How to be more interesting

How to be more interesting

I used to be terrified of being boring. Networking events made me wonder if my small talk sucked. Coffee meetings were similarly nerve-wracking. And when I talked during team meetings, a single yawning co-worker could make me forget my point.

But then, I started paying attention to how the most interesting people around me held others’ attention. I realized that just like you could learn to be a better leader or more effective negotiator, you could learn to be more engaging.

And that’s awesome news for your career. When you’re interesting, everyone you meet—from your boss to your future business partner—wants to be around you. Not only will you make more connections, but those relationships will be easier to maintain and strengthen.

To reap these benefits, check out the six ways to become a more interesting person. (Bonus: You’ll never fear small talk again.)

1. Pursue Interesting Topics That Have Nothing to Do With Your Career

Last week, I spent roughly 10 minutes explaining to a product manager why I’d shown up to a two-hour session about a profession I’d never tried and probably never would.

“I’m just curious about package design,” I told him.

The truth is, I regularly go to meetups and talks on topics that are completely unrelated to my ambitions. 90% of the time I end up learning a bunch of cool new things—giving me some great conversation fodder.

For instance, at that packaging panel, I learned manufacturers spray a coffee aroma onto the lids of their instant coffee jars so you get a whiff of java when you open one. I also discovered bubble wrap’s original purpose was textured wallpaper.

Fun facts aren’t the only thing you’ll take away—you’ll learn how to talk to virtually anyone and expose yourself to new ideas.

So, hop on Meetup.com or Eventbrite and start looking for events you’d normally never attend. Or, if going to an event isn’t feasible, make an effort to read articles or nonfiction books that you wouldn’t normally be drawn to.

2. Have a “Yes” Month

If you want to become more interesting immediately, borrow Daily Muse Editor-in-Chief Adrian Granzella Larssen’s trick. Larssen makes a point of saying yes to every invitation she gets, no matter how random, unappealing, or exhausting it sounds.

The great part about doing this? You literally can’t lose. When you end up at the inevitable dud, you’ll walk away with a story. When your experience takes a turn you were never expecting, you’ll walk away with an even better story. And when everything goes as planned, you’ll have a cool anecdote about, say, the Q-tip millionaire you met while playing Frisbee or the cave expedition you went on.

The idea of accepting every request might sound exhausting — especially if you’re an introvert, like Larssen. She copes by giving herself a firm time limit (usually one to two months). After your “yes” period is up, you can go back to being more selective with your time.

3. Try an Experiment

It’s nearly impossible to resist articles like, “I Gave Up Social Media for a Month and Here’s What Happened,” or “The Three Weeks I Spent Eating Only Hot Dogs.”

These are compelling because, well, people doing out-of-the-ordinary things always are. Giving yourself a challenge is therefore guaranteed to make you more interesting.

And there’s no reason your experiment has to be unpleasant. Emily O’ Mara, a software consultant at Oracle, ate 101 cheeseburgers in her mission to find the most delicious. Writer Kevin Roose, meanwhile, documented his attempts to create the perfect morning wake-up.

However, if you want to be more interesting and more productive, consider a more traditional challenge. Ideas include temporarily renouncing caffeine or alcohol, turning off your phone after work, or eating lunch away from your desk every day for a week.

From the process to the results, you’ll have plenty to talk about. (Just don’t proselytize — telling people they must stop drinking coffee is the opposite of interesting.)

4. Listen to Podcasts

Lastly, I’ve noticed my conversations with fascinating people are always filled with “I heard on this podcast …” or “According to this episode of [podcast] . ”

It makes sense: Podcasts are chock-full of surprising stories, details, and facts, so listening to them gives you an awesome source of topics.

Plus, they’re the perfect alternative (or complement) to books. You can’t read while you walk your dog or run errands, but you can easily stream an episode of say, Planet Money.

I recommend listening to a healthy mix of topics you’re interested in and topics you’re unfamiliar with. For instance, roughly 50% of my subscriptions focus on tech, business, design, and social psychology: in other words, my core interests. The other 50% is completely random, ranging from food and film to Disneyworld and architecture.

Striking this balance gives me a fountain of information on almost every topic—meaning it’s far easier to talk to people with different interests.

(Need some suggestions? Check out 51 awesome podcasts you’ll want to download right now.)

5. Learn New Facts

Interesting people tend to know trivia for every occasion. Maybe you order a charcuterie board, and they announce there’s a bank in Italy with a vault just for Parmesan cheese. Or you spot a wild deer, and they tell you about the British crew that kept a live reindeer on their boat for six weeks during World War Two.

These facts are interesting—so you automatically think of the people providing them as interesting, too.

As a bonus, a relevant but surprising piece of information never fails to spark a fun conversation.

I’ve built up a mental repository of trivia by subscribing to Now I Know, a daily email newsletter for strange-but-true facts. You can also buy a trivia calendar. Or follow writer A.J. Jacob’s lead, and read the encyclopedia. It might sound tedious, but you’d be surprised at how much entertainment is packed between A-ak and Zyzzyva.

6. Listen More

It might sound counterintuitive, but the most compelling people spend a lot of time not speaking.

Listening to others makes you more interesting for a couple reasons. First, you pick up a ton of interesting information—which you can then use down the road with different people. For example, a couple months ago I met a woman who’d grown up in a remote Alaskan fishing village. She told me tons of cool tidbits; as result, when I met a CEO who’d just gotten back from Anchorage, I had a long mental list of potential questions and conversation starters.

In addition, talking only 30 to 40% of the time guarantees that you won’t accidentally ramble. It can be tricky to tell when the other person is going from “engaged” to “bored but politely pretending otherwise.” If you naturally stop before this point, they’ll find you far more compelling.

And the final reason? As Dale Carnegie pointed out in How to Win Friends and Influence People, everyone’s favorite subject is themselves. Ironically, putting the conversational focus on them will you seem more interesting.

As you can tell, being interesting isn’t effortless—it actually takes a lot of hard work. But once you start captivating everyone you meet, that hard work will definitely pay off.

It’s easy to be boring. It’s harder to be interesting. Want to learn how? Jessica Hagy offers the following advice, excerpted from her book “How To Be Interesting.”

Go exploring.

Explore ideas, places, and opinions.

The inside of the echo chamber is where all the boring people hang out.

Expose yourself.

To embarrassment. To ridicule. To risk. To strange events and conditions. To wild ideas. To things that make you cringe. To strange vistas and new sounds. Trust me. It’ll be fun.

Become a spy.

People watch. Eavesdrop. Lurk. Loiter. Listen. And you’ll learn the secret codes of others. Every day can be an interesting recon mission.

Tweak the schedule.

Wake up before the alarm. Steal moments between stoplights to compose poems. Sneak off to a moonlit spot when you’d otherwise be watching something on a glowing screen. Work at night and play in the daytime. Carve out hours for the dreams you’ve been putting off. There’s always time to explore. You get to decide when it is.

Keep asking why.

Parents hate it when kids do it.

And on and on. But try it. You’ll be surprised at how quickly a simple Why? can turn into a fascinating Because.

Share what you discover.

And be generous when you do. Not everybody went exploring with you.

Let them live vicariously through your adventures.

Instigate.

Do not wait until tomorrow. Say, do, or make it now. Go where you need to be. Do not wait to be invited places. Host your own parties. Do not sit by the phone. Pick it up. Spread the word. Press the buttons. Buy the tickets and enjoy the show.

State the obvious.

What’s known to you is often a mystery to others. Your old fact is someone else’s new lesson. Your simple task is someone else’s impossible chore. Your mind is full of treasures that no one else has seen. Pass them on. An idea shared is not diminished: It’s multiplied.

Do something. Anything.

Dance. Talk. Build. Network. Play. Help. Create. It doesn’t matter what you do, as long as you’re doing it. Sitting around and complaining is not an acceptable form of “something,” in case you were wondering.

Sign up.

Join a club. Take a class. Volunteer. Have a party. Take a meeting. What we do shapes who we are. Be someone who’s been there, done that, and wants to do new things tomorrow.

Earnestly enjoy yourself.

Irony gets in the way of experience. Drop the pretense, and you’ll have room to carry the day.

Sing along to cheesy pop music. Enjoy things that are out of style. Make silly faces. Stop stifling your giggles.

Give yourself permission to enjoy yourself.

Tinker.

Start with a wonder. How does this work? What makes that happen? Then poke. Take things apart and put them back together. Push buttons. Change settings. See how the pieces fit. See what powers the engine. See how interesting it all is.

How to be more interesting

I’ve posted a lot of research from experts on getting people to like you, being influential, and having great conversations. What’s the best way to use all this information to be more interesting?

1. First, don’t be boring.

Sometimes the best offense is a good defense. Look at it like the Hippocratic Oath of conversations: Do no harm. We’re all terrible at realizing when we bore others because, well, we all think we’re just fascinating. The number one tip for never boring anyone comes from Scott Adams: Be brief, be positive. If you’re always to the point and stay upbeat, it’s extremely hard for anyone to accuse you of being poor company. But sometimes you do need to speak a little longer to make sure things don’t get stilted. The Art of Civilized Conversation offers another good tip: Is anyone asking you questions about what you’re saying? If not, maybe it’s time to end the story or ask the other person a question.

(More rapport building techniques are here)

2. The most captivating people are often good listeners.

Impressing people can be great but it can also devolve into status jockeying, one-upmanship, and envy. People love to talk about themselves and there are a dearth of good listeners. Let the other person talk. It gives their brain as much pleasure as food or money:

Talking about ourselves — whether in a personal conversation or through social media sites like Facebook and Twitter — triggers the same sensation of pleasure in the brain as food or money… [Barking Up the Wrong Tree].

You can make an excellent impression by saying amazingly little. Ironically, the people we like the most often say the least.

(Learn how to listen like a hostage negotiator here)

3. Talk about the other person’s interests.

This is straight from Dale Carnegie and if you’re not that socially adept, this is as straightforward as it gets. Why struggle to guess what most people might find generically interesting? Ask people what they’ve been up to or what their hobbies are. Then talk about that. You’re now 80 percent of the way there. If you know about the subject, the similarity will bond you. If you don’t, ask them to explain and be a great listener as they talk about something they love.

(More on the science behind Dale Carnegie’s classic here)

4. Have three good stories.

Comedians don’t just talk about anything when they’re onstage. They have their act rehearsed. You don’t just trot into a job interview and say whatever’s on your mind. Always have three good stories on hand that reliably entertain, inform, or engage. Another tip from Scott Adams: People are generally more interested in stories about people rather than things. Drama, gossip, and reality TV are successful for a reason. We all find human behavior fascinating. On the other hand, most people don’t want to hear about the features on your new iPhone.

(More on how to tell good stories here)

5. Don’t forget charisma.

It’s not all about the words. Some people are engaging but if what they said was transcribed, it would be unimpressive. When you’re speaking emotionally, the words only account for 7 percent of what get conveyed. Seven percent. Voice tone and body language are far more important.

One often quoted study (Mehrabian & Ferris, 1967) found that of all the information conveyed to another person when we say something that is emotional (not informational), only 7 percent is contained in the actual meaning of the words we use. [The Heart of Social Psychology: A Backstage View of a Passionate Science].

Laugh. Smile. Be passionate. Gesture. Modulate your voice. Don’t just sweat the words.

6. Be somewhere interesting.

Got a say in where you’ll be at, as with a date or meeting? Pick someplace stimulating. Context matters. In general, we’re lousy about realizing where our feelings are coming from. Research shows excitement from any source is often associated with the person you’re with — even if they’re not the cause of it. Why do people find musicians so captivating? The music and the crowd stimulates emotions — and we viscerally associate those with the band.

Why does this happen? Ariely thinks it might have something to do with “misattribution of emotions”: “Sometimes we have an emotion and we don’t know where it’s coming from, so we kind of stick it on something that seems sensible.” In other words, your strong feelings about the music might make you think you’re having strong feelings about the lead singer [MIT Behavioral Economist Dan Ariely].

(More on the power of context here)

7. And most importantly: Live an interesting life.

Remember the theme of Don Quixote: If you want to be a knight, act like a knight. If you don’t read, watch, and think about generic things, generic things are less likely to come out of your mouth. This doesn’t need to be expensive or difficult. Hang out more often with the most interesting people you know. The friends you spend time with dramatically affect your behavior — whether you like it or not. The Longevity Project, which studied over 1000 people from youth to death had this to say: The groups you associate with often determine the type of person you become. In The Start-up of You, Reid Hoffman and Ben Casnocha talk about how the best way to improve particular qualities in yourself is to spend time with people who are already like that. The best and most reliable way to appear interesting is to live an interesting life. And to pursue that ends up being far more rewarding than merely making a good impression on others.


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More from Barking Up the Wrong Tree.

It’s easy to be boring. It’s harder to be interesting. Want to learn how? Jessica Hagy offers the following advice, excerpted from her book “How To Be Interesting.”

Go exploring.

Explore ideas, places, and opinions.

The inside of the echo chamber is where all the boring people hang out.

Expose yourself.

To embarrassment. To ridicule. To risk. To strange events and conditions. To wild ideas. To things that make you cringe. To strange vistas and new sounds. Trust me. It’ll be fun.

Become a spy.

People watch. Eavesdrop. Lurk. Loiter. Listen. And you’ll learn the secret codes of others. Every day can be an interesting recon mission.

Tweak the schedule.

Wake up before the alarm. Steal moments between stoplights to compose poems. Sneak off to a moonlit spot when you’d otherwise be watching something on a glowing screen. Work at night and play in the daytime. Carve out hours for the dreams you’ve been putting off. There’s always time to explore. You get to decide when it is.

Keep asking why.

Parents hate it when kids do it.

And on and on. But try it. You’ll be surprised at how quickly a simple Why? can turn into a fascinating Because.

Share what you discover.

And be generous when you do. Not everybody went exploring with you.

Let them live vicariously through your adventures.

Instigate.

Do not wait until tomorrow. Say, do, or make it now. Go where you need to be. Do not wait to be invited places. Host your own parties. Do not sit by the phone. Pick it up. Spread the word. Press the buttons. Buy the tickets and enjoy the show.

State the obvious.

What’s known to you is often a mystery to others. Your old fact is someone else’s new lesson. Your simple task is someone else’s impossible chore. Your mind is full of treasures that no one else has seen. Pass them on. An idea shared is not diminished: It’s multiplied.

Do something. Anything.

Dance. Talk. Build. Network. Play. Help. Create. It doesn’t matter what you do, as long as you’re doing it. Sitting around and complaining is not an acceptable form of “something,” in case you were wondering.

Sign up.

Join a club. Take a class. Volunteer. Have a party. Take a meeting. What we do shapes who we are. Be someone who’s been there, done that, and wants to do new things tomorrow.

Earnestly enjoy yourself.

Irony gets in the way of experience. Drop the pretense, and you’ll have room to carry the day.

Sing along to cheesy pop music. Enjoy things that are out of style. Make silly faces. Stop stifling your giggles.

Give yourself permission to enjoy yourself.

Tinker.

Start with a wonder. How does this work? What makes that happen? Then poke. Take things apart and put them back together. Push buttons. Change settings. See how the pieces fit. See what powers the engine. See how interesting it all is.

Many people see themselves as boring or not very interesting. As a result, they minimize social contact, or feel self-conscious and awkward when interacting.

Having a self-image of being uninteresting can lead to isolation and loneliness, while eroding self-worth.

A fascinating inquiry is to explore what makes us interesting. Is it our net worth, our accomplishments, or knowing people who are popular? Maybe these factors create a curious image that some people find appealing. But do we want people to find our image interesting or find us interesting?

The key to making us interesting is not what we’ve achieved (although this might have superficial appeal), but rather who we are as a person. We become more interesting as we know and show our authentic self to people. We bring more aliveness to our relationships as we notice and reveal our true feelings and desires. It’s not what we’ve done with our lives, but sharing the life that exists within us in this moment, whatever it happens to be — taking the risk to reveal our true emotions and desires.

Let’s say we’re on a date and feel an attraction. Do we communicate that or keep our feelings inside? If it’s the first date, we might bide our time and get to know the person better. But if we say nothing — if we reveal little about ourselves — how we feel about things, or how we’re experiencing our time together, the person may think we’re not interested in them… or that we’re not very interesting.

Nurturing a connection involves expressing our fears, hurts, hopes, and joys. We convey what delights our heart, what makes us feel alive, and what keeps us up at night. We take a risk to share these things. If we never reveal ourselves in a way where a person can “feel” us as a human being, we risk being boring. If we stay in our head or become overly self-protective, we remain isolated.

This is not to say that we should have no boundaries. We don’t want to scare people away with sloppy boundaries or make assumptions about how intimate they want to be with us. We need to gauge what we feel safe sharing and what might wait for another day — when more trust has grown.

Being Attentive to Others

We also become more interesting as we show genuine interest in knowing another person. How often does someone appear to be curious you! It feels good when it happens, yes? I would suspect that a person who extends attention to you and knows how to listen becomes interesting to you. Can you offer that same gift of listening to others

Deep listening means quieting our mind and being present to hear another’s feelings, thoughts, and concerns. Notice where your attention goes when you’re with someone. Does it wander off? Are you preparing your response? Can you return to the present moment and be curious about the person across from you? Can you ask them questions about themselves — and gauge your comfort level in asking more questions based upon their response?

Throughout the life of a relationship, we nurture connection by finding a rhythm between revealing our inner experience — and listening to others’ experience.

Cultivating Connection

Relationships flounder or deteriorate when we withhold our important feelings from each other. I often notice how couples often offer their analysis, opinions, and criticisms of each other, but not their feelings and longings.

They might say, “You’re selfish and uncaring,” but not disclose the felt experience that underlies these hurtful judgments, which might be something like: “I’ve been missing the connection I once felt with you. I’m lonely for you. I feel scared that we’re drifting apart and worried that we won’t find our way toward each other.”

We become more interesting — that is, we create a climate for an interested and alive connection — when we expose our tender, vulnerable feelings. Hearing our partner say “You’re self-absorbed” is likely to push us away. Hearing “I want more quality time with you” or “I enjoy your company” is more likely to pique our interest and move us to listen and respond positively.

Approaches that help us connect with our felt experience, such as Focusing (Gendlin), can help us connect with ourselves more deeply. Our relationships can deepen by sharing our experience with others. But first we need to be mindful of what we’re experiencing and then find the courage to reveal it to selected people.

Becoming Interested in Life

A key to initiating and sustaining intimate relationships is to not be so concerned about being interesting, but rather pursue a life where we become interesting to ourselves and where life becomes fascinating for us. Are we doing what nourishes us, enlivens us, and expands us? Are we following our interests in music, art, dance, nature walks, gardening, yoga, meditation, or whatever might help us feel good? Are we living a mindful, connected life (as much as possible) or are we going through the motions — living what psychologist Tara Brach calls a “trance of unworthiness.”

As we become more engaged with life, we feel more alive. We live with more meaning and poignancy. We enjoy moments of good humor, joy, and laughter. We share our experience and are receptive to others’ experience.

We become more interesting because we are interested — in people, in life, and also in ourselves. We are interested in growing and living with more love and joy in our heart. All this attracts people toward us. And remember to be gentle with yourself. All of this takes practice. We don’t have to do any of it perfectly.

If you like my article, please consider viewing my Facebook page and books below.

Last medically reviewed on September 17, 2017

How to be more interesting

Everyone wants to be that charming, magnetic person at the party who everyone wants to talk to. Not everyone is naturally gifted with that kind of charisma. But according to a fascinating thread on question-and-answer site Quora, everyone has the potential to become interesting — or at least more interesting than they are now.

In response to the straightforward question, “How do I become an interesting person?,” CEOs, speakers and other professional (and amateur) charmers shared some of their tips and tricks that can transform anyone from dull to delightful.

1. Be curious.

The easiest way to be interesting, according to several respondents, is to be interested. “Curiosity leads to the accumulation of new experiences or viewpoints with which to view the world,” explains Moses Namkung, a quant analyst at Google. Which gives you plenty to talk about and ways to meaningfully connect with others.

Helpfully, “knowledge has never been as accessible as it is now,” insists CEO Evan Asano, who advises those looking to up their curiosity quotient to “read, listen to podcasts, find great websites. Learn from interesting people.”

2. Do new stuff regularly.

Being curious and consuming information is one great way to become more interesting, but so is doing new stuff. “You collect interesting tidbits by experiencing the world,” writes Shakespearean director and software engineer Marcus Geduld. The key “is doing stuff that changes you. It doesn’t have to be a huge change, and usually it won’t be. It could just be that you went to a new restaurant or learned a new fact. you have to make yourself interesting by doing interesting things,” he adds.

Asano calls this “seeking adventure,” though he doesn’t necessarily mean big, scary adventures like trekking across the Sahara or jumping out of a plane. “Adventure doesn’t have to mean traveling to another another country or involving expensive gear,” he notes. “Seeking adventure can be through travel, sports or the outdoors, but it definitely means getting out of your comfort zone.”

3. Have a passion.

You can acquire stuff to say by consuming information broadly (‘be curious’) or by seeking out fresh experiences (‘do new stuff regularly’) but you can also make yourself more interesting by delving more deeply into subjects you already know something about. “Interesting people have hobbies they pursue passionately,” writes Asano.

4. Kill the small talk.

Talking about the weather might be safe but it’s also guaranteed to be boring. “Small talk is verbal static,” warns Jeff Kirkendoll-Chapman, a customer service rep (aka “professional talker,” according to Kirkendoll-Chapman). Still, he says there is some value in chatter about the weather, at least as a starting point. “In the static, people will drop keywords that matter to them. Your task is to identify those words and focus your responses to draw that person out.”

5. Actually care about people.

“Everyone’s favorite subject is themselves,” Kirkendoll-Chapman believes. Therefore, if you can’t get interested in others, they’re not going to find you a very congenial conversation partner. “When someone talks about their kids, or their lack of snow tires, or what happened on The Voice or Games of Thrones or whatever… You have to care. If you don’t genuinely care, then you need to do an Oscar-winning performance that you care,” he adds.

6. Hone your storytelling skills.

Having something to say is only half the battle, you also need to know how to say it. This is where storytelling skills come in very handy. “Storytelling is a deliberate act. You don’t just dump whatever is on your mind into the conversation; you purposefully shape it to make it interesting,” explains Geduld.

“You need to learn what’s too long and what’s too short, which depends on your audience and their moods (you need to learn how to read people); you need to learn to make your experiences visceral, which means describing the cheesecake you ate in a way that makes your listeners taste it; you need to learn how to to tease by withholding information until people are itching for a payoff; you need to learn about story structure: beginnings, middles, and ends,” he elaborates.

7 Be your (weird) self.

Your quirks are what make you interesting. Trying to fit in all the time is a sure fire way to sand off the rough edges that others will find fascinating. Founder Julian Reisinger urges readers to “be a true original.” He explains that “most people try to fit in in order to be liked. True originals don’t bend their behavior to match the expectations of others,” though he cautions that “staying true to yourself doesn’t mean pissing other people off intentionally. Knowing when to shut up is an art in itself.” Asano likewise recommends that if you want to be interesting, you should be bold enough to “be unconventional.”

What made the most fascinating people you’ve ever met so interesting?

How to be more interesting

There are few pleasures in life better than a great conversation. When you truly connect with someone, time stands still, space contracts, and you leave whatever event you were at feeling truly alive.

On the other hand, there are few miseries worse than a night of endless small talk. An evening of surreptitious glances at the bar and awkward silences will leave you as drained and depressed as a night of new friendships will leave you exhilarated.

So how do you turn one into the other, moving from small talk drudgery to genuine human connection? You get better at small talk, obviously — or to be more accurate you learn how to get beyond small talk and into the realm of real conversation. Quora can help.

The question-and-answer site crowdsourced wisdom for a user who wanted to know how to get better at small talk, gathering useful tips for anyone who wants to grow their circle of connections and make their next event way less boring (for all involved).

1. Be more interested.

If you want small talk to be more interesting, the surest route is to be more interested in your conversation partner. “If you are running out of things to say, you are not interested enough in the person you are talking with,” insists angel investor Kai Peter Chang in the thread’s most popular answer.

“If you don’t fundamentally care about the person you are speaking with, that will show,” he writes. “So the first fix is your own attitude — if this is someone you don’t care about that you are simply pretending to care about, cut your losses, say ‘it’s nice to meet you’ (yes, lie) and move on.”

Writer Ellen Vrana offers some advice: “Imagine a robot saying ‘I find you interesting.’ Creepy. Words alone don’t work. To convey a genuine sense of interest, you have to emote. Lean forward. Make eye contact. Show them that you are listening and care.”

2. Ask open-ended questions.

There’s absolutely no trick that can make one-word answers exciting, so the only solution is to avoid them. It’s all about phrasing, insists art director Craig Weiland. “When you ask someone a small-talky question, be aware of how the question is phrased, and always defer to open-ended structure in your phrasing of questions rather than ones with a simple yes or no answer,” he advises.

“For example, ‘Are you here with your family?’ is a question that can be answered with a simple ‘yes’ and then you’re left holding the bag again. ‘Whom are you here with?’ invites them to share new information of their own, introducing new subjects of conversation to discuss. If they reply, ‘My family,’ then you can ask about them, since the other party brought them into this themselves,” he elaborates.

“Get out of small talk phase by asking simple questions that require more than one word ‘yes/no’ answers and pay attention to the responses,” writes entrepreneur Daniel Da Vinci, concurring with both points one and two in a single sentence.

3. Leverage your environment (or your wardrobe).

Talking about the weather or the traffic is the classic example of this strategy, but there are other, less painfully cliched ways to use your environment as a conversational springboard. Software engineer Robert Rapplean suggests “commenting on something in your environment. their clothing or jewelry,” for example.

It’s a technique that’s endorsed beyond Quora as well. On HBR recently, professional speaker (and therefore serial event attendee) Dorie Clark suggested a variation on this theme.

“Wearing a distinctive clothing item can be a great icebreaker, whether it’s a Madeleine Albright-style signature brooch (which can spark a conversation about the trip to Italy where you bought it), a tie from your alma mater (‘you’re a Longhorn, too. ‘), or colorful socks,” she writes, adding, that “you can also let your conversations be guided by someone else’s sartorial choices. Psychologist Richard Wiseman wrote about one man with a unique networking strategy; to avoid habitually gravitating to people just like him, he would pick a color in advance and then make a point of seeking out people wearing that color to initiate conversations and make connections he otherwise wouldn’t.”

4. Play the student.

Small talk can seem pointless and unstructured — and therefore totally painful — but most everyone understands both the how and why of teaching. So one trick is to turn an aimless chat into a learning session.

“If there’s a subject you’re not familiar with, just be honest with that person and 9 out of 10 times they’ll teach you about it,” says entrepreneur Michael Wong. “It helps if you show a healthy interest though and put effort into following what’s being said.”

5. Gamify for your own amusement.

Boredom is usually a two-way street. If your conversation partner is bored, so are you. But the opposite is also true. If you’re having a blast, it’s likely others will enjoy talking to you. So “gamify for your own amusement,” suggests social cause marketer Keirsten Lindholm. Before entering an event, she chooses a topic to find out more about and then uses small talk as an opportunity to complete her self-appointed mission.

“Sometimes I feel like finding out about secret hobbies, favorite volunteer activities or how their industry is changing,” she says, adding that “trading ideas is like weaving a story together of playful banter and should probably be regarded as foreplay to possibility. The possibility of more time with one another.”

6. Be more interesting.

If the first principle of good conversation is to be genuinely interested, an important corollary is to be more interesting. Small talk is only as small as your reservoir of topics and experiences. Expand your store of anecdotes and opinions and you’ll expand your conversational possibilities.

“Get out there and experience new things!” urges respondent Belinda Kwan. “You need to build your repertoire of interesting experiences (not only for the sake of having good conversations, but for the sake of enjoying your life).” Good advice on the topic exists if you’re not sure about how to go about becoming more interesting.

7. Give up on lost causes.

Finally, don’t forget that you’re not required to find every human being on the planet interesting (it would be weird if you did). The best thing you can do sometimes is cut your losses and end a stalled conversation in order to move on and chat with someone with whom you have more rapport.

“There are a few people who are as dull as toast. No, that’s an insult to toast. Dull as a toaster that doesn’t have toast. You won’t connect with everyone. No one does,” Vrana reassures readers of the thread.

What’s your favorite trick for better conversations?

How to be more interesting

Apr 11, 2018 · 4 min read

Everyone wants to be funny.

Really, we do. Sometimes we’re shy to admit it but everyone wants to be That Guy or Girl, the one who can crack people up with a sharp one-liner.

This is not (necessarily) fuelled by a secret desire to forge a stand-up career, but because being able to make people laugh gives the impression you are socially skilled, cool to be around, loving life, POPULAR.

Of course this is often a faca d e; some of the greatest comics in history have struggled with anxieties, depression and reclusiveness. Humour can be a temporary way of turning the darkness outwards instead of in.

Being genuinely funny is an art — and it’s difficult. Not many people can consistently pull it off (without alcohol), nor should they try. Contrived humour ( “did you hear the one about…”), especially when it doesn’t fit your personality, will peg you as more fool than funny.

While it’s true that being funny can boost your popularity, striving to be popular is a dumb goal. Striving to be anything you’re not in order to get something you want is a dumb goal.

But there’s nothing wrong with trying to be — and have — more fun. And there’s everything right in trying to make life lighter and sweeter for the people in your world.

Here are some ways to rev yourself up. If you don’t think you’re boring (or don’t know), take the test here. You might be surprised (or freaked out).

1. Make your goals spicy.

Check what you’re aiming for this month, this year and in life. If your goals make you feel tired and bored then you’re probably tired and bored with life and tired and boring to be with. Throw out the list and make a new one full of things that light you up.

2. Drop the cool act.

If your reason for getting up is to post air-brushed selfies and keep everything you say and do lined up with your Personal Brand, go away, you’re making us yawn. Don’t take yourself so seriously. You are not as cool as you think — no-one is.

3. Tell stories but know when to stop.

Telling a great story will make you a people magnet. Not knowing when to stop will do the opposite. Be aware of the difference.

4. Hide your phone from yourself.

Visible phones give others the impression you’d rather be somewhere else. Or you’re waiting for someone cooler to call. We’re all guilty of this but once you get over your offline angst, being phone-free will help you stay in the moment.

5. Initiate something. ANYTHING.

Get off the couch. When was the last time you came up with a spontaneous activity for you and your partner/family/friends — then followed through on it? Surprise them and they’ll look at you with fresh eyes.

6. Take the muzzle off.

Voice your opinions; try hard to lock your inner critic in a cage. Even if you struggle with shyness or social anxiety, take a tiny risk. You can’t get through life saying all the right things and having everyone love you — not even close — so get in the game now.

7. Screw with your routines.

Don’t be and do same old, same old, every day. Change it up. Enough said.

8. Do (or try) interesting things.

It will give you interesting things to talk about. It will give people something to ask you about. Mostly, it will give you more investment in your own life — and that excitement will radiate through you.

9. Take a conversation somewhere.

Be curious. When talking to someone, wait for their response and take it somewhere that relates to THEM. Then do it again. All roads shouldn’t lead back to yourself.

10. Smile.

I know, being told to smile is patronising. But when you see someone laughing and smiling in the world it’s human nature to want a piece of that. Also smiling is very, very easy. Why not do the simple stuff first?

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