How do you keep conversations flowing?

Good conversation can be a great indicator of chemistry. If the conversation flows, you tend to be more comfortable with a person. Stilted conversation has the opposite effect. So what can you do to get more comfortable having conversations? How do you keep conversations flowing?

Here’s how I do it:

Draw out stories

If you want to keep a conversation flowing, make sure that you’re always trying to draw out stories. That means avoiding questions and lines of conversation that can be answered in one word or in a short sentence, and embracing questions and lines of conversation that have to be answered with an anecdote. Why did they choose their career path? What made them move to the city they’re in now? What are their hopes, dreams, and aspirations? The more you engage them in conversation, the easier it is for the conversation to flow.

No small talk for small talk’s sake

I don’t think there is anything inherently wrong with small talk. Sure, it’s not the most useful way to learn about someone, but it has it’s purpose. It’s a bridge that can take you to where you want to go. You don’t ask a stranger how long they’ve been single immediately after you get their name, small talk gets you there, because it bridges conversations. You absolutely can use small talk to get to know someone, as long as your small talk eventually leads to meatier conversation. If you want to ask someone about their long-term romantic goals, you might use small talk to bring up something like how long they’ve been single.

Figure out their interests. Ask about their interests. Repeat.

If you want to get someone talking, ask them about their interests. Actively engage with them, ask questions, ask for explanations, dig deep into their interests. Then, repeat. Ask them about their interests, or learn more about an interest. If they’re into the newest superhero movie, ask about the characters, ask about the history, ask why they got interested in the first place. If they’re super into home improvement/real estate shows, ask them about their favorite shows, their favorite personalities, their favorite moments on these shows. And then Repeat.

Ask questions you want to answer

If you ask someone a question, unless that question is incredibly specific to them, chances are good they’ll ask you the same question. You ask where they went to school, they ask you the same. You ask what they do for a living, they ask you the same. If you know that being asked about your career is something you dread, don’t ask them about their career. They might ask you and you should answer, but if you’re the person asking the questions, focus on asking questions you’d want to answer. This will not only help the conversation flow, because it’s easier to answer questions you want to be asked, but will also help you both learn about each other.

Progress the conversation

All those tips are fine on their own, but you should remember that your goal should be to advance the conversation. We talk about conversation using terms like “flow” because we associate progress and movement with a good conversation. Try to build on each conversation, and move it forward. What moving a conversation along looks different from person to person, but for most people it follows a basic formula.

Discuss a topic, ask a more in-depth question about that topic until you exhaust the topic.

Ex. How many siblings do you have? What are their names? Where do they live? Are you close? Who are you closest with?

Once you exhaust a topic, move on to another topic. At the end of a conversation you should know more about the person than when you started talking.


These tips work for me, and I think they’ll work for you. If you’re struggling to have conversations that flow, give my tips a shot.

Good Luck Out There.


Also published on Medium.

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