We’ve all been there, trying to have a conversation with someone new and exciting, and it’s just going nowhere. You try everything, jumping from one topic to the other and nothing clicks.
Do you like music?
Yes.
What’s your favorite music?
All kinds.
What’s your favorite food?
IDK, I like a lot of stuff.
Do you watch TV?
Yeah.
What do you watch?
Lots of stuff.
What’s going on? Is it your fault? Are they not enjoying this conversation at all? Is this just the most boring person ever? Why aren’t they engaging?
The problem is that these questions either aren’t open-ended or (somewhat ironically) they’re TOO open-ended.
When it comes to starting a conversation there are three types of questions:
These are sometimes called closed-ended questions because a simple yes or no answer closes the question.
They’re very good for exchanging simple information, but not so great for starting conversations. That’s because your brain considers the exchange closed once you’ve given or gotten the answer, and even if there are follow-ups, it breaks up the flow of conversation in your brain. It’s never a good thing.
These are the questions you remember from grade school. Who? What? When? Where? Why?
They’re also called open-ended questions because the answer can be just about anything. Things like “What’s your favorite food? Who’s your favorite actor? Where is your dream vacation?” They can have hundreds of answers and can open the door to discussion or disagreement.
The sheer number of answers available can also be a problem. If you have too many options to pick from, sometimes your brain just shuts down. Have you ever asked someone what their favorite song is? Only to watch their eyes go blank as their brain crashes because it’s trying to remember every song they’ve ever heard? If your questions are too general, you’re going to get a packaged answer, or the dreaded “I don’t know.”
Sometimes these are called “choice questions.” These are simple questions that give the person being asked the choice between two options (though sometimes more). While they are technically another form of closed-ended questions, they’re more complex and engaging. These are usually the best choice when trying to break the ice or strike up a new conversation.
The best way to start a new conversation, or keep one going, is by asking this or that questions. That’s because they require thought and engagement, but aren’t going to have an overwhelming number of answers. They also leave the conversation open to follow-up questions or having the question turned around on you, both of which mean the person you’re talking to is engaging!
As an example, if someone asks you if you prefer hip-hop or rock music you’re thinking about an answer, you might even be thinking of what your favorite songs or artists in that genre are. A question like that is going to be far more engaging than one that can go anywhere, or nowhere.
This or that questions are also great because they can be adapted to any setting. They can be a casual way to get to know coworkers or have a conversation on Snapchat or Tinder. As you get to know someone better, you can ask flirty, even dirty this or that question.
The great thing about this or that questions is that they feel simple and conversational. There’s not the same pressure to be amusing as if you were playing a game, plus offering to play a game can feel a little awkward and forced if it’s your first conversation.
That said, this or that questions can easily be turned into a game if you want your conversation to feel a bit more unique and exciting.
“Would you rather…” is the most popular variation of this or that question, and one that can allow you to show off your creative sense of humor by coming up with funny questions, or creative ways to answer the other person’s questions.
Questions can be simple, and in the same vein as the basic, this or that questions, like “Would you rather never have dessert again, or never have pizza again.” They can be about things like daydreams or fantasies, like “would you rather be able to fly or teleport.” Some of the best Would You Rather questions are absurd, like the (in)famous “Would you rather fight 100 duck-sized horses or 1 horse-sized duck?”
Of course, like this or that questions, would you rather questions can also be dirty and involve real or imagined sexual fantasies.
This is a way to get the person you’re talking to engaged as well. You ask this or that questions until they give an answer you don’t agree with, then you switch, with them asking the questions until you give an answer they don’t agree with.
Of course, this requires a bit of cooperation and honesty, but if you can’t get that, there’s no game that’s going to work.
The beauty of this or that questions is that they’re pretty simple, but if you’re having a hard time getting started, or you’ve run out of ideas, here are some new this or that questions to ask.
Whether you use this list or make up your own, this or that questions are the best way to get to know someone new and keep a conversation going!