Fun Questions to Start Up a Conversation

Fun Questions to Start Up a Conversation

With the holidays approaching, there will be many opportunities for us to gather with friends and family to enjoy each other’s company and socialize. Sometimes these get-togethers are with people we know well and other times we find ourselves having to strike up conversations with complete strangers. Being prepared with a list of fun questions to ask can help you spark a conversation with someone you may not know very well. When I was a kid, one way my family sparked conversation was to ask silly or fun questions during conversations at meals or get-togethers. Here are some fun questions to ask people of all ages:


Would you rather...

These were great questions my family loved since I had brothers; we felt that the grosser the questions were, the more exciting and interesting our talks would be. For example, “would you rather eat a dirty sock or a bug, and why?”. It was fun to see what each person felt was the better of the two outrageous items.


Here are some other ‘would you rather’ questions that I have been asked or heard before:

  • Would you rather lose your sight or your hearing? Why?

  • Would you rather live in a tent but have all the money in the world, or in a mansion with a pool and internet but only get 10 bucks each day?

  • Would you rather have all thumbs on your feet or all pinky toes on your hands?


Thinking Outside the Box

If you would like to pose some fun questions around critical thinking, here are some questions based on the ideas presented in Dr. Daniel Khaneman’s book, “Thinking Fast and Slow”, which is a great read that gets you thinking and talking about things that are outside-the-box.


Ask both of the following pairs of fun questions regarding risk vs reward:

A. Would you rather have your test score increased by 5% for sure?

-Or -

B. Would you rather take a 50% chance of increasing your test score by 10%?


Follow up with a slightly rephrased question to get them thinking from a different perspective:

C. Would you rather lose 5% off your test score?


D. Take a 50% chance of losing 10% on your test score?


What Dr. Khaneman found when he asked people these slightly different types of questions, is that most would choose A and D, where one is a sure thing and the other is risky. This shows that in general, people prefer to avoid risk when it comes to gains, and will take on more risk if it involves losses. This really goes against reason so it makes for a great conversation starter!

Using these fun questions to strike up a conversation about the different ways we go about decision-making can help anyone think more critically and objectively when weighing their options. It will make you stop and purposefully think about things in terms of what there is to gain, to lose, and the risk involved.


Fun Questions about Christmas

Since it is the Christmas season, open-ended fun questions about Jesus are great to get people talking. Here are a few that have started many great conversations:


If you were an animal in the manager what would you describe to other animals what you saw when Jesus was born, or when Mary and Joseph came to stay there?


Why is Jesus like a candle?


What is the difference between a Christmas song and carol?


What Christmas song/carol is represented by these words?

[Q]Embellish the interior passageways

[A]Deck the Halls


[Q]  In a distant location, the existence of an improvised unit of newborn children’s slumber furniture

[A] Away in a Manger


[Q]Move hitherward the entire assembly of those who are loyal in their brief

[A]O Come, All Ye Faithful


[Q]Listen, the celestial messengers produce harmonious sounds

[A]Hark, the Herald Angels Sing


You can find more examples of these online if you and other enjoy trying to figure out song titles with a more elaborate wording to them.


Riddling Fun Questions Pinterest

Another way to use fun questions to keep the conversation alive is through the use of riddles. Riddles can be found all over the internet. Here are some great ones that I have heard over the years and still love using today.


[Q]You are a bus driver and pick up 2 people from the first stop and 4 people from the second stop. At the third stop, 3 people get off and 5 get on. At the last stop, 5 people get off and 1 gets on. What is the name of the bus driver?

[A]This would be where they should tell you their actual name.


[Q]What 8-letter word has “kst” in the middle, in the beginning and at the end?  

[A]Inkstand has “in” in the beginning, “kst” in the middle and “and” at the end.

Fun Questions Involving Problem Solving

If you find yourself in a conversation with people that like to talk about math, try one of these out:


[Q] Can you spot which algebraic or mathematical rule was broken in the following series of equations?

[A]Step 1. A = B

Step 2. A^2 = AB (By multiplying both sides by A)

Step 3. A^2 = B^2 (By substituting A with B)

Step 4. A^2 - B^2 = AB - B^2 (By subtracting B^2 from both sides)

Step 5. (A-B)(A+B) = B(A-B) (By factoring)

Step 6. Then cancel (A-B) from both sides by dividing by (A-B), so…

A+B = B

Step 7. 2B = B (By substituting A with B).

Step 8. 2 = 1 (By dividing both sides by B.


How could this be? How can 2 equal 1? The problem with this question is that we divided both sides by (A-B) in step 6, but the problem lies in that A equals B, so if you subtract the two, you get 0, and one should know that you cannot divide by 0, as that is impossible to comprehend, as 0 can fit into anything an infinite amount of times. So by using an irrational procedure, you result with an irrational answer.


Here’s another math question I’ve used to get the conversation started with my students over the years:


[Q]If you have a barrel of water and you need to measure out just one gallon, how do you do this if you only have a three-gallon container and a five-gallon container?

[A] 1. Fill the three-gallon bucket -- pour the 3 gallons out into the five-gallon bucket.

2. Fill the three-gallon bucket again.

3. Pour two gallons to fill the bigger bucket to the top. Then you have one gallon left in the smaller bucket.


This last one is a riddle that I have given as extra credit to students here at Enlightium Academy: sorry students, I will not be using it this year because I am sharing the answer in this article for you to use while socializing this season.


[Q]If you have 6 black socks, 4 blue socks, 8 brown socks, and 2 red socks in your sock drawer, what is the minimum number of socks that you need to pull out in the dark to be sure you had a matching pair?

[A]Since there are only four colors, you will need to grab five to guarantee that there will be two of the same color.


No matter which fun questions you ask, it is just great to get family and friends thinking and engaged in conversation with one another. If you're looking for an education option that helps your child develop the ability to make conversation while stretching their brain, consider Enlightium Academy. We are a fully accredited online private Christian school that allows students to work at their own pace with a flexible schedule. Our affordable tuition, individualized curriculum, and simple admissions process maintains the advantages of a home school education while also preparing students for college. Additionally, Enlightium offers record-keeping and has worked with families in all 50 states to meet state requirements. Feel free to call us at 866-488-4818 if you have any questions about transferring to Enlightium Academy. With the second semester approaching quickly, we would love to share what it would look like to enroll your student in Enlightium Academy. Enjoy making conversation while using this list of fun questions and feel free to share some unique ideas of your own!


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