Laugh at yourself first.
Yep, that’s it. Sounds simple, but it’s very hard for many people.
If you’re too insecure or uptight, you’ll have a hard time making anyone laugh (even Jimmy Fallon—and he laughs at everything).
Jack: Wow, that’s an awesome tattoo.
Jill: Thanks, my husband George actually drew it for me.
Jack: Really? That’s cool.
Not a very funny interaction, huh? What if Jack playfully admitted a weakness instead?
Jack: Really? I wish I could draw like that—I could probably draw a stick figure, but that’s about it. My skills don’t get much beyond sticks—and half the time I can’t even draw straight lines!
Why It Works
If you want to be funny, you need to be able to laugh at yourself first. Think about your favorite comedian—there’s a strong chance he or she relies on a heavy dose of self-deprecating humor —they know their own weaknesses or shortcomings and aren’t afraid to point them out in a humorous way. It’s easily one of the most common comedic techniques.
Now think about the person or people who make you feel comfortable. Likable and easy-going people are usually comfortable in their own skin and have embraced their character flaws. They are okay with being a little vulnerable. Such people are the first to admit they aren’t perfect and are happy to laugh at their personal quirks. They’re quick to admit funny mistakes or episodes of forgetfulness. They use their flaws to their advantage.
Few people want to listen to a braggart rave about how well he did on a test or how many sports cars he owns. But everyone enjoys hearing about the time you made a fool of yourself at that party—especially if you can laugh about it after the fact. Being okay with (and poking fun at) your own flaws helps you let your guard down, and it lets others take their guards down, too. It’s a small reminder that nobody’s perfect and that we’re all in this together—and that’s ok—that’s the message you’re sending. The end result is that people will often like you more after you expose an inner flaw or embarrassing experience, even of the small or trivial variety. Funny people realize their weaknesses and insecurities can actually make some interesting and entertaining conversation material.
In the olden days—I mean, in the days before GPS—I was riding in a car with my new boss, and she asked me how to find our destination. I responded rather bluntly, “I’ll be honest, I’m navigationally impaired… I’m probably the worst person to ask for directions. If I say turn ‘left,’ you’re probably better off turning ‘right!’” She quickly admitted that she, too, was horrible at navigating, and we both had a few laughs over who was worse! It was a great bonding experience.
I was chatting recently with comedian Sarah Cooper, and her number one tip for being funny in conversation was to start with honesty. Be transparent first, and the funny will come. I thought that was great advice. A perfectly groomed man sitting next to you wearing a perfectly fitted suit isn’t funny. But if the perfectly groomed man in a perfectly fitted suit accidentally squirts Dijon mustard on his pant leg, now there’s potential for funny. Don’t be afraid to take off your mask and show people your flaws. A magic thing happens when you take down your façade; you help others loosen up as well. The social tensions melt away, and the playfulness and fun seep into the interaction.
What are some of the imperfect traits, feelings, and behaviors behind your hard exterior? Irrational fears can be hilarious—what’s one of yours? Afraid of cockroaches? Talk about how you’ll never travel to NYC because you heard about how many cockroaches live there. Even though you may have a serious fear, you realize that it might be a little irrational, but you’re inviting others to laugh at you regardless.
What about recovering from a verbal blunder? Be quick to admit your mistake and make light of it next time. Arming yourself with a few comments that help you recover from mistakes will help you bounce back from mistakes (don’t think about that too hard, folks). The next time you find yourself flustered or embarrassed by a mistake, try turning the anxious situation into a lighthearted event with a self-deprecating comment like:
That story seemed so much better in my head.
That’s the first thing that popped into my head… I need to work on my internal filters!
Evidently, it was not a smart move for me to skip coffee this morning!
We shouldn’t take my car—it will probably break down on the way there!
I just completely butchered that expression, didn’t I?
I probably should have proofread more before sending it. Now you think I can’t spell above a 4th grade level!
When you take advantage of mistakes instead of ignoring them, you’re more likely to venture down fun and engaging tangents rather than experiencing awkward moments. Attempting humor is not easy because it’s not predictable—the risk involved can be unsettling and scary. That’s why it’s so important to be able to laugh at your mistakes—because mistakes are inevitable. (Sometimes, the mistake is the funniest part!) If you’re constantly afraid of making a mistake, you’ll never be funny. But if you learn to laugh at yourself, or your failed attempt at being funny, or your botched storytelling, or your awkward impersonations, you’ll begin to have the ability to make people laugh.
Stay social, my friends.