Funny Things to Say to Someone I Don't Really Know
Humor has a way of making friends of strangers. Find a way to say something funny to a person that you don't really know, and it will work to break the ice between you. Whether you are the class clown or quiet and shy, you can use humor to help others relax. Just be sure to never put the other person down in the process -- the goal is to laugh with him, not at him.
Tell a funny anecdote about yourself, to make the other person laugh and also help him to get to know you better, says communications expert and author of the book, "Small Talk, Big Results," Diane Windingland. For example, you might say to a new classmate that you don't know well, "The other day I tripped running from the change room after gym class. I would have been less embarrassed if it hadn't been because my shoes were on the wrong feet." Funny stories about your life show that you don't take yourself too seriously.
Make a funny observation about the situation shared by you and the person you don't know well. If you are riding on a bus together, say something like, "If this bus runs any slower, that elderly man is going to pass us in his scooter." Choose something that you have in common or something common to both of you at the moment, but be sure not to complain too much. Unless you can be hysterically funny, keep your complaints to a minimum.
Simple one-liner jokes can be used with people whom you don't know well. Some simple examples from Academic Tips.org include "A computer once beat me at chess, but it was no match for me at kick boxing," "A day without sunshine is like ... night," or "What do you call a boomerang that doesn’t come back? A stick." Just be careful not to go over the top or become bothersome with these types of jokes. If the other person smiles or laughs, consider it a success and move on.
4 Comical Hypothetical
A comical hypothetical usually starts with the words, "Wouldn't it be funny if..." according to Mark Peters in the "Psychology Today" article, "Conversation: Wouldn't It Be Funny If..." For example, you might say to your new acquaintance, "Wouldn't it be funny if our desks all faced the back of the room and the teacher couldn't see our faces?" Your new friend would then chime in with his own funny addition such as, "I could yawn and nod off as much as I wanted and never get in trouble." The idea is to set up a funny imaginary situation and build from there.