Dear Red Monkey,
I often feel anxious when chatting to friends—say I’ve been invited to a braai or a lunch or whatever—and it’s especially bad when the people there aren’t natural conversationalists. I end up mentioning the weather, and then there’s a lot of chat about the weather. But later, there are these awkward moments of silence. I think, “Now what?”
I try the usual things: asking how people are doing, what they’ve been up to, and so on. But then another silence creeps in, and I—as usual—get nervous and just start saying anything that comes to mind. I know I’m overthinking things. Maybe people are just tired. Maybe they’re thinking about what they’re going to do tomorrow. Maybe they’re trying to come up with something to say themselves.
Still, I always feel embarrassed afterward. I worry that I hogged the conversation, said too much, or bored people. Maybe silences are fine? I don’t know. Some people are amazing at getting the conversation going—they can talk non-stop, especially about themselves. Others are more reticent, and they don’t “egg you on,” so it’s hard to keep things flowing.
Sincerely,
The Scaredy Cat Conversationalist
Dear Awkward,
I’m not entirely sure what your question is. Are you saying you’re boring? That you haven’t mastered the art of conversation? That you’re hopeless and need rescuing? Don’t you have anything to say?
Perhaps write in again and be more specific.
But since you’re here—and we’re talking—I’ll share a few tips, even though I’m not from the chattering classes myself.
First off, don’t overthink it. Be natural. Let things flow. Sometimes conversation is a stream, sometimes a trickle, and sometimes just a nice shared silence. If you’re worried about keeping things going, try making a simple statement rather than asking endless questions. For example: “I watched a great show the other night—it really surprised me.” That’s a statement. And if someone wants to jump in and share what they’ve watched, they will.
Asking questions is fine, but if you fire off too many in a row, you’ll sound like a customs official. So mix it up. Share a little about yourself, then open the door: “I went to a few shows recently and really enjoyed one at the Baxter. Have you seen anything good lately?” That’s a gentler, more engaging way to connect.
Of course, tailor your topics. Don’t ask about theatre if you know someone hasn’t been out in months. Read the room. The occasion, the people, the mood—it all matters. And the golden rules? Avoid deep philosophical debates, religion, politics, personal confessions, and please don’t skinner. Nobody likes a gossip, even if they lean in to listen.
Anyway, if you really want help, be more specific next time. As for me, I’m a red monkey—not a red carpet regular—so I rarely speak to humans. And when I do overhear them, honestly, I think they’re talking the biggest load of nonsense anyway.
With a shrug and a swing,
Red Monkey
About: Dear Red Monkey
Dear Red Monkey is not known for sound advice, and not especially trying to be.
Red Monkey tolerates the angst of human beings with a twitching tail and a raised eyebrow, but never truly understands them. Advice is delivered with a whimsical paw, a touch of mischief, and absolutely no guarantees. Read at your own risk—and preferably with a banana in hand.
