The Art of Keeping a Conversation Alive
Simple ways to ask better questions, listen more closely, and keep the conversation flowing long after hello.
Published: Aug 23, 2026
Knowing that people with strong social connections tend to live happier and healthier lives, you muster the courage to walk across the room at a party and introduce yourself to someone you don’t know. You exchange pleasantries — and then the conversation sputters.
Now what?
Your mind starts racing as you search for something interesting to say. What should I ask next? Am I talking too much? Is this getting awkward? Before long, you’re so focused on keeping the conversation going that you stop listening to what the other person is saying.
As I wrote last week, the first hurdle is getting started. The next comes right after you say hello, as you’re figuring out where the conversation might go.
Fortunately, keeping a conversation going is a skill that gets easier with practice. I’ve picked up a few tricks over the years, and most begin with listening and letting what the other person says guide where you go next. Here are a few ideas that have worked for me.
Asking better questions
Some conversations trade a few facts and leave us knowing almost as little about the other person as we did at the start. Others take off within minutes. You’re swapping stories, discovering things you have in common, and 10 minutes later, you already feel a connection.
What’s the difference? Often, it’s the questions we ask. Charles Duhigg, author of Supercommunicators, talked about this when I interviewed him for my podcast. He calls them “deep questions — questions that invite people to talk about what they think and feel rather than recite facts.
Think about the questions we routinely ask someone we’ve just met: Where do you live? What do you do? Where did you grow up? There’s nothing wrong with any of them, but the answers often leave us searching for another question.
Change those questions slightly, and you give the conversation somewhere to go. What do you enjoy about your work? What was it like growing up there? What brought you to the neighborhood?
Charles summed up the idea this way: “Don’t ask about the facts of their life. Ask them about how they feel about their life.” The answer is likely to tell you something more interesting about the person — and, if you’re listening closely, give you an idea of what to talk about next.
Have a backup plan
No matter how comfortable you are talking to people, there will be times when your mind goes blank. That’s why I keep something in my back pocket, like a question or an observation that can give the conversation a nudge when it needs one.
For me, that’s often humor. A joke or a playful observation can break the tension and put people at ease. Humor comes with some risk; I’ve told plenty of jokes that landed with a thud. When that happens, you laugh at yourself and keep going.
Your backup plan doesn’t have to be funny. Keep a few reliable questions handy, like “What brought you to the event?” or “How do you know the host?” You’re not memorizing a script; you’re simply giving yourself somewhere to go if the conversation stalls.
The best material often comes from the conversation itself. Return to something the person said earlier: “You said you just got back from Italy. What was your favorite part?” Listen closely, and you’ll find another thread to pick up and another reason to keep talking.
Be the host - even when you're the guest
Here’s one last idea: Step into a different role the next time you’re with a group of people. Think of yourself as the host, even when you’re not. Look around and find someone standing alone. Introduce yourself, then bring them into a conversation.
A good host wants everyone to feel comfortable and included. There’s no reason the person whose name is on the invitation has to do all that work.
This approach also takes some of the pressure off. Instead of worrying about what other people think of you, you start thinking about the people around you. Who doesn’t know anyone yet? Who could use an introduction?
That small shift in mindset can change the way you experience the room. Instead of waiting for someone to make you feel welcome, you’re looking for ways to bring others in. You’re creating the connections that make it a good party in the first place.
All the best,
Jim
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Written by 1-800-Flowers.com Founder and Chairman, the Celebrations Pulse letters aim to engage with our community. By welcoming your ideas and sharing your stories, we want to help you strengthen your relationships with the most important people in your life.
AUTHOR
Jim McCann is the founder and chairman of 1-800-FLOWERS.COM, Inc. as well as a business leader, author, and philanthropist with a passion for helping people deliver smiles. Devoted to helping others, he also founded Smile Farms, a 501(c)3 organization that provides meaningful jobs in agricultural settings to young adults and adults with developmental disabilities.
