Robin Sutherns | Sep 16, 2021 | 0
250 Good Questions - Ask One to Easily Start a Conversation
New? Start here.
Knowing good questions to ask is essential...
...Because asking questions is the most powerful way to get to know someone. Of course, not all questions are equal. Having the right questions to ask prepared goes a long way in helping you to connect with people more effectively.
And I know it sounds too good to be true, but the right question to ask someone can change your life. It can lead to new relationships and help current ones to grow. Having good questions to ask can also just be a fun way to pass the time. You never know what could happen, and that's what makes questions so fun.
This handy list of questions to ask people is your secret weapon for social situations. You can memorize your favorites, or simply pull them up on your phone as needed. We've compiled questions to ask that fit any mood, person, and goal. Use them wisely.
11 Best Conversation Topics
Coming up with ideas for conversations isn't always easy. Everyone draws a blank at some point. It happens.
This list of conversation topics is your key to smooth and easy discussions. It's your mental Rolodex that you can turn to when you just can't think of something to say.
Whether you're chatting with a new co-worker, an old friend, or a crush, these conversation topics kill those awkward silences and keep the verbal river flowing.
Some of them will help you to learn about the other person, and others will simply give you some food for thought. Not all conversations have to be deep. Sometimes just chatting for chatting's sake is all you need.
Here are the 11 best conversation topics:
1. Where do you like to go when you eat out?
Food is always a fun conversation topic, and you might even learn about some local eateries you weren't aware of.
2. Do you like to cook?
Again, food is great conversation fodder, and you might learn a few new recipes.
3. Could you live without the internet?
These days, the internet is essential. What would life be like without it?
4. Most memorable birthday?
Everyone loves talking about their favorite birthday experience. It's pure positivity.
5. What would your perfect day be like?
The imagination can run wild with this one.
6. When are you happiest?
Another conversation that just makes people smile.
7. What's on your bucket list?
People love talking about their hopes and dreams for the future.
8. Do you have any trips coming up?
Traveling is always a safe conversation topic. Plus, it gives them the opportunity to get excited about their next vacation.
9. What's something you could teach me about?
This question shows that you're interested in and respect them. it also shows that you're an open-minded person.
10. What is your favorite hobby?
Simple and sweet. What do they love to do in their spare time?
11. Do you have/have you ever had any pets?
Pets are like an extension of their owners. There's always a funny story or two that comes with talking about pets.
14 Best Conversation Starters
These conversation starters spark discussions. They're direct questions that give the other person a specific topic to wax about. That's what makes them so useful.
Sometimes these questions to ask someone may feel a little random. Embrace it! Some of the best conversations come right out of left field. People like hanging out with someone who can keep them on their toes.
Use these conversation starters sparingly. After all, your goal is to start a conversation, not interrogate your company. Listen to their responses, and give your own. The art of conversation is a two-way street.
Here are the 14 best conversation starters:
12. What’s the best comedy movie you’ve ever seen?
Share some laughs about your favorite scenes. If you haven't seen it, you've got a new movie to check out.
13. What’s your favorite song and why this particular one?
Music is always a great conversation topic, and you might get a new song for your playlist.
14. What’s been the best concert you’ve attended?
A good concert is a magical experience. Talk about the best of the best.
15. Do you drink coffee or tea?
If neither, how do you function?
16. If you were stranded on a deserted island and you could have only 1 item, what would it be?
A classic question that always yields interesting answers.
17. Do you believe in luck?
Or do we make our own luck?
18. Do you prefer cats or dogs?
They say there are two types of people...
19. What is the best thing that happened to you during the past week?
This question is great because it's current and upbeat.
20. What are some of your long-term goals?
Knowing a person's goals really gives you insight into who they are.
21. What did you have for dinner last night?
This question is great because it requires zero effort to answer, and it can lead to other conversations about food.
22. What is your favorite meal of the day?
Followup: favorite dish for that meal?
23. What do you do for a living?
A person's career is a major aspect of who they are.
24. What’s the most useful thing you own?
If you don't have one, you might want to go pick one up.
25. What is your spirit animal?
This is a funny question, but it can say a lot about the person. After all, answers like an owl or a lion tell you a lot.
8 Best Questions to Ask
This list is the cream of the crop. Some of the questions will make you think. Others help you get to know the other person better. They're extremely versatile.
If you're in a rush to find some solid questions to ask someone, this list should treat you right.
Here are the 8 best questions to ask:
26. What is the first thing you notice about a person?
This question helps you to understand how they perceive people.
27. What are some challenges you think the next generation will face?
This conversation gets the imagination flowing. It can lead to fascinating discussions about the future.
28. What three habits will improve your life?
This question shows you value the other person's input, and you may learn a thing or two.
29. For what in your life do you feel most grateful?
This question is great because it's deep, but not too intrusive. It can be light and easy or more in-depth, depending on how the person answering feels.
30. If you could have lunch with one person alive or dead, who would it be?
A classic question that tells you a lot about the other person without getting too personal.
31. What is your favorite season, and why?
This is another question that tells you a lot about the person without going too deep. It can also help you to appreciate the beauty of other seasons.
32. Do you have any guilty pleasures?
Everyone has that song or movie that they secretly love.
33. If you could only eat one food for the rest of your life, what would it be?
This question might make you hungry.
14 Best Get to Know You Questions
Nobody is 100% an open book. In order to understand what makes people tick, you need to ask them questions.
These are the best get to know you questions for connecting with someone. They also help the other person get to know you.
Some of these questions may seem surface-level, but the responses you get can really tell you a lot about the other person. Read between the lines.
Here are the 14 best get to know you questions:
34. What’s the number one item you would save from your burning house?
A person's most treasured item can say a lot about them.
35. What really makes you angry?
We all get a little peeved from time to time. What's their trigger?
36. What is your favorite thing about your career?
Talk about the positive sides of working.
37. What makes you laugh the most?
Learning about a person's sense of humor is an amazing way to bond with them over some laughs.
38. Aside from necessities, what one thing could you not go a day without?
This question helps you to understand what they truly value most in life.
39. Are you a clean or messy person?
40. What does a successful relationship look like to you?
Everyone has their own unique idea of what a perfect relationship looks like.
41. What is something you like to do that other people would probably consider "weird" if they knew?
Weird doesn't always mean bad. Humans tend to have unique characteristics, and that's what makes us special.
42. What was your upbringing like?
Learning about a person's childhood provides insight into who they are today.
43. If you had to describe yourself in five words, what would they be?
This question might take some thought, but the answers can be very revealing.
44. What goals do you have for the next five years?
A person's hopes and dreams are a part of who they are, and who they will be.
45. What big life changes have you recently experienced?
Recent experiences can play a major role in a person's attitude and behaviors.
46. What is your favorite holiday?
This conversation is light and easy, but it also helps you to understand who they are.
47. What is the first thing you would do if you won the lottery?
Donate to charity or hit the bar? The answer can say a lot about their priorities in life.
7 Best Questions to Ask a Girl
Whether you're chilling with your crush, going on a first date, or just hanging with a female friend, you want to be entertaining. At very least, you don't want to be silent! These questions to ask a girl give you something to say.
Having questions in mind and ready to go naturally inspires confidence. After all, when you study for a test, you feel less nervous, right? It's the same principle.
Besides helping to fill the silence, these questions can tell you a lot about the person you're with. They also show her that you're interested in her.
Sometimes a good conversation is one of the best memories after a hangout session, so don't overlook the importance of having solid questions prepared. After all, your natural charm can only get you so far.
Here are the 7 best questions to ask a girl:
48. What have you learned from your past relationship?
Every relationship's end is a new opportunity for growth. Share your wisdom.
49. What is the most important thing that guys should understand about the girl, and it seems to you that they do not understand?
There's nothing wrong with a little self-improvement.
50. What is the most useless thing you've ever bought?
We've all squandered our money on something that ended up in the junk drawer.
51. Which decade do you think had the best sense of style?
Bellbottoms in the 70s? Day-dresses in the 30s?
52. What is your silliest fear?
There's no shame in unreasonable fear.
53. If you had to compare yourself to one fictional character, who would it be?
This question can help you to understand how she views herself, and the type of person she would like to be.
54. What is the worst pickup line you've ever heard?
Most girls have heard a few stinkers in their day. Laugh at them, but please don't use them.
10 Best Questions to Ask a Guy
These questions to ask a guy are geared towards a male perspective. Whether you're vetting a new co-worker, shooting the breeze with your boys, or making small talk at the office, these questions will keep the conversation interesting.
Feel free to tweak these questions to fit your specific situation. Sometimes these questions will also spawn new conversations. Just go with the flow. Keep it light, easy, and natural, but don't be afraid to get into deeper discussions if they arise.
Here are the 10 best questions to ask a guy:
55. What’s one thing people would never know about you just by looking at you?
A lot of guys have interests and passions you would never expect.
56. What’s the sweetest thing you’ve ever done for a girl?
Feel free to shamelessly steal his idea next time you're trying to do some charming of your own.
57. Have you ever made a decision that changed your entire life? If so, what was it?
This question can lead to some fascinating conversations.
58. Would you rather go out or stay in on a Saturday night?
Are they more of a party person or a chiller?
59. What’s the craziest thing you’ve ever done for a girl?
We've all done it. Share your stories of reckless romance.
60. Where do you like to go to have fun?
You'll learn about him, and you might find out about a cool new thing to do in your area.
61. What is your favorite thing about being a guy?
Besides being able to stand while you pee, of course.
62. What is your most useless skill? Most valuable?
Men are all about their skills, no matter how pointless they may be.
63. What's the best bad decision you ever made?
That moment that seemed so wrong but turned out so right.
64. What is the best pizza topping combination?
Everyone loves pizza.
8 Best Questions to Ask Your Girlfriend
No matter how long you've been together, sometimes you run out of things to talk about with your girlfriend. That's where we come in.
This list of questions to ask your girlfriend is perfect for long drives, dinner conversation, or just for hanging out on the couch. Some of them help you to connect with her on a deeper level, others are just for making small talk.
Asking your girlfriend questions is a great way to let her know that you still care about her. Relationships take work and time. These questions help you strengthen your bond.
Here are the 8 best questions to ask your girlfriend:
65. What did you always wanted to try but never found the courage to do?
Listen to her answer, and help her achieve her dreams.
66. Do you enjoy being out in nature?
If so, maybe a camping trip is in order?
67. What’s the best way to spend a rainy afternoon?
Hopefully it's cuddled up with you.
68. What's the silliest reason you've ever gotten into a fight with someone?
Sometimes dumb fights happen. Hopefully hers was with someone else!
69. What slang or trend makes you feel old?
What are the kids up to these days?
70. How are you really?
This question, though simple, can actually be very meaningful. Communication is essential to the success of any relationship. It's nice to check in every once in a while.
71. What was the most thoughtful gift you ever received?
Take note and try to outdo it.
72. What’s the best topping/ice cream combination?
This question should probably be followed by an impromptu date to your local ice cream parlor.
11 Best Questions for Couples
These questions for couples all have one thing in common: romance!
Use these questions to get to know each other better. Use them to improve your relationship.
Keep an open mind, and make sure you give your own answers too. It's important that these questions aren't one-sided. Use them to ignite conversations.
Here are the 11 best questions for couples:
73. What does love look like to you?
Everyone has their own idea of what love means and is. Try to find common ground and create your perfect idea of love together.
74. What is your favorite dessert?
Take note and treat her to it.
75. When was the first time you became aware of me?
Sharing memories is a wonderful way to reconnect and remember why you're together in the first place.
76. Do you remember the first thing we said to one another?
This is another question that pushes those nostalgia buttons.
77. What's your favorite memory of me?
Make sure you have a fond memory of her ready to talk about.
78. What is your favorite way of spending time with me?
Whatever it is, make it a point to do it more.
79. If you were asked to give me a nickname, what would it be?
This is a fun question that can get silly.
80. What’s the one secret you’ve been too embarrassed to tell me?
Be warned: she's going to want you to share one too.
81. If there’s one thing you’d want to change about me, what is it?
Try to be open-minded. This can be a sensitive subject, but it can lead to positive changes in the long run.
82. If we hadn’t met each other, where would you be right now?
It's interesting to think about how one person can change the course of another person's life.
83. What would your dream home look like?
Planning for and dreaming about the future is a great way to bond with your partner in crime.
6 Best Questions to Ask Friends
There's a lot you probably don't know about your friends.
But if you have some questions to ask friends at your disposal, you'll constantly discover more about them.
And the best part? It'll only bring you closer together.
Here are 6 best questions to ask friends:
84. What time of the day do you feel the most energetic and what do you usually do in those moments?
To be productive, you have to maximize the time you have. Here are some helpful tips.
85. What’s the coolest thing about science?
In the words of Bill Nye, Science rules. Was it the Falcon Heavy Launch? How about Crispr?
86. What’s your idea of Heaven?
A spa day? A hunting day? Everyone has a different definition of Heaven.
87. When are you most yourself?
We all need to tone it down sometimes. When can you let it all out?
88. If you won 100 million dollars, what would you buy first?
Your safest option is to not tell anyone.
89. What’s the best sound in the world?
The popping of bubble wrap? Children laughing hysterically? The words, "I Love You"?
6 Best First Date Questions To Ask
So you landed a date. Congratulations, stud – now it's time to get ready. Pick out an outfit, make some reservations, and prepare your social game with these first date questions.
It's no secret that coming up discussion fodder can be tough, especially when it's your first time meeting someone. Mantelligence is your virtual wingman here to help.
Asking questions is the best way to get to know someone and determine if they're a good match or if you should keep fishin' the pond. Quality questions yield quality answers, so don't overlook the importance of preparing some solid openers.
Here are the 6 best first date questions to ask:
90. If you could wave a magic wand right now and have your life be perfect, what would that new life look like?
This is a roundabout way of finding out what a person's goals and aspirations look like.
91. What could you spend all day talking about?
This question helps to get her to open up by giving her the opportunity to choose her own topic of conversation.
92. On your last vacation, did you plan everything out beforehand or go with the flow?
This seemingly simple question can actually shed light into what type of person she is.
93. What’s your favorite thing about your best friend?
This question helps you to understand what qualities she values in a person. Take note.
94. If you had a dinner party and had to invite a musician, a politician, a famous couple and only one family member, who would you invite? Bonus points: What would you be serving, where would you have it, and what would be on your dinner playlist?
This is a big question that can take plenty of time to answer – perfect for first dates when you want to fill the awkward silences.
95. What do you like to do when you're not working?
Get some ideas for your next date with this question.
10 Best Would You Rather Questions
The "would you rather" game is timeless. Not only is it a blast, but you can learn a lot about the other person.
Some of these would you rather questions are extremely difficult. That's what makes them so fun.
Would you rather questions are great because they give the other person two clear options to choose from. At the same time, the answers can spark new questions and conversations too.
Use these questions to get the game going, but don't be afraid to come up with some of your own too!
Here are the 10 best would you rather questions:
96. Would you rather go camping in the woods or stay at a beach resort?
Are they more of an outdoorsy type or a lover of luxury?
97. Would you rather be half your height or double your weight?
Either way you're next mirror experience is going to be a weird one.
98. Would you rather be an ugly genius or a hot moron?
Beauty or brains?
99. Would you rather be itchy or sticky for the rest of your life?
There's no good answer here. Choose the better of two evils.
100. Would you rather have the hiccups for the rest of your life, or always feel like you need to sneeze but can't?
Yes, you would be making that pre-sneeze face all of the time.
101. Would you rather eat a gallon of mayonnaise or four sticks of butter?
It's the diet of champions.
102. Would you rather end the life a single human being or 500 cute baby animals?
Either way, you're a monster.
103. Would you rather relive the same day for 365 days or lose a year of your life?
Would you go through a Groundhog Day scenario or just chock one year up to loss?
104. Would you rather sell all of your possessions or sell one of your organs?
How important are your things to you?
105. Would you rather be forced to dance every time you heard music or be forced to sing along to any song you heard?
Whatever answer you choose, you're going to be a hit at parties.
9 Best Random Questions to Ask
Sometimes a random question is the best question. It's fun to surprise people, and a question out of nowhere keeps things interesting.
These random questions to ask don't need any rhyme or reason. Whatever the setting or mood, just toss them in the mix.
Here are the 9 best random questions to ask:
106. If you were in a band, what kind of music would you play?
And what would your band be called?
107. If you had to run away from everyone then where would you hide yourself?
In a van down by the river? In a treehouse in the woods?
108. What do you think is the cleverest animal and why?
Which animal secretly knows exactly what it's doing?
109. If you had to be one cartoon character, which would you choose?
You would still live in the normal human world.
110. Would you abandon your phone, internet, family, and friends for three months for a prize of 1 million dollars?
And you're not allowed to tell anybody.
111. What is the word you absolutely hate people for using?
Some words just make the skin crawl.
112. What is the most beautiful thing in nature?
Flowers? Mushrooms? Waterfalls? What's the most magical thing on Earth?
113. What is your favorite type of candy?
What makes your sweet tooth happiest?
114. How do you feel about clowns?
Clowns tend to be a love-them-or-hate-them (or be terrified by them) topic.
8 Best Interesting Questions
If you're uninteresting, you're boring.
Become more of an individual by trying out our best interesting questions in your next conversation.
Here are the 8 best interesting questions:
115. What are You Expecting from This Relationship?
This is a curveball of a question simply because you don't expect people to ask it. But you deserve to know.
116. Do Loud Noises Bother You?
Some people enjoy the liveliness of a crowded place. Others cannot stand it.
117. What have you forgotten?
118. If you had two hours left on earth what would you do?
A fun one to answer. It's a shame you can't watch The Lord of the Rings all the way through.
119. Who makes you laugh more than anyone?
Get a friend who you can act ridiculous with.
120. What’s the best gift you’ve ever given?
Be proud of the gifts you give people, especially if you put a lot of thought into them.
121. How many times a day do you look in the mirror?
Tomorrow, keep a tally. Windows count too!
122. If 100 people in your age group were selected randomly, how many do you think they’d find leading a happier life than you?
Does the majority have it tough or are things just fine?
8 Best Fun Questions to Ask
Sometimes you just want to keep the mood light and easy-breezy. These questions help you do just that.
These fun questions to ask don't require any touch thinking or emotional involvement. They're pure fun – plain and simple.
Here are the 8 best fun questions to ask:
123. If you were guaranteed the correct answer to one question, what would you ask?
This is a great question because it can go anywhere.
124. What is an obscure food that you have eaten that most people never tried?
There are a lot of interesting dishes out there. Some are divine, and others are abysmal.
125. What is your favorite three-word sentence?
This question gives you both the chance to be creative. You can also have categories like "funniest," "scariest," and so on.
126. If you had to live a week without internet, what will you do to keep yourself busy?
Read a book? Hit the gym? What would you do during the worst week of all time?
127. What was the most awesome excuse you ever made?
Did you call out of work because you got "sprayed by a skunk?" What's that ridiculous excuse that somehow worked?
128. What’s the worse topping to put on a pizza?
Feel free to get creative with this one. Keep it edible though.
129. What's the worst topping to put on ice cream?
It's probably the pizza you made in the previous question.
130. What’s the most ridiculous thing you’ve ever heard someone say out loud?
Some people have no filters.
8 Best Funny Questions to Ask
Never underestimate the power of humor. Sharing laughter is one of the most effective ways to form a lasting bond with anyone.
Even if you have absolutely nothing in common with the person you're talking to, these funny questions to ask will help to break the ice.
Just because they're lighthearted doesn't mean that these questions won't go a long way in connecting you with someone. Use them sparingly though – you don't want to come off like you're doing a standup act. Always leave your audience wanting more!
Here are the 8 best funny questions to ask:
131. What product do you think the world could go on without?
There are a lot of useless gadgets out there. Which is the most pointless?
132. If one animal was made the size of a whale, which would be the scariest?
A whale-sized mosquito is nightmare fuel.
133. What is the worst song lyric you have ever heard?
And how loud can you belt it out in public?
134. What is the craziest thing you’ve seen somebody do at the workplace?
Workplace freakouts often lead to hilarious stories.
135. What is the worst thing your mom caught you doing as a kid?
Kids do some pretty funny stuff, although the parents might not think so at the time.
136. What is that one joke that you cannot tell without laughing hard?
Everyone loves a good joke.
137. Who is the most annoying celebrity according to you?
And can you do an impression of them?
138. What fun activity from your childhood has been completely ruined for kids today?
This is why we can't have nice things.
7 Best Ice Breaker Questions
Everybody knows how much a polar bear weighs.
Be more original with your ice breaker questions by trying some of our best below.
Here are the 7 best ice breaker questions:
139. What good happened to you today (or this week)?
It's easy to get caught up in the negative aspects of a day. Focus on the good when starting a conversation with someone.
140. When you are gone, what would you like people to write for your obituary and why?
141. What responsibility would you gladly give up? What would you not give up?
Being an adult isn't easy. What would lighten the load?
142. "Where were you living between the ages of 7 and 12? What were winters like then and how was your home heated during that time?
This is an off-the-wall question but it's very specific (which is funny). Try it out and let us know how it works!
143. What do you like best about your house or apartment?
If your place of living feels drab, consider buying some cacti and succulents! They're hard to kill and will make any room feel much more comfortable.
144. What is your middle name and why were you so named?
Middle names are great because they're almost pointless.
145. Where is your happy place?
You should have a happy place; a place in your mind you can visit to relax. Or even a real, physical place.
6 Best Weird Questions to Ask
These weird questions to ask are a bit loony, and that's why we like them. After all, sometimes getting weird just feels right.
Everyone has their own bizarre idiosyncrasies. That's what makes people special.
Flaunt your strange side with these wacky questions.
Here are the 6 best weird questions to ask:
146. What smells make you happy?
Some people love the smell of gas at the gas station. What weird odors make you smile?
147. If you could pick any animal to talk, which would it be?
Bonus points if you can imitate its voice.
148. What's the most bizarre chewing gum flavor you can come up with?
And what amount of money would it take for you to chew it?
149. What are the five words that you use the least? The most?
This question might take some thought, but the answers can be hilarious.
150. Would you rather be tiny as a fly or massive as a dinosaur?
Both sound terribly inconvenient.
151. If you were a snake, how long would you want to be?
It's a perfectly reasonable question.
13 Best This or That Questions
These this or that questions are great because they make things easier for the other person. You give them two choices, and they decide on one of them. It's that simple.
The beauty of these questions is that the answers can spark more in-depth discussions. Don't be afraid to ask someone to explain their answer. Sometimes it's fun to have a good-natured argument over why one answer is preferable over the other.
Here are the 13 best this or that questions:
152. Burgers or tacos?
This is a question that may make people cry.
153. Money or fame?
What's worth more?
154. Too warm or too cold?
And how do you find relief?
155. Pepsi or Coke?
156. Beard or mustache?
157. Early bird or night owl?
Early to rise or late to sleep?
158. Classic or modern?
Past or present?
159. Smile or eyes?
Which holds more beauty?
160. Fast food or mom’s cooking?
161. Batman or Superman?
Who would win in a fight?
162. Call or text?
Which is better and why?
163. Plane or train?
Is it about the journey or the destination?
164. Sweater or hoodie?
Which one warms your heart more?
6 Best Truth or Dare Questions
Truth or dare questions turn any gathering into a party. Either you're going to learn some juicy secrets about the people you're with or you're going to be entertained by some lighthearted foolishness – it's a win-win.
Truth or dare is only fun if everyone participates. It's an unspoken rule that if you start the game, you have to fulfill your duties to the bitter end. If you don't like your truth or your dare, well, that's just too bad. Of course, you want everyone to have a good time, so keep your questions and dares on the positive side.
These questions and dares will get you started, but don't be afraid to get creative with your own ideas. After all, where you are and who you're with makes a big difference in how the game goes.
Here are the 6 best truth or dare questions:
165. After you've dropped a piece of food, what's the longest time you've left it on the ground and then ate it?
5- second rule? 10-second rule? Where do you draw the line?
166. What was the last thing you searched for on your phone?
Be careful: you might be required to show the proof.
167. How would you rate your looks on a scale of 1 to 10?
This scale goes to 11.
168. What's the most unflattering school picture of you?
Bonus points if you can bust out your best blunder years shot.
169. Would you wear your shirt inside out for a whole day if someone paid you $100?
In other words, what is the true cost of your dignity?
170. Give someone your phone and let them send one text to anyone in your contacts.
What could possibly go wrong?
6 Best Personal Questions
Sometimes you want to get to know a person on a deeper level.
Asking personal questions is a great way to get there!
Personal questions deal with topics that most people aren't comfortable talking about to just anyone.
But if you ask, you'll be surprised at how many people will answer the questions below!
Here are the 6 best personal questions:
171. What do you spend most of your time doing?
Talk about hobbies with people. It's a great way to bond.
172. What do you spend way too much of money on?
If you can't answer this yourself, it's time to make a budget.
173. How do you calm yourself when you get angry?
Something to keep in mind: Getting angry is a choice. You control your emotions and how to respond to things.
174. What was the last time you tried to something to look cool but it ended in utter embarrassment?
Whenever this happens, it's best to own it.
175. What is the most impressive skill you have?
Even if it's useless it's probably still kind of cool.
176. What’s your “go to” video or gif for a laugh?
It's always stressful when people don't laugh at a video you show them.
8 Best What If Questions
If you're going to ask what if questions, they might as well be the best. These questions allow for great speculation that can lead into incredibly interesting conversations.
Choose a few from the list below and drop them into your conversation when you feel the moment could use a little mind blowing.
Here are the 8 best what if questions:
177. What if computers took over the world?
We've all thought about it, so, what if?
178. What if someone wrote a story about you? Would you be considered a hero or a villain in your story?
A new way to make people think of their own lives.
179. What if we found live dinosaurs living on a remote island?
Are you visiting the park or staying home?
180. What if you could change one thing about the world? What would it be?
It's just one thing so you know it's going to be important to them.
181. What if you woke up and discovered you were the only person on earth?
Are they lonely, scared, or ready for an adventure?
182. What if you were offered the opportunity to go into space?
Would you be brave enough for the greatest adventure of your life?
183. What if you could marry someone famous, either living or dead?
Find out who everyone's favorite stars really are.
184. What if you could start your life all over? What would you do differently?
One of the great questions of all time, and every answer is interesting.
8 Best Deep Questions to Ask
These deep questions to ask are best used with someone you already know. Some of them can be a bit personal, and they really make you think.
Of course, if you feel comfortable with someone, asking a deep question can strengthen your bond. Just don't be pushy about it. Pay attention to the other person's body language, and if they're not feeling it, dial it back.
Deep discussions have a time and a place. Sometimes they're planned, but more often than not, they happen spontaneously.
If you find yourself having a deep discussion, it's important that you contribute too. If you want the person you're talking with to open up to you, you need to give them something in return. Be willing to give your own answers, and try to create a comfortable, judgment-free environment.
Here are the 8 best deep questions to ask:
185. What is the biggest change you want to make in your life?
And what steps will you need to take to succeed?
186. What do you consider to be the highlight of your life?
What was the pinnacle of achievement? Can it be outdone?
187. What is your best piece of advice?
Heed the answer. Good advice is priceless.
188. What do you think is the best feeling in the world?
What is pure bliss?
189. What is one thing you don’t understand about yourself?
We all have qualities that don't really have any rhyme or reason.
190. What is something beautiful you see every day?
It's important to see the beauty in the small things.
191. What was the single, best realization you have ever had?
This question can help you to come to some important conclusions of your own.
Simple and sweet.
7 Best Most Likely To Questions
Using most likely to questions is a great way to learn more about the person answering and the other people you know.
When you really want to maximize the experience, you have to go with the best most likely to questions out there, which we've put together here.
Pick your favorites and start asking around, since everyone already knows you're most likely to ask a most likely to question.
Here are the 7 best most likely to questions:
192. Who is most likely to give all their money to charity?
Find out who is considered the most generous person you know.
193. Who is most likely always to be happy?
Hang out with that person.
194. Who is most likely to have weird phobias?
Get the answer, then ask the person.
195. Who is most likely to get in a fight?
Avoid getting that person angry.
196. Who is most likely to be the first one to die in a zombie apocalypse?
When you see that first zombie, don't team up with this guy.
197. Who is most likely to invent something useful?
A great way to find out who the most creative and mechanical person is you know.
198. Who is most likely not to take a shower for a week?
You probably know just by the smell test.
7 Best Hypothetical Questions
Hypothetically, if you're asking hypothetical questions, do you want to ask the best or the lamest? Hypothetical or not, the answer is always the best.
With these hypothetical questions, you'll have people thinking, laughing, and starting great conversations. Choose your personal favorites and try them out at your next gathering.
Here are the 7 best hypothetical questions:
199. Would you rather lose £100, or be given £10 million and have to set it all on fire and watch it burn?
It may be incredibly painful to watch the money burn, or it may be a whole lot of fun.
200. Would you rather eat only one meal every three days of whatever you want, and only peanuts in between to keep you alive; or eat whatever you want, whenever, but have no sense of taste?
A crazy way to make people think about how much they like food.
201. If you had a choice between having a tail or losing a leg, which would you choose?
The tail would certainly make it easier to share your mood.
202. What would you do if you only had 100 blinks left before losing your vision?
Use really good duct tape.
203. If you did not exist, what would you be doing now?
Let everyone's minds pretzel at that one.
204. How would human life be different if crocodiles could fly?
205. Can you afford to feed a dinosaur?
Ask the guy always bragging about how he can cover the tab for everyone.
8 Best Existential and Philosophical Questions to Ask
The answers you get to these questions can really provide some fascinating perspectives about a variety of topics, so pay attention. Look at the resulting conversation as a learning experience.
These questions really make you think, so use them sparingly. Dwell on the answers, and trade takes. Sometimes you might want to try playing devil's advocate to try to inspire deeper thoughts.
Always be kind and understanding, and be willing to change your mind. An open mind is the key to successful existential and philosophical discussions.
Here are the 8 best existential and philosophical questions to ask:
206. To what extent do you shape your own destiny, and how much is down to fate?
Are we in control or just flowing down the river of life?
207. Should people care more about doing the right thing, or doing things right?
What's more important: ethics or ideal results? Do the ends justify the means?
208. Is a “wrong” act okay if nobody ever knows about it?
Discuss morality and what constitutes good and evil.
209. What do people strive for after enlightenment?
Once you've made it to the top, where do you go from there?
210. If lying is wrong, are white lies okay?
Is it ever okay to bend the truth for the overall good?
211. Can we have happiness without sadness?
Can there be one without the other? And if so, is pure happiness ever possible?
212. Does sound happen if nothing is present to hear it?
If a tree falls in the woods...
213. Does observation alter an event?
You may want to look into the double-slit experiment for this one.
24 Never Have I Ever Questions
You'll need this popping list of never have i ever questions to dig deep really quickly. We're all so sick of small talk. Lots of us are still learning how to navigate intimacy. We use the traditional, tried, and true get-to-know-you games as anchors for inquiry.
Our beneath each prompt input lets you know what each says about your personality and/or the questions you're really asking of the people around you.
Here are 24 never have I ever questions:
214. Never have I ever played Never Have I Ever.
You're saying that you're new to the process so you appreciate everyone's patience while you get in the groove.
215. Never have I ever 'cleaned up' by piling everything into a closet.
You're better than that and you get to the root of the cause.
216. Never have I ever pretended to laugh at a joke I didn't get.
You're secure in yourself and authentic where others might succumb to peer pressure.
217. Never have I ever had a near-death experience.
You've never been so close to that edge but you have curiosity about and respect for those that have.
218. Never have I ever played Candy Crush.
Just because someone says click here doesn't mean you will. Bright colors don't send you into autopilot.
219. Never have I ever crept on someone I just met on social media.
Clearly you're not on social media enough to be tempted.
220. Never have I ever lost sunglasses that I was already wearing.
That piece of plastic weighing on the bridge of your nose is not something you can zone out.
221. Never have I ever gotten stitches.
You really want to hear about the accidents had by those who have had their flesh sewn shut.
222. Never have I ever had a paranormal experience.
Aliens are everywhere but they hide well from the normals.
223. Never have I ever woken up and couldn’t move.
Consider yourself lucky.
224. Never have I ever looked through someone else’s phone without their permission.
You have enough integrity not to snoop and you probably don't have extreme jealousy or trust issues.
225. Never have I ever said I am never drinking again.
You're a moderate social drinker who doesn't overdo it, at least when it comes to substances. Maybe retail is another story...
226. Never have I ever tried guessing someone's password.
By putting this out there, you're trying to suss out the folks in the room who aren't above creeping into your business if they had the chance.
227. Never have I ever pulled a push door.
This one is a gauge of who will admit they walk around on mindless autopilot and who's reading the words in front of them at all times.
228. Never have I ever checked through my phone media to remember the night before.
It's an alcoholic breathalyzer test built into a prompt.
229. Never have I ever farted in an elevator and pretended it was not me.
How can one even pretend in this case? You're trying to figure out who's zen or shameless enough to fart freely.
230. Never have I ever spied on my neighbors.
Either your neighbors don't inspire much interest or you're so focused on yourself you aren't drawn to compare your life to that of your neighbors.
231. Never have I ever Fallen asleep on the bus and passed my station.
This might allude to a person's inability to relax or it might praise them for being vigilant.
232. Never have I ever kept a wallet or money that someone dropped.
It doesn't mean your a saint just because you have; who wouldn't keep cash that has no clear original owner?
233. Never have I ever called in sick to work because I was hungover.
Yet another gauge of someone's impulse to escape into drinking weighed against their sense of responsibility toward their job.
234. Never have I ever deleted a post on social media because I had a low percentage of “likes.”
How shamed are you by numbers?
235. Never have I ever made a wish at a fountain.
This is a measure of one's whimsy and belief in the magical ways of the universe.
236. Never have I ever been stood up by my date.
Just because you haven't doesn't mean you're reliably irresistible. It also could mean you don't date much, for whatever reason.
237. Never have I ever tolerated a bad movie to impress my partner.
The whole "bad movie" thing is a chance to make snap judgments. It might seem like a bad movie because you don't understand it. The same goes for "bad peop
11 Best Newlywed Game Questions
Entertain your wedding guests with these mischievous newlywed game questions.
We have some surefire laughs on your betrothal day that will take the gathering to a new level of intimacy.
Here are 11 newlywed game questions:
238. Which one of you is the first to wake up in the morning?
This reveals who gets to stare lovingly at the still sleeping figure of their beloved.
239. When it comes to replacing the toilet paper roll, should the paper go over or under?
The mundanities of life create alliances. There are the over folks and the under folks.
240. Who is terrible with directions and gets lost easily?
This person might also just enjoy the spontaneity of exploring new avenues and the challenge of getting oneself unlost.
241. Among the two of you, who believes in ghosts?
Connection to the spirit world and belief in the beyond is a riveting characteristic.
242. Which of you is pro at fixing things in the house?
Who breaks and who fixes?
243. Which spouse is a picky eater?
The questions of "What should we eat tonight? Pizza? Chinese? Sushi?" get all the more complicated.
244. Who is better at remembering important dates?
Who will remember the anniversary of this day in 20 years?
245. What would you do to make it a perfect Sunday?
This question is a white canvas for dreams.
246. Who gets to hold the remote?
Who is in charge of channel surfing, and who's got too many other hobbies going on to care what streams through the tube?
247. What subject was likely the weakest subject for your mate in school?
Creative or analytical, that's what's being asked.
248. Who is more likely to bring home an abandoned kitten or puppy?
And so the family begins.
5 Interview Questions
With resumes becoming more and more generic due to the proliferation of coaching available in a competitive job market, the interview questions you ask to create the ideal team for your company are more important than ever.
Here are the 5 best interview questions:
249. What’s something you’d be happy doing every day for the rest of your career?
How steady is their vision for responsibility and consistency?
250. How important is physique to you for a healthy relationship?
This is erring on the personal side of things for the typical job interview, but hey, it cuts down to someone's primal attractions and values even if it would take one heck of a rare company mission for this one to be appropriate.
251. How do you define success?
This is a very dry and boring question, which gives much more credit to a person who can actually answer it with creativity and gusto.
252. What would your pet say about you if we asked for a reference?
A person's outlook on the wisdom of animals says everything about their ability to be compassionate, intuitive, and emotionally connected to the people around them. Honestly, professional and personal boundaries are starting to blur and it's not always a bad thing.
253. How can you say that a certain process is effective?
This is a great question because it seeks into a candidate's awareness and mindfulness around what constitutes results. If all they can spout off are numbers, beware. Results are in employee morale, ethics, and integrity as well.
How to Start a Conversation
Knowing how to start a conversation is an incredibly valuable skill, and like any skill, the more you do it the better you get.
Here is how to start a conversation:
1. Feel out the setting
You don't want to start an existential conversation at the water cooler at work. Who you're with and where you are make a huge difference in choosing the right questions to ask.
Be aware of your company and what the appropriate level of conversation is for that specific social situation.
These questions are meant to be used in a casual way. Don't blurt them out as soon as you meet someone. Wait until the right moment, and then ask them. You don't want the other person to feel like they're being interrogated!
Striking a conversation and engaging with another person is fun, so keep it that way. Even deep conversations should be approached in a friendly, non-intrusive way.
3. Pay attention to body language
Never force a conversation. If the other person simply doesn't feel like chatting, just enjoy the silence. There's no hard rule that says you must be chatting constantly.
Be conscious of how the other person reacts to your questions. If they don't seem to be enjoying themselves, try using one of the lighter, easier questions ("would you rather" and "this or that" questions are great for lightening the mood).
Conversation is a two-player game. Look at it like tennis. You serve the question, and the other person hits it back. Now, do you hold onto the ball? Of course not. You hit it back-and-forth.
Sometimes you're going to need to do the hard work if you want to go deeper with a conversation. Offering a tidbit of personal information can help the other person to feel more comfortable opening up to you. There's nothing wrong with making yourself vulnerable if you trust the other person.
On the other side of the coin, being a little goofy can help the other person to be willing to get a little silly too. Be a conversation leader, and the other person will follow naturally.
5. Let the conversation end when it ends
Even the best conversations will come to an end. Don't be the guy that beats a dead horse. You can always revisit discussions later, but you don't want to keep asking more and more questions.
When the conversation is over, move on. These questions give you plenty of material to work with, so mix it up.
Downloadable and Printable List of Questions to Ask
Here is a downloadable and printable list of questions to ask (right click the image and select Save Image As...):
You've reached the end of the master list of questions to ask. You're now fully equipped to spark conversations with pretty much anyone, anywhere, at any time.
While you may be a lean, mean, question-asking machine, try not to let your robotic side take over. The ability to have a conversation is one of humanity's greatest achievements, so keep it human!
Be yourself. Be charming. Be friendly. Be genuine. Keep an open mind, and remember to listen to your conversation partner. It doesn't matter how many questions you have to ask if you're not actively paying attention to the answers. Being a good listener means people will want to start conversations with you.
Now get out there and enjoy connecting with people via the art of conversation. It's a beautiful thing.