Knowing several examples of homonyms and how to use them makes you a ninja in the dojo of witty repartee. Homonyms, like ninja, are very clever and sneak around; they pop up when you least expect them. A homonym is a word that looks and/or sounds like another word with a different meaning, so it's really important to keep an eye out.
Don't be afraid, but be wary: homonyms lurk all over the English language. It's as if they are there to confuse people. Luckily, the confusion results in a plethora of surprises and funny situations. Most jokes hinge on confusion since people find the unexpected exhilarating and entertaining. If you can get a couple examples of homonyms into your active vocabulary, you'll be the life of the party, and everyone will love to speak with you.
These jokes are not the kind you want to bring out when you're trying to win friends and influence people, but looking at them will help show the splendor of homonyms.
Consider this age-old zinger:
Q: What's black and white and red all over?
A: A newspaper!
It's difficult to imagine a time when this joke was funny, but it's easy to see why it was. The "red" in the question is obviously the color because it comes after two other colors. But when the punchline is unleashed on the hapless hearer of the newspaper joke, he finds that he couldn't have been more wrong. He should have heard "read." There's a momentary flash of confusion followed by the euphoric ah-ha effect. The ah-ha effect usually ushers in a volley of ha-ha's, and fun is had by all.
Historic figures are not immune to the hilarity of homonyms either.
Q: What's purple and conquered the world?
A: Alexander the Grape!
Not quite the knee slapper either, but this joke is an even better example of homonyms in action. Grapes are purple, and "grape" sounds close enough to "great" to act like a homonym here, but that's not nearly all. Concord is a type of grape, and "concord" is a homonym with "conquered." It's really quite clever when you think about it, and the leaps of the mind to make all those connections in a few moments is pretty amazing not to mention enjoyable.
Another thing that's great about homonym jokes is that they make sense of an entirely absurd scenario:
A string walks into a bar and asks the bartender for a Singapore Sling. The bartender regards him with a scornful eye and says, "We don't serve strings here!" Downtrodden but resilient, the string leaves the bar with a theory of how to get back in. He messes up his hair, ties himself up and walks right back in. The string orders another Singapore Sling. The bartender leers at him and says, "Aren't you that string that was in here just a second ago?"
"Nope," the string says, "I'm afraid not."
A lot is going on in this absurd little anecdote, but most of what's funny lies in the homonym in the punchline. "I'm afraid not" sounds exactly like "I'm a frayed knot," which is truly what the protagonist has become by the end of the story. Of course, there's the idea of a string ordering a "sling," which is a cocktail, a weapon made of string, and a word that rhymes with "string." Then there's the bit about a string having a theory, making it a string theory. However, as much fun as one's brain might have making those connections without its owner's knowing it, the homonym at the end is the part of the joke that really brings the thing home.
Naturally, these are all kids' jokes and not for everyone, but the better you get at using homonyms and recognizing them in your daily interactions with people, the more you will impress others with your wit. Next time someone is talking about gene therapy at the office, you can comment on the fact that young people purposely cut holes in theirs for fashion and that, although you don't understand the waste of good denim, you support their right to choose. If you try it too early in the morning, you might reap little more than strange looks. If you keep smart company after coffee though, you'll harvest at least a few chuckles.
Not all homonyms are created equal, and not every example will render desired results. Indeed, your miles may vary with every homonym pair. Start listening to people and how people's statements can be interpreted differently from how they intended. Also, there are great spots online to find out more about homonyms.
Another reason to pay attention to your homonyms is that they are very easy to get mixed up when they matter. It's hard for fastidious writers to respect those who are discourteous to their grammar, so you don't want to appear too lazy to keep track of your homonyms!
Here are some examples of homonyms that are commonly messed up (especially online):
The last example has some 1337 speak in it because much of the internet seems unable to get their homonyms straight. A n00b is someone who is new at something, and 1337 means elite.
Homonyms are pretty easy if you're paying attention. Remain vigilant, and you will quickly earn your black belt and become the envy of everyone you meet.