5 Tricks I Stole from Comedians to Talk to Strangers as a Socially Awkward Person
Owning your awkwardness will show you wonders.

Silence is a response I get a lot, especially when I’m hanging out with a new group of people. I don’t know whether it was what I said, or they’re just allergic to my voice. But a cloud of awkwardness would always settle for a good few seconds after I voice my thoughts out.
The thing is, they don’t know they’re acting that way.
So, I opt to stay quiet. Listening to their story of how Connor was flat out rejected after giving a drunk confession was more entertaining anyway.
Oddly, “Why are you so quiet?” is always what I get in return when I am quiet.
So I decided, sigh, you know what, let me dig up the secrets that I got from comedians but never really bothered to use and unleash my hidden superpowers: the ability to talk like a not socially awkward person.
1. Acknowledge the awkwardness
Awkwardness is a familiar feeling for a comedian. Throughout their careers, they would have jokes that fell flat. It’s inevitable. Hell, even the most successful ones now still have those moments.
But acknowledging that they just made a bad joke is what makes them good comedians. Because then, they would know that knock-knock jokes aren’t funny for the people in a certain place. Or how they realize that sometimes situational humor just doesn’t work.
I wasted years trying to kid myself that this is not awkward at all every time I talk to someone new. I ended up overthinking about what to say or what not to say. I ended up filtering most of who I am.
Now that I’ve learned to let the awkwardness be, it feels like a long-time friend casually chilling with me. The conversation flows better, and I didn’t even have to wreck my brains out for the topic.
2. Comment on your awkwardness
Many good comedians comment on the silence they get after delivering a bad joke. They know that owning up to it is better than feeling embarrassed or ashamed.
The small or a silly comment of “Well, that went nowhere..” will most likely pop the awkward bubble and make at least a few people chuckle.
I have more than enough shares of awkwardness to try this one trick with various people, and 98% of the time, it works.
Once I said, “Well, this is awkward” or “Why are we so awkward?” with a touch of playfulness, the ice breaks.
3. “Anyway” is a magic word
In some cases, comedians would proceed to the next joke instead of acting on the failed joke. This works too, but the transition wouldn’t be as smooth.
Similar to them, I usually use the word “anyway”, to move on from a topic that made people feel somewhat uncomfortable or other awkward instances.
When you said “anyway”, most of the time, people will focus more on what comes after that and forget everything before the word was uttered.
“How are you?”
“Hm? You too!”
…
“ANYWAY, how’s … ?”
4. Pretend you want to be there
A part of a comedian’s job is to act. No one cares if the comedian’s in a bad mood, they had come to laugh. Therefore, the comedian’s job is to do just that. If they have to pretend for it, then so be it. Or at least that’s what I learned from listening to Pete Holmes’ podcasts.
As a socially awkward person, I find it nerve-wracking every time a stranger comes up to me and start a conversation. I want my peace, damn it.
No hard feelings for them, but I really don’t feel like making anybody feel even remotely awkward right now.
Alas, wishing was never a good enough spell to change their minds. So I pretend to want to be there.
I may not owe this stranger the way comedians owe their audiences for paying to watch them. But I do owe this stranger some kind of respect, especially if they mean no harm.
5. It’s still good even if the conversation is bad
“I don’t judge a bomb by if I’m not getting laughs. I judge a bomb by whether or not my back is sweating”
That is what Pete Holmes said in his podcast with Adam Sandler. They’ve had shows where they were fully into the role, but the reaction wasn’t so good. They’ve had spectacular shows, but they were in a daze.
But bad reactions are just a reaction. Adam Sandler said, “I did pretty good because I stayed fucking strong up there.” and that is what matters.
Even with all the tricks mentioned, the conversation can still go south. A trick to not see it as a failure, but rather from whether you put an effort even when it’s not going the way you wanted or not.
Maybe, you just haven’t met the right audience yet. There’s the right audience out there thinking, “HAH I get what you mean!”
Final Thoughts
I’m no comedian, but these five tricks have definitely help me in the last few years:
- Acknowledge the awkwardness
- Comment on the awkwardness
- “Anyway” is a magic word
- Pretend you want to be there
- It’s still good even if the conversation is bad
With that said, if I can do it, I’m sure you can too.
In case if it doesn’t, well, they created a whole genre based on social awkwardness, and some people would love to see it (Check out cringe comedy).
You’ll eventually find someone who will love your awkward self.
