How to be an irresistible conversationalist and make people laugh more

“The key to being a good conversationalist is probably a genuine unselfish interest in others. That, and practice.” -Frank Crane

A lot of people have a difficult time with conversations with strangers, even acquaintances. I know I do. As Cal Fussman once penned: “We all know the feeling of wanting to do something so well and so badly that we try too hard and can’t do it at all.”

But I’ve worked hard to become a better conversationalist. I find I can make people laugh easier than before. And the #1 lesson I’ve learned?

Give All Your Attention — Even If You’re Bored

In the past, I’d gauge my interest in a person within seconds of meeting them. If I found them boring, uninteresting, or weird, I’d mentally decide, “This conversation will go nowhere. How can I get out of this?”

The truth is, people are hyper-sensitive to this rudeness. You can’t fake interest in a conversation without the other person knowing. Even if are bored, you can always be polite and discuss topics more for the other’s benefit.

But if you want to be a great conversationalist, you can’t be rude. People know.

You’ll probably still get bored during some conversations. That’s bound to happen. But it’s no excuse to be rude. Best-selling author Tim Ferriss put it this way: “Treat everyone like they can put you on the front page of the New York Times.” 

Someday, you just might run into that person.

People-Pleasing Actually Doesn’t Work

If your primary method of conversing involves flattery and pandering, you’re on track to be a bad conversationalist.

People don’t want empty praise or generic kudos; they respond to a real connection and honest conversation. As Emmy-nominated comedian Whitney Cummings once said of people-pleasing:

“You’re not pleasing anybody. You’re just making them resentful because you’re being disingenuous, and you’re also not giving them the dignity of their own experience. It’s patronizing.”

You’ve probably been guilty of over-flattering; we’ve all been there with our boss, our in-laws, a cute stranger. One time, I met Steve Forbes at a cocktail party and I was the most kiss-ass suck-up you’d ever seen. I doubt he remembered me despite my endless praise of him.

If you want to be a great conversationalist and create genuine laughs and connection: don’t flatter. Don’t pander. Be honest and frank.

Conversations can be awkward and stunted, leaving you feeling tense and unsure of what to say. For many people, they’re not trying to make people laugh — they’re just trying to get through it without looking like an idiot!

We can do better. The world needs better conversationalists, and will reward those who take the time to develop that skill. The best conversationalists in the world are the ones who secure better jobs, connect with more influential people, attract more attention and success, and inspire more confidence in others.

How do you do this?

Model successful conversationalists and do what they do. Invest in yourself.  

The largest rewards are often the result of small changes. Focus on being a little better, every day — the rewards for being a better conversationalist are astounding.