Level Up: How To Be The Most Interesting Man In The World

When we talk about attraction, one of the things that doesn’t get brought up often is that you need to be interesting. The truth is that people don’t want to date someone who’s boring. Being boring is an attraction-killer; even the most gorgeous people in the world lose their appeal when you can’t have a simple conversation with them. On the other hand, the most attractive people are the ones who are interesting. They’re the people that folks want to talk to. They hold people’s attention, not because of their looks or their social value but by virtue of being who they are as individuals. As one of my friends put it: “I married my husband for the entertainment value he brings, and I am never, ever bored.”

It shouldn’t be much of a surprise that interesting people are desirable. After all, one of the keys to becoming someone worth dating is that you have to be someone people want to spend time with. It’s a key part of The Grimes Test: what do you have going for you beyond the bare minimum? What do you do besides… well, exist?

The thing is: like social skills, being interesting isn’t a binary. It’s not a case of “you’re interesting or you’re not”. It doesn’t take that much to be a more fascinating, captivating person. You just have to understand what it takes to be interesting.

Learning these secrets will help you live an amazing life and be the most interesting person in any room.

Do Interesting Shit

OK, So this I admit sounds a little dismissive… but there’s a point to it. Most people don’t do anything. Their lives are a matter of endless, joyless repetition: wake up, go to work, come home, go to sleep. If they’re feeling especially edgy one day, they might go to a movie… in the middle of the day.

Part of what makes somebody interesting isn’t whether they can spout random facts or their views on any particular issue, it’s that they’re active participants in their own life. They live a life that’s varied, active and multidimensional. Their lives are more than just passive consumption of other people’s creations. Passivity at its core gets you nowhere; interesting people don’t wait for others to provide them with opportunities or openings. They direct and shape their own lives.

Of course, this brings up the question of “OK… what should I do?” And the answer is to ask yourself: what would someone you find interesting do? What are some of the qualities of the people who interest you? These can give you some starting points about what you want to try doing. Pick options that have little to do with your job or day to day life. Maybe you’d like to travel. Maybe you’ve wanted to try making sushi. Perhaps you just want to learn more about graphic design. Maybe you’ll do a rope course or participate in an escape room. You might go to an outdoor shooting range and fire machine guns and blow up cars.

However, you don’t want to treat having an active life as one of constant one-upsmanship. One of the mistakes that a lot of people make is that they assume that to be interesting they have to take things to extremes. If they’re not BASE jumping, backpacking to exotic locales or swimming with sharks, they’re not interesting or EXTREME enough.

And while partying with rockstars can make for some fascinating stories, that isn’t the only way to be interesting. Being interesting is simply about having a diversity of experiences and interests and being able to share them. Often it’s not a case of going broad but deep. You may not be able to travel to Europe, but you can explore your town and get into its histories and mysteries. The mundane is often only boring on the surface; it’s how you relate to it that makes it fascinating. One of the best conversations I recently had with a friend – someone who hosts a popular show about doing things like breaking into cars and jumping off buildings – was about getting lost on a road trip and accidentally finding a diner in the middle of nowhere with the best burgers in Texas.

Cultivate Your Intellectual Curiosity

Part of what makes someone interesting is how they engage with the world around them. They don’t just absorb things as they come; they grab on, interrogate it, examine it and absorb it. It’s very hard to be bored or boring when you let your curiosity drive you. There’s always something new and fascinating to learn.

If you want to be more interesting, you want to let that sense of curiosity and discovery drive you. The more you explore the world you live in, the broader a perspective you gain. That, in turn, makes you more fun to talk to.

The first thing you should do to be more interesting is to make a point to read for pleasure. A surprising number of people – over a quarter of Americans, in fact – don’t read. Not can’t. Don’t. This makes them almost absurdly boring to talk to. You, on the other hand, want to have a broad base of reading material. Read histories, biographies and books about social growth and trends. Being better informed helps give you a wider understanding of the world and why things happen.

Just as importantly, read fiction – specifically fiction by people who are different from you. Read books written by women, by queer authors, by people of other nationalities and by people of color. Reading stories from people who are unlike you opens you up to voices and perspectives that are different from your own. It broadens your view of the world and helps you understand and connect with amazing people you might otherwise never get to know.

The more you read and the more you learn, the more you’ll have things to talk about in almost any situation. A wider base of knowledge, even if it’s not the deepest, can open up conversational opportunities you’d never expect. You’re in a much better position to talk to more people than if you focus like a laser on only one thing.

Podcasts are another valuable avenue for exploring your intellectual curiosity. From Radio Lab to My Favorite Murder, there’s a wealth of knowledge to be absorbed out there. When shows like S-Town are dominating the discourse, finding a variety of podcasts can help keep your brain engaged and improve your life socially.

While you’re at it: take classes and attend seminars, just for the sake of satisfying your curiosity. Maybe you’ll take lessons in making cocktails. Or you might get a hankering to learn the basics of podcasting or video production or the history of Moorish Spain. Don’t focus on things that have a direct application on your life; just indulge yourself in trying things you might never do otherwise. You may never have a practical reason to, say, take an iado class, but it adds dimension to you as a person. It is just one more facet of who you are that helps you stand out from the crowds of of the bland and boring.

Talk To Strangers

In a moment of supreme irony, one of the important parts of being interesting is also one of the most neglected. While it’s easy to picture The Most Interesting Man in The World holding court at a party, people forget that interested is interesting. It’s all too common that people fall into traps of trying to out-cool the people around them, jockeying for status by having the coolest experience, the best stories. While being the center of attention can be fun, being a good listener can be even more valuable.

Most of us like to talk, but we rarely find an audience. More often than not, we encounter people who aren’t listening; they’re just waiting for their turn to talk. Someone who is interested while listening, however, is invaluable. We love finding people who legitimately want to hear what we have to say – and that makes you someone they will want to spend time with. When you become interested in the people around you, they feel appreciated and validated. After all, when people feel like they can tell you anything, they’re going to want to spend more time with you. And the more you get used to talking to strangers, the easier it is to meet new friends… and new lovers.

More importantly, however, being interested in others will make you more interesting, because of the way it will connect you with others. Interesting people are natural networkers; they let that natural curiosity create connections with people they meet. Everyone has a story after all, even if they don’t realize it. When you’re curious about them and want to get to know more, you become the person who elicits those cool stories. I’ve had conversations with strangers who insisted they’re nobody special and later revealed that they discovered sunken ships while scuba diving or made a living as a gold miner. You never know who you might meet or what might happen if you don’t take that first step of simply showing interest in getting to know them.

Meeting interesting people makes you more interesting because of the way it gives you more experiences. Maybe you’ll come away with a cool story about someone you met while you were traveling. Or perhaps taking interest in that stranger will lead to a friendship that will then lead to a different adventure. Maybe the person you struck up a conversation with at the bar will be able to get you into a concert you could never get tickets for. You might get invited to join them elsewhere and meet more interesting people and join them in their shenanigans. Even if you don’t end up with a new lifelong friendship, expressing interest in others and wanting to hear their story will lead to opportunities for you to cultivate your own.

Now to be sure: this can be hard for a lot of people. And that’s actually a good thing. Why? Because…

You Need to Get Out Of Your Comfort Zone

The thing that makes people interesting is how they do things that other people often don’t. That difference, that willingness to do the unusual, to explore the unexplored or to simply dare to do things differently makes them more fascinating to us because, frankly, most of us like comfort for our own good. Don’t get me wrong: having a comfort zone is good; it gives us a place where we can relax and be at ease. But at the same time, it can also be a limitation. When we become loathe to leave the known and comfortable, we make it much harder for interesting things to happen.

After all, there’s a reason why so many beloved stories focus on people who are driven out of their everyday lives. Luke Skywalker, Bilbo and Frodo Baggins, and Harry Potter all start with having their status-quo upended and being forced to leave it. It’s the story of what they do once they leave and how – or if – they return that makes them so compelling. They have to change and adapt to new circumstances and grow as a result.

The problem, though, is that safe and comfortable is, ultimately, boring. Change and difficulty – even something as minor as overcoming approach anxiety and talking to strangers – is part of what makes us more interesting, even when things don’t go well. Discomfort is often about pushing past your limits and growing into the person you can be instead of who you are currently. Change may be scary, but change is necessary – especially when you’re not satisfied with how you are now.

This is why if you want to be interesting, you have to take risks and do things that you might never do otherwise. It can be as extreme as going travelling abroad on your own or as simple as going to a rosé tasting with strangers because fuck it why not? Maybe you’ll try going on a hike that ends with rappelling down a canyon, even though you have a crippling fear of heights. Maybe you’ll take a public speaking class. You might end up getting “volunteered” to be part of a stage show with a magician… or knife-throwing Chinese acrobats.

Just remember: the point isn’t to succeed or overcome things – though that can be great. The point is simply…

Err on the Side of Stories

The single thing that interesting people have in common is that they all have stories. It’s a natural byproduct of living an active, varied life; you end up with stories because you’ve put yourself in position to make things happen. Again, it’s not that the stories have to be extreme; it’s great if you end up exploring a ruined temple in a jungle surrounded by a minefield¹ but an interesting story could just as easily be about meeting your best friend at a random bar in Anaheim or that road trip you took to Luckenbach.

Your rule of thumb for being more interesting should be “could this lead to an interesting story later?” If the answer is “yes”, then do it, even if you’re not sure how it’ll turn out. After all, making mistakes can make for as good – or better – stories as success. What did you do, why did it go wrong, how did you fix it or get out of it? How did you react, what was the fallout, did things get better or worse? Being interesting isn’t about avoiding conflict, it’s about how it happened. Getting stuck up that tree isn’t as important as how you ended up there in the first place and what you did about it.

So do things that challenge you, that scare you or that you might never do in a million years otherwise. Take road trips because it might be fun. Try new foods that you’d never eat in a thousand years. Take vacations to places you might never visit in other circumstances.

The more experiences you have, the more stories you collect… the more interesting you’ll be.

1. Also a true story [↩]