Conversation Kickstarters

When you’re just getting to know someone or you’ve only just met them for the first time, conversational lulls are not uncommon. Sometimes that’s ok and you both just mutually part ways or make an excuse to go say hello to someone else. But what do you do if you want to keep talking to each other? What do you do after you’ve run through the basics and no longer know what to say?

At this point you have a few options: one, you could give it up. You could just “Let it go” Frozen style and find someone else to talk to, even if you kind of liked that person. But as someone who basically lives and breathes social awkwardness on a daily basis, I’ve adopted more of an option two based strategy: ask another question. So today I’ve put together a short list of some of my favorite conversational kick starters.


“Tell me more about…”

Going this route is good for a few reasons. One, it passes off the ball of conversation from you to them. This gives you more time to think of what you might actually want to ask them about a little later and gets you out of the hot seat for a minute or so. Two, asking for more details is an easy way to show that you were listening earlier. It means that you remembered something they said and shows that you were paying attention. Third, the more you know about something, the more likely you are to have follow up questions. It keeps the conversation moving instead of stalling at superficial levels. For example:

A: So what do you do?

B: I’m a writer.

A: Tell me more about that.

B: Well, I write for….I write about…I worked on this piece with…

A: How did you get started? Was it something you’ve always wanted to do? Where do you find the inspiration?


“What’s your favorite…”

When people have a passion for something, it’s pretty much impossible to get them to shut up about it. Their whole face lights up, too. I love it. If you can get people talking about what they like, then the conversation goes from being superficial to something a lot more meaningful. For example, say that you have an interest in restoring antique cars. Since I don’t drive, cars aren’t really my thing, but your interest in the cars proves to me that you are a passionate individual and that you’re patient enough to go through the challenge of restoring them. Now I know two things about you that I didn’t know before. If we happen to discover a common interest from this question, that’s perfect. If not, I can still ask a lot of questions about something I may not know anything about. Like, antique cars. Because even if we don’t share the interest, I can still appreciate your dedication to the things that you’re passionate about; I still want to get to know you more so that we can find our common ground.


“If you had a whole day to yourself, and could really do anything, what would you do?”

This is probably my favorite question to ask people. Firstly, because there’s a wide variety of answers you can get from it. I’m constantly surprised by the things that people come up with. It will tell you if they’re adventurous, easygoing, spontaneous, etc. And from that one line you can ask loads of follow up questions. Is this something they’ve done before or something new that they’ve always wanted to try? Where did they hear about it? Is it a nostalgia thing? Even just how quickly they respond to this question will tell you a lot about them. Did they think about it for a while or just blurt out the first thing that came to mind? It’s a great question, but the drawback is that it sometimes takes too much thought depending on the situation. So be careful where and when you use it so that you don’t stall the conversation even further.


“If you could have any superpower, what would it be and why?”

Call me crazy, but I’ve always loved these sort of questions because I think they’re great icebreakers. Does your conversation partner laugh before answering? Do they think about it really seriously? Is their superpower a funny one like the ability to talk to animals or a serious save-the-world one? How people respond to questions like this can tell you a lot about their personality and their interests. It also takes a conversation from something dreadfully serious and professional to something more fun and relaxed.


Have any other good suggestions for conversation kick starters? Let me know in the comments down below!



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