confidence.
3. Discover how to intentionally practice handling awkward moments.

The fastest way to build social confidence? Seek out awkward moments.

Sounds weird, right? I get it—I spent most of my life avoiding them.

At seven years old, I jumped into a pool at a birthday party—still wearing my socks. The laughter wasn’t the fun kind. It was the pointing, snickering, “Why are you wearing socks?!” kind. Awkward! So I immediately called my parents to pick me up and spent the next few years avoiding birthday parties altogether.

I was always the tallest kid in class, which meant people assumed I was great at basketball. But I was king of the airballs. When someone was tempted to pick me for their team in PE, I’d hear a whisper: “No, don’t pick Ali.” Awkward! And on the rare occasions I did end up with the ball? I got rid of it immediately—passing before I could even think about taking a shot.

A few years ago, I was on a panel at the American Psychological Association when someone asked me a fantastic question. I smiled and said:

“Great point, Glenn!”

“My name’s Jim.”

Awkward!

So I did the completely rational thing of never saying anyone’s name again at a conference:

• “Good to see YOU.”
• “Hi FOLKS.”
• “Great question, esteemed COLLEAGUE!”

Have you done this? Replayed a conversation, cringing at every word? Dreaded looking weird or saying the wrong thing? Maybe even made things more awkward by trying to avoid awkwardness?

When you struggle with social anxiety, you live in fear of your awkwardness being revealed to the world. So you try to avoid awkward moments at all costs.

But what if awkwardness isn’t the enemy—it’s the answer?

What if avoiding it is making your social anxiety worse?

And what if leaning into awkwardness is the fastest way to build real confidence?

True Story 📖

Northern California, November, 2000 

It was my senior year of high school, and my heart was racing. I was a mess of awkward sweat—not because of a test, but because I was about to reveal something I was sure would end my relationship.

“Can we talk after school?” I asked my girlfriend, Nhu-An. “There’s something important.”

We had been dating for a few months now and talked on the phone every night…except Wednesdays. I kept making up excuses why: 

• I have to do homework (she knew I was a slacker). 
• I’ve got a family thing (on a Wednesday?).
• I have to clean my room (which I can do while on the phone). 

All this lying wasn’t just awkward—it was unsustainable. If I wanted a real relationship, I had to stop dodging and start being honest.

After school ended, we circled the campus a few times, waiting for everyone to clear out. My stomach was in knots. I was sure she was going to break up with me. 

I took a deep breath and whispered:

“I'm a Trekkie. And Star Trek: Voyager airs on Wednesdays. That’s why I can’t talk on the phone…unless it’s a rerun.”

Silence.

Then she smacked my arm.

“That's it?! I thought you were dying!”

I had spent the whole day convinced she’d never want to see me again. Instead, she was just confused why I’d made such a big deal about it.

Over the next few weeks, we had long conversations about why Star Trek meant so much to me.

“It’s actually really cool that a TV show had this effect on you. Most people just watch TV, but it doesn’t make them a better person.”

That moment taught me that awkwardness wasn’t my enemy—it was the price of real connection.

Here's What We Know 🧠

People with social anxiety are wired to experience awkward situations in 3 different ways:

1. We see more awkwardness.

We’re wired to pick up on any sign of disapproval or rejection, even if it’s not really there. One person frowning in a room full of smiles? We zoom in on that. Awkward!

2. We feel more awkwardness.

Even when people are saying nice things, just knowing we’re being watched can make us feel awkward.

3. We remember more awkwardness. 

Our brains remember awkward social situations more vividly than wins.

All of this feeds this loop of social anxiety: We believe social situations must go perfectly, or else they’ll be awkward disasters. 

The Social Anxiety Loop:

1. Avoidance – We dodge social situations that make us anxious.
2. Overthinking – When we can’t avoid them, we overanalyze every possible misstep.
3. Self-Sabotage – We freeze up, overcorrect, or actually make things awkward.
4. No Recovery – Since we never practice handling awkwardness, we don’t know how to bounce back.

Like when I jumped in the pool with my socks, or constantly passed the ball in PE, or started calling everyone “YOU”. 

Awkwardness isn’t the problem—it’s the path forward.

That’s what Nhu-An taught me: that awkwardness is just part of every social interaction. No matter if you are talking to a stranger, an aquiatance, or a romantic partner, things are going to get awkward. It’s normal, temporary, and never as big of a deal as our anxiety makes it seem.

We can’t escape awkwardness. But we can get confident with the mess.

Think About It Like This 💡

Imagine watching a movie where nothing surprising happens. No tension, no awkward exchanges—just people saying exactly the right thing at the right time, smoothly navigating every interaction. 

Sounds dull, right? 

That’s life without awkward moments. It’s predictable, forgettable, and missing what makes human connection real.

Take my favorite movie of all time: Jurassic Park. It’s full of dinosaurs, yes—but also awkward moments.

• Dr. Grant getting stuck with the kids – At the start, he wants nothing to do with them. But thanks to a few near-death experiences, he discovers how much he actually cares—and by the end, he’s practically their adoptive dad.
• Dr. Hammond’s failed tour – He’s certain Jurassic Park will be flawless. But when the tour flops—no dinosaurs, no excitement—he’s forced to face the truth: he can’t control nature.
• The lawyer fixating on profits – Instead of discussing ethics, he’s drooling over how much money they’ll make. Cringe. But without this awkward moment, we’d never get Dr. Malcolm’s legendary line: “Your scientists were so preoccupied with whether or not they could, they didn’t stop to think if they should.”

Now imagine Jurassic Park without these moments—just scientists calmly discussing dinosaurs. No tension. No chaos. No fun. Not exactly a classic, right?

Real life works the same way. Awkward moments feel uncomfortable, but they’re what make relationships real and conversations unforgettable. If you never risk being awkward, you’ll never build deep connections. You’ll miss out on the best moments—the ones people remember, laugh about, and connect over.

Try It Out ✨

Want to build real social confidence? Stop editing out the weirdness. Lean into it.

Everything thinks confidence means you know exactly what to say. You never make mistakes. You know things are going to go perfectly. 

That’s a steaming pile of dinosaur crap.

We don’t build confidence by avoiding awkwardness—we build it by experiencing it. Some conversations will fizzle. Some silences will stretch too long. Some jokes won’t land. And that’s exactly how you learn.

We have to learn that awkward moments aren’t fatal and we can work through them, recover from them, and yes something use them to form a deeper connection. 

Researchers call this social self-efficacy—your belief that you can handle social situations, even the awkward ones. And the best part? You don’t need to be perfect to improve it. In fact, research shows it goes up when you practice navigating awkward moments—like in social anxiety group therapy.

Here’s the good news. You don’t have to be in therapy to practice the exercises that help you become more confident. You can do them on your own. I’ve run this treatment for over 10 years and here are my favorite exercises for social confidence.

Step 1: Pick an Exercise

🦕 Visitor Center (Awkward but You're in Control)

These are small steps to practice mild awkwardness—just make sure to do them in daylight and safe, public spaces.

• Say something slightly incorrect on purpose. Like misnaming a dinosaur—“Is that a Brontosaurus?” when you know it’s a Brachiosaurus.
• Ask for directions to something obvious. Like standing in front of a Starbucks and asking where the nearest Starbucks is.
• Wear mismatched socks or a small, silly accessory. Nothing too wild—just enough to feel a little self-conscious.
• Sit in a public space and do nothing—no phone, no book—just observe. Like a scientist in the control room—watching, not acting.
• Order something at a café, then “oops” and ask to change your order. Mildly awkward, but harmless.
• Intentionally make a silly typo in a text. "No thanks I'm good" becomes "No thanks I'm food".

🦴 Raptor Paddock (Real-Time Awkwardness)

These exercises push your comfort zone and help you manage awkwardness in real-time:

• Join a conversation instead of waiting to be invited. You have to be quick, but they might just accept you...
• Purposely let silence sit in a conversation before responding. Think of it like standing still when the raptors are watching—stay calm!
• Walk up to someone and pretend you know them. “Hey Andrew!” and see their reaction.
• Ask a stranger to take a selfie with you. Mild social discomfort that builds tolerance.
• Go to a store checkout with a small item and pretend you don’t have enough money. “Oh no! I’m short 50 cents. Should I put it back?” and see what happens.
• Now you’re fully out in the wild, testing your ability to handle full-blown social awkwardness.

🦖 T-Rex Territory (Facing the Big Fears)

• Take a survey in a crowded place. You could ask, "Who's more dangerous – President Biden, President Trump, or a T-Rex?"
• Purposely say something silly in a group and let it sit. “I just realized… velociraptors totally remind me of oversized turkeys.”
• Go to a crowded place and pretend you can’t find your friend. Say “Has anyone seen Nora?” to random people and wait for responses.
• Trip on purpose in a public place. Great for dealing with embarrassment directly. Even better if you have a bunch of papers or books to drop.
• Order coffee, take a sip, then return it, saying you actually wanted tea. Handling mild conflict is a great confidence booster.
• Call a restaurant to order food, then call back immediately to cancel it. Awkward, but harmless.

Step 2: Predict

• Write down what you're worried might happen.
• Now ask yourself—how likely is that really? 0-100%

Step 3: Reflect

• What actually happened?
• Did anyone react the way you feared?
• What did you learn from this experience?

Remember the goal here isn't for things to go well. It’s to accelerate your development of social confidence by getting you a lot of experience with awkward social situations.

If you want to learn more about how social anxiety works, check out lesson 1 in this series. And for more on social skills to make things less awkward, read lesson 2.

Which level will you try this week—Visitor Center, Raptor Paddock, or T-Rex Territory? Reply and let me know—I’d love to hear how it went and what you learned!

Until then, boldly go! 🖖🏽

—Dr. Ali

P.S. The awkward conversations never stopped between Nhu-An and me. We kept dating, got married in 2014, and to this day, I still feel awkward every time I ask, "Are you done with Gilmore Girls so I can watch Star Trek?"

Summary 📝

• There's no "perfect" way to be social.
• Everyone experiences awkwardness - you're not alone.
• Real confidence comes from messy experiences, not perfect preparation.
• Start small, but start somewhere.

Dive Deeper 🤿

📺 YouTube: I talk about similar social anxiety exercises in my Top Social Anxiety Tips for Confidence video. 

📚Read: For a refresher on how these types of exercises work, check out this lesson: Expand Through Experience: Building Real-World Confidence. If you are overwhelmed during these exercises and can't stay focused on the social situation, check out my rapid-response skills for anxiety.

👨🏽‍⚕️ If these self-help strategies aren't working, a mental health professional can provide individualized support. Check out my recommended resources to take your next step.

📺 YouTube: Check out this fun video featuring my wife discussing what it's like to be married to a psychologist.  

🔬 Research Behind This Lesson: 

• Lazarov, A., Abend, R., & Bar-Haim, Y. (2016). Social anxiety is related to increased dwell time on socially threatening faces. Journal of Affective Disorders, 193, 282–288. https://doi.org/10.1016/j.jad.2016.01.007
• Turner, S. M., Beidel, D. C., Cooley, M. R., & Woody, S. R. (1994). A multicomponent behavioral treatment for social phobia: Social effectiveness therapy. Behaviour Research and Therapy, 32(4), 381–390. https://doi.org/10.1016/0005-7967(94)90001-9
• Rukmini, S., Sudhir, P. M., Bhaskar, A., & Arumugham, S. S. (2021). Identifying mediators of cognitive behaviour therapy and exposure therapy for social anxiety disorder (SAD) using repeated measures. Journal of Affective Disorders Reports, 6, 100194. https://doi.org/10.1016/j.jadr.2021.100194
• Albano, A. M., & DiBartolo, P. M. (2007). Stand Up, Speak Out: Client Workbook. Oxford University Press. https://doi.org/10.1093/med:psych/9780195308945.001.0001