Just a few more tips on what not to say in conversation, then next week I'll move to what *to* do.
Talking about People the Other Person Doesn’t Know. Telling an anecdote from someone else’s life, someone no one in the current conversation knows, is not usually a good idea unless the story has a strong emotional pull, e.g., they got all their skin burned off in an arson they started. Most people do not care about people they don’t know. Call us hard-hearted, but that’s how humans are. Tell your own stories about your own life.
Asking Vague, Generalized Questions. Do you like being asked “What’s new?” I don’t. I hate it. I do prepare myself for being asked this because it will always be asked of me by three or more people at even a small party. But it’s a hard question for most people to answer. It puts them on the spot to come up with something that will be interesting to you. Asking a generalized question makes people feel boring. You never want someone’s reaction to one of your questions to be “Damn--have I even done anything new or out of the ordinary in the last week? I really haven’t, have I? Geez, I’m boring.”
Think of the questions you don’t like being asked. These are the same ones other people would be thrilled not to have to answer. So don’t ask them.
Trumping the Other Person’s Story/Cleverness. If you are starting to tell a story because it’s better, funnier, more awful than the one the other person just told, stop yourself. It will come off as one-upmanship. No one wants to be with someone who makes her feel her story was boring, not good enough, etc. You want to make others feel good about themselves when they’re around you. A conversation is not about you building your own self-esteem. It’s about building the other person’s self-esteem by enjoying her stories, being interested in her life and finding her jokes funny.
It’s perfectly fine to contribute your own anecdote about your hellish Christmas with the family after someone else has just finished telling hers, but don’t do it to trump her or because you feel jealous that she’s the center of attention when your story is so much better. Tell your story because you can relate to the other person’s tale, and because you think others will actually enjoy your story (not only that you will enjoy telling it).
Am I saying that you are going to crush someone’s self-esteem if you tell a better story than she does? No--unless the person is really insecure. But you do not want someone to walk away from a conversation feeling that she came out as second best. Conversation is not a competition. *Neither* of you should walk away thinking your story was second best.
Making Obscure References that Only Amuse You. Tell those in your head. Not out loud. No one likes to have a joke or reference explained to her. Don’t do it. Ever.
Putting Yourself in a Bad Light. It’s one thing to laugh at yourself, which invites others to laugh *with* you, and another to put yourself down, which invites others to say “Oh, you’re not that bad,” or “Poor baby.” Or “What a loser.” It’s the difference between “I emailed this girl on Nerve and she never even emailed back and she was the only one on the site that was interesting to me” [Loser], and “So I check my Nerve account and I’ve got these messages from some woman who lives in Albuquerque and another woman who wants to date only green-eyed Libras, and I’m like, I can’t date either one of these women. They’re both illiterate. I live in New York, I’m a Taurus and I have brown eyes” [Funny].
P.S. It does not matter if the joke on yourself is a vast exaggeration as long as it’s funny. If you’re tempted to tell a story that makes you look bad, pathetic or lacking control over your own destiny, make sure it will make people laugh. The only exception to the it-must-be-funny rule is if you’re talking to someone whom you want to say “Poor baby, poor baby” or to your therapist.