5 Artful Ways To Keep a Conversation Going

Have you ever found yourself in a conversation with someone, and suddenly the conversation ends with awkward silence?

You panic because you can’t think of things to say to keep a conversation going. Your face grows red and your brain goes blank, as you grasp for a verbal lifeline to save you from looking like a shuffling, bumbling idiot.

It happens to all of us — we meet someone, chat for a few minutes, and then run out of things to say and the conversation begins to stall. The weather topic has been covered. You’ve discussed each other’s jobs. And you’ve talked about your kids. So now what?

The great gift of conversation lies less in displaying it ourselves than in drawing it out of others. He who leaves your company pleased with himself and his own cleverness is perfectly well pleased with you.  -Jean de la Bruyere

When you don’t have strategies to keep a flagging conversation alive, it can rob you of the opportunity to get to know other people. It can also undermine your confidence to initiate a conversation in the first place.

It’s common to encounter a few bumps when conversing socially, but knowing how to keep a conversation going can help you build meaningful and interesting relationships.

Want to learn how to never run out of things to say in a conversation?

5 simple strategies on how to keep a conversation going.

Pick one of these techniques to make a conversation interesting:

1. Keep a conversation going by asking great getting to know you questions.

One way to invite the other person to talk is by asking open-ended questions.

man and woman talk curbside how to keep a conversation going

Rather than asking questions that can be answered with a  “Yes” or “No,” prepare some questions in advance that encourage people to talk and share more detailed information about their lives.

Have these questions handy, and review them before you enter a social situation that you know will involve one-on-one conversations.

For example, you might ask, “How did you and your wife meet?” Or “How did you decide to get involved in your career field?”

These are interesting questions that can draw out an intriguing story or another detail that can keep the conversation going.

As the person is talking and sharing personal information, listen for areas of commonality and shared interests which can open new channels of discussion.

At the end of this post, you’ll find a few more good questions you might use in future conversations.

Related: 30 Conversation Topics To Kickstart Your Speaking Confidence

2. Keep a conversation going by being an active, conscious listener.

When making conversation, we tend to focus on what we are going to say next after the person pauses speaking.

Fearing that awkward silence or eager to get a word in, we fail to really hear what the other person is saying and show them the respect that makes a conversation truly a gift.

Listening is just as important as talking in a conversation — maybe even more so.

The reason why so few people are agreeable in conversation is that each is thinking more about what he intends to say than what others are saying. -Francois de La Rochefoucauld

Being an active listener requires taking part in the conversation, and building the rapport between you and your conversation partner.

Skilled and active listening requires focused attention on what the other person is saying, using eye contact, affirmative nods, and affirmative words.

It also involves paraphrasing or mirroring what the speaker says to show you understand, as well as asking questions and making appropriate, relevant comments.

women sitting talking how to keep a conversation

Think about a good conversation as a ball bouncing back and forth.

Receive what your partner has said, and then add a little bit to it before bouncing the ball back for more. This back and forth is likely to create a deeper conversation that will last quite some time.

3. Keep a conversation going by avoiding one-word answers.

In addition to refraining from asking questions that can be answered with one word, always elaborate when someone asks you a simple question.

Maintain the conversation by giving more detail to your answer than the questioner might expect, like offering not just the name of the college you attended but also what you studied or the fraternity or sorority you were a part of.

Related: 10 Good Communication Skills You Must Know

Providing your conversation partner with this extra information gives them more opportunities to relate to your story and ask you something else to continue the conversation.

It increases the likelihood that you and the person you are talking to will connect on some level and throws them a verbal lifeline to keep a conversation going.

4. Be yourself to keep a conversation going.

You may second guess everything you ask your conversation partner, especially if this is the first time the two of you have met. You might be a bit stiffer and formal with someone you don’t know well.

couples on deck overlooking ocean how to keep a conversation going

It’s common to wonder how this person will react to a question or a story, so you may hold back or be less of yourself so you don’t give the wrong impression or unintentionally offend.

To make conversation continue to flow, don’t filter your true personality. Just be yourself, and ask good questions that come to mind or say what you are thinking (within reason!).

The best way to practice making conversations last is by being authentic and open with people who you already know.

Maybe you are with a friend or a co-worker who you don’t know on a deep level, but you have crossed paths with him or her several times.

Take the opportunity to step out of your comfort zone a little and talk about some topics you normally wouldn’t discuss. Or ask a deeper question that is a bit more personal or probing.

You can generally tell from someone’s body language whether or not they welcome more intimate conversation.

It’s refreshing to realize that you can say or ask whatever is on your mind without the fear of being judged.

Of course, don’t ask anything inappropriate or controversial, but generally, people love to talk about themselves, and they are likely more focused on how they appear to you rather than what you have said.

Being authentic can open up a huge arena of topics and good conversations to have that will help you get over those awkward moments of not know what to say.

5. Say “Tell me more” to keep a conversation going.

Rather than asking a specific question, ask your conversation partner to simply tell you more about a topic that they have mentioned.

This allows them the opportunity to take the conversation wherever they want and talk about what is most important to them.

It also forces them to do a bit of the thinking when it comes to keeping the conversation going and puts the ball back in their court to do the talking. This buys you a bit of time as well when you are stumped for something to talk about.

Asking someone to tell you more about something also shows them that you are interested in what they have to say.

They will recognize that you are giving them control of the conversation, and they will be flattered that you find them engaging enough to expound on the topic.

If you struggle with being shy or a lack of confidence when it comes to talking to strangers, use these tips to continue the conversation so you will never run out of things to say.

Related: 27 Small Talk Topics

Practice these conversation skills with people you feel comfortable around, so you have more confidence when you enter a setting with new people.

If you know how to skillfully keep the other person talking, you will not have to worry about stumbling on your words or saying the exact right thing the entire time.

Also, be sure to engage in the conversation with great questions, active listening, and authenticity, and you will bypass those awkward silences and uncomfortable moments when your mind goes blank.

20 Questions to Ask to Keep a Conversation Going

If all else fails when you’re trying to hold the conversation momentum, go back to strategy #1 and ask interesting questions. Not only does this help bridge that awkward silence gap, but also it allows you to learn more about the other person.

And the odds are, the other person will return the favor by asking you the same or a similar question so that you begin to build a bond of understanding and connection.

Consider asking some of these 20 questions:

  • Where did you grow up and what was your childhood like?
  • Do you enjoy reading, and if so, what type of books do you read?
  • What do you feel really passionate about or curious about?
  • What is one of the highlights of your life this past year?
  • What is the biggest challenge you’ve overcome recently?
  • Do you have any big goals for the year, and if so, what are they?
  • If you could go back and change anything in your life, what would it be?
  • How do you like to relax and decompress?
  • Would you consider yourself more of an introvert or extrovert and why?
  • If you could live anywhere else, where would you want to live?
  • What are some things on your bucket list?
  • What would you consider your “superpower” — something that you’re really good at?
  • Where do you see yourself in five years?
  • What kind of movies (or music) do you like?
  • If you could meet anyone in the world and have a conversation with him or her, who would it be?
  • Where is your “happy place?”
  • If you won the lottery, what would you do with the money?
  • What is a typical day like for you?
  • What would you consider your top five values in life?
  • What do you prefer — the beach or the mountains — and why?

Did you find any value from these tips to keep a conversation going?

I hope you enjoyed these ideas for making conversation. I hope you’ll use these ideas for how to keep a conversation going to help you when you’re in a social setting, and the dialogue begins to falter.

Which conversation strategy was the most inspiring and helpful for you?

Would you like to help others improve their conversations?

There are people all over the world who get stuck in that awkward conversation moment and don’t know what to say next.

Would you willing to share the love with your friends and family (and thousands of other people) on your preferred social media channel?

This act of kindness will bring you good conversation Karma!

In social settings, your conversation can stall and feel awkward. Learn how to keep a conversation going with confidence.

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