Random Conversation Starters

1. What was the last funny video you saw?

Always fun to follow up on the question by watching the video they thought was funny. I’m sure you’ve got
a few funny videos to share as well.

2. What do you do to get rid of stress?

Everyone gets stressed out at times, and everyone deals with it differently. Find out how they deal with it and
maybe pick up some extra stress relief tips for you.

3. What is something you are obsessed with?

This is a great question because you can follow up with lots of questions about what they are obsessed with. I
guarantee they’ll have plenty to talk about when it comes to what they geek out on.

4. What three words best describe you?

Find out how they view themselves, and don’t forget to ask follow-up questions about each of the words they
chose.

5. What would be your perfect weekend?

See what they are into, and you’ll have plenty to talk about. Everyone loves talking about things they love.

6. What do you think of tattoos? Do you have any?

If they do have tattoos, there is probably a story behind each one. And if they don’t have any, well it’s good
to know what they think about them.

7. What’s your favorite number? Why?

This one is a little off the wall, but you never know, you might get an interesting answer. Especially by
asking, “why?”

8. What’s the most useful thing you own?

Sure, this one is good for a general conversation starter, but what is really nice is being able to get some
ideas on what works well and is generally awesome to have.

9. What’s your favorite way to waste time?

Similar to the perfect weekend question, this question tries to get at what they really enjoy doing so that you
can both talk about that.

10. Do you have any pets? What are their names?

Are they an animal person? And how clever are the names they gave their pets?

11. Where did you go last weekend? / What did you do last weekend?

A pretty common conversation starter, but sometimes the best ones are the ones people are used to.
12. What are you going to do this weekend?

Very similar to the last one, another oldie but a goodie.

13. What is something popular now that annoys you?

Time to channel some cranky old man vibes. Kids these days, with their stuff and their things and their hair.
You know, that type of stuff.

14. What did you do on your last vacation?

Vacation stories! Bad or good, everyone likes talking about their vacation. Just duck out before they start
showing you pictures.

15. When was the last time you worked incredibly hard?

Whether it’s their job or a personal project, you can see what they put their heart and soul into.

16. Are you very active, or do you prefer to just relax in your free time?

Find out if they are all about the gym or all about the couch. To each their own!

17. What do you do when you hang out with your friends?

See what they like to do when they are social, talk about that activity if you can.

18. Who is your oldest friend? Where did you meet them?

This is a great question because it often leads to some wonderful stories from when they were younger. I
mean, who doesn’t like reminiscing about the good old days?

19. What’s the best / worst thing about your work/school?

Tailor this question to the person you are talking to, whether they work, or they are a student. Also, some
people like to let off steam, and some like to keep it positive so you can choose which way you want the
question to swing.

20. What is your favorite song? What kind of music do you like?

21. What were you really into when you were a kid?

Every kid goes through phases when they are REALLY into one thing. Now you can find out what they
obsessed about when they were a kid.

22. If you could have any animal as a pet, what animal would you choose?

This one is fun because a blank check pet choice can lead to some great answers. And you can always
transition the conversation into pets they had/have.

23. Have you ever saved an animal’s life? How about a person’s life?

Who doesn’t like listening to or telling a hero story? I’m sure it will lead to an interesting story. Even if it
isn’t about them, and just about someone they know who saved an animal or person’s life.

24. If you opened a business, what kind of business would it be?

25. Who is your favorite entertainer (comedian, musician, actor, etc.)?

Pop culture and entertainment are great topics for conversation, and this question is a good entry point into a
larger conversation about what kind of entertainment they like.

26. Are you a very organized person?

Does everything have its place, or does their stuff roam about?

27. Have you ever given a presentation in front of a large group of people? How did it go?

Public speaking is high up there on the biggest fears people have. So, I’m sure if they have, it probably left a
big impression.

28. What is the strangest dream you have ever had?

Sure, talking about dreams can be dull, but who knows, if you are talking about the strangest dream they’ve
EVER had, it might be pretty interesting. Or not. Let’s see!

29. What is a controversial opinion you have?

So, don’t immediately start bashing their opinion if you don’t like it. I mean, you asked the question after all.
Let them explain why they have the opinion and their reasoning behind it. Not everyone has to have the same
opinions as you. And if it’s super out there or evil, well it’s good to know so you can avoid them in the
future.

30. Who in your life brings you the most joy?

An awesome question for keeping it positive, and they’ll be talking about someone they love, so it’ll be easy
to jump into a conversation about whoever that person is and why they are so awesome.

31. Who had the biggest impact on the person you have become?

This one may or may not have the same answer as the previous question, so you might want to choose either
this one or the previous one depending on the type of conversation you want to have.

32. What is the most annoying habit someone can have?

Find out what annoys them, chances are it probably annoys you too. Then it’s easy to step into a
conversation about annoying habits.

33. Where is the most beautiful place you have been?

This one will probably lead to a good travel story. And conversations about travel are always fun.

34. Where do you spend most of your free time/day?

Find out what their day to day looks like. It’ll be easy to start up a conversation about anything of the things
they do on the regular.
35. Who was your best friend in elementary school?

Time to get nostalgic about how life was when you both were growing up!

36. How often do you stay up past 3 a.m.?

Are they a night owl or an early bird, time to find out! This can easily transition into a conversation about
what they like to do in their free time.

37. What’s your favorite season? Why?

This question will probably conjure up some wonderful memories linked to your and their favorite season.
Have fun reminiscing!

38. Which is more important, having a great car or a great house? Why?

Do they care more about showing off to others or having awesome stuff for themselves? Always good to
know! And you can easily transition into a conversation about cars you/they want or dream houses.

39. What animal or insect do you wish humans could eradicate?

Probably going to get a lot of mosquito answers. But depending on where you are and if they have a special
hatred for a creature, you might get a different answer. If you get the mosquito answer, you could always talk
about the best way to get rid of the evil pokey buzzing things.

40. Where is the most beautiful place near where you live?

Similar to the question about the most beautiful place they’ve seen but this time it’s local! Who knows, you
might get a tip on an awesome local spot.

41. What do you bring with you everywhere you go?

Sure, you’ll get the normal keys, cellphone, purse/wallet, answers, but you might get to hear about a cool
keepsake / lucky charm that means a lot to them.

42. How much time do you spend on the internet? What do you usually do?

Find out what sites they enjoy, chances are you probably enjoy some of the same sites. You can swap good
people to follow or suggestions for interesting sites.

43. What is the most disgusting habit some people have?

An earlier question talked about annoying habits; now it’s time to get gross with it and find out what disgusts
them.

44. Where and when was the most amazing sunset you have ever seen?

This one is another way to get into a good conversation about travel.

45. Which recent news story is the most interesting?

So, I had to make this one a bit vague, but it can lead to an interesting conversation about recent events. And
you might just hear about something you didn’t know happened. Just make sure to steer clear of politics.
46. Where is the worst place you have been stuck for a long time?

Whether it’s at an airport, after a car broke down, or something else, we’ve all had times where we’ve had to
wait for a seemingly endless amount of time. There is a good chance it’ll lead to a good story.

47. If you had to change your name, what would your new name be?

This one is a little creative and fun. They might have to think about it for a bit, or they may have an answer
right off. Don’t forget to ask them why and what might be a good last name as well.

48. What is something that really annoys you but doesn’t bother most people?

Everybody likes sharing and complaining about what annoys them. Now you can find out what weird quirks
annoy them.

49. What word or saying from the past do you think should come back?

There are all kinds of words and sayings from the past that have fallen out of use. It can be a lot of fun to
dust them off and put them into modern sentences. If you both can’t think of any, there are plenty of lists
online.

50. How should success be measured? And by that measurement, who is the most successful person you
know?

This question can lead to some surprisingly deep answers. A lot of how we view the world is based on what
we consider to be worthwhile, and this question tries to get at the heart of that to find out what is most
important to the person.

51. What is your guilty pleasure?

Everyone has something they absolutely love but might not be in line with how people view them or how
they view themselves.

52. Was there ever an event in your life that defied explanation?

Time to learn about some cool mysteries! This one quite often leads to several good stories.

53. If you could learn the answer to one question about your future, what would the question be?

A fun question that helps you figure out what is important to them.

54. Has anyone ever saved your life?

This one can get quite personal and sometimes tragic. So just a heads up, you might want to save this one for
when you know the person well.

55. What benefit do you bring to the group when you hang out with friends?

Every member of a group has their duties. Time to find out what role they play! Plus, you can expand the
conversation into what they usually do when they hang out with different groups of friends.

56. How often do you curse? And what’s your go-to string of curse words?
This question is definitely unique. You’ll have to judge the situation and who you are talking to in order to
see if this question is a good fit for the situation. It can be fun, though.

57. What trends did you follow when you were younger?

Each generation has its trends. And if you are of a similar age, there is a good chance that you both share
some similar trends that you followed.

58. What do you fear is hiding in the dark?

This is a great question to get into a conversation about fears that you both share.

59. What was the best period of your life so far? What do you think will be the best period of your entire
life?

Another question that leads to a lot of fond memories and stories to tell, but also lets you know how hopeful
of the future they are and what their ideal life would look like.

60. What do you do to improve your mood when you are in a bad mood?

Everyone needs to blow off steam sometimes. With this question, you can see if you share some stress relief
techniques.

61. What is the silliest fear you have?

Another one about fear, but this one is more lighthearted. Everyone has fears that they know are irrational.

62. What are some things you want to accomplish before you die?

The classic bucket list question. It’s great because it shows you what they want out of life and what is most
important to them. And it’s easy to split off into a conversation about any of the things they mention.

63. What is the best room in your house? Why?

Are the all about food and the kitchen? Perhaps they prefer to sleep or chill on the sofa? Or maybe there is a
special reading nook they have. This is another question that helps get a conversation going about what they
do in their downtime.

64. Who is someone popular now that you really like? Why do you like them so much?

This one serves as a great stepping stone into a conversation about celebrities and other people in the
limelight.

65. Where is the best place to take a date?

This one you’ll have to be selective with, it’s not appropriate for all situations, but you might be able to get
the low down on a good spot you didn’t know about. Just don’t let the conversation stray into their dating
life, that can get a bit awkward. And if you need date ideas, we have a ton!

66. What smell brings back great memories?

67. What’s the best pet name you can come up with for a specific type of pet? (Like these orange cat names.)

Go for funny names, puns make great animal names. And you could tailor it for a pet that they have or would
like to get.

68. How often do you help others? Who do you help? How do you help?

This is a great question to see how empathetic and prosocial they are. And can lead to conversations about
volunteering or times they’ve helped others.

69. What are you best at?

With this one, you might learn about a hidden talent, or perhaps a hobby you didn’t know about. Both can be
the beginning of an excellent conversation.

70. What makes you nervous?

Very similar to the fear one but a little bit broader. It can be something happening in their life right now,
something that happens regularly, or something they think is likely to happen in the future.

71. Who is the funniest person you’ve met?

Not necessarily a comedian, but a friend or family member who always manages to make them laugh. It
definitely could spin off into a conversation about comedians, though, which would also be fun.

72. What weird or useless talent do you have?

Wiggling ears, burping the alphabet, farting on command, humans are weird, and we all have some weird
and useless talents that are fun to talk about.

73. What are some strange beliefs that some people have?

Be careful with this one, because they may end up labeling one of your beliefs as strange. Just be ready not
to take their answer too personally.

74. Who would be the worst person to be stuck in an elevator with? How about the best person to be stuck in
an elevator with?

Hypothetical questions can be a blast to talk about. And this is a fun one to ponder.

75. What was the best birthday wish or gift you’ve ever received?

Hopefully, everyone has had a super thoughtful birthday wish or gift given to them. It’s a perfect question to
get in a conversation about past birthdays.