How to Stop Being Boring
A guide to not getting "left on read"
Why do people zone out when you talk? Why aren’t people jumping at the chance to meet up with you?
Sure, everyone’s busy. But people make time for what matters to them. Everyone knows someone so engaging that you’d gladly rearrange your schedule just to have dinner or a long conversation with them. So when it comes to being someone others genuinely want to spend time with, the old dating adage applies: "if they wanted to, they would."
So why don't they? It turns out, there's both an art and a science to being interesting, and everything from what you think to what you wear plays a role. Today, we look at the steps you can take, both big and small, to be the most compelling “you” you can be.
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Seek to Be Interested, Not Interesting
Perhaps the world’s second worst crime is boredom. The first is being a bore.
-Cecil Beaton
Before you begin “making yourself interesting,” you’ve already taken a wrong step by focusing on yourself. At least, that’s according to writer-philosopher Alan Watts, who wrote about the great paradox of interest; to become interesting requires you to lose sight of yourself in something external:
You don’t get the full development of human personality by trying to cultivate personality. Did you ever hear of anybody who had true personality who got it through taking a course on how to win friends and influence people? Or how to be a real person? You never did. It’s rather: when you forget about your personality, and you become interested in something else, that you become interesting to other people.
Rarely is someone’s personal life so compelling that it suffices as a topic of dinner conversation. Rather, the people who hold other’s attention are those who animate their conversation with the zeal of the truly passionate. Studies have shown that the traits that make people seem boring are things like being passive, obsessed with one’s own life/problems, and displaying low to no enthusiasm. People considered interesting, however, were more able to contribute information to conversations, or able to share their thoughts and feelings while not centering things around themselves.
The best way to contribute information is to know it, and, to Watt’s point, the best way to know a lot about something is to become so enamored with it that it makes you forget yourself. Even if you can’t immediately think of a subject that makes you feel that way, there are ways to brute force this effect.
Writer/journalist Malcolm Gladwell once explained his method for finding stories as picking something mundane, like shampoo or pasta sauce, and researching until he found what was truly interesting about that topic. With a bit of patience and effort, anything can be compelling, if you only dedicate enough time to find it fascinating.
Fortunately, however, it’s likely you already have interests and won’t need to pull a Gladwell by researching random topics. Simply giving way to your natural curiosity and diving headfirst into things will give you enough to start.
But spending hours on something that makes you forget yourself is not enough. In fact, the main way most people do so is actually making them more boring, not less…
Track Your Phone Use (and Be Horrified)
Be very careful, then, how you live—not as unwise but as wise, making the most of every opportunity.
-Ephesians 5:15-16
If you’re like a majority of the world, you (likely) have a problem with life-deadening screentime. So if you haven’t already, activate whatever personal screentime consumption metrics you can and watch your beliefs about your digital habits crash into the cold jagged cliffs of reality.
Research shows people vastly underestimate how much time they spend basking in digital light. In a way, this makes perfect sense. Insensitivity to sloth, like insensitivity to any sin, is the result of a gradual hardening against its aggressions on the soul. The more you indulge, the more calloused you become, and the less you take stock of what it’s doing to you.
Psychologically, this can act as a defense mechanism to maintain your sense of self as a “good person” when you continuously act in ways that contradict that belief. As a result, you either modify your bad behavior or your perception of that behavior. Recognizing the problem with quantifiable data, and being shocked enough to change, is an important first step.
The reason this comes up in a discussion about being interesting is that endless reels or Twitter scrolling can feel like developing an interest, while the format itself actually prevents this from happening. This is due to “context switching,” where the frequent bouncing of your attention from one topic to another in rapid succession prevents the retention of meaningful information. That interesting reel on exotic animals or a scientific formula will be a non-memory when you try to summon it up at your next dinner party, and the deficits in working memory and lower recall means almost nothing you saw doomscrolling becomes a part of your knowledge bank.
This black hole of time and empty educational calories makes you less interesting than a person who spent those hours doing things they can remember. So if you think you’re boring people, managing screentime is a necessary first step on the road to recovery.
But even if you put the phone down and stare at the wall to recover your attention span, it isn’t enough, because there’s still an active element required of you…
Stop Waiting For Life to Happen
I have led a toothless life, he thought. A toothless life. I have never bitten into anything. I was waiting. I was reserving myself for later on—and I have just noticed that my teeth have gone.
-Jean Paul Sartre, The Age of Reason
In The Beast in the Jungle, author Henry James tells the story of John Marcher, a man living in dreadful anticipation of some great calamity he senses will someday befall him. Marcher can’t explain the nature of this catastrophe, which stalks him like a beast hidden in a jungle, but he knows it will be ruinous. Not wishing to afflict anyone with his curse, Marcher makes few friends, and refuses to court the one woman who expresses interest in him. By the end of the novella, Marcher comes to a frightening realization that the tragedy that would define his life was just how little he lived, waiting for it to start.
Similarly, many people spend their lives with what you could call Harry Potter syndrome; waiting to be discovered not for what they have done, but simply because they contain some hidden greatness or are intrinsically “special.” This thinking places all the effort on others to discover why they should care about you, and the truth is, it’s your responsibility to give people a reason to be interested. This passive mentality is pure poison to an aspiring interesting person, as it is entirely inward focused and the exact opposite of Watt’s advice.
So no, no one is coming to save you from your uninteresting life, but the good news is, no one is going to stop you from starting an interesting one, either.
And this being Letters from the Old World, we can’t help but make a bit of a sartorial suggestion to start you off.
Wear Your Interests on Your Sleeve
From the wreckage that was the mid-2000s pick-up artist “scene” came one piece of advice worth incorporating into your wardrobe: the idea of “peacocking,” or wearing interesting pieces of jewelry or clothing that inspires curiosity. By having something that invites questions from others, you not only provide entry points to conversation, but you share niche passions which would otherwise not be brought up.
But while pick-up artist “peacocking” is clumsy and ostentatious, picking a wearable conversation piece can — and ought to — be as subtle as the pattern on a tie or pocket square. Take, for example, Evan’s cufflinks in the photo below, which feature an engraving of his home state:
Small accessories like this are meant to be noticed eventually rather than immediately. You don’t want to draw attention to them, but you’ll probably be surprised by how often they come up organically in conversation. You don’t have to dress tacky like the free money guy, just wear something that has special meaning for you, and let things take their course from there.
You Are On Your Own
There are dozens of ways to break get granular about this topic (like suggestions to join a club, hone a skill, work on your public speaking, etc.), which is why this quick overview is simply intended as a springboard. Once you identify the main issues that stand in your way, you can focus on becoming passionate about something outside yourself, putting down the anti-memory formation devices, and taking action any way you can.
But beyond that, the way that you in particular will become a person worth knowing must be left to you. We can’t tell you to learn all about a certain topic or to pursue a certain athletic/intellectual endeavor and pretend it’s one-size-fits-all advice. At the end of the day, it’s simply about finding the things that speak to you in such a way that you can’t help but live your life in their pursuit, and make people want to know how your search is going.