All the Conversation Tricks I Use to Be (Somewhat) Less Awkward

IntrovertDear.com conversation tricks awkward

After divorcing in my late twenties, I found myself in the uncomfortable position of having to date for the first time in my adult life. The first date I went on was with a guy I had met through a friend. I asked him to go to a concert with me, hoping the booming music would cover how bumbling I was.

After the show, we sat in a little bar nearby sipping beers. Cue my awkwardness, and loooong uncomfortable silences. I had no idea what to say. He asked me questions, and I gave short, cryptic answers, ending practically every statement with a pleading, “You know what I mean?”

For the first time in my adult life, I realized I had no idea how to do this thing we humans call “conversation.”

Eventually, exasperated from trying to extract words from the hot ball of awkward I had become, he dropped that dreaded question:

“Why are you so quiet?”

As an Introvert, I Didn’t Need All That Chatter

It wasn’t the first time I’d heard that question. My teachers, peers, and coworkers had been repeating it my whole life.

But I didn’t think of myself as “shy” or even “quiet.” I thought of myself as someone who just didn’t need all that chatter. Or attention. I could work things out on my own in my head without saying them out loud. Besides, a lot of the things people said to each other (“Nice weather we’re having!”) seemed fake and contrived.

Later in life, I discovered that I’m an introvert, and my penchant for quiet made sense.

(Not sure what an introvert is? Check out this definition.)

After that date left me curled in the fetal position and never wanting to leave my house again, I realized I needed to work on my conversation skills. I was always going to be an introvert∂ — someone who felt most at home in solitude — but if I ever wanted to go on second dates (or make new friends, get along better with my coworkers, etc.), I needed to figure this “talking” thing out.

I’m still a pretty quiet (and somewhat awkward) person. I’m never going to be the most popular person in the room, a pick-up artist, or a natural schmoozer. But I’ve gotten to the point where interacting with strangers doesn’t scare me anymore, and sometimes it can even be fun. I’m also now (finally) in a happy, committed relationship.

Here are my conversation tricks.

Conversation Tips to Talk Better and Be Less Awkward

Go First

One of the first things I noticed was that I often waited for the other person to make the first conversational move. But the people who were good at talking didn’t wait for an awkward silence to settle in — they jumped right in and asked the other person a question.

So I bit back my fear and tried it. I noticed that going first gave me a sense of control. And when I’m more in control of an interaction, I tend to do better. It also made me seem confident.

When you go first, don’t worry about saying something profound. It’s okay to open with something like, “How’s your day going?” or “What’s new?” As much as we introverts loathe small talk, it can serve an important purpose: It helps two people warm up to each other, and you can use it to probe for more interesting things to talk about.

Which brings me to my next point.

Transform Small Talk Into Deep Talk

Ironically, I do much better conversationally when I’m talking about the meaning of life, a difficult problem I’m facing, or a hot current events topic. My interest in the subject naturally propels me forward and helps me think of things to say. Ask me about the weather or my weekend plans and I flounder.

I’ve found that the trick is to turn small talk into deep talk. A simple way to do this is to ask open-ended questions. As I explain in my book, open-ended questions can’t be answered with just a simple one or two words. They invite the other person to tell a story.

For example:

Instead of… “What do you do for a living?”

Try… “How’d you end up in your line of work?”

Instead of… “How was your weekend?”

Try… “What was your favorite part of this weekend?” or “What are you looking forward to this week?”

Instead of.. “How long have you been living here?”

Try… “What do you like about this area?”

Another tactic is to pair “why” questions with “what” questions. “What” questions  focus on the facts (“What college did you go to?”), while “why” questions are more interesting: “Why did you choose that college?” You’ll learn more about what makes the other person tick, and the conversation will naturally unfold in a more interesting way.

Say It Loud

Like many introverts, I have a naturally quiet voice. Sometimes people don’t even hear me because literally my volume is like a whisper in a construction zone.

At one point, I wondered if simply talking louder would make people respond differently to me. So I did an experiment: I raised my voice just slightly above my normal mouse-like decibel when I ordered my Subway sandwich.

To my surprise, people looked up and paid attention. Again, I seemed more confident than I really was.

I’ll be honest, I still have to remind myself going into social situations to use my “loud-confident voice.” Don’t laugh. This is my reality.

Say What’s Actually on Your Mind

I used to feel like I never had anything to say. But then I started tuning into my inner voice. Turns out, there were tons of thoughts and feelings flying through my headspace at any given moment. I had simply fallen into the trap of thinking I couldn’t say them out loud. I worried that other people would judge me for them.

If someone’s comment makes you think of an interesting study you read, tell them about it. If the song playing in the coffee shop makes you remember your childhood pet parakeet meeting an untimely death, say it. If something exciting happened today at work and you can’t stop grinning about it, tell the story.

Similarly, try making an honest admission. There’s something surprisingly charming about being completely honest. Even one honest admission quickly builds intimacy because it draws people in makes them let down their guard.

Here are some honest admissions you might make:

  • “Parties aren’t really my thing. To be completely honest, I’m feeling pretty overwhelmed right now.”
  • “I don’t like IPAs. Like, at all.”
  • “I’m really proud of that.”
  • “Ouch! That hurts my feelings.”
  • “This feels awkward.”
  • “I’m ready for some me time.”

Of course, don’t take this one to the extreme. You probably shouldn’t mention that your coworker’s new haircut makes her look ridiculous or that your date sounds like a lawn mulch machine when he chews his salad. Tactfulness, people.

You’re not going to do these tricks perfectly the first time. That’s okay. But you’ll get a little better each time you try.

And when the date is over or the work day ends, there is always Netflix and quiet time. 

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Read this: 12 Things Introverts Absolutely Need to Be Happy

Learn more: The Secret Lives of Introverts: Inside Our Hidden World, by Jenn Granneman 

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Jenn Granneman is the founder of IntrovertDear.com and the author of The Secret Lives of Introverts: Inside Our Hidden World. She also cohosts The Introvert, Dear Podcast and blogs for Psychology Today. For most of her life, Jenn felt weird, different, and out of place because of her quiet ways. She writes about introversion because she doesn’t want other introverts to feel the way she did.