When Your Joke Goes Bust, Adjust

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Have you ever tried to say something funny, only to realize not everyone realized it was a joke? So then you try to explain that you were kidding, but at that point it’s awkward and you just prefer to crawl into a hole?

Now I’m not talking about people that say things they actually mean but try to pass them off as a joke because they’re too passive to say what they really mean (“Oh, you never return my stuff! I’m just kidding…”). That drives me crazy.

No, I’m talking about the opposite scenario, where you really DID mean something as a joke but the person thought you were serious. You quickly realize your sense of humor doesn’t mesh with the other person's, and you have to adjust for future interactions.

It’s happened to me a couple times lately. Here are two scenarios:

Flop #1:

Recently I met a colleague of a friend (let’s call him Andy) from back in Houston. I knew they had gone to medical school together, but after talking to him found out they went to undergrad together, too. Trying to make friendly conversation I said, “Oh, wow, I bet you could tell me some good stories about Andy from back in the day!”

The man was silent for a minute, thinking. Then he shook his head and said quite seriously, “No, not really.” Silence.


Truly I wasn’t really fishing for adventures at drunken frat parties or embarrassing stories. I was simply trying to break the ice, make conversation. It was the type of comment where you would expect a laugh or at least a smile and then move on to talk about the weather or whatever small talk you discuss with someone you just met.

It was a bit awkward after that.

Flop #2

I picked up my daughter from preschool and found this in her cubby:


I’m pretty sure it was supposed to be a snowman. I laughed, joking with the teacher that we had a Picasso on our hands. As I gathered up her things I overheard the teacher telling another mom that she saved a piece of her son's artwork for the end of the year art show. I interjected, “What, you didn’t want this one for the art show?” I had a huge smile on my face and thought it was pretty clear that I was kidding. I mean, come on. Look at it.

But the teacher looked mortified and stammered… “Well, we can only save one piece from each student and….”

Oops. Apparently she thought I was serious. I felt terrible and tried to backpedal and explain that it was a joke, no hard feelings that my kid’s "snowman" wasn’t saved. It was awkward and I left feeling dumb. The last thing I wanted to do was make that sweet teacher feel bad. Once again, I was just trying to make funny conversation and it backfired.

What Have I Learned?

First off, not everyone has the same sense of humor. And that’s ok. I can adjust. The first guy I’ll likely never see again, and if I do I’ll be polite. But let’s face it, he’s never going to be my BFF. Honestly he wasn’t very much fun. On the other hand, I LOVE the teacher and of course see her all the time. But I realized I needed to make adjustments on my interactions with her. She is super sweet but more serious and clearly doesn’t get the sarcasm I like to spew out (perhaps a little too often). And that’s fine. It takes all types and she is one of the nicest people around.

This is also a transferable lesson to professional life. People do this all the time in business, often without even realizing it. Some clients are serious and want only facts, while others like to chit chat and joke around. We present material differently to clients, bosses or potential customers based on their personality style. I recently took a test on communication styles teaching the differences between facilitator, promoter, analytical and controller personality types. Once we know how people think and process information, we know better how to sell to them. Formal training can help. So can trial and error, which is clearly how I’ve been learning lately.