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.
Coming up with ideas for conversations isn’t always easy. Everyone draws a blank at some point. It happens.
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 11 of the 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.
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 14 of the 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.
Really… there isn’t one questions to ask that is the best. Because, think about it, every situation is different. Sometimes, you’re looking for something to ask a coworker… sometimes it’s your significant other… sometimes it’s your best friend. And, it’s different depending on your goal. Maybe you want to get to know someone better… maybe you want to have a deep conversation with your significant other… maybe you’re just trying to start a conversation with someone new.
So, it’s better to know handful of questions, for a handful of different situations. Use the table of contents above to help find what you’re specifically looking for. But if you’re just looking for a few of the top questions, see the next section!
If you’re in a rush to find some solid questions to ask someone, this list should treat you right.
Here are 8 of the 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.
Nobody is 100% an open book. In order to understand what makes people tick, you need to ask them questions.
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 14 of the 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.
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 7 of the 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.
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 10 of the 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?
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 8 of the 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.
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 11 of the 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.
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 10 of the best would you rather questions:
84. 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?
85. 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.
86. Would you rather be an ugly genius or a hot moron?
Beauty or brains?
87. 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.
88. 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.
89. Would you rather eat a gallon of mayonnaise or four sticks of butter?
It’s the diet of champions.
90. Would you rather end the life a single human being or 500 cute baby animals?
Either way, you’re a monster.
91. 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?
92. Would you rather sell all of your possessions or sell one of your organs?
How important are your things to you?
93. 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.
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 9 of the best random questions to ask:
94. If you were in a band, what kind of music would you play?
And what would your band be called?
95. 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?
96. What do you think is the cleverest animal and why?
Which animal secretly knows exactly what it’s doing?
97. If you had to be one cartoon character, which would you choose?
You would still live in the normal human world.
98. 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.
99. What is the word you absolutely hate people for using?
Some words just make the skin crawl.
100. What is the most beautiful thing in nature?
Flowers? Mushrooms? Waterfalls? What’s the most magical thing on Earth?
101. What is your favorite type of candy?
What makes your sweet tooth happiest?
102. How do you feel about clowns?
Clowns tend to be a love-them-or-hate-them (or be terrified by them) topic.
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 8 of the best fun questions to ask:
103. If you were guaranteed the correct answer to one question, what would you ask?
This is a great question because it can go anywhere.
104. 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.
105. 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.
106. 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?
107. 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?
108. What’s the worse topping to put on a pizza?
Feel free to get creative with this one. Keep it edible though.
109. What’s the worst topping to put on ice cream?
It’s probably the pizza you made in the previous question.
110. What’s the most ridiculous thing you’ve ever heard someone say out loud?
Some people have no filters.
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 8 of the best funny questions to ask:
111. 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?
112. If one animal was made the size of a whale, which would be the scariest?
A whale-sized mosquito is nightmare fuel.
113. What is the worst song lyric you have ever heard?
And how loud can you belt it out in public?
114. What is the craziest thing you’ve seen somebody do at the workplace?
Workplace freakouts often lead to hilarious stories.
115. 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.
116. What is that one joke that you cannot tell without laughing hard?
Everyone loves a good joke.
117. Who is the most annoying celebrity according to you?
And can you do an impression of them?
118. What fun activity from your childhood has been completely ruined for kids today?
This is why we can’t have nice things.
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 6 of the best weird questions to ask:
119. What smells make you happy?
Some people love the smell of gas at the gas station. What weird odors make you smile?
120. If you could pick any animal to talk, which would it be?
Bonus points if you can imitate its voice.
121. 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?
122. What are the five words that you use the least? The most?
This question might take some thought, but the answers can be hilarious.
123. Would you rather be tiny as a fly or massive as a dinosaur?
Both sound terribly inconvenient.
124. If you were a snake, how long would you want to be?
It’s a perfectly reasonable question.
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 13 of the best this or that questions:
125. Burgers or tacos?
This is a question that may make people cry.
126. Money or fame?
What’s worth more?
127. Too warm or too cold?
And how do you find relief?
128. Pepsi or Coke?
129. Beard or mustache?
130. Early bird or night owl?
Early to rise or late to sleep?
131. Classic or modern?
Past or present?
132. Smile or eyes?
Which holds more beauty?
133. Fast food or mom’s cooking?
134. Batman or Superman?
Who would win in a fight?
135. Call or text?
Which is better and why?
136. Plane or train?
Is it about the journey or the destination?
137. Sweater or hoodie?
Which one warms your heart more?
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 8 of the best deep questions to ask:
138. What is the biggest change you want to make in your life?
And what steps will you need to take to succeed?
139. What do you consider to be the highlight of your life?
What was the pinnacle of achievement? Can it be outdone?
140. What is your best piece of advice?
Heed the answer. Good advice is priceless.
141. What do you think is the best feeling in the world?
What is pure bliss?
142. What is one thing you don’t understand about yourself?
We all have qualities that don’t really have any rhyme or reason.
143. What is something beautiful you see every day?
It’s important to see the beauty in the small things.
144. What was the single, best realization you have ever had?
This question can help you to come to some important conclusions of your own.
145. How’s life?
Simple and sweet.
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 8 of the best existential and philosophical questions to ask:
146. 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?
147. 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?
148. Is a “wrong” act okay if nobody ever knows about it?
Discuss morality and what constitutes good and evil.
149. What do people strive for after enlightenment?
Once you’ve made it to the top, where do you go from there?
150. If lying is wrong, are white lies okay?
Is it ever okay to bend the truth for the overall good?
151. Can we have happiness without sadness?
Can there be one without the other? And if so, is pure happiness ever possible?
152. Does sound happen if nothing is present to hear it?
If a tree falls in the woods…
153. Does observation alter an event?
You may want to look into the double-slit experiment for this one.
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 are 5 steps to help you start a conversation more effectively:
Step #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.
Step #2: Relax
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.
Step #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).
Step #4: Participate
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.
Step #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 List of Questions to Ask
Here is a downloadable 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.