Spark Conversation With These 35 Creative Questions


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No more awkward silences!

One of the most common things I hear from clients is that they avoid social interactions, dates, or even dating situations all together because they never know what to talk about.

So, in this article I’m going to arm you with 35 conversation-sparking questions to ask the next time you’re stumped.

Just make sure nobody catches you checking your notes…

1: What’s something you’ve always wanted to do, but haven’t yet?

Everyone — everyone has a list of things that they’ve not yet accomplished, but want to. Granted, some lists will be longer than others, but you will always get at least one answer from someone even if they have to think about it a little bit.

This is a great way to open the door for follow up questions, find out about more things they already have done, and learn more about their core values.

2: What is your favorite book?

Do they read?And, if so, what genres interest them? The information people choose to absorb tells you a lot about them.

3: What are your love languages?

A key factor in making a relationship work.

4: What’s a part of life that you’d do over again, and one that you wouldn’t?

For me, NOT high school.

5: What’s the greatest achievement of your life (so far)?

How much time do you have? (Just kidding).

6: What’s the most adventurous thing you’ve ever done?

Make sure they’re not boring.

7: What’s one of your guilty pleasures?


8: Do you believe aliens exist?

(Obviously they do).

9: If you could live anywhere in the world, where would it be?

Los Angeles, or Monte Carlo!

10: What do you picture your retirement to look like?

Family, friends, fun.

11: How do you show your love to people?

Make sure that they actually do.

12: If your life was turned into a movie, who would play the role of you?

Mine is The Rock, obviously.

13: What’s the most important lesson you’ve learned from failure?

Too many to count (lots to talk about there).

14: What is the greatest advice you’ve ever been given?

Make sure they’re open to receiving feedback.

15: If you had to do a TED Talk right now, what would your topic be?

This is always a fun question.

16: Do you believe there’s an afterlife?

Dun dun dunnnn.

17: What is one food that you’ll never eat again?

I’m down for whatever.

18: Do you believe everything happens for a reason?

I think we create the reason after it happens.

19: If you could solve one global problem, what would it be?

Lots to choose from.

20: If you could have a conversation with anyone (living or dead), who would it be?

21: How did you end up on your current career path?

22: If you could live for 24 hours with no rules or limits, what would you do?

23: What’s something you used to love that you don’t anymore?

24: What’s your relationship like with your parents?

25: What do you like most about yourself?

26: What are you most grateful for?

27: What do you value most in a relationship?

A big question.

28: If you could instantly speak any other language, which would it be?

Cultural curiosity is important.

29: What is the most (non-physical) attractive quality in a person to you?

Make sure they don’t just want you for your smokin’ bod.

30: What couple (fictional or real) is the “ideal couple” to you?

This could be very good, or very bad…

31: When you picture your life in 5 years from now, what does it look like?

This is a great way of seeing if you have similar visions of the future.

32: What’s the biggest challenge you’ve ever overcome in your life?

33: How do you want people to remember you when you’re gone?

We may not live forever — but we can create something that does.

34: What is one thing you absolutely MUST do while you’re on earth?

35: What makes you happy and fulfilled?

This is possibly one of the most difficult questions for people to answer, but also the most telling. Is it their contributions to society? Their kids or family? Having a soft bed to sleep on at night?

The key to these questions is asking them in a fun but thought provoking way — some are deeper than others, but all of them will give you a glimpse into a person’s identity and help you learn about them in ways that most people don’t.

Everyone can ask “what do you do?” or “How about this weather?”

But, not everyone will ask the more fun, more challenging, more thought provoking questions.

And — remember — the key to great conversation is having the ability to actively listen. Most people love telling you about themselves, and asking these questions will open up the space to do exactly that.

If you can trade these questions back and forth, you’ll never run out of things to talk about.

James Michael Sama is an internationally recognized speaker, author, and personal development coach.

Finding success in creating hundreds of viral articles and videos on building limitless confidence and healthier relationships, James has accumulated over 38 million visitors to his website and a collective social media following of over 400,000.

James speaks at live events and in the media across the U.S. and has become a go-to expert with outlets such as CNN, Bravo, The New York Post, The Huffington Post, The Daily Beast, CNBC, The Boston Globe, CBS, and more.


  1. Miss Bougie on August 5, 2022 at 1:44 pm

    Love these ideas. Well done, James!

  2. Irma Bryant on August 5, 2022 at 1:51 pm

    Thank you for another great read! Keep ‘’em coming.

  3. Brigitt HooSang on August 5, 2022 at 7:36 pm

    You generally have good topics, THIS one, I love!!!!!

  4. Lonstermash (@reallonstermash) on August 26, 2022 at 1:56 am

    Love it! Great conversation ideas

  5. Brigitte on February 23, 2023 at 7:41 am

    Very good idea’s of things to talk about with someone when first getting to know one another…
    I hate siting there having small talk…I’m not big on small talk. I like a deep, intelligent, & fun convo and these really are some good topics! Thx James!

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