7 Steps To Start Having Amazing Conversations Over And Over Again

image - Flickr / Nicolas DECOOPMAN
image – Flickr / Nicolas DECOOPMAN

The more I talk to people, the more I realize that conversations, connections, and closeness have less to do with your external attributes and more to do with your vibe, genuineness, and willingness to enjoy someone else’s company.

Truth is, I’m not a special person: I’m short, I have acne (I’m turning 27 soon), and I’m introverted. Sometimes I stutter. Sometimes I don’t want to talk to anyone. Sometimes my hair has a life of its own.

And the more I talk to people, the more I realize that none of that matters. So what does matter?

Well, here are a few lessons I’ve picked up over the years that have helped me escape my comfort zone and feel comfortable around strangers. Now, I’m no suave conversationalist and I still deal with my barriers; but tips these have helped immensely with talking to strangers, meeting new friends, and having some odd adventures, and I hope they help you too.

Let’s start with the basics:

1. Your Vibe

Imagine telling a stranger, “It’s a beautiful day,” in a monotone voice with a dreary expression on your face.

What you say doesn’t matter — it really is how you say it.

Now, when you’re with your friends, you could slightly lift one eyebrow and everyone would know what you mean. But when you’re talking with someone who’s never met you before, that context doesn’t exist. Therefore you really need to “overact” so that your emotion, energy, and enthusiasm are clear.

When about to initiate a conversation, I always remind myself to start with more energy than the person I’m talking to.


2. Mean What You Say

There was another problem with the previous example:

The tone didn’t match the words.

This isn’t just your vibe; it also shows you don’t actually believe what you said. You’re just talking to talk, and no one enjoys chatting with someone who’s forcing conversation.

For example, if you’re in your 20s, asking a college student, “What are you working on?” fits because they will assume you’re either (a) a student too, (b) do something related, or (c) want to talk about college. If you’re an old, shaggy dude (and I see this a lot), this will fall flat on your face because the student knows you don’t really care.

Instead talk and ask about things you really care to know. And if they say something you don’t know or care about, be truthful about it. I might even say something like, “I don’t know anything about what you just said, but based on your enthusiasm, it sounds really fun.”

3. Commit and Practice “Full Engagement”

I’m still working on this concept. Basically, when talking to someone new, commit fully to the interaction. I used to think you had to act detached and “cool” with your body facing away and your arms hugging on nearby chairs, but that’s the equivalent of dipping your toe into a pool: you’re not really in or out. As a result, you’re muddy with your intentions and no one will want to lead the conversation unless — and I’m being honest here — you’re very attractive. (If you’re very attractive, people tend to be happy just to talk to you so you can fuck up and still get decent reactions. People like me, however…)

The problem I just described is also called “playing it safe” — you’re not completely involved so, if the conversation goes sour, you won’t get outright rejected. But that’s a weak play. It’s like “laying up” in golf because you’ll avoid a bogey, but never get the birdie.

Instead, go all in and put your attention and energy behind your words. (That will cover the previous two rules as well.) You’ll have a positive vibe and deep meaning behind what you say. And ince I’ve tried “full engagement” in conversations, I’ve almost never been rejected. Weird.

My fear got in my way.

4. Stop Asking So Many Questions

“What do you do? Oh, how is that? How long have you been doing that? What do you like about it? What do you hate about it? Why did you choose to do that? Did you study that in college? What company do you work for? What do you do for them? Oh wait… I already asked that.”

I hate question trains. It’s another weak play — you’re not opening up and adding value; you’re just subtly asking them to jump through hoops. Unless they like you (and why would they if you haven’t shared anything about yourself?), they’ll eventually stop talking. Also, if you’re using a question train because you can’t think of anything else to say and just want to keep talking, you’re just forcing conversation.

Do NOT force conversation. Instead, create opportunities for them to share their story by showing them that you’re willing to do that too.

Bad example:

“What do you do?” (Don’t ask this, by the way — it’s a rookie question.)
“Oh, I’m a bookkeeper.”
“Oh okay. Do you like it?”

1. Do you even care? (Be honest now.) 2. How do you think they like it?

Better example:

“What do you do?”
“Oh, I’m a bookkeeper.”
“Oh that’s interesting. Okay, funny story: my dad’s an accountant and, when I was a kid, I used to work in his office to do bookkeeping.”
“What? Really?”
“Yeah! I still remember how fucking frustrating it was when the books didn’t balance! I would look all over to see where it was.”
“Yes! Haha.”
“And when I finally found it, I would, like, jump out of my seat and throw my arms up.”
“Haha, yes! I know that feeling.”
“So what do you do when you’re not battling the books?”
“Well! I blah blah blah…”

Now they’ll be way more likely to open up. (And yes, I did work as a bookkeeper in my dad’s CPA firm when I was like 10. Never lie.)

Question trains can also be deceptively selfish. Rather than sharing anything unique about yourself, you just ask questions to perpetuate the conversation. Do this with a random stranger and the conversation will sputter. But if do this with a person who MUST answer your questions (like in professional setting, among colleagues, etc.), you’re making them do all the work.

5. Appreciate Them

Two hours ago, I met a girl who worked sales in a furniture store. She actually really enjoyed what she did and laughed when I made a joke about how I would nap on all couches. Then I said, “I like that. That’s very unique… I rarely meet people who are into sofas.”

It stuck.

The truth is, when someone tells you something awesome, interesting, unique, deep, or detailed, you MUST appreciate what they said. Otherwise, you’ll show that you didn’t really care (even if you actually did).

But compare this to an approach I saw a few days ago at a Starbucks at Cedar City, Utah:

This guy (who was, admittedly, very good-looking) was flirting with one of the baristas. At one point, the barista said she recently lived in Japan for three years. He immediately said, “Cool… so what time did you start working today?”


She just spent an enormous chunk of her adult life abroad and you didn’t show one shred of curiosity?! C’mon now. One, that’s insincere and, two, that just shows you’re talking just to talk. (Of course, when I started talking to her, she told me about her experiences in Okinawa, asked me a lot about my time in South Korea and Taiwan, and made me a free drink. Hmm, how about that?)

6. Do NOT Let Go

With any new conversation, there will be lulls. Do NOT take your attention off — in other words, don’t look away, play with your cellphone, continue with your work, etc. Stay engaged and maintain some eye contact.

Be comfortable with the silence.

Silence is inevitable with any conversation. But you have to appreciate it, too. Maybe after a joke, there will be a lull. Keep your gaze going. Smile. Relax. Maybe they’ll say something to break the silence and you can go from them and maybe not. If not, you can say something. Anything. (As I said in Rule Number One, it really doesn’t matter.)

But if you lose a connection, it’s insanely difficult (and try-hard) to re-break their concentration to resume the conversation.

7. Accept That Not Everyone Wants To Talk To Strangers

Even if you do everything right, there’s still a chance someone will be unreceptive of your conversation. If that’s the case, don’t get upset or worry about it because, ultimately, the goal with any conversation is to give something of value (fun, acceptance, etc.) not get something of value.

It’s small, but it makes all the difference.

My Last Word:

Now, there are way more tips and tricks available (and there are some doozies), but these are the basics that helped me immensely over the past few months. I still struggle with these every now and then, but when it all clicks, the time will just melt away and you’ll have yourself a new friend that you might know better than even their closest friends.

“Yeah, but is it worth it to do all this to talk to people? I mean, it’s like you’re doing this all for them and trying too hard and acting too mechanical.”

It hear people tell me that sometimes. But the people who say this are typically the same people who don’t talk to anyone (and if they do, it’s hit-or-miss). Moreso, following these guidelines actually makes your conversation MORE authentic because you’re being transparent with what you want, like, and find interesting.

Good luck. If you have any questions, just hit me up. Thought Catalog Logo Mark

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