The Awkward Person’s Guide to Making Conversation

Given the number of articles on how to sustain light conversation, talking to people seems like an overwhelmingly unpopular and occasionally excruciating custom that doesn’t come naturally to most. You’d think that if so many people hate small talk, we could just do away with the practice entirely, but apparently getting rid of things that shouldn’t exist is not how the world works.

Image result for pirates of the caribbean 2017 imdb
Look, I liked the first movie, but this… (From

For my compilation below, I’ve drawn from articles and my own experiences. I’ve also consulted people who’re exceptional conversationalists as to what they attribute their conversation-sustaining skills.

1. Share details about yourself until you find common ground.

Keep throwing them out there until you find something that interests your conversation partner. The idea is to quickly bypass superficial niceties by offering segues into topics on which you can easily elaborate if requested.

Person: How are you?

Me: Not bad. I think any day I survive the DART is a good day. You?

Person: Oh, cool. I’m good.



Me: Sometimes I feel utterly alone in the world.

2. Ask them questions.

The content of conversation matters much less to people’s ultimate impression of you than how you made them feel during the talking. Get them talking about themselves by asking relevant questions.

Me: So what city were you born in?

Person: New York.

Me: What high school did you attend?

Person: Uh, Stuyvesant—wait, are you taking notes?

Me: What’s the name of the street on which you grew up?

Me: What’s your mother’s maiden name?

Image result for hacker
Me trying to hack a computer. Also, points if you remember my password rant. (From

3. Have them bear the brunt.

This is actually a legitimate tactic I use. I have this friend who I used to see every day in class, and he’d always greet me by asking me what I’d been up to since I last saw him. I struggled to come up with interesting things to say for the better part of a semester before I became suspicious. Turns out he goes on the offensive as a diversion—best defense is a good offense and all that.

Person: Hey, how—

Me: *aggressively* HOWWASYOURWEEKEND?

Person: Uh… I, uh… let me think.

Me: Excellent.

Person: I went kayaking. It was fun. You?


Me: This backfired.

4. Repeat the last thing they said back to them in the form of a question.

When you search for tips on how to sustain conversation, this strategy is what comes up most often, so presumably, it works. Parroting people helps with the flow and, more importantly, makes it their turn to speak without your having to actually contribute anything.

Person: … and what’s surprising is that it actually works.

Me: It actually works?

Person: Yeah. They’ve even done studies on it and everything. I can show you.

Me: I can show you?

Person: … Are you repeating after me?

Me: Are you repeating after me?

5. Be prepared with the basics.

Stock responses are always a necessary fallback if you’re not a fan of thinking on the spot; you can at least buy yourself some time. If all else fails, at least show people how you’re able to hear words and then say words back.

Box office employee: Have a great time!

Me: Thanks, you too!

Airport security: Have a great flight!

Me: Thanks, you too!

Lunch lady: Have a great day!

Me: You’re welcome!

6. Play a game.

The author of The Art of Mingling, Jeanne Martinet, recommends abandoning stiff formalities and injecting playfulness into small talk with strangers. She’ll ask for three characteristics of your company, for example, and then try to guess it. This success of this method, I’m assuming, is weighted pretty heavily on your ability to be a good guesser.

Me: Give me three hints about your job and I’ll try to guess what you do.

Person: Majored in chemistry. I treat people who aren’t feeling well, and the job’s pretty high pay.

Me: You’re a drug dealer!

Image result for unimpressed doctor
Would you believe this is the second result for unimpressed doctor? (From

Alternatively, if we take creative license with “game”…

Me: You interested in playing a game?

Person: Yeah!

Me: Cool. I spy with my little eye… a ghost.

Person: A what?

Person: *looking around*

Person: Nicole?

Image result for now you see me now you don't cat in the hat
Magic. (From

After all, as they say… in terms of conversation, if at first you don’t succeed, self-destruct immediately.

Seriously though, conversation is a two-way street. As long as you’re not completely unresponsive and do show interest, the demise of small talk is never wholly your fault. So whether you follow these tips, which mostly shift responsibility to the other person and make them feel bad instead, or simply find common ground in how inane conversation makes you uncomfortable, don’t give up. Worst comes to worst, just blame it on the other person anyway; I’ve found that usually helps.


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(Lead image from

8 thoughts on “The Awkward Person’s Guide to Making Conversation

  1. I’ve always relied on a combination of 3 and 5. They work particularly well with self-absorbed types who like to hear themselves talk and don’t care if you answer a question about the new deck furniture with “me neither.” Hmm. Now I wonder why I bothered spending time with those people.
    Oh. Yes, I do remember your password rant. Do I win something? Yes it has been nice weather.

    Liked by 1 person

  2. One major breakthrough I had in not failing to hold conversations occurred when I started taking guitar lessons. My teacher said improvising a jazz solo was a little bit like having a conversation–you put together bits of what you know works, and usually it turns out okay. (My reaction: “Uh, there are tricks you can use to get you through conversations???”) But from that point on, I started noticing tried and true questions and phrases other people used in conversations and using them when I talked to other people.

    Liked by 1 person

    1. That makes sense, though improv just scares me in general. You know, a couple months ago, I was meeting with a group to practice a speech for the next day, and this guy, trying to describe how tired he was, said he felt like talking had become freestyling. Basically, he was so exhausted that he had no idea what was coming out of his mouth as he said things. And I was like, oh yeah? That’s how ALL my conversations are, ALL the time.
      So no one won, really.

      Liked by 2 people

  3. Public conversation is not for the weak either. Once started there has to be a plan in place to terminate what should not have started in the first place. But once started, to disengage politely requires skill and tact. There are five ways to end a conversation. 1) scratch yourself vigorously and say, “I don’t know what they are, either. All I know is that they jump very high. 2) How many crackers does it take to fill up a cracker consuming parrot? 3) Do you know how many times I’ve wanted to say I love you, and I’m feeling much braver now? 4) Every conversation that I’ve had on this planet ends when someone thinks. 5) The best conversation terminator is just after something important has not taken place. 6) You can’t talk or count, and aren’t sure why.

    Liked by 1 person

    1. You make very interesting points, and I personally would prefer someone say any of these things to me over banal “how are you”s (but then, maybe they think the same of me and we just both assume the other party wants to make polite conversation. What a tragedy)


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