Questions to Keep a Conversation Going

Luckily, there are lots of things you could do to keep your conversation alive. Read this article to find the best questions to keep a conversation going, and never have a boring conversation again! Forgetting what to say in the middle of a conversation is the worst thing that could happen to anyone. Especially when speaking to someone for the first time, it's normal to be tongue-tied.

Asking questions helps move the conversation forward and ensures nobody is bored. Depending on the type of questions you ask, you also get to learn fun, interesting facts about the person you're talking to.

There are different types of conversational questions you could ask.

  • Funny Questions - You could try asking funny questions to lighten the mood. This is great when the conversation has become dull or boring.
  • Deep Questions - You could ask deeper questions that prompt serious discussions. While it's important not to ask too many serious questions, especially in a casual conversation, deep questions often prompt long, interesting discussions that help keep the conversation alive.
  • Flirty Questions - If you're talking to someone you like, there's no harm in slipping a few flirty questions to them. These questions shouldn't be overly flirty but enough to intrigue them.

It's always recommended that you ask questions linked with stories. For example, asking 'what was the first book you read?' could lead to a conversation about the novel the person read and extend to a conversation about books in general. This way, the conversation continues long after the question is answered.

To assist you, here are some great questions to hold a conversation with;

  • Have you ever had an obsessive partner?
  • Do you enjoy taking lots of pictures?
  • What are your goals in life?
  • What is the weirdest dream you've ever had?
  • Do you have a favorite number or letter? If yes, why?
  • What's the craziest thing you've ever done?
  • What's your favorite season?
  • Are you a Marvel or DC person?
  • What was the worst date you ever went on?
  • What is the best piece of advice you've been given?

Questions to Ask to Keep a Conversation Going

We all know the feeling when you're talking to someone, the conversation is going great, then suddenly, there's this silence, and none of you know how to fill it. These situations are always very uncomfortable, but you never have to worry about that happening again!

These questions are helpful in all situations, whether it's a first date, a conversation with a friend, etc. Or maybe you want to know the person on a deeper level; these questions will help you out.

Some funny questions you can ask to keep the conversation going include;

  • What was the silliest trendy thing you did when you were younger?
  • What would a reality show starring you be like?
  • You just won a million-dollar lottery; what is the first thing you'd do with the money?
  • What would a book about your life be called?
  • Have you ever had a crush on a cartoon character?

You could also ask deeper questions, such as;

  • What's your favorite memory?
  • What are you most passionate about?
  • Are you a religious person? If no, why not?
  • You've just been gifted with a new superpower; what would it be?
  • What are your biggest regrets in life?

If you feel the conversation is getting too serious, don't hesitate to deviate from the deep questions and ask simpler, more casual questions such as;

  • Do you procrastinate a lot?
  • Are there habits you have that you wish you could erase?
  • What's your favorite Disney character?
  • Do you have any obsessive habits?
  • If you could know the day you die, what would you do?

These questions will ensure that you never run out of things to say in a conversation

How to Carry on Conversation Over Text

It's always easier to talk to people over text than in person. When texting, if you forget what to say, you could do some research or think about what you want to say.

However, if you're speaking to someone for the first time, conversations over text can be hard and often boring. You need to know the right things to say while texting.

Here are a few ways you can carry on your text conversation properly;

  • Start the conversation with a question - Questions are a powerful way of getting someone's attention. Plus, if you start with a question, you don't have to think about what to say during the conversation.
  • Ask deep questions - Yes, you don't want to seem invasive, but you also don't want to be boring! They're already used to being asked casual questions, so it's time to try something deeper. You can start simple, like asking them about their childhood memories and sharing some of yours too!
  • Use emojis and memes - If you're chatting with a friend, it a crush; emojis and memes are great ways to boost the conversation.
  • Don't dwell on dead conversations - Let's imagine you're chatting about movies. You've been speaking for 15 minutes, the person was interested at first, but now they're growing bored. The best thing to do is let it die.

Don't try bringing up old conversations; look for a new topic to talk about.

One thing is for sure. If the person you're talking to gets bored when texting you, they probably won't want to meet you in person. So you have to find a way to captivate them while texting.

Interesting Questions to Keep a Conversation Going

If you want to have an interesting conversation with someone, you need to know the right questions to ask.

These questions will help you build rapport with someone you're speaking to for the first time. They are deep enough to be interesting and casual enough to hold that light, conversational tone.

These questions can work with both young and older people. You could also learn lots of fun and interesting facts about people.

Here are some top-quality questions to keep a convo going;

  • If you could travel anywhere in the world, where would you go first, and why?
  • Do you ever want to get married?
  • What is something you recently developed an interest in?
  • What is your biggest motivation?
  • If you could get an answer to any question, no matter how hard it is, what would you ask?
  • Are you an introvert or an extrovert?
  • Have you ever fallen in love?
  • What events have impacted you the most in your life?
  • What is your idea of the perfect date?
  • What do you view as your greatest accomplishment?
  • What's the most important thing on your bucket list?
  • Do you believe in miracles? Why?
  • What is your favorite novel? Did it impact you in any way?
  • Have you ever taken big risks in life?
  • Do you think your parents were the most influential people in your life when you were younger?

Make sure you're not the only one asking questions. Try to get the other person in the conversation to ask you questions too. This way, it won't be a one-sided conversation. You may learn new things about yourself as well.

Remember that these questions are just for fun, so don't overthink or take them too seriously.

How to Spice Up Text Conversation

Tired of having the same boring conversations over text? No worries. There are lots of interesting things you could do to drive the boredom away. Or maybe you're just tired of having repetitive conversations? You can always spice up your texts by trying these three things;

  • Ask Questions - If you're texting someone and feel the conversation is becoming boring for both of you, the best thing to do is ask each other questions. These could be lighthearted questions all for fun, or they could be deep questions to discuss. Either way, questions always help fill up awkward moments. You also have extra time to think of what to say while the other person answers your questions.
  • Play A Game - What better way to liven up a conversation than by playing a game. It could be something as simple as 'would you rather…?' to an exciting game of 'truth or dare!
  • Exchange Stories - You could tell stories about meaningful events in your life or just random, comedic things that happened to you.

All these things are sure to spice up your text conversations. If you decide to tell stories or ask questions, try to talk about things you're passionate about. This makes it harder to run out of conversation topics.

Things to Talk About When Bored Texting

There are lots of light and serious topics you could talk about while texting. They include;

  • Work / School - Try and get them to talk about their work or school. What work do they do? Are they living their dream job? What are their favorite subjects?
  • Pets - People love talking about animals. Ask them if they have any pets or if they're planning on getting one.
  • Sports - Maybe you both bond over your love for sports. Do they play any sport? Who are their sport idols?
  • News - Maybe you're both into government and news. Ask them about their political views and thoughts on current world matters.
  • Hobbies - This is a great way to spice up your text messages and get to know the person better. What do they like to do for fun?
  • Music - Everyone loves talking about their music taste. Ask them what genre they like the most? Do they have a favorite band? Have they ever been to a concert and would they like to go to one?
  • Movies and Books - Ask them what their favorite movie is. Or maybe they enjoy reading a lot. What's their favorite novel? Why do they like it so much?

When choosing a conversation topic, pick something that you feel will interest your partner. Also, try to choose a topic closely linked to the conversation you were having and a topic that interests you.

Remember that follow-up questions are very important in conversations. When they're done talking about a specific topic or question, ask follow-up questions to show that you're listening and are interested in what they are saying.

Questions to Ask in a Boring Conversation

Even when talking with our closest friends, sometimes the conversation could dry up. These fun, casual questions will ensure that you never feel bored in any conversation again;

  • What's your favorite video to watch for a laugh?
  • What's your comfort movie or novel?
  • What song do you listen to a lot?
  • What's the most interesting app on your phone?
  • What's one thing you wish you had done when you were younger?
  • Have you ever accidentally sent someone a text that wasn't meant for them?
  • What is the most stupid thing you've ever bought for yourself?
  • What happens a lot in movies but rarely happens in real life?
  • If you could enter into a movie, TV show, or novel, what would it be?
  • What are you most passionate about in your life?

When asking questions, remember to answer some questions too. You don't want the conversation to seem one-sided.

Also, try to be creative with your questions. The whole point is to ask entertaining questions that will interest both you and your partner, so don't be boring!


With the help of these questions and ideas, you'll never have another boring conversation or text ever again.

One good thing to remember when having a conversation is not to overthink. Also, remember to space your questions; it's not an interrogation; it's a conversation. A lot of people think too much and ask too many questions. This makes them come off as overbearing and boring.

Keep this in mind as you use these conversation tips to strike up fun, entertaining conversations!

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