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.”

Esoteric Man


It was difficult for me to evaluate the advertising executive trying to sell my wife on radio ad space in a fair way, because he dressed like every guy I hated in high school. I knew I was being unfair, but as Anaïs Nin said, “We don’t see things as they are, we see them as we are.” Certain things are the way they are, but they’re complicated by the way things were, and we cannot escape their influence.

The guy’s checkered pants reminded me of one of my many arch rivals in high school. The checkers were multi-colored, of course, but some of those colors were pink, and my arch rivals wore pink. Most of the guys I detested in high school wore pink. The ad exec wore sensible shoes, John Lennon spectacles, and he wore his hair in a messy coif. He was also a people person that knew how to relate to us, the folks, and I didn’t want to have anything to do with him before he said twenty words.

“I don’t even have cable!” was the most memorable thing this nouveau hipster said to punctuate the fact that he didn’t watch TV. “I only have Netflix, because my kid enjoys some show, but that’s the only reason.”

“Wow!” is what we were supposed to say in the space he provided. “You’re so esoteric, and philosophical! You’re what they call ‘a with’ it dude!” The hipster mentioned the name of the show his kid enjoyed, but it was as irrelevant to him as it was us. But talking about his kid helped us relate to him, right? Even though he was, of course, divorced, and he only saw his kid on weekends. Yet, he only dropped some info on his kid. He didn’t want us to know much about his kid, because he probably didn’t. He wanted our focus on him and his preferences. 

He was a flood of useless information about himself. He was on the edge of his seat wondering what he was going to say next. He was a serious man who didn’t take himself too seriously, but he could get out of control at times too, and he knew that I knew that’s just the way he was, even though I never met him before.

“I don’t drink soda! It’s gross!” he said to initiate another preferences portion of our conversation, so that our sales meeting could be delightfully informal. He found his preferences so esoteric and philosophical, and he found that if he added a personal touch to his conversation it would culminate in a sale. This portion of the conversation gave schlubs like us a point where we could relate to this salesman. He was being real for us to sell himself in the manner all salesmen know is fundamental to obligating customers to fork over a dollar.

As the two of us listened to this man, he presumably decided he was losing me at one point in our conversation, so he decided to focus his energy on me. He directed his energy at talking more often, when his focus should’ve been on talking less. This esoteric ad exec struck me as the type who has always been able to talk himself out of a pickle. His modus operandi (M.O.), I can only assume, was focused on creating more chaos in the minds of his clients, so that they didn’t have time to consider if a sale would be beneficial to them or not. I think he watched the tactics that law enforcement officials use in a drug bust. Break in, crash things, smash things, and scream a bunch of things at high volume to dismantle the central nervous system of the alleged perpetrators, so they don’t know what is going on, until the scene is secure. I think he saw that method as a way to sell ad space.

I’m not sure, if this ad exec decided to disregard transitions in his stories, or if he wasn’t a fella who employed transitions, but his stories began to arrive in such a flurry that I lost my place in his stories a number of times, and I ended up forgetting almost everything he said. He was turning red at various points, and he began yawning in others. This suggested to me that his brain wasn’t receiving enough oxygen, but it was obvious that he preferred an oxygen depleted brain to a lost sale.

“Wow! You must really be smart,” those without control of their sardonic nature would say to the list of this man’s preferences. This is the type of response that an esoteric man expects from a TV watching, soda drinking, Neanderthal. He didn’t get it, this time. This time, he got a guy who stared at him with silent ambivalence, waiting for him to get back to the whole reason we came to him for in the first place.

“You know?” was the only transition that this man didn’t completely abdicate. It was the only form of punctuation this man had left to let his listener know that a sentence was complete. He mixed in a couple “You know what I’m saying?” questions to prevent losing me with redundancies, but that was the extent of his variation.

“Yes!” I replied to put a verbal foot on the floor and keep his transitions from spinning out of control. I almost screamed it once, but the parental, patience practice of counting to ten was all that prevented the outburst.

He engaged in an “aren’t we guys stupid?” chat that everyone considers harmless fun. When that didn’t achieve the desired result from me, he flipped to the “we’re all really stupid anyway” pop psychology, gender neutral nuggets, and the two of us were supposed to laugh heartily at those stories, because we could both relate to dumb people humor. It reminded me of a heavy metal band’s lead singer attempt to reach his audience by mentioning the fact that he actually rode in a motorized vehicle on the paved roads of my hometown. “Today as we were driving down MAIN STREET…” YEAH!

He was a nicknames feller. Even though he didn’t apply such nicknames to me, I’m quite sure that he calls more than one male in his life “dawg”. He probably also calls a couple of them “Bra!” and he bumps fists with them as he works his way past their cubicle. I don’t know if he has any authority in his place of work. If he does, I’m sure he asks all his peeps to call him by his first name, because he’s an informal fella who wants informal relationships with all of his peeps. I’m sure he has an open-door policy, and that all his top performers are “rock stars!” He’s a people person who’s not afraid to let his hair down. If one of his peeps has a name that begins with a B, I’m sure he calls them ‘B’, or ‘J Dawg’ if their name starts with a J. He’s also the esoteric guy in the office that conforms to group thought when called upon to do so. I’ve been around his type so often that I can pick them out of a closet from fifty yards away. They all have nihilist beliefs in private, and they don’t bow to the man, until that man is in the room, and then they turn around to insult “the dude” the moment after he leaves the room and they hear the click of the door closing.

We didn’t talk politics, but I’d be willing to wax Brazilian if it’s revealed to me that we see eye to eye on anything. He’s the type who seeks “a third way” of governing. He strives to avoid labeling. He prefers the open-minded perception. He pities those simpletons conditioned to believe that there are actually very few forms of government from which to choose, and that there are only two viable political parties in this country to run it. Their type knows of another way. They don’t have specifics, but they feel sorry for those of us that have bought into the system. They are open-minded. They are extraordinarily intelligent, and they equate their intelligence with their morality. They are thoughtful, and they are wonderful. We are wrong. We attach these labels to them, and they are “truly” so much more.

When he eventually swerves into the whole reason we came to see him in the first place, I’m gone. I’m beyond listening. He thinks he’s warmed me up with his ‘look at me’ chatter, that he considers good bedside manner, but in reality I’ve begun to feel so sorry for him, and his pointless attempts to sound interesting, hip, funny, likable, intelligent, esoteric, philosophical, and personable, were so overwhelming that I shut down and missed the first two minutes of his sales presentation when he finally started it.

“We guys don’t seek medical attention.” He smiled after that one. He thought that was polite guy, fun chatter. He surveyed my reaction. He told me he enjoyed sports, and then he asked me if the San Diego Chargers were still in existence. I normally would’ve enjoyed such ignorance of my arena, but I realized that I didn’t care if he knew anything about the Chargers, the NFL, sports in general, or anything else. This was a huge accomplishment for this guy, whether he knows it or not, for as anyone who knows me knows, I get off on personal preferences. I want to know what books a person reads, what movies they like, what music they enjoy, and what restaurants they frequent. I love top ten lists, the reasons behind why another’s rankings. Some have informed me that this is one of my more annoying attributes. This esoteric ad exec didn’t have to face any of my more annoying attributes, because he managed to achieve a nearly unprecedented place of me trying to avoid the subject of personal preferences. I just wanted him to stop talking.

The quiet types have something to hide, is a description we’ve all come to accept in one form or another. It could be true, in some cases, but I’ve experienced a number of quiet types who simply don’t know what to say or when to say it. I’ve met other quiet types who have been slapped back for saying what they think so often that when they have a thought on a particular matter, they’re frozen by the fear that you’ll uncover something about them if they voice their opinion, so they usually find it more comfortable to say nothing. When a person talks and talks, we naturally assume they are as advertised. We assume that they’re the “open book” they’ve told us they are so many times that they can only be trying to convince themselves. They are extroverts who are conversant on so many topics that we can’t think of anything that they could possibly be hiding, until we walk away from them with the realization that they didn’t say anything. They just said a whole lot of nothing on nothing topics. We might label that obfuscation and misdirection. We might consider that an art form normally associated with magicians, but talkers can display a talent for this art form too. They just don’t use their hands … as often.