On Being Funny & Connection

One of my favorite first date questions is: What do most of your close friends have in common?

I’d say the majority of my best friends are funny.

I don’t think I’ve prioritized funniness above all else when curating my inner circle—it seems to have happened naturally.

A big part of being funny is the ability to surprise the other person. If you always know what someone is going to say next, odds are they’ll never say anything that makes you laugh. Laughter is a spontaneous reaction of surprise and joy.

Saying something unexpected requires you to have novel thoughts. So, you have to be a somewhat original thinker to be consistently funny. There are of course other elements to being funny such as timing, delivery, and physicality. Because of this, not all original thinkers are funny — not every dog is a poodle. But all funny people are original thinkers.

When I think about funniness this way, it makes sense why my friends are funny. One trait I do prioritize when choosing friends is original thinking.

At least once a week, my two roommates and I will sprawl out on one of our beds or circle around a little snack in the kitchen and debrief. The charm lies not just in the sharing, but in not being able to fully anticipate their responses. I know they’ll treat me with kindness and compassion and the basics of friendship, but I’m always curious about the next words out of their mouths. I think this curiosity is what keeps friendship interesting and fun and gives it the lifeblood to last years and decades.

How can we encourage more surprising thoughts? Is it better to know what people usually say and think to spark new, surprising ideas, or is the opposite true?

Sometimes knowing the conventional response hinders creativity. You see this in action on dating apps. People will look at other profiles and then craft their own, and suddenly, everyone hates pineapple on pizza, orders tequila for the table, and loves The Office.

Yet, having a pulse of the zeitgeist feels key to being funny. My funniest friends like to read, are deeply interested in other people, and spend at least some time online.

Humor is a rebirth of life’s fragments—snippets of conversation, art, memes—gathered like scraps of metal, melted down, and fashioned into something new and unexpected. A simple soda can tab, in the hands of someone funny, becomes a spoon.

I like to think about why I love my friends.

Understanding the roots of love in our relationships can lead to more relationships and a deeper appreciation of them.

Connection feels rare and special to me. In the film “Before Sunset,” Celine reflects “I guess when you’re young, you just believe there’ll be many people with whom you’ll connect with. Later in life, you realize it only happens a few times.” The optimist in me wants to believe connection is on tap. I do believe you can get better at accessing it. But it still feels like something you have to stop and take notice of.

Connection often begins with admiration—for someone's wit, discipline, or creativity. We’re drawn to people who expand our world, who inspire us to finally make progress on our New Year’s resolutions.

Henrik Karlsson, in his essay “Looking for Alice,” suggests showing “the inside of your head in public, so people can see if they would like to live in there.” Sharing what matters to us not only reveals who we are but also invites others to see if they resonate with our essence.

The more I’ve shared my interests, writing, and projects, the more I’ve increased my surface area for connection.

It’s often said that you have to love yourself first before focusing on loving someone else. Discovering what interests and excites you, pursuing it wholeheartedly, and sharing it with the world is a form of self-love. It only makes sense that more connection will fill your life as a result of it.