300 of the best conversation starters questions
22 Dec 2020 admin

300 of the Best Conversation Starters

In theory, starting a conversation is easy. You simply say “hello, my name is…” and voila, you’re having a conversation. Of course, this is easier said than done because you need something to talk about after you say that. Preferably something that doesn’t involve the weather. Check out these amazing conversation starters.


It gets even more daunting when you consider that every conversation actually consists of several, sometimes even dozens of smaller conversations. The art of conversation involves knowing when to ask new questions when there’s a lull and keep the other person talking.


Most importantly, you should never worry about asking questions to keep a conversation going. People’s impressions of you are based entirely on how you made them feel, and asking questions is a great way to make them feel interesting and important.

What Makes a Good Conversation Starter

Before we get into the questions (and boy do we have a lot of them!) let’s take a quick second to go over what makes a good conversation starter.


  • Open-Ended. A good conversation question has multiple answers, and cannot be answered with just “yes” or “no.” If it can, the conversation is likely to end exactly one word after you ask your question.
  • Clear Prompt. If your question is too broad or too vague, the effort involved in thinking up the answer can make a person check out. That’s not to say that deep questions don’t have their place, but maybe save the meaning of love, life, and the universe for your second date. Instead, try “this or that” or “would you rather” questions.
  • Fun and Engaging. Most importantly, your questions should show a fun, creative side. Asking questions that are a little off the wall will make a conversation more fun and memorable than asking something they’ve answered hundreds of times already, like “where do you work?”

The Best Conversation Starters 1-50

1. What are you currently obsessed with?

This one gives the other person a chance to gush about whatever their current number one thing is, without the pressure of having to definitively pick a favorite.

2. What was your childhood obsession?

Another great prompt, but his one allows some nostalgia, and maybe a little humor. You might even have some childhood memories in common that you can geek out about together.

3. How do you like to decompress?

You can learn a lot about someone from how they relax after a stressful day. Some people might have a cute little routine, other people just need to shut their brains off.

4. How would you sum yourself up in a tweet?

A variation on the classic “three words to describe yourself question. Asking a person to condense everything about themselves to a couple of short sentences will get them to highlight their most meaningful values and experiences.

5. What’s your dream vacation?

Someone’s idea of fun and relaxation says a lot about them. It can also lead to you bouncing vacation ideas off each other, brainstorming, or even reminiscing about past vacations.

6. What’s your perfect day off?

People have different philosophies on their days off. Some people just need some R&R. Others want to pack in as much excitement before they go back to a boring job. No matter what they need from their day off, everyone has a different idea of what makes it perfect.

7. What’s the most useful thing you’ve bought for less than $20?

A lot of the stuff we use every day we’ve spent a fair amount of money on. This one needs a bit of thought, but everyone is likely to have an offbeat creative answer.

8. What do you want your first/next tattoo to be?

This is going to be a bit more effective than asking about their last tattoo because not everyone has one. Asking about a first/next tattoo lets them talk about things they think are cool or important. If they already have tattoos, you can pivot to asking about the stories behind them after.

9. What trend do you not “get”?

There’s a lot going on in the world, and no one is going to like all of it. Sometimes talking about something that they dislike or are just plain confused by can help you feel a bit more sane.

10. What’s the shortest amount of time you’ve held a job?

Odds are this is going to lead to either a story about a terrible job/boss, or an embarrassing one about getting fired. Both can be fun… if they’re willing to laugh at themselves a bit.

11. What’s your idea of a perfect night in/out with friends?

Go out or stay in? A night you’ll never forget, or one you’ll barely remember? How a person really cuts loose tells you a lot about them.

12. What would your theme song be?

This is less about a favorite song and more about how a person thinks about themselves or wants to be perceived.

13. If you could keep any animal as a pet, what would it be?

No holds barred, no boring answers. If laws, money, and space weren’t an object, what animal would be the best pet?

14. Who is your favorite actor/actress?

This is several questions in one. Who’s their type? What kind of movies do they watch? Do they value acting talent, comedic ability, or someone who does their own stunts? A lot to learn from a very simple question.

15. What actor/actress can’t you stand?

On the other hand, everyone has an actor that they see and know a movie is about to be unwatchable. Is it because they’re terrible and only get cast in bad movies, or is it something else?

16. What’s your favorite movie?

If they’re really into movies they probably have a favorite. If they watch a lot of movies or don’t have a strong opinion maybe the better question would be “what’s the last movie you loved?”

17. What’s the worst movie you’ve seen?

Dunking on a terrible movie is a lot of fun. Just don’t get defensive if they name one of your favorites.

18. What movie would you say is “okay” but seriously overrated?

Again, don’t go right to defense if they name one of yours. Some classics and Oscar winners don’t seem like all they’re cracked up to be, which ones don’t they love?

19. Would you rather be contrarian or correct?

Some people like to have the right answer, other people just like to argue. AKA the “STEM or Humanities” question.

20. What habit is an instant “turn off” for you?

What’s something other people do that they can’t stand? Also, a decent way to avoid shooting yourself in the foot.

21. What’s the most beautiful place you’ve visited?

It could be somewhere local, or a place they crossed the world to find. A great way to ask about travel experiences without making the homebodies feel self-conscious?

22. What’s your earliest memory?

It might be something silly, or it might be a formative memory. It’s a fun question to ask and answer either way.

23. Are you a night owl or a morning person?

Be sure to follow up this question with “why” or what they like about being up late/early otherwise it’s not a question that has a lot of places to go.

24. When was the last time you pulled an all-nighter?

A school project that they put off too long, a trip gone awry, a video game they just had to beat, this question is sure to have an interesting answer.

25. Would you rather it be always summer or always winter?

This question requires some thought, and will naturally lead into a conversation about favorite activities for that season.

26. Do you prefer spring or fall?

This one is similar to the above but allows the other person to talk about specifically what they like about the season.

27. Would you rather have a mansion, or go on an expensive vacation every year?

Assuming each is mutually exclusive, this is a fun question because they’ll have to think about which would be more enjoyable. It can also lead into conversations about dream homes or dream vacations depending on which answer they pick.

28. What (besides your phone) do you never leave home without?

Their phone is the obvious answer, which is why we’ve ruled it out. This can lead to some interesting answers about everyday-carry items and daily routines.

29. What’s the last “fun fact” you learned?

People love sharing trivia, and making this question about the last fun fact they learned makes it a bit easier to think of an answer. Try to have a follow up besides “that’s crazy” to keep the conversation going after.

30. What’s the longest you’ve been stuck at an airport? (or in traffic, if they haven’t flown)

Travel stories are fun, and what’s more memorable than the story of a trip gone wrong? This is another great way to start talking about trips and vacations.

31. Would you rather fly or take the train?

Flying gets you there quicker, but you miss a lot of the scenery, or do you? They’re sure to have some thoughts.

32. If you had to go into witness protection, what would your new name be?

Put a bit of spin on the classic “if you had to change your name” question. You can even turn it into a story of what their new life would be like.

33. Who is the most overrated superhero?

Superman. It’s Superman. If you want to talk about why Superman is overrated, fire away with this question as is, or ask them who besides superman is overrated.

34. What do we really need a new word for?

Maybe it’s a word from a different language, maybe it’s something that you can only describe with a sentence, like “the feeling you get when you think you lost your phone, but it’s actually in your other pocket.”

35. What’s your guilty pleasure?

Ice cream? Rom-coms? Trashy reality shows? Loosen up a bit and laugh about the things you enjoy but really shouldn’t.

36. What song lyric do you always mishear?

Another chance for some self-deprecating humor. This one is a mix of trivia and pop culture, which is always fun.

37. Which friend are you?

That can be “friend” or “F.R.I.E.N.D.” What role do they play in their friend group, or what famous sitcom friend are the most like?

38. What’s the most useful curse word?

If you’re using this list to brush up for a work event, you should probably skip this question. Otherwise, this can be a fun (but certainly not PG) way to break the ice.

39. What’s the nerdiest thing you do?

Giving people permission to geek out about something they think they might be judged for otherwise is a great way to get a conversation going.

40. What gives you an instant mood boost?

This is a fun, upbeat conversation starter because it’s about things that are fun and upbeat. What do they do to turn their day around?

41. Would you rather know how you die or when you die?

On the other hand, you can get a bit darker with it. Anything that gets people thinking will get them talking.

42. What’s the #1 thing on your bucket list?

The big one, the crowning achievement of their life. People love to talk about their goals and dreams, and this is the biggest.

43. What’s the most achievable thing on your bucket list?

Something they’ve always wanted to do, just haven’t gotten around to yet. You can share ideas, and if you’re looking for fun activities to do together, this can be a great way to plan.

44. What’s the silliest thing you were afraid of growing up?

Another chance to laugh at yourself, while giving the distance of time and maturity so it doesn’t sting too much.

45. Do you cry more at happy endings or sad endings?

If you’re looking to build some connection and vulnerability, this question is a great lead-in. You can talk about emotions in something low-stakes, like movies.

46. If you could make one room in your house twice as big, which would it be?

A question to start people thinking about their homes and what they use them for. Also a fun lead-in to talking about things like dream homes, or what the perfect version of whatever room they pick would be.

47. Do you like Christmas or Thanksgiving more?

There’s a lot to be said here IF you follow up with questions about why, and what their favorite parts of each are.

48. What’s your hidden talent?

This is a great one because it allows you to show interest in them and their talents in addition to just getting them talking.

49. Would you rather be average at everything, or the best at one thing?

There are pros and cons to each, and a lot to go back and forth on if you’re willing to take the opposing position.

50. What’s the last time you laughed until it hurt?

This one is especially great if you’re trying to keep a conversation going with a group. Letting people share funny stories and sights they saw.

The Best Conversation Starters 51-100

51. The book or the movie?

This one can be general or specific. And if they have a preference in general, is there an exception?

52. Would you rather re-watch your favorite show, or try a new show you know nothing about?

The safety and comfort of the 100th viewing of The Office or take a chance on something new?

53. What would be the best book/TV show/movie world to live in?

Another chance to learn a lot about someone with several questions in one. Do they prefer to be safe and comfortable or strike out on an adventure? Would they rather live in a world with spaceships or dragons? Or neither?

54. What would be the worst book/TV show/movie world to live in?

Same question, but in the opposite direction. There’s a lot of strong choices for this one, maybe make a list instead of just trying to pick the worst.

55. What was the first movie you saw in theaters?

This can be a fun way to explore early memories and formative experiences. Did it instill a lifelong love of movies, or did they not sleep for a week?

56. What was the last movie you saw in theaters?

This can open up a discussion for current pop culture without putting them under pressure for not being 100% tuned in and up to date on everything.

57. Do you prefer ebooks or physical copies?

Another question-behind-the-question here, so there’s a lot of places to go once they answer. How often do they read, what kind of books do they read, where do they do most of their reading?

58. What’s always better homemade than store-bought?

This one brings up a mixture of strong opinions and nostalgia, a surefire way to get anyone talking.

59. What’s always better store-bought than homemade?

On the other hand, some things are just more convenient from the store. Unless they have recipes they want to share?

60. What food defined your childhood?

Note, this isn’t quite the same question as “your favorite food growing up.” Maybe it’s something they haven’t had since then, maybe it’s a food their parents always made that gives you some insight into who they were/are.

61. What musical artist do you secretly love, but would never admit?

This one requires a little bit of vulnerability, as it’s likely to open everyone up to a bit of gentle ribbing, but it’s a fun way to start talking about music in a way that’s not just listing bands you like.

62. What’s your go-to good mood song?

The sun is shining, the birds are singing, everything is right in the world. What song is playing in the background to make it a perfect day?

63. What’s your go-to bad mood song?

Is it a surefire pick-me-up? Something that matches your mood and lets you process? Or do you need something that gets you mad and fired up?

64. PC, console, or mobile? Which console?

Ultimately the goal here would be to talk about favorite/memorable games, but a bit of lead-in helps set the stage and gets people into the right mindset.

65. What everyday thing screams “the future is now!”?

The future is now, we just don’t always realize it. Maybe it’s something silly, or maybe they have a serious answer. This one is a fun way to put a spin on talking about the stuff we see every day.

66. Would you rather text or call?

This one might be a bit redundant if you’re already having the conversation via text, but it can also be a way to learn more about someone.

67. iPhone or Android?

There’s likely to be some strong opinions about this one. This can be a great lead into what sort of hobbies and everyday activities they have, or a way to pivot to favorite apps and games.

68. Sci-fi or Fantasy?

Some people say they’re the same thing, but real heads have thoughts.

69. Pop or Rock? Rock or Rap?

“What’s your favorite” can be a little too vague for something as pervasive as music. Try narrowing it down a bit first, and then you can talk about favorite songs and current trends.

70. What was the last good season of The Simpsons?

It’s been on TV for as long as anyone can remember, and there’s a lot of opinions floating around about which the really good seasons were. From here you can talk about favorite jokes and episodes, or move on to other shows.

71. Marvel or DC?

Both have massive cinematic universes to talk about, or maybe you’ll get someone who has been reading the comics since long before the movies were a cultural phenomenon.

72. Would you rather communicate solely with emojis, or without them entirely?

They’re certainly useful, but are they too useful to go without? Or not useful enough to rely on fully?

73. Which fast food restaurant is the worst?

With a couple of regional exceptions, there’s not a ton of great fast-food restaurants out there, so “best” is a middling and subjective question. Now, worst? You could talk about which is the worst for hours.

74. What’s the fanciest meal you’ve ever had?

This can be a fun one. Was it part of a once in a lifetime trip, a work party they felt totally out of place at? A fancy party they hosted themselves?

75. What sequel is better than the first entry?

There’s not a lot of these, but they’re out there. They’re also subjective, so you can spend a lot of time talking about this one.

76. Which reboot is better than the original?

Everything is getting rebooted these days. By “infinite monkeys on typewriters” logic, at least one of them has to be better than the original. Which ones stand a fighting chance?

77. Where would you go on your dream vacation?

Unlimited time, unlimited budget, what kind of answers can your friend(s) come up with? Or is it somewhere they’ve been already?

78. Glitzy tourist destinations, or hidden gems?

This can be a great way to get to know a person, while also being a prompt for travel stories. Some people like having all the comforts of home while they travel, other people like the bragging rights of having been somewhere few people have heard of?

79. Would you rather have robot arms or robot legs?

Alternatively, what part of your body would you replace with a bionic part? Or how much of your body would you replace with bionics if you could?

80. What’s the best piece of tech you own?

For most people, this is probably their phone, but there are plenty of other options as well. This question can be a great way to talk about what people invest their time and money in.

81. What gadget in your kitchen is the most useful?

Maybe they don’t cook a lot and it’s just their microwave. If they do a lot of baking it’s probably a Kitchenaid. Maybe it’s a fancy coffee maker or something that whips up sweet treats.

82. What do you think the next big technological breakthrough will be?

What’s just around the corner that they’re excited about? Talk about what downsides it might have, or what would make it even better!

83. What problems do you think technology will solve in the future?

Time to open it way up. What’s going to be the ultimate triumph of technology? Teleportation? Solving world hunger? Create drinking water from the ocean?

84. What’s your favorite piece of clothing?

This is another one that will indirectly tell you a lot about a person. Maybe it’s something expensive, or sentimental, or just really comfy.

85. Summer vacations or winter vacations?

Both of these have their advantages, and can also be about when it’s best to get away from work. Try to follow up on the conversation wherever it goes.

86. Would you rather ski or stay warm in the lodge?

Or whatever the applicable equivalent is. The point is, is it better to stay warm and out of the cold, or be out having adventures in it? From there move onto winter sports or cocoa recipes (or winter cocktails for a more adult audience).

87. What’s the best winter food or drink?

Speaking of cocoa recipes, is there anything that goes better with watching snow fall outside? If so, what is it?

88. What special holiday traditions does your family have?

Most families are going to have traditions that center around the winter holidays, but you might get some fun answers about other holidays as well.

89. If you could create a new holiday what would it be?

National “I don’t want to go to work day” maybe? Or something (or someone) underappreciated that needs their own day on the calendar. Chances are, if it’s something that they think deserves a holiday, they’ll be willing to talk about it for a while.

90. Would you rather go to a big school or a small school?

A big school where you can blend in with the crowd and have all the programs and resources, or a small school where you know everyone and get special attention from the staff? The same question could apply to corporations and employment.

91. Buffet or sit down restaurant?

It’s the classic quality versus quantity question, and a great way to pivot into favorite foods and restaurants.

92. What’s the weirdest food you’ve ever eaten?

Was it something they had while traveling? An attempt to appease a relative? Regardless, it’s likely going to result in some great stories.

93. What would be your final meal if you were on death row?

A bit morbid, but it’s a much more meaningful question than just asking about favorite foods. Are they going out on a bang, or would they rather have something familiar and comforting?

94. Would you rather be able to stop time or fast forward it?

Skip boring moments, or have time to prepare and react to anything? Don’t forget the follow-up, what would they do with the ability they chose.

95. If you could send a message to yourself at any age, what would it be, and what age?

This is a surprisingly deep question masquerading as a silly one, so it’s a great question to ask to get people talking about major moments in their lives.

96. If you never had to pay for one item again, what would it be?

This one will get them talking about their values and priorities. Will they pick something they use a lot? Something they think should have been free in the first place?

97. Would you rather learn that aliens are real, or vampires are real?

Kind of a variation on the “sci-fi or fantasy” question, this one can also deal with fears and ambitions, so can be a great way to start talking about serious topics in a silly way.

98. If you could scale any animal down to the size of a cat and keep it as a pet, what animal would you pick?

Would a tiny elephant be a cute pet? How about a lion the size of a housecat? Or maybe the ability to keep a great white shark in a fish tank?

99. What would be the best law to be exempt from?

A fun question to explore the way a person’s morality may or may not be constrained by the law. And if they say “murder,” run.

100. What’s the best practical joke you’ve ever played on someone?

The Best Conversation Starters 101-150

Was it something tame? Did it go way too far? This is a chance for people to tell stories about themselves, and give you an insight into the kind of person they may be.

101. If you had no restrictions where would you live, and what kind of house would you have?

No restrictions, up to and including the laws of physics. So let’s hear about those moon mansions and undersea apartments.

102. What’s the best one-liner joke you know?

Put them on the spot a bit, and let them show off their sense of humor without the need to remember elaborate setups and punchlines.

103. Would you rather be able to read minds or understand animals?

What would be the advantages and downsides of each? Maybe they get enough from people as is, or are sick of being lied to.

104. What quote from a TV show or movie do you use regularly?

Another fun way to start a conversation about media, this one involves insight into the shows and movies that live in their head 24/7.

105. What’s the most ridiculous item you’ve ever bought?

Impulse purchasing, drunken shopping, and more. Everyone has a story of money not-so-well spent, and it can be a fun way to get people laughing that doesn’t sting too much.

106. Would you rather own a bookshop or a museum?

Theoretically, they’re both lives of quiet discovery, but there are crucial differences. If they’re excited about the prospect of either, it could open up a world of related topics.

107. What would be the most useless superpower?

Technically a superpower, not so technically useless. This is a chance for them to show off their creativity and sense of humor. Or maybe just dunk on Aquaman.

108. When was the last time you yelled at someone?

This could be a question about righteous fury or something embarrassing that happened because of stress.

109. When was the last time you went on a road trip?

Whether this is a regular occurrence or something they have fond childhood memories of, this one is bound to get some stories.

110. What would a restaurant made just for you look like/serve?

Another end-run around the entirely too broad “what’s your favorite food.” This can also be a question about the atmosphere, service, drinks, and a bunch of other things.

111. What’s the smartest thing you’ve seen an animal do?

Anyone who has a pet has stories about smart things they’ve seen them do. Or maybe it was something they saw at the zoo or even a viral video.

112. What apocalypse do you think is the most likely? The most fun?

Sure, Mad Max is probably more likely than zombies, but is it more fun? If society is going to collapse, it should at least have the decency to turn into a giant playground.

113. What company do you avoid at all costs?

Maybe it’s the principle of the thing, maybe they had a bad experience with them in the past. Everyone has companies they’d sooner avoid.

114. Would you rather make naptime or snacktime a thing in adult life?

Kindergarten got a few things right. Which would they rather see implemented in the workplace? Or maybe they have a better idea?

115. Would you rather only be able to yell or only be able to whisper?

One’s more embarrassing, one’s more inconvenient. What kind of person are they?

116. Would you rather do stand-up or improv?

Some people are funniest off the cuff, others would rather have time to prepare. What would they prefer?

117. What would be the weirdest food to put peanut butter on?

Another chance to show off some creativity and humor. What wouldn’t peanut butter be good on?

118. What are the best and worst casino games?

Do they have a system? Do they not mind losing as long as it’s not boring? Do they go to the casino for an entirely different reason?

119. What’s your favorite holiday movie?

There are classics, there’s kitsch. Then there’s the most important question: does Die Hard count?

120. What were the best and worst things about where you grew up?

People love talking about childhood memories, and this question provides some direction and nuance for the question.

121. What movie is only good the first time you watch it?

Twists in movies are great, but if they’re not done right they’re completely unwatchable afterward. Or maybe the shock or humor wears off in other ways. What movie is only good once?

122. What is the oldest thing you own?

A childhood toy? A family heirloom? Maybe they replace everything they own every five years? This is a fun way to start talking about memories and valued possessions.

123. What’s the newest thing you own?

Some people have to have the newest of everything. Others keep everything until it is completely nonfunctional (or beyond).

124.  Would you rather only be able to watch classic (20 years old) movies/TV shows, or only new ones?

Is pop culture something they engage in mostly to talk about with other people? Or do they find something comfortable and stick with it? What would be the hardest to give up from either era?

125. What’s the weirdest conversation you’ve had on a plane/bus/train?

You meet some interesting people when you have to share a space to get somewhere. Who was the most memorable?

126. What’s the weirdest thing you’ve overheard?

Sometimes you hear stuff that just doesn’t make sense, even knowing the context. What’s the last thing they heard that made you do a double-take?

127. What noise will always wake you up, no matter how deep asleep you are?

Obviously your alarm, but some things will make you sit bolt upright out of a dead sleep. Sometimes they’re funny, sometimes they’re terrifying. What are they?

128. What awful movie do you love?

Another opening for some teasing, but if everyone is willing to laugh at themselves, it’s a good way to see what their standards for “so bad it’s good” are.

129. What would you rename so the name makes more sense?

Trash pandas. Sky rats. Spaghetti cake. What should be renamed so their names make more sense?

130. What values are most important to you?

This one requires some introspection and openness, which makes it a great question if you’re trying to make the conversation a little less casual.

131. What’s the fastest you’ve ever regretted a purchase?

Buyer’s remorse is real, and it hits even faster when what you bought breaks before you even got it home. When’s the last time that happened to them?

132. Would you rather say everything you were thinking, or hear everyone’s thoughts?

The choice seems obvious until you think of just how many people are around you, thinking all the time.

133. What food did you use to love until you ate way too much of it?

Was it a Halloween candy they made themselves sick on? A pizza topping that they can’t think of without feeling woozy? This works for other things. Shows they watched to death, or songs they’re sick of.

134. What’s something obsolete that you still use?

Sometimes it’s easier to keep doing things the old way. What’s something they never bothered to update?

135. Would you rather be half an hour early or 15 minutes late everywhere you went?

They’re both inconvenient, they’re both embarrassing, but chances are, everyone has one they’d pick, and one they’d rather die than do.

136. What’s your favorite drink?

Coffee? Water? Soda? Cocktails? What their favorite drink is, and how often they have it can say a lot about a person.

137. What would your dream home be like?

If you give a person time to talk or walk through it room by room, this one can keep people talking for a long time.

138. What’s your dream car?

Is it a classic muscle car? The newest supercar? Something that doesn’t exist yet? If they’re really into cars this one can take up some time too.

139. What would you rate a perfect 10/10?

Some things in life just cannot be improved on. What are they?

140. What job would you be terrible at?

This one has a few different dimensions. Maybe the job involves skills they just don’t have or doing things they’re not comfortable with. Maybe they’d just really really hate it.

141. What’s something you’ve always wanted to be better at?

Maybe it’s something they haven’t had time to practice. Maybe it’s something they can’t get better at no matter what they try. If they’re willing to be open about it, learning about someone’s weaknesses can be a good way to get to know them.

142. What do you wish you understood better?

Maybe it’s a personal shortcoming, maybe it’s something that just plain makes no sense to anyone.

143. What’s the perfect way to start the day?

Not what their current morning routine is, goodness knows that’s not always the same thing. But if they had total control over how and when they woke up, and what they did after, what would it look like?

144. Would you rather sleep 8 hours a night, or take four 2 hour naps throughout the day?

It’s the same amount of sleep either way, but one might let you manage your downtime better, or break the day up better.

145. What day do you always look forward to?

Is it a holiday? Their birthday? The weekend? Payday? Everyone’s calendar has a day circled (if only metaphorically) what’s theirs?

146. Would you rather live out of an RV, or stay in the house forever?

What’s more important to them, flexibility or stability? What would it take to make either arrangement worth it?

147. What trend are you waiting to come back around?

All trends repeat every 20 years, at least that’s how the saying goes. Maybe they missed it last time or just kept all the clothes until they came back in style. What’s going to be most welcome when it starts happening again?

148. If you could stay one age forever, what would it permanently be?

Maybe it’s a year or two older than they are now, maybe it’s younger. What would be the perfect age to be forever?

149. Would you rather stay young until you die at a normal age or age but live forever?

If fairy tales have taught us anything it’s that eternal life and eternal youth aren’t the same things. But which is better?

150. What’s your idea of an adventure?

Is their life pretty tame, and an adventure is going to a new part of the city? Or have they had such an exciting life that only illegally base jumping in a foreign country counts?

The Best Conversation Starters 151-200

151. Would you rather be great at a hobby that very few people have heard of or average at a hobby that lots of people also do?

Is it better to be the best and have no one to play with, or play with a lot of people, many of who are better than you?

152. Would you rather be a master blacksmith or woodworker?

Two old-timey skills. One is still more practical today, but is the other one cooler?

153. What hobby would you take up if you had the time and/or money?

Some things look undeniably fun, but require tons of time and money. Which one of those activities would they pick? Or maybe they just don’t have enough time to pick up a new hobby at all.

154. What would your first act be if you were the dictator of a small nation?

A chestful of self-awarded medals and the uncontested rule of an island nation. What are they doing first?

155. What “luxury” couldn’t you live without?

You can learn a lot about someone by what things they think are always worth the money. Maybe you agree, maybe you don’t. Talk about it.

156. What long-dead historical figure would make the best president if resurrected?

They’ve been dead for 100 years or more, but if you taught them how to use the internet and gave them a few days, we’d have world peace. Who is it?

157. What makes you a good person?

This is another question that requires some introspection. Everyone is the hero of their own story, find out why they deserve to be.

158. What would your evil twin most likely do to ruin your life?

Or conversely, if they were the evil twin, what would they do to ruin the good twin’s life? What soap opera shenanigans can they come up with?

159. What’s your favorite smell?

Smell is heavily linked to memory, so it’s likely to be something nostalgic. Or maybe it’s just something that smells really yummy, like freshly baked cookies.

160. What’s the last charity you donated to?

Not as accusatory as “when’s the last time you donated to charity” or “do you donate to charity.” This question is a great way for people to share their values and priorities.

161. What’s the best compliment you’ve ever gotten?

People don’t get complimented enough, so the compliments we get tend to stick with us. This is also a great way to find out what people like most about themselves.

162. What was your biggest “never doing that again” moment?

When you learn from the school of hard knocks, you don’t usually need to repeat classes. What was a lesson they’ll never forget?

163. What quintessential school experience did you never have?

The prom. Detention. Food fights. House parties. What scene from a high school comedy did they never get to live out?

164. What was your “clique” in school?

No matter how well they got along with others, there was a group they gravitated towards. What was it?

165. What’s the best gift you’ve ever gotten?

Something practical? Something heartfelt? An experience they’ll remember forever? You can learn a lot about someone by the type of gifts they enjoy most.

166. Would you rather be a teenager forever, or a senior citizen forever?

One can drink, one can’t, both have about a 50/50 chance of being allowed to drive. What’s the better choice? Or is it just a question of least bad?

167. What would be the best and worst fragrances for a candle?

Another chance to be creative and funny, and maybe a little gross in the latter case.

168. What’s your best scar story?

Scars are like tattoos with better stories. Best case scenario it’s a cool story, worst case it’s funny or embarrassing.

169. What story describes you best?

Maybe it’s a story from their childhood that explains why they are the way they are. Maybe it’s something that some up the way they feel about life and everyone around them. What’s the story that sums them up perfectly?

170. What’s a terrible thing everyone should try once?

Some terrible experiences are incredibly instructive. Which universally awful experience would make the world a better place if everyone had it?

171. What’s something you haven’t grown out of?

Stuffed animals? Cartoons? LEGOs? Sugary cereals? Sometimes being an adult just means there’s more money to spend on kid’s stuff.

172. What’s the worst advice you’ve ever gotten?

There’s plenty of bad advice out there. What’s the last warning they were able to safely ignore?

173. What’s something you wish you had started doing when you were younger?

Maybe it’s an act of self-improvement that would have made life easier now. Maybe it’s a skill or hobby they wish they were better at. What is it?

174. Where would you feel most out of place?

Some people can fit in anywhere. Some people can’t. Where would they struggle to fit in?

175. If you wrote a book, what would it be about?

Everyone has a book in them, or so the saying goes. What’s theirs about?

176. If you could create one rule that the whole world had to follow, what would it be?

The 11th commandment. The platinum rule. If only everyone could be convinced to just do this one thing… what is it?

177. Would you rather be in prison for a year, or solitary for a month?

It’d be over quicker, but could they stand being alone with nothing to do for an entire month?

178. What rules were meant to be broken?

We all know the saying, but what rules, exactly are they talking about?

179. Would you rather have a million dollars you could only spend on clothes or a quarter-million you could spend on anything?

Sure it’s more money, but could they really spend that much on clothes? Is there a clever workaround to the problem?

180. If you give a billion dollars but had to give up anything you didn’t spend after a week, what would you do?

How quickly could they spend a billion dollars? And what would they have bought for themselves at the end of it?

181. Is it better to be smart but lazy or hard-working but average intelligence?

Which would make them happier? Which is a better recipe for success?

182. What’s something that’s free but you’d happily pay for if it wasn’t?

The best things in life are free. It stands to reason that at least a few of them would still be the best, even if you had to pay for them.

183. Would you rather always wear underwear when you shower, or always wear underwear over your clothes?

Offbeat, a little embarrassing, and there’s definitely no right answer.

184. Would you rather have skin that changes color when you change moods or tattoos that show everything you did yesterday?

One way or another, it’s going to be a lot harder to keep secrets. Which would be less embarrassing?

185. Would you rather lose all your teeth, or lose all your hair?

Is it a question of what’s more embarrassing? What’s the easier fix? Find out their fears, or priorities when it comes to their appearance.

186. What do you think is your best feature?

Give them a chance to brag about themselves. It’ll make them feel good, especially if you agree.

187. Would you rather have the same phone or the same car forever?

Both need to be replaced every so often, for obvious reasons. But what if that wasn’t an option? Which one couldn’t they do without?

188. Would you rather be blind or be deaf?

Nothing zany about this one, just practical, real-world possibilities. Something everyone has thought about and should be able to approach sensitively.

189. Would you rather have eyes that record everything, or ears that record everything?

And then, correcting hard in the other direction. Which one would be more useful? More fun?

190. What’s your sick-day routine?

Once they’ve called in to work, what does the day look like? Ginger ale? Soup? Game shows?

191. Would you rather always wear clothes that were too big or clothes that were too small?

Is there a good choice here? Too big might be more comfortable, but it’ll definitely look shabbier.

192. Would you rather be 10 feet tall or 1 foot tall?

That’s enough to be either the shortest or tallest person in the world by almost a full foot.

193. Would you rather wear high heels to bed or slippers everywhere you go?

A really zoomed-in version of the “comfort or appearance” debate. And how often would you have to replace your sheets if you wore stilettos to bed?

194. What’s your go-to comfy outfit?

It’s the weekend. Nowhere to go, nothing to do. What do they wear when they don’t have to move for 48 hours?

195. Would you rather wear sweatpants for the rest of your life, or never wear them again?

On the one hand, they make formal sweatpants. On the other, they’re still very obviously sweatpants.

196. How would your life be different if you had four arms?

Would the extra multitasking abilities be worth the fact that shirts would never fit right again?

197. Is it better to be too hot or too cold?

One small part of the “summer vs winter” debate. Also applies to wardrobe, thermostat settings, and preferred shower temperature. (Maybe don’t lead with that last one)

198. If you could have a bionic hand with a tool for each finger, which would the tools be?

Swiss army hand! What five tools would be worth the upgrade?

199. If you had one year to live, what would you do?

Bucket List speedrun time. How would they make their last year on earth meaningful?

200. Would you rather have the same shoes forever or the same haircut forever?

This one will be especially difficult for people who need to stay up to date on everything. What’s the biggest priority?

The Best Conversation Starters 201-250

201. What would be the first thing you did if you suddenly woke up and were a foot taller?

Are they still a somewhat normal height, or suddenly one of the tallest people in the NBA? What needs to change right away? What can wait?

202. If you could only have one food for breakfast, what would it be?

If they had to have the same breakfast over and over again, every morning, what would they choose? And what are their thoughts on turning into their dad?

203. Would you rather have a mullet or a perm?

Easily two of the least cool things to come out of the 80s. Which one would be more livable?

204. If you had to swap teeth with one animal, what would you pick?

Try to keep things normal and choose something like a chimpanzee, or go wild with it and pick a wolf or a duck.

205. Would you rather be homeless for a week, or live with your worst ex for a month?

This is going to be a very obvious choice for a lot of people, but it could easily go either way. Be sensitive, there might be some painful stories attached to this one.

206. Would you rather sleep on a bench, or on an insanely comfortable bed someone has died on?

Would their back or their brain make it harder to fall asleep? With the right follow up questions, this one could go in some interesting places.

207. How many cats is too many?

Does it make a difference if they’re indoor or outdoor cats? And how many cats is WAY too many?

208. How many dogs is too many?

Same as above. Is the number for too many dogs bigger or smaller than too many cats? Are 3 huskies more than 3 terriers?

209. Would it be worse to have no arms or no legs?

Not being able to walk, or not being able to grab things with your hands. Which would be harder to overcome?

210. Would you rather smell terrible and not know it, or have to live with someone who smells terrible?

Anxiety vs. discomfort. Fight!

211. Would you rather always be the hottest person in the room, but boring or the funniest person in the room, but plain?

Really just a question of how hard they want to work for attention, and what they want to be remembered for.

212. Which holiday has the best treats?

Every major holiday has its iconic foods and treats, but which is the best? It’s got to be down to Christmas, Easter, or Halloween, or is there another?

213. What’s your favorite comic?

There are webcomics, syndicated cartoons, superhero comics, even manga. Both the genre and the ultimate choice will say something about the person.

214. What’s your favorite cookie?

Girl Scout cookies? A classic from grandma? An embarrassing number of Oreos? What’s their choice, and why?

215. Would it be worse to be permanently thirsty, or permanently nauseous?

They’re both unpleasant, and both can be fixed. But which would be worse if it never went away?

216. Would you rather have hands for feet or feet for hands?

Probably hands for feet, right? Or would that make walking too hard? You could probably still type with your thumb toes…

217. Would you rather be able to shapeshift, or turn invisible?

In terms of practical results, there’s a lot of overlap here, but also some crucial differences that could tell you a lot about the person.

218. What website do you spend the most time on?

This one is pretty telling as well. It’s probably social media of some kind, but the differences between Facebook, Twitter, Reddit, and Tumblr are all going to be informative if you ask them why they made their choice.

219. What was the last thing that made you say “that was close”?

Stories about close calls can be exciting to both hear and share. You’re bound to get some fun answers out of this one.

220. What’s the biggest red flag a person can have?

You hear it, and you start backing away slowly. What’s the biggest thing someone can do to save you the trouble of getting to know them?

221. Would you rather be a wonderful dancer or a wonderful singer?

They’re both creative in their own way. They can both bring fame and fortune. Which would be preferable?

222. Would it be worse to lose your ability to speak, or lose your ability to read?

This one is going to come down to the way the other person socializes. Things like how important they think education and information are going to factor in as well.

223. What’s the most important thing in your home that you spent less than a dollar on?

This one might take some creative thinking, but everyone has something in their house that costs less than a dollar. It’s just a question of finding it.

224. What everyday thing will future generations not understand?

As technology, society, and the planet itself evolve, there are things we do every day that will be seen as unnecessary, wasteful, or incredibly luxurious by future generations. What’s an example?

225. What was the last thing you splurged on?

Another way to find out what people value and prioritize. What a person spends money on, especially their big “splurges” is a great way to get to know them.

226. What’s the most unrealistic thing you see regularly in movies?

It might be something they learned in their job or a dialogue tick that makes no sense when you think about it. Answers to this question are likely to be amusing and informative (but might ruin a few movies for you(

227. Would you rather re-do elementary school, or re-do high school?

Is this a question of reliving their glory days, getting it right, or just going back to a simpler time?

228. What was the most memorable thing one of your teachers did?

It could be a lesson that stuck with them, a hilarious mistake, or something else. Everyone had that one teacher, what did they do?

229. Would you rather understand every language you hear, or be able to play any instrument you pick up?

Seems like one is more practical and one is more impressive, but which is which? Is there a hidden downside to either of them?

230. What WOULD you wish on your worst enemy?

Sure, there are all kinds of terrible things that people wouldn’t wish on their worst enemies. But what is just painful or inconvenient enough to wish on your worst enemy?

231. Would you rather only be allowed to watch live-action or only watch animated shows/movies?

With the growing prevalence of animation, there are more choices than ever to watch. But if they had to choose, which would they give up? And what would be the hardest from each category?

232. Do you think it’s more likely to find aliens on other planets, or that they’ll come to us first?

Most stories about aliens involve them finding us first, hence the name aliens, but what if we’re the most advanced beings in the galaxy?

233. Would you rather rule the world, or live in a world without conflict?

Peace or power? Or if they had power, do they have a plan for peace?

234. Would you rather be the captain of an old-school pirate ship, or own a private jet with unlimited fuel?

There’s plenty of adventures to be had with each, but which they choose will depend on what they consider an adventure, and the directions their imagination takes them.

235. If you were immortal with one exception, what would be the thing that could kill you?

First off, the question is if life is meaningful if it doesn’t have an end, but if that’s too deep, just have some fun finding unlikely loopholes in your immortality.

236. Would you rather be a great scientist or a great athlete?

In a lot of ways this boils down to being famous or making a great contribution to society, but there are other aspects to it as well.

237. If you could build a hotel anywhere, where would it be?

A tropical paradise? Antarctica? Go even wilder and put it on another planet? What’s the one place everyone would be excited to visit.

238. Would you rather have everything in your house be the same color or a different color?

One’s boring and might make things hard to find. The other is bound to be an eyesore. Which would be easier to get used to?

239. If you could change the rules of any game, what would you change?

Whether it’s a professional sport or a classic board game, there must be a small (or large) change that would make it more exciting. Share some ideas.

240. Would you rather give up streaming video, or give up social media?

No Netflix, Hulu, Youtube, or no Twitter, Facebook, and Snapchat? Which would be harder to give up?

241. What’s something you spend way too much doing?

A slightly less positive version of the obsessions question, or maybe it’s something they’re sick of having to do. Either way, it’s an insight into their daily life.

242. Would you rather be a king thousands of years ago, or an average person now?

It’s a question of wealth and power, or wifi and plumbing. Which is more attractive?

243. If you could give any movie a sequel, what movie would you choose?

Some movies are perfect as is, but some are too good not to revisit. Finding out which move exists in that sweet spot tells you what kind of movies they love.

244. If you could see any historical monument when it was new, which would you choose?

This is a double whammy. First, it’s a question about where they’d most want to visit, but it’s also a question about what historical moment they find most exciting.

245. Would you rather be in jail or in a coma for five years?

They’d be removed from society for the same amount of time, but which has the greater downsides?

246. What meal can you cook well enough to impress a date?

Another chance for them to brag about their skills, but also a question about what their favorite foods are. It can also be about what foods they think are impressive or romantic.

247. Would you rather be able to see a week or 100 years into the future?

See exciting visions of the future, or see just far enough to change things? Or is it the other way around?

248. What’s the most expensive thing you’ve seen in real life?

A fancy car, a mansion, a rare collectible. What’s something extremely expensive they’ve seen for themselves?

249. Would you rather be on the run for a crime you did commit, or be imprisoned for a crime you didn’t?

Is it better to be in trouble that you deserve or have a resolution even if you didn’t deserve the outcome?

250. Would you rather have 1 wish today, or 10 wishes 10 years from now?

As long as they don’t wish for unlimited wishes, this is a question primarily about delayed gratification.

The Best Conversation Starters 251-300

251. Would you rather never have to wait for your food at a restaurant, or never hit a red light again?

Waiting isn’t any fun but is it a crucial part of the experience, or something they’d gladly do away with.

252. Would you rather grow 10% every year, or shrink 10% every year?

Either of these can get out of hand quickly, but which is preferable?

253. Would you rather do a freestyle rap or 5 minutes of impromptu standup?

Public performance is a major fear for most people, but each of these things has different challenges or required skill sets, so it’s sure to be an informative question

254. What’s better, instrumental music or acapella?

Or maybe the question should be which is worse? If they have strong opinions about either of these, they’ll be able to introduce you to some new musical artists.

255. What would you do if you were the last person on earth?

It’s the ultimate “what do you do when no one is around” question. How would they stay sane if there was no one else to talk to?

256. Which celebrity has the most interesting life?

Wild parties, expensive vacations, and more. Sure celebrities seem like they have it all, but who seems like they’re really going the extra mile?

257. Which celebrity do you think has the most normal/boring life?

On the other hand, who seems like they just curl up and watch Netflix on a Saturday night?

258. Would you rather end every phone call with “I love you” or always have a 50/50 chance of calling your partner the wrong name.

They’re both awkward, but is one more likely to cause trouble than the other? Or could they get used to one more easily?

259. You have 30 seconds to ruin a wedding, what do you do?

Creativity and chaos, both fun things to talk about. And it’s the most dramatic moment in any romantic comedy.

260. What’s the first book you remember reading?

This tends to be a formative memory, or at least the chance to reminisce together.

261. Would you rather be lost in the desert or the jungle?

There are dangers and difficulties with both, but which would be harder to survive?

262. What conspiracy theory do you think is most likely?

There’s a lot of them out there, they can’t all be fake, right? Which conspiracy they think could be true says a lot about how they view the world.

263. Would you rather know everything about space or everything about the ocean?

This one will tell you about the form and priorities of their curiosity. There’s a lot of unknowns about both, which is more exciting? Which is more useful?

264. Would you rather always know the exact time, or always have exact change?

Both are mild conveniences, but is there a way you could make them even more useful? This is another great way to learn about their creativity and priorities.

265. Would it be more embarrassing to publish your search history or your camera roll?

This one could get a little too private, so be careful who you ask, but it can also be a way to share a laugh.

266. If someone had been in a coma for the last 20 years, what would surprise them most?

A lot has changed in the past 20 years, what would be the biggest shock for someone who has been asleep since then?

267. If you were to join the military, which branch would you choose?

This question is examines an intersection of their skills, values, and at least a little bit of what they think is cool.

268. Would you rather have a self-mowing lawn or self-cleaning dishes?

These would both make life quite a bit easier, but would one save substantially more time than the other?

269. What’s something you think people only pretend to enjoy?

Some things just seem so boring and unenjoyable that you just think “no one actually enjoys this, it’s got to be an elaborate practical joke.” What are some examples they can think of?

270. What would be the biggest headlines of your life?

Not the biggest headline that happened during their life. Instead, if there was a newspaper all about their life, what would the biggest headlines be?

271. What’s the best cheap meal you know how to make?

Everyone has a few meals they can whip together for not a lot of time or money. This is another great way to get some insight into their daily life.

272. Would you rather only wear suits or only wear sweats and a t-shirt?

Both are going to be out of place most of the time, but which would be worse? Whether they’d choose to be underdressed or overdressed can say a lot about a person.

273. Would it be harder for you to give up coffee or soda?

Two of the most common, if least severe addictions that people have. Which one would be the bigger sacrifice?

274. Would you rather always have a healthy heart, or always have a healthy brain?

Having your mind or your body give out are the biggest fears about getting old. Which would be the better to be immune from?

275. If you had to play on a professional team for one game, which sport would you pick?

How they make their decision is going to say more than what their decision is. Are they picking it because it would be fun, for the exposure, or because they’d had a shot at actually playing some time?

276. Would you rather go to a concert or a play?

Both have social elements. Both are a way to take in some culture. Do they prefer the energy of a concert or the contemplation of a play?

277. What’s the fastest you’ve ever seen someone get fired?

This one can be a bit gossipy, but it’s sure to produce some funny stories.

278. Would you rather have amazing pizza once a year, or average pizza whenever you want?

Do they really like pizza, or really like pizza? It’s all a question of priorities and how they enjoy the things they love.

279. Milkshakes or sundaes?

Ultimately they can have the same ingredients, but there’s probably going to be a strong preference. Why?

280. Tater tots or french fries?

Fried potatoes with a soft center, another snack with the same ingredients, but which is better?

281. Sweet or savory breakfast?

Breakfast is one of the most chaotic meals of the day. You can have cake for the entire meal! If they had to choose either the classic sweet options or the savory, which would they choose?

282. If you had to give a 15-minute lecture right now, what could you give it on?

This is a chance for them to share something they’re knowledgeable about, or passionate about, or something that’s both. This is a great way to break the ice and make them feel interesting.

283. Would you rather have to eat all your meals with a toothpick, or drink all of them with a straw?

One’s slow and picky, the other is fast but it’s not likely to be enjoyable. Do they value their time or enjoyment more?

284. What’s the dumbest argument you’ve ever had?

Talking to some people can be like banging your head against a wall. Having someone who can sympathize with that struggle can make a fast friend.

285. Who would be the best celebrity to go out drinking with?

Who seems like they know how to have a good time? This question will give an insight into who their favorite celebrities are, but also what their idea of a great night out would be.

286. What’s your “hear me out” recommendation?

Some things are great but a little hard to explain. Maybe it’s a TV show that takes a while to pick up, maybe it’s a movie that’s too weird to describe. Give them the chance to ramble a bit, and maybe you’ll have a new favorite.

287. Would you rather always have full wifi/phone signal, or always have full battery on all your devices?

What’s a bigger convenience? Or which is the bigger frustration? This can be a good way to figure out how they organize their life.

288. Would you rather give everyone a car, or get rid of all cars forever?

Would it be an act of charity, or would getting rid of cars make the world a better place? It’s a thought-provoking question, and if they’ve thought about it before, they’ll probably have some strong thoughts as well.

289. If you had to cobble together a meal but could only choose one item from each restaurant, what items would you choose?

Who has the best fries? The best burger? The best drink? Or would they go in another direction entirely for their Frankenstein meal?

290. Would you rather marry the most attractive person in the world or the best cook in the world?

Beauty doesn’t last forever, but neither will your health if you’re eating like a king every night. Which seems more important?

291. Would you rather have every movie spoiled for you before you watched it, or never get to see the last 5 minutes?

Some people think that knowing how a movie ends makes it more enjoyable. Some people definitely don’t. Which one are they?

292. If you were to travel back to the stone age, what technology could you reproduce?

We take a lot of things for granted, and we think we know how most of them work, but what would it actually be possible to recreate in a pinch?

293. Would you rather have a clean kitchen and a filthy bedroom, or a clean bedroom and a filthy kitchen?

Would the convenience of a clean kitchen make up for the bedroom being a disaster, or would the embarrassment of a messy kitchen be a price worth paying to have a tidy bedroom?

294. If you got paid $100 for each consecutive time you rewatched a movie, which movie would you pick?

Even at a hundred dollars a pop, any movie is going to wear out eventually. Which movie would give them the best shot at making the most money?

295. What podcasts have you listened to from the very first episode?

This could be a bit of a “before it was cool” brag, or it could be a chance to talk about something they’re so excited about they listened to the entire backlog. Either way, it’s obviously something they care about.

296. Do you prefer to watch movies in the theater, or at home?

The theater is a whole experience, but not one that everyone enjoys. Watching at home certainly has its advantages. Or maybe there’s a compromise. Home theater anyone?

297. Do you watch episodes as they come out, or binge the entire season at once?

Another question that deals with how they consume pop culture. If they like to talk about shows, or otherwise run the risk of having them spoiled, they probably watch it as it comes out. Other people hate cliff-hangers and having to wait on story arcs.

298. If you were in line for the last spaceship to leave earth, what would you tell them to make them take you?

This is a chance to brag about themselves in the biggest way possible. Gun to their head, what do they bring to the human race?

299. Would you rather have a billion dollars and have every purchase you make published and criticized, or a million dollars you could spend however you want?

Is privacy worth 999 million? It is for some people.

300. If you could pick any two people to be your shoulder angel and shoulder devil, who would you pick?

Saints and celebrities. Conquerors and comedians. Who would be the best duo to guide all your life choices?


In Conclusion

With 300 questions to ask for any occasion, now you can breeze through conversations, and let the other person (or people) do more of the work. Whether you ask them to a group, gamify them, or just use them to make small talk less painful, we hope they help!


And be sure to check back, we’ll be adding more soon and check out the blog

50 Philosophical Questions That Would Make You Doubt Your Whole Existence