Why I LOVE Awkward Conversations (and want to have as many as I can)

Tell me if this scenario is familiar. It’s late at night and you’ve just arrived at the hotel to check-in. You’re face to face with the receptionist sitting hunched over in an ill-fitting suit. Dried Kolgers instant coffee stains the cracked skin around his mouth. Violet circles ring his eyes which shift lazily from his dusty monitor towards you. “Checking in?” he says dryly.

After handing over your ID and watching him slowly type away on his computer, you slowly muster up the courage to ask something. “Is there… any possibility to get a… free upgrade?” you stammer. His coal-black pupils flick towards you as the corner of his mouth curls into a mocking grin. His left eyebrow rises ever so slightly. His countenance reminds you of the look one makes if asked to give away the winning lottery ticket.

“No, I’m afraid we can’t do that.” He replies. You can tell he’s using every last ounce of what energy he has to hold back from mocking your arrogance. He hands over your key card, and you immediately turn around and scurry into the elevator.

“Well that was awkward,” you think to yourself.

If you’re like me, the above scene has happened many times in a myriad of different places and with a myriad of different people. Each time I’m left feeling like I’ve embarrassed myself, that I’ve done something stupid, that I should probably not do the same thing again.

Screw that I say. Screw that.

Awkward conversations are awesome, and I want to have as many of them as possible. Here’s why.

“A person’s success in life can be measured by the number of uncomfortable conversations he or she is willing to have.” — Tim Ferriss

1. If you don’t try, you won’t succeed.

How do you know if the front desk won’t give you an upgrade if you don’t ask? How do you know the girl in the back of your chemistry class won’t be down for a date if you don’t ask? How do you know Matthew McConaughey won’t offer his autograph if you don’t ask?

So what if you don’t succeed your first five, twenty, a hundred times. Your awkward conversation will yield that free upgrade, and even if it’s one in a hundred, it’s worth it.

2. You’re probably not as awkward as you think.

Remember the last awkward conversation you had with a peer, say a fellow student or coworker. You’re trying to make a new friend, and they just don’t seem to be on the same wavelength. You try to be friendly, and you end up pretty much apologizing for interrupting their day. You’re thinking to yourself “why did I bother to try anyway?” Now imagine if you had asked the same set of questions to the classmate or coworker you’re friendliest with. Probably not awkward.

What I’m trying to say here is that you could probably act the same way with two different people and one could be an awkward interaction and the other would be perfectly normal. If that’s the case, you’re not awkward. The other person is.

Too often do we attribute the cause of awkwardness to ourselves. You’re not as awkward as you think.

3. Most of the time you’re either not going to see the other person again or they won’t care.

So you’re at this networking event, and you’re trying to figure out what you can possibly say to the suited banker standing across from you. The conversation is dying. In fact, the conversation was probably never alive in the first place. You blurt out something dumb, hoping that this will lead to something, that leads to something else, that just maybe end up as an internship offer at his firm. Maybe it’s some pointless story about your crazy uncle in Hawaii. He looks utterly unimpressed.

Here’s my take on this situation. First, props to you for trying; you couldn’t have known he’d be such a bore unless you tried to strike something in the first place. Second, he’s probably got a million things on his mind that by the time you submit your resume, he’d forgot this even happened. Third, even if he did remember this “awkward” encounter, I guarantee it was a much bigger deal for you than for him.

The above situation is going to play out a thousand times in subtly different variations in our lives. Let’s embrace them for what they are — just another road bump — and move on to the next opportunity.

4. Okay let’s say you are actually objectively awkward. Awkward conversations are your best way of becoming un-awkward.

Let’s say you’re really, really bad at the violin. Like your bow hits the string and suddenly every pane of glass around you shatters into a million pieces. Like cats hurl themselves out of windows to escape the sound of your “music.” How the hell do you get better?

You practice more. You do the thing you’re bad at over and over again. You approach the task knowing that with each up and down of your bow, you’re one iota better than before.

Are conversation skills any different?

If you’re actually bad at conversing, why not thrust yourself into more situations, be your totally awkward you, and think to yourself, “what could I do to smooth over some of the rough patches of this interaction?”

Maybe every awkward situation is just an opportunity for us to rise higher and be better.

5. What’s the worst that can happen?

Pretend for a moment you’re a soldier and you’ve just been shot in the chest by an arrow from the opposing army. The steel tip feels like it’s protruding out the other side of your spine. It hurts real bad.

Now, let me offer you a superpower. As long as you forget about that arrow, as long as your mind is somewhere else, as long as you ignore the pain, the arrow disappears. Your wound could rapidly heal. Would you receive the gift?

I think the feeling of awkwardness is a lot like this arrow. So often, when we’re put in awkward situations, we feel like a part of us has been injured.

What if I told you that the cure was simple as forgetting about it? Let the awkward moment pass and the wound will seem as if it were just a trick of your imagination. In the worst outcomes of your awkward situations, the danger you feel is imaginary. You may be shooed away. You may be snickered at. You may be belittled. But if you choose to forget, these wounds pretty much never existed in the first place.

Next time you ask yourself if you’re willing to put yourself into that awkward position, remember this superpower. You’re practically Superman if you believe it.

“Find out what you’re afraid of and go live there.”

— Chuck Palahniuk

I’ll wrap up this blog post by sharing what was probably my most awkward memory. It was TechCrunch Disrupt in San Francisco back in 2014. Freshly graduated Alex strolls down the aisles of booths promoting the most exciting up-and-coming start-ups around the world. A few booths down there’s someone with a booming voice conversing with a pair of bespectacled founders in plaid shirts and blue Levi’s. He’s fervently gesticulating with his hands, drawing large O’s and I’s in the air before him. After a few minutes, he reaches out his hand towards the founders, shakes their hand, and turns towards the next booth.

I sprint after him and stop right before he reaches the next stall. I lock eyes with the man for a second and involuntarily gulp. “Mark,” I say, mouth suddenly parched. “would you take a photo with my friends and me.”

“Sorry. I’m busy,” replies Mark Cuban without a moment of hesitation. In a split second, he’s back to looking through the display at the next booth. My feet are suddenly lead. I twist my torso back to friends a few feet behind, swiveling my heavy head side to side. No luck.

22-year-old me thought this was the pinnacle of awkwardness. 28-year-old me looks at this, and for the reasons I’ve written above, thinks otherwise. And if I ever have the chance to speak with Mark Cuban again, I’m probably not asking for a selfie.

With that I say, go forth, have more awkward conversations, make a fool of yourself, and know that it’s only a big deal if you let it be. Oh, and if you get that upgrade to the deluxe suite, I’m expecting an invitation to come over and hang out.

Yours in awkwardness,

Alex