60 Icebreaker Questions To Jumpstart a Dull Conversation


Last Updated on January 27, 2021

Whether you’re readying yourself for your maiden date or that all-too-important meeting with your clients, one thing is for sure – there will be moments of tense silence punctuated with blank stares and awkward fidgeting. Usually, these are the moments when you can’t figure out the next most appropriate thing to say.

You wish a pin could drop on the floor so you can make a great deal out of it and keep the conversation flowing. Or that it could suddenly start to snow in the middle of a hot summer afternoon, even if that means kick-starting a romantic conversation on a meteorological note.

However, neither of these things will likely take place. The only way out of these tense, awkward moments of silence is to arm yourself with the best icebreaker questions.

We’ve prepared some of the most thought-provoking icebreaker questions that will spark great conversations and encourage real bonding with your date, friends, clients, or even office colleagues on a teambuilding retreat.

Hobby Icebreaker Questions

Hobby-related questions, as the name implies, are intended at getting to know what the other person loves the most.

These questions are more common on maiden dates where you’re not already acquainted with the other person.

1. What is your favorite hobby?
2. Are you a movie or a music person?
3. Do you have any hidden talents? What are they?
4. If money and time were no object, what would you be doing right now?
5. What’s your favorite type of day? (Rainy, snowy, windy)
6. What are some of your favorite games to play?
7. What has taken you the longest to get good or decent at?
8. What food do you love that many people might find a bit weird?
9. What is your favorite sport or physical activity?
10. What is your favorite thing to do by yourself?
11. What is your idea of fun?
12. Who was your favorite teacher in school and how did they impact you?
13. What two things do you consider yourself to be very good/bad at

Personal Icebreaker Questions

It’s natural for a person to lie about their hobbies or to not have any specific hobbies at all. After all, most of us are so trapped in the 9 – 5 rat race that we hardly ever find time to pursue our pastimes.

If you find the answers to the above hobby icebreaker questions unsatisfactory, you might consider the following personal questions. These questions are more profound and will enable you to discover a lot more about the other person besides their hobbies.

1. Are you a morning or evening person/Are you an early bird or a night owl?
2. How into self-improvement are you?
3. How would you describe yourself?
4. What’s the best thing you expect out of this relationship/friendship?
5. What’s the worst thing someone has ever done to you that you found incredibly difficult to forgive?
6. What’s the one thing in your daily routine that you wish you could eliminate?
7. What are some of your guilty pleasures?
8. What is your biggest pet peeve?
9. What would you like to be remembered for?
10. Where do you see yourself in 5/10/20 years?
11. Would you rather be the funniest or the smartest person in the room?
12. Would you rather be the person giving or taking advice?

Reflective Icebreaker Questions

Reflective icebreaker questions are thought-provoking and are mostly intended at getting the other person to reflect on their past life and things that are dear to them.

When you pose these questions, don’t expect an answer immediately, unless the respondent has an excellent memory or is way too creative.

1. Have you ever wished death on anyone and if yes, who was it and why?
2. If you could choose an age to remain forever, which age would you choose?
3. If you could go back in time and make little changes to your childhood, what’s the first thing you’d change?
4. If you were added five more years to your lifetime, would you rather establish a medical research center or a charity organization?
5. If you won a lottery of $1 billion, what would you do with all the money?
6. What’s that moment in your life when you felt a complete sense of peace and harmony?
7. What’s the best thing you’ve got going on in your life at the moment?
8. What’s the most incredible thing you’ve done in your life?
9. What is the most amazing fact you know?
10. What is your earliest childhood memory?
11. What is your most treasured material possession and why?
12. What takes a lot of time but is totally worth it?

Career-related Icebreaker Questions

Career-related icebreaker questions are resourceful when you’re trying to get to know your work colleague, boss, job applicant, or client better.

As you may have guessed, these icebreaker questions should be plain and direct.

1. What do you expect from this job?
2. Do you have prior experience in a similar job?
3. How did you lose your previous job?
4. What’s the best/worst job you’ve ever done?
5. Growing up, what did you want to become?
6. What’s that one important skill you believe could transform this company?
7. What’s your absolute dream job?
8. What’s your retirement plan?
9. What aspects of the company do you think require the most improvement?
10. Would you rather be employed or self-employed?

Fun Icebreaker Questions

One of the best things about fun icebreaker questions is that they can apply in numerous situations. The questions don’t necessarily have to be relevant to the theme of the occasion. Instead, you can use them to spark just about any conversation.
Plus, fun icebreaker questions also allow you to gauge the other person’s sense of humor and creativity.

1. Are there any interesting things your name spells with the letters rearranged?
2. If you were left on a deserted island with either your worst enemy or no one, which would you choose? Why?
3. If you were to be cast in a movie, would you rather be the hero that dies in the end or the villain that lives?
4. If you were to be in only one place for the rest of your life, where would that be?
5. If you were to bring back any fashion trend, what would it be?
6. Have you ever been mistaken for someone famous? And if yes, what’s the name of that person?
7. What is one article of clothing that someone could wear that would make you walk out on a date with them?
8. What’s the most embarrassing thing you’ve ever done and believe you might still do if given half the chance?
9. What’s the most popular joke that you don’t find funny at all?
10. Would you rather get back with your ex or get down with your best friend’s girlfriend/boyfriend?
11. Would you rather know how the world began or how it will end?
12. Would you rather lose your wallet or lose your phone?
13. Would you take a trip to the moon knowing very well that you’ll never come back?

Wrap Up

Evidently, there are numerous icebreaker questions that you can ask to jumpstart a conversation and keep it flowing. Just remember to avoid overly scary, boring, or subjective questions. Instead, keep the questions fun, simple, relaxed, and if possible, relevant to the theme of the occasion.

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