9 Tips for Being Funny

Learning how to be funnier will make you more appealing in everyone's eyes.

After yesterday's post — in which I suggested that if you have trouble being funny, and you want to laugh with your boyfriend or partner, you should do things like watching comedies or reading The Onion — it occurred to me that my friend Teddy Wayne, who is not only a novelist but also a very accomplished humor writer, might have some better ideas. So this morning, after I did a little begging (and hog-tied him to the porch, threatening to force-feed him sea kelp and saltwater taffy if he didn't give in), he agreed to share his secrets with me. I think it's safe to say these rules will go a long way in helping you crack people up. I know I will be referring back to them myself in the weeks to come.

1. Play on the juxtaposition between what a listener thinks will happen and what actually happens in the story you tell. Freud talks about this in his Wit and Its Relation to the Unconscious. To give you an example, let me tell you more about that hike I went on over the weekend — the one I had to be rescued from? Yeah. When I called 911, I was crying, exhausted, and completely disoriented, worried I wouldn't make it to the clearing where the fire department had parked to begin their search for me. The 911 operator kept me on the phone, and said, "We have a good sense of where you might be from the GPS monitor but we're worried you may not be very close to the access road. Continue walking till you see any kind of landmark and then tell us what it is." About 60 seconds later, I was saying: "Oh! I see something in the distance. It's ... it's red ... and ... it's a truck! And on the side it says ... Oh! Oh. It says, um, Fire Department?"

2. Use the rule of three. Give two standard or fairly serious examples, and an absurd third one. For example: "The men I like best are the ones who are tall, dark, and not living in their mother's basement."

3. End on a funny word or phrase. Do this when the funniest part of a joke or quip is a single word or phrase. As Woody Allen once said, "I don't feel comfortable changing in front of a man of my own gender."

4. Build up the tension. Many conventional jokes begin with long stories that include many irrelevant or unnecessary elaborations or details because the more involved a person becomes in the story — and the more distracted she becomes by the story — the more likely she is to care about (and to be surprised by) the ending. It's a bit like he's holding his breath while you tell the story, and the longer he has to hold it, the bigger the burst will be when he finally lets it out.

5. Take something someone said earlier and play on it. For instance, a while back, Teddy was with a friend of ours when she bought a new purse. Two different salespeople said to her, "Oh, what a fun bag." Later in the day, when I met up with Teddy and her, I said, "That's such a great bag!" And Teddy said, "No, no, not great. Fun."

6. Have a running joke. In this blog, my baby fireman fetish is one of our running jokes. My penchant for jailbait is another. Part of what's appealing about a running joke is simply feeling like you're in on it; another appeal arises when you work the running joke in at an unexpected moment or in a surprising way. (Sort of the way I did when I talked about having to be rescued by the Lebanon Fire Department and then said, "Yep — I'll do anything to meet a firefighter, won't I?")

7. Discern between self-deprecation and self-pity. Everyone loves self-deprecating humor — but you should be careful to make sure you're poking lighthearted fun at your foibles in a way that makes it clear you recognize your shortcomings but have basic confidence or self-respect. (Conan O'Brien is a master of this, Teddy says.) One way to make sure this is happening is to do it with a figurative twinkle in your eye — or a literal smile. By signaling that you're joking — with a raise of your eyebrows and a grin, for instance — people will understand that you're not complaining.

8. Look for opportunities to be ironic. Make a statement that contradicts something that has just been said. For instance, if someone tells you you're a good listener, you might say "What was that?" (Teddy loves that one.)

9. If you're teasing someone, do it with affection. Don't come off as nasty or judgmental. Tease someone with the idea that you're doing it in a way that shows your affection for the person in question — shortcomings and all. One thing Teddy loves to nudge me about is the way I always say — both in person and on my blog — "What do YOU think?"

But, um ... What do YOU think? Folks, if you have more tips to add, please speak up. And if you use any of these to make a good joke, let us know what you did!