The Art of Making People Laugh: How to Tell a Joke That Lands

Humor is a powerful tool. It can break the ice in awkward situations, lift someone’s spirits on a tough day, and even diffuse tension in the most uncomfortable circumstances. But there’s an art to telling a joke that lands. Anyone can crack a punchline, but creating the kind of humor that people genuinely connect with takes skill, timing, and a bit of personality. Jason Colotario’s Laugh Lines: A Journey Through Life’s Funniest Moments offers a behind-the-scenes look at how humor can become a bridge between people, how to use it effectively, and how a well-placed joke can make all the difference.

So, how do you craft a joke that hits the mark every time? Let’s break down some key takeaways from Colotario’s experiences as a humorist and dive into practical tips that will have you telling jokes like a pro.

1- Keep It Relatable

One of the most important things to remember when crafting a joke is to make it relatable. Colotario highlights how humor is at its best when it connects with people’s everyday experiences. Whether it’s poking fun at the awkwardness of a grocery store run or making light of those parenting moments that everyone can identify with the most successful jokes are the ones that make people say, “I’ve been there.”

In his book, Colotario reflects that humor doesn’t need to be grand or complex. For instance, a simple dad joke, like the one he shares in the grocery store, can create instant connections. When you joke about something people experience, they are likelier to laugh because they see themselves in it.

Tip: When considering your joke, ask yourself: “Who can relate to this?” A joke about spilling coffee on your shirt might not make sense at a black-tie event, but it will resonate with someone who’s had a hectic morning. The simpler, the better.

2- Timing Is Everything

A joke is only as good as its timing. The correct setup and punchline at the right moment can turn an average joke into a hilarious one. Jason Colotario shares how humor is often about finding the perfect moment to insert a joke, especially in everyday situations. It’s the difference between telling a story that drags on and a perfectly timed one-liner that catches everyone off guard.

In Colotario’s personal experiences, the delivery often differentiates between a joke falling flat or getting the laugh it deserves. For instance, his experience with a dad joke at the checkout counter—where he quipped about Matthew McConaughey’s house—wasn’t about the joke itself. It was about knowing when to tell it. The cashier had had a long day, and Colotario’s timing was just right to lighten the mood.

Tip: Practice waiting for those natural pauses in conversation. It’s not just about what you say but when you say it. Make sure the timing fits the flow of the moment to maximize the impact of your punchline.

3- Be Confident—Even If It’s a Risk

Sometimes, a joke is a gamble. As Colotario admits, humor can be risky, and there are moments when you throw out a joke without knowing if it will land. But confidence is key. Even if the joke doesn’t get the laugh you hoped for, committing to it fully can make the experience fun for everyone involved. In his book, Colotario shares a moment in a grocery store where, despite the joke being a little out there, the confidence in his delivery turned what could have been an awkward interaction into a shared, lighthearted experience.

People are often drawn to confidence. If you believe in your joke—corny or clever—there’s a good chance other will, too. Confidence helps to disarm any potential awkwardness, and even if the joke doesn’t land, the energy you put into it can keep the mood upbeat.

Tip: Don’t hold back. If you’re unsure if a joke will land, go for it anyway. A confident joke can make an awkward moment funnier, even if it doesn’t get a huge laugh.

4- Don’t Force It

There’s nothing worse than a forced joke. When humor feels too rehearsed or unnatural, it often falls flat. Colotario emphasizes the importance of letting humor flow naturally. Humor should feel organic; not like you’re trying too hard. The best jokes are the ones that come in spontaneous moments or unexpected situations. Colotario’s anecdotes about making people laugh in real life, from a grocery store to family events, highlight how humor works best when it feels genuine.

Humor that arises naturally often feels more authentic. When you force a joke, it can feel out of place. Humor should enhance a conversation, not feel like a distraction from it.

Tip: Don’t feel pressured to be funny all the time. Some of the best jokes come out of the blue, so let your humor arise naturally from the moment. People appreciate jokes that feel authentic.

5- Laugh at Yourself

Finally, one of the most important lessons in Laugh Lines is learning to laugh at yourself. Colotario shares personal stories about his mistakes—like the time he messed up a bathroom repair or his “Screech”-like singing performance—and how those moments have become sources of laughter. He reflects on how embracing life’s absurdities, rather than taking yourself too seriously, can make you more endearing and funnier.

When you can laugh at yourself, others will be more likely to do the same. It shows humility and a willingness to embrace imperfection. Plus, people love self-deprecating humor—it’s down-to-earth and relatable.

Tip: Don’t be afraid to share your embarrassing moments. A story about your latest blunder can be a great way to get others to relax and share their own experiences. People love to laugh with you, not at you.

Conclusion

Telling a joke that lands isn’t about having a great setup or punchline—it’s about connection. Humor is a bridge that connects people, breaks down barriers, and lifts spirits. From Colotario’s journey as a humorist, we learn that the art of telling a great joke lies in relatability, timing, confidence, and a willingness to embrace the lighter side of life. So, the next time you’re about to tell a joke, remember: it’s not about being perfect. It’s about creating a moment of shared laughter and making someone’s day a little brighter.

Crafting the perfect joke is a skill anyone can master—and with the right approach, it could be the key to making real connections, lightening the mood, and bringing a smile to someone’s face.