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. Listeners don’t have to be cool or beautiful either. They can be old, young, smart, dumb, boring and fascinating. 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 musicians told me to avoid the “chitter-chatter, chitter,-chatter, chitter-chatter ‘bout schmatta, schmatta, schmatta”. The movies told me to be the quiet, mysterious type everyone looks to for reaction. They told me if I wanted elusive charisma, I should be silent.

“Don’t listen to them,” The Ghost of Present Rilaly would whisper into my ear. “Silence doesn’t make you look cool. Silence makes you look silent.” Silence lands you in the corner of the room not knowing what to do with your hands. No one remembers you when you are silent.

There’s a reason former athletes and the beautiful are silent. They don’t have a lot to offer.

“How do you know so much about such stupid stuff?” the beautiful might ask. If we’re bold enough to answer, they’ll say, “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 a long time 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 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. My best friend enjoyed talking to people. I found that so confusing 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 would talk with old people about old people stuff. Their conversations were absolute nonsense. He didn’t care, and he was having one hell of a good time doing it. I thought he 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 know anything about that,” he said. “I just want to have a good time.”

“It goes against code,” I said, in whatever terminology I used at the time. He didn’t care. He didn’t tell me he didn’t care. He wanted to be cool, like Matt Dillon, and all that, but some part of him enjoyed the art of conversation so much that he couldn’t control himself. When some old man got angry about the cost of a Hershey’s chocolate bar, my friend turned to him and encouraged the rant. What? Why? When an old person starts in you’re supposed to walk away. When he first started doing it, I thought it was a bit. I thought he was trying to pull a thread on the old man to get him going. After numerous interactions of this sort, I realized my best friend was respectful and deferential. He just enjoyed talking to people of all stripes. He 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 the superficial side to just talk to whomever happened to be near him in the moment.

It took me a long time to see that my friend might be onto something. It took a job where my employer forced me to engage with customers that I realized I could and should tap into my superficial side. I got all tied up in the shoe-gazing, grunge virtue that suggested you were all a bunch of fakes, and I was living real. As usual, when you accuse someone else of being fake too often, it’s usually because you are. I was a nice Midwestern kid trying to pretend like I was a Northwestern rock star. At that point in my life, I still believed that the artistic persona was an important one to maintain, but I learned to maintain that persona while tapping into a superficial side. I did that to remain an employee with high scores, but I learned to tap into that persona in my off work hours too, and I found that I had a lot more fun in life doing so.

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 in their skin 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 we are. 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 just as inferior as we are. They’re just normal people living normal lives, and they enjoy engaging in casual conversation.

3) Pretend to be interested in what they have to say. How often are we so interested in being interesting that we forget to be interested? 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 receive a return on our investment. One of our favorite conversation topics is us, and when we show them we’re interested in them, they are going to be more interested in us. One of the keys to this is to avoid testing it out too early. If we begin speaking too early, their smile 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 overwhelm them with interest.

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 you forget to be interested in what they have to say.  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 proper timing of a 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 way 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.

6a) Be a Great Listener. Some suggest that listening is a lost art. I’d argue that it never was. I’d argue that people in Aristotle’s era, Shakespeare’s, and every just about every dot in human history had the same complaint about human nature. “Nobody listens to anybody anymore.” Are you listening to people when you say that? I’ve been called a great listener in enough venues that I’m starting to think it’s true. I am fascinated by the people around me, and why they think what they do, and I have to tell you that it’s a great way to make friends. The one problem with being a great listener is when you’re known as a great listener, people don’t want you to talk. They much prefer that you listen to them, be fascinated with them, and find them funny. As I’ve written throughout this piece, those of us seeking to make friends will have to work through this in their own way, but if we lay the foundation of being a great listener people will be drawn to us.

6b) Ask Active Listening Questions. Asking active listening questions not only prompts the speaker to launch or continue, it makes them feel interesting. There are few things people enjoy more than an active listening question about the story they’re telling. The questions we ask are relative to their conversation, but some of the times, a simple “Why did you do that again?” can do wonders to show we’re not just following along and that we’re interested, but that we want to hear more. Some listening prompts might feel so obvious to be almost stupid, but soon after we drop them, the speaker picks the ball up and eagerly runs with it. As I wrote earlier, people love it when we make them feel interesting, and they might love being funny more, but the final leg of my version of making friends and influencing people might endear the speaker to you more than any other. If we phrase our question just so, it makes them feel like your resident expert on the subject in question. Active listening prompts not only shows that you’re listening it suggests that you trust that they know the truth of the matter.

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 else, 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, for anyone who asks the five questions regarding how to implement them, 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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