Conquering Casual Conversation


“Talk,” is one of the many pieces of advice I would give my younger self if I could go back in time, “and not every conversation has to involve deep, impactful, and important subjects. Some of the times, you just talk for the pure enjoyment of talking to people. Our listeners don’t have to be cool or beautiful either. They can be old, young, smart, dumb, and the boring and interesting. Talk to the fascinating and the boring. Talk about matters consequential and inconsequential. If we talk long enough, we might find, we just might find, that the boring are far more interesting than the interesting.”

The movies and the music told me to avoid the “chitter-chatter, chitter,-chatter, chitter-chatter ‘bout schmatta, schmatta, schmatta”. They told me to be the quiet, mysterious type everyone looks to for reaction. They told me if I wanted elusive charisma, I needed to be silent.

“Don’t listen to them,” The Ghost of Present Rilaly would whisper into his ear. “Silence doesn’t make you look cool. Silence makes you look silent.”

There’s a reason former athletes and the beautiful are silent, because they don’t have a whole lot to offer anymore.

“How do you know so much about such stupid stuff?” they might ask. If we’re bold enough to answer, they’ll add, “Huh, well I was much too busy getting busy in high school to learn about such nonsense.” If we’re then bold enough to remind them that high school was so long ago, we’ll realize that that persona we tried so hard to attain didn’t accomplish half of what we thought it would. “You think everyone is looking at the guy shaking his head in the corner? Nobody remembers any of that. It might seem so pointless in the beginning, but developing the skills necessary to talk about absolute nonsense actually adds something to life.”

1) Learn how to be superficial. I was confused, embarrassed, and mortified to see my best friend engage in superficial conversations about nothing. He did it so often that I was embarrassed to be around him at times. When he talked to a fella, I had no problem with it. When he started up a conversation with a young woman, I kind of envied it, but this guy didn’t make discerning choices. He’d talk with anyone. He started up conversations with old people and other less desirables. The conversations were nonsense. He didn’t care, and he was having one hell of a good time doing it. I thought my friend was a fraud, and when I called him out on it, do you want to know what he said? He had the audacity to say, “I was enjoying myself.”

“Where’s your integrity my man?” I asked him.

“I don’t care about that nonsense,” he said. “I just want to have a good time.”

It goes against the codes we worked so hard to follow to be superficial, but it’s an artform in some ways that pays off in numerous ways. My best friend wasn’t smarter than me, and he wasn’t one of those types who knows a little bit of something about everything. He just knew how to talk to people. He learned how to put the important, artistic personae aside and tap into his superficial side to just talk.

2) Be confident. I know this is easier said than done. Most of us are insecure, and we all have moments when we’re not sure of ourselves. If most of us are unsure of ourselves, then most of us are unsure of ourselves. Unless our listener was an athlete or a beautiful woman in high school, chances are they’re as uncomfortable, insecure and nervous about themselves as we are. The trick is spotting it. I was on a date with an incredibly beautiful woman. I was as nervous and unsure of myself as ever. I pulled out of the parking lot and circled back. I wanted to back out. When I finally stood before her, she blushed. My confidence soared as I realized she was as nervous as I was. It taught me the simple and emboldening fact that most people are as nervous about meeting new people as I am. If we watch them long enough, we’ll spot it. It might be a blush, a stutter, or an uncomfortable look away, but everyone has a tic of some sort. If we’re observant, we’ll see something that informs us that most people are not as superior to us as we fear. They’re just normal people living normal lives, and they enjoy the uncomfortable revelations that can occur in casual conversation.

3) Pretend to be interested in what they have to say. Conversations are a two-way street, and if we’re able to convince them that we’re interested in what they have to say, we’ll find most of that interest returned. We all know talkers, and some talkers just want to talk. When we show them interest, they find it intoxicating. We can see this when we begin speaking. Their smile quickly fades, they become distracted by anything and everything around them, and the minute we finish speaking, they start in again. Displaying an acute focus in what another person has to say is one key to making friends, but some might find our interest so intoxicating that they’ll want to compound it without a return on our investment. We can deal with that element later, if the two of us develop a sustained friendship, but if our goal is to make more friends, the key is to show interest in them.

One thing we covet more than being interesting is being funny. Some people aren’t funny, but if we want to be friends with them: laughter is the best medicine. No matter how common or dumb their joke is, laugh. Laugh about how dumb their joke is if that’s what it takes. Laugh if they messed the joke up. They won’t know why we’re laughing if we do it right. If we do it right, we’ll find them coming up to us with their jokes over and over again. If we do it right often enough, we could become their go-to person with their jokes.

If you’re anything like me, when you meet someone new for the first time, you’re so insecure and nervous that the go-to is to try to be so over-the-top interesting and funny that we forget to be interested in what they have to say. How often are we so interested in being interesting that we forget to be interested? I write pretend we’re interested, because if we pretend well enough and long enough we might accidentally convince ourselves that we are interested.

4) Tell self-deprecating humor, but don’t overdo it. If something works, and self-deprecating humor almost always does, we have a tendency to do until it doesn’t. There is a tipping point, however, where we might accidentally affect their impression of us. Everyone loves the “But what do I know, I’m a dummy” conclusion to a provocative thought. If we do that too often, though, they might walk away thinking we’re dumb. Why wouldn’t they, it was the impression we gave them one too many times.

5) Find a through line. One of the many reasons the show Seinfeld was so popular is that nonsense is funny and fun. Some of the best friendships I have in life were based on nonsense. Example, Michael had a habit of making a drink face before he even reached for his can of soda. He reached out for the soda with an ‘O’ already on his face. He grabbed the bottle and inserted its contents into the ‘O’. I never knew we had a drink face, until I met Michael. I never thought about the timing of the drink face, until I met him.

“Michael, you need to wait until the drink is almost on your face before you make a drink ‘O’,” I said. “You make your drink faces far too early.”

“Women don’t like a man who makes a drink face too early,” Cole added. “It freaks them out.” A lifelong friendship between Cole and I was born that day.

Another friend and I loved the comedic stylings of Don Knotts, and we both hated caramel apples, because we hated the feeling of caramel on our nose. On that note, another bonding agent can be hating the same things. You both might hate beets, accidentally stepping in puddles, or people who make old man sounds when they sit. Whatever the case, there’s always some nonsense you can bond over. It’s your job to find it.

6) Find active listening prompts. There are few things people enjoy more than an active listening question about the story they’re telling. The questions we ask are often relative to their conversation, but some of the times, a simple “And why did you do that again?” can do wonders to show we’re not just following along, we’re interested, and we want to hear more. Depending on who the person is, they’re not used to people being so interested in what they have to say, and as we said in point #3, interest generates interest.

These little tidbits seem so simple that they couldn’t possibly work, and they may not. As someone who has, at times, suffered from situational stage fright, because I wanted to be more entertaining, funnier than everyone else in the room, and so over-the-top everything, I realized that I had a tendency to lock myself up by over-complicating the situation before me. Some of the times, these situations are complicated and tough to read, but some of the times they’re relatively simple. Getting a read on conversations can be similar to making reads in sports. Some of the times, depending on the level of competition, we can win a game all by ourselves, but most of the time, we damage our team’s chance of victory by trying to do too much. When we experience the latter, we learn to let the game come to us. It’s all confusing and situational, and the best advice comes from the immortal lyrics from You’re the One that I Want by John Farrar, for the movie Grease: “Feel your way.”

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