08/28/2014 03:10 pm ET Updated Oct 28, 2014

How to Use Jokes, Irony and Sarcasm

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A few days ago, I was standing at the ticket booth of a theater asking to have a couple of tickets reprinted because my friend had left them in his car. I tried to be funny and said to the ticket seller, "My stupid friend forgot his ticket. Could you please reprint them?" My friend said nothing at the time, but a few days later, he told me he was really offended by being called stupid.

What I saw as humorous, he saw as hurtful. Of course I felt terrible and wondered how often I use joking, irony, even sarcasm, which I see as humorous, but which can be perceived as insulting. How can one tell when it is okay to joke and when it isn't? Realizing I had been insensitive to one of my best friends and that only a close friend may feel confident enough to say, "You hurt me," I worried that I do this to others who, unbeknownst to me, also react negatively.

Teasing, joking and making fun of ourselves and each other can often create intimacy, diffuse barriers and bond friends and colleagues. Joking about myself with self-deprecating remarks is usually OK, but even then some people are literal and will reply to my remark about being so stupid about something with, "No, no, you are not stupid -- you're smart." To the question: "How are you?" I have answered with the absurd statement: "I'm perfect and improving," and then been told in a parental tone, "No one is perfect."

I often use irony as a reverse of the expected. For instance, if someone says, "I will have to work late for the next few days," I might say, "How exciting!" as opposed to "What a bummer." It really says the same thing; the tone of voice highlighting the intended incongruity.

Sarcasm is a different story. It can by funny, but hurtful at the same time. Never use it with someone who would not feel free to reciprocate or who might be especially sensitive. An example of sarcasm used at White Sands, the retirement community where I live: our executive director said, "We are getting a new bus." A resident retorted, "In our lifetime?"

I joke and use irony with people I am fond of -- I assume they know I like them and will take it with a grain of salt -- but this is not necessarily true. Some people feel vulnerable when joked with.

I am not very good with boundaries and tend to cross the line thinking I am being terribly funny, when, in fact, I'm being hurtful. The problem is that people seldom admit to being hurt, because that makes them feel even more vulnerable when they think they are under attack. Even if your intent is clearly to be humorous, they may be wonder if you have a secondary motive because some jokes have an element of truth.

How to tell why a joke you have just told has gone sour? One way that may help is figuring out what went wrong by looking at the following components.

1. The Teller: What was your intent, to be funny or punishing?
2. The Receiver: Do you know if this person has a potential sensitivity to a particular topic?
3. The Content: Topics such as race, gender, religion, sexual orientation, politics and one's appearance may be off-limits for some people.
4. The Tone: The tone of voice should indicate whether the statement was meant to be a joke.
5. The Culture: Some cultures allow kidding in ways which would be unacceptable in another culture, each family also has rules about which types of teasing are acceptable.

It is important to apologize for a perceived slight and when in doubt... don't!

We all love the sound of laughter, which is our reward for having been funny. Humor depends on an element of surprise. All in all, adding fun to our lives by whatever means is a worthy endeavor and, notwithstanding the possible pitfalls, it is worth the attempt.