250 Questions To Spark Conversation & Get To Know Someone

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250 Questions To Spark Conversation & Get To Know Someone
Love

Sometimes we all need a little help with keeping the conversation flowing. Whether you're on a date or just meeting someone new, it's good to have questions to get to know someone on hand so you can break the ice and really get to the core of who someone is.

Meeting someone new can be difficult for introverts (and even extroverts!) when it comes to small talk. There are so many factors that go into what’s discussed and when something is brought up. 

You just have to take the social factors into consideration before conversating, because as we all know, there are certain questions for certain times. 

Like if you are trying to get to know someone on a date, then you ask a series of questions or play a game where you go back and forth asking each other questions to get to know each other a little better. 

Then there are times in a relationship when you ask the deep questions and others when you ask the flirty ones.

RELATED: 20 Good Questions To Ask A Guy To Really Get To Know Him

In a relationship, you may even have to interact with your date’s kids or siblings, so even having some appropriate questions on hand will help you gain major brownie points with your partner and it will also help the children become more comfortable around you as well. Children are usually shy around adults and can be hesitant to talk. So, if you have ready to go questions about things they like, then they may open up to you quickly because you are talking about things they can relate to. 

So, here is a great list of questions to get to know someone, which will help you get more comfortable with each other. 

Questions for a first date

It may feel weird at first when you start talking with your crush or someone you're romantically interested in. But when you have some questions tailored to getting to know each other, it will be so much easier to start talking with each other. 

Sometimes starting with the most harmless of questions will help you get more comfortable with each other. Also, asking non-threatening questions lets you see if you have some of the same things in common. 

These are good questions to talk about in person or through text when you are trying to decide whether this person may be worth pursuing. 

These questions just break the ice and keep things from getting awkward. 

1. What's your favorite color?

While it may seem like a very surface-level question, knowing someone's favorite color can actually tell you a lot about their personality — at least if you believe in color psychology

2. What was the last book you read?

Asking this will help you learn about their fantasies or interests. People usually read books that are related to what they desire or a topic of interest for them. 

3. Do you have pets?

This question seems basic but could one of the most important things you ask. If you both have a pet, you could use this as a segway into a pet playdate. If they don't have any pets, you can at least find out their stance on pets. What if they hate dogs? Now you know not to waste your time. 

4. What do you like to do in your free time?

Figuring out what someone likes to do in their free time will give you an idea of what your time with this person would be like. It will also answer a lot of questions you may have about compatibility. If you don't enjoy the same things now you know you can move on.

5. What is your favorite movie of all time? 

This is a simple question to start a conversation and see a little bit of their personality shine through. If you've never seen their favorite movie maybe you can suggest watching it together as a second date.

6. Who is the most fascinating person you've met? 

Asking this question will help you to find out who is influential in their life and who they value. 

7. What's your favorite alcoholic and non-alcoholic drink? 

This is another easy conversation starter and can lead to other questions like "what's your favorite local bar or coffee shop?"

8. Where have you traveled?

Traveling is not something everyone has had the chance to or wants to do. If one of your goals is to find someone you can travel the world with, then you might want to find out if this person has any interest in leaving their hometown. 

9. What are your hobbies? 

Similar to asking what someone does in their free time, this will answer a lot of compatibility questions. If you have a similar hobby or have never tried one of theirs, that can be a great idea for a second date.

10. What's your favorite international food?

Asking this question will let you know if they are a risk-taker or not. If they only ever order chicken tenders, they probably aren't huge risk takers off the menu either.

11. What's your dream job?

This will help you gain perspective on their goals and ambitions. 

12. What are your personal goals?

Similar to the above question, this will help you see where their goals lie. It will also give you insight into whether or not this person is worth your time. If they see themselves with kids in five years and you don't see that for yourself, you can end things now.

13. Who's your favorite book you read? 

This question will help you to find out if they even like to read or what topics and writing styles spark their interest. 

14. What's the last TV show you binge-watched?

This is an easy and fun way to find out what their sense of humor is or if they love true-crime. You can see if you both have the same guilty pleasures. 

15. Who is your favorite actor/actress?

This is another fun one. This is a carefree, no pressure question that leads to others, like "what is your favorite movie they've been in?", etc. 

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

If you are complete opposites in this area, you might not be compatible. If he gets up at 5 am but you like to stay up until 2 am, there will be some fundamental issues.

17. What's your favorite restaurant?

This lets you know the kind of food they enjoy and helps you choose something to do for a second date.

18. What would you do if you had enough money to not need a job?

Questions like this will help you discover their passions and dreams. A person's passion tells you a lot about them. 

19. What would your perfect vacation look like?

Asking this will help you find out their hobbies as well as if they vacation for adventure or stress relief.

20. What are your top three favorite songs?

Music choice is something that you should at least have a little bit in common. If you love rap but he only listens to country, you'll have some very annoying car rides in the future.

21. What's something everyone should try once?

I like this one because you can't lose. You not only find out something of importance to them but you also have something new to try if it doesn't work out. 

22. What's the best thing that happened to you this month?

This will show you how optimistic this person is. It's very likely that nothing super exciting happened to them, but if they still manage to come up with some kind of silver lining, they're a keeper.

23. What do you do to unwind? 

This gives you insight into what someone considers relaxation as well as what kind of stress they are unwinding from.

24. Where is the strangest place you have visited? 

Asking this will help you understand this person's level of crazy. 

25. What household chore do you hate?

This question is fun and breezy. A great way to break the ice and find out if they are a neat freak!

26. What is your worst fear?

In my opinion, this one is very important. What if they will never kill spiders for you or go on a roller coaster???

27. What's your favorite app on your phone?

This will show you where their interests lie. If his favorite app is Instagram, he might be an influencer. If his favorite app is his food log, then he's probably a health nut.

28. What is the cutest animal?

This is another fun ice breaker and maybe even a good segway into asking them to go to the zoo with you.

29. What is the ugliest animal?

Trick question... there are no ugly animals. 

30. Who is the kindest person you know?

Asking this will shine some light onto who he values and looks up to in his life.

31. Do you have any odd talents?

This will help to break them out of their comfort zone and they might even show you their talent!

32. Which country do you never want to visit?

If their answer to this is your dream destination, you might want to run. Or at least hope they're open to changing their mind.

33. How have you changed since high school? 

If they can't answer this, this person is not relationship material. Imagine if you were still the same person you were in high school... This question should show you how they've grown as a person and where their maturity is at. 

34. What's the most relaxing situation you could imagine? 

This helps you learn what is stressing them out and how they like to unwind.

35. What's the most beautiful view you have ever seen?

Asking this will show you if they have had the opportunity to travel as well as how easy or hard it is to impress them.

36. If you could live anywhere in the world, where would it be? 

This is another question that will give you insight into whether they ever want to leave their hometown or not.

37. Would you like to be famous? 

This gives insight into whether or not they are over-the-top materialistic. If they are overly enthusiastic about wishing they were famous, they might be a little less genuine than you'd like. 

38. What's the most recent thing you've done for the first time? 

This shows you adventurous he is and how often. If he says he went bungy jumping last week, you know you're in for a wild ride. 

39. How did you meet your best friend? 

Learning more about the important people in someone's life is a great way to get to them without asking super hard questions. 

40. When was the last time you walked for more than an hour? 

This tells you more about their fitness activities and hobbies. Do they go to Disney once a month? Do they enjoy power walking?

41. What is the best and worst ice cream flavor? 

Easy ice breaker and an awesome way to suggest getting ice cream for your second date.

42. How much personal space do you need to feel comfortable? 

This question is very important and helps you find out their boundaries. If they are super touchy-feely and you're not touching them at they might think you don't like them. If you are touching them and they express that they need a lot of personal space, you know to back off. 

43. What do you like but are kind of embarrassed to admit? 

Getting to know someone's guilty pleasures helps to break down walls and have an easy conversation.

44. What's your favorite smell? 

At the very least this will tell you what kind of perfume and candles to avoid when you're around this person. On a deeper level, smells symbolize different things for different people. Learn what smells symbolize for them.

45. What skill have you always wanted to learn?

This shows you what they are curious about and if they are a lifelong learner. If they are interested in learning something you are both interested in, you can try a class together for a bonding experience. 

46. What are the top three things you like to talk about? 

If they say three things you have absolutely zero interest in, you know to end things now.

47. What are people often surprised to learn about you?

This is an amazing question to find out if you're judging a book by its cover or jumping to conclusions.

48. What small things brighten up your day when they happen?

If they say something wholesome, you know you've found a keeper.

49. What's the most ridiculous thing you've done because you were bored?

We've all done weird stuff when we're bored, so be prepared to answer this about yourself as well.

50. What's your favorite holiday?

Asking this will show you how much he gets into the holiday spirit. Is he going to do a couple's costume with you if things work out?

RELATED: 5 Deep Questions To Ask A Guy To Find Out Who He Really Is

Romantic questions to ask

Now, this set of questions is for when you have started pursuing each other more in your relationship. These are good questions to know the answers to and they can give you a great insight into your partner. 

Some are light, some are lusty, and some will get you thinking. It's just important for you to make a mental note of some of their answers to specific questions like a dream date, so that you can make their dreams reality, within reason of course. 

51. What's your dream date night? 

Finding out their dream date will give you an idea of something nice to do for them in the future. 

52. What makes you feel the most loved? 

Learning someone's love language is super important if your goal is to have effective communication.

53. What's most important to make your relationship last? 

If you're thinking long term, this question will give you a map of how to get there. 

54. What do you love most about me? 

Listen carefully... If they can't come up with something, run! This question should be easy to answer and make you feel reassured. 

55. What's your favorite romantic movie?

Their favorite romantic movie will give you an idea of what their dream romance is like.

56. What kind of music puts you in the mood?

Take notes and play this the next time you want to heat things up.

57. What's your love language?

This is an awesome way to find out what they need to feel loved. 

58. What was your first impression of me when we met?

This is a nice way to feel reassured in your relationship because it will show you how you've progressed.

59. What's your favorite way I touch you? 

This gives them the opportunity to tell you what they want more of and maybe what they want less of if something makes them uncomfortable. 

60. What physical feature of mine is your favorite?

Ask this when you're feeling like you could use a little self-esteem boost. 

61. What's your idea of a perfect date?

Finding out what they want to do for fun together will help you understand what they consider quality time. 

62. What song do you think of when you think of me?

Even if they don't have one come to mind right away, this will give them the opportunity to do something nice for you and find 'your song'. 

63. What could I do to improve our relationship?

It's important to have small check-in's like this to find out how things are going and If they need to improve in any way. 

64. When was the first moment you wanted to kiss me?

This will spark a romantic memory for both of you and definitely lead to a passionate kiss. 

65. What do I do that helps you calm down?

Part of being in a relationship is helping your loved one to cope with stress. Asking this will help you understand how you can do that for them.

66. When are you the happiest with me?

Their answer will show you what they enjoy doing together the most. 

67. What was your favorite part of our first kiss?

This is another question to ask if you want to spark some romantic memories of your first few special moments together. 

68. When and what was the first moment you knew you were in love with me?

This is a great way to find out how long your partner has been falling for you. Not everyone says 'I love you' as soon as they feel it. 

69. What do you say to others when you talk about me?

If they don't tell their friends or family about you, you can assume they want to keep things casual or just aren't there yet. This will tell you where they are in the relationship. 

70. What's one thing you want to do with me that we haven't done yet?

Now you have an idea for your next date!

71. What great adventures do you think we'll achieve in the next 5 years?

This will help you find out if they see a future with you. If they get super freaked out by this question, they probably aren't thinking long term.

72. What do you think I find most attractive about you?

This will show you what they are confident about in themselves.

73. What's been one of the funniest times we've had together?

Want to lighten the mood? This is a great way to visit memory lane and remind him of a great time you had together if maybe today wasn't so great.

74. What's your biggest relationship dealbreaker? 

The most important part of compatibility is having similar values

75. What do you like best about our relationship?

As mentioned before, little check-ins like this are vital to make sure you're on the same page and things are going smoothly.

76. Is there anything you're afraid to accomplish that I can help you with? 

Heping your partner to feel like you support them will help you bond. They will have an easier time trusting you if they know you have their back.

77. What values are most important in a relationship?

Always ask this when you start to get serious with someone to make sure you have similar outlooks on love and life. If your values aren't in alignment, fundamental issues could arise within the relationship.

78. Has anything surprised you about our relationship?

This allows your partner to have an opportunity to tell you things that are on their mind whether they're good or bad. 

79. What's your favorite memory with me?

Reflecting on memories as a couple will help you strengthen your bond. 

80. What moment would you want to relive again and again?

Finding out what their favorite moment with you is, is a great way to find out how to plan similar dates in the future. You can even try to recreate their favorite moment as a cute date idea that shows you listen.

81. What is something little I do that makes you smile?

Your partner will find this question sweet and it will give them the opportunity to tell you what they want more of.

82. What's your most scandalous memory of us?

This question is a great one to ask if you're looking for things to get steamy. Reminiscing on past romantic moments will help to set the mood. 

82. What can I do to spice up our love life?

Checking in with your partner is about the physical aspects of your relationship is equally as important as checking in with them about emotional aspects. Finding out if their physical needs are being met will help your relation stay strong. 

83. What do you think is most important for communicating in our relationship?

Again, it's important to know if needs are being met in your relationship. Knowing how your partner prefers to be talked to, especially during an argument, will help your relationship stay healthy.

84. What weaknesses do you see in our relationship? 

Hopefully, nothing comes to mind when you ask this but if something does you have just opened up a conversation to fix it.

85. Has anything surprised you about me?

We all like to discover what someone's first expectation of you was. This is a fun question to see what they were expecting and how different it is from how you are. 

86. What strengths do you see in our relationship?

Discovering your strengths will aid in healthy communication, intimacy, and overall a lasting relationship.

87. Is there anything you'd like me to be willing to change?

Communication is key! It's important in a relationship that we acknowledge that sometimes we need to work on our behavior as well. Your partner may be uncomfortable with certain things and asking this will help them to find their voice. 

88. What goals would you like to set up for our relationship?

Asking this question will help you see how long term of a commitment they expect you to have. If they do see a future long term, now is a great time to discuss when you want to buy a house, etc. It's important that you are on the same page about these topics. 

89. What can I do to encourage you on a regular basis? 

This is another question that will show your partner your support. Even if they don't have an answer they will appreciate knowing that you truly care.

90. Is there anything about me you might not know but want to know?

Continuing to learn new things about each other will keep the romance alive and the spark burning. It also gives your partner reassurance that you're an open book.

RELATED: The 5 Most Important Things To Know About Someone Before You Start Dating Them

Funny questions to ask

Sometimes when you are with either your date, partner, family, or anyone else important to you, you need some sort of list of questions to spark conversation. These funny questions are light and usually spark interesting conversations, especially when you need to lighten up the conversation. 

91. What is the best WiFi name you have seen?

Most of us have seen some pretty strange and sometimes hilarious WIFI names. This will have you both cracking up.

92. What's the most ridiculous fact you know?

Everyone knows random, silly facts about things they're interested in. Finding out their list of random facts will be a good insight into their topics of interest. 

93. Is a hotdog a sandwich? Why or why not?

This question is silly and asking it will have you both laughing before they can even answer. 

94. What conspiracy theory do you believe?

This is a great conversation starter and kind of a secret way to see what kind of off-the-wall beliefs they might have.

95. What is the funniest joke you know by heart?

Asking this will lighten the mood and give them the opportunity to show off their humor. 

96. Toilet paper: over or under?

This is an important debate to have if you see any kind of future scenario where you will live together. Personally, I'm an over person and could never share a bathroom with an under. 

97. What's the weirdest recurring dream you have?

Many dreams make absolutely zero sense at all, and recounting them call be hilarious. This is also a good way to dig deeper into dream meanings and see what's going on in the subconsious!

98. Does pineapple go on pizza?

The answer is yes — but all kidding aside, this is a fun question to help you know if you're both on the same side of the pineapple pizza debate. 

99. What is something everyone looks stupid doing? 

Asking this will have you both hysterically laughing. If you're lucky you can get them to perform their answer.

100. What's the best type of cheese?

If you're the kind of person who loves to put together cheese boards, this is an important one. If you're not cheeseboard compatible, are you even compatible at all?

101. What's the longest-running inside joke you've been a part of?

Inside jokes are usually shared between family and friends. This will show you who they're close to and what their sense of humor is. 

102. What would be the absolute worst name you could give your child?

I find this one to be important if you plan on having kids. What if your dream name is their deal-breaker?

103. What's the weirdest thing a guest has done at your house?

Funny stories like this are a great way to get to know each other and now you know what not to do if they invite you over as a guest.

104. What's the most embarrassing thing you have ever worn?

This question will show you what embarrassing phase they went through in middle school or high school.

105. Which body part do you wish you could detach and why?

If they have a serious answer to this question, change your phone number and move to a foreign country to ensure they will never find you. 

106. What's the most spontaneous thing you've ever done?

This is a good way to see just how impulsive they can be, and will probably lead to a good story!

107. What would be the worst "buy one get one free" sale of all time?

This is a great way to figure out if someone would be a good shopping partner. 

108. What sport would be the funniest to add a mandatory amount of alcohol to?

You guys can try this at home if you want to make this even funnier. 

109. What would be the coolest animal to scale up to the size of a horse?

This question will make you both smile and show what some of their favorite animals are. 

110. What set of items could you buy that would make the cashier the most uncomfortable?

Asking this funny question will show you what they consider to be weird.

111. What two totally normal things become really weird if you do them back to back?

This one will show their values in sneaky ways. If they mention two things you'd be totally fine with doing back to back, you might not be compatible. 

112. What movie completely changes it's plot when you change one letter in its title? What's the new movie about?

This question will show their creative side and leave you both with a case of the giggles. 

113. If you were transported 400 years into the past with no clothes or anything else, how would you prove that you were from the future?

This is another one that requires them to get pretty creative. You guys could go on and on about this one because the possibilities are endless. 

114. Where was the most embarrassing place you've farted?

This will break down some serious walls and break all of the ice. If they can get through this embarrassing of a question, there's a good chance they'll open up to you about much more.

115. What fictional character is amazing but would be insufferable to be around in an everyday setting?

Asking this will help you learn their favorite movies and shows without having to ask a basic question. 

RELATED: 100 'Getting To Know You' Questions To Ask On First Dates

Hard questions to ask

Now, instead of being light, sometimes you need to dig in and discuss very deep topics that give you a great idea of a person. These are good questions for friends and potential romantic partners. 

Don't be surprised if they cannot answer some of these questions, because you may not be able to answer them either. They can give you something to think about and help you personally decide what you need the answer to be for you to feel comfortable in a relationship. 

116. If you could give everyone just one piece of advice, what would it be?

Asking this question will really give you some good insight into their priorities in life.

117. What wrong assumptions do you make about people?

This is the easiest way to figure out how they judge other people, and how they may be judging you.

118. What's the most essential part of a friendship? 

This question is important because if you're looking for a relationship with them, you'll need to be friends with them first and foremost!

119. What says the most about a person?

With this question, you will either get a super cute answer or a shallow one. 

120. What are some things that are OK to occasionally do but definitely not OK to do every day?

This is a great way to learn more about their hobbies!

121. Are you an introvert or an extrovert?

Very important! You can probably already make your own conclusion after meeting them...

122. What's one thing you would change about yourself?

How confident are they? If confidence is an attractive trait for you, this is an important one to ask!

123. Are you religious or spiritual?

Make sure to be respectful and open-minded!

124. Which parent are you closer to and why?

Because when is it not cute to hear someone talking about how much they love their parents?

125. Is what you are doing now what you always wanted to do growing up?

This is a good way to see if they stick to their goals.

126. Would you ever take back someone who cheated?

Asking this can really show you what they value in a romantic relationship.

127. When do you think a person is ready for marriage?

A forward, but telling questions that may just help you find the one!

128. What makes you feel accomplished?

What drives them in life? This is how to find out!

129. What's one of your favorite childhood memories?

This is a great way to see what they value in life — and also might give you a good date idea in the future if it's something you can recreate!

130. What's your biggest regret in life? 

We all have something we wish we could go back and change. It's not an easy question to answer, but the takeaways are important!

131. What would you do if your parents didn't like your partner?

You can see how much they care about what their parents think, which is important to some people.

132. Are you confrontational?

Does this line up with your personality? This is a good way to find out if you are compatible with them.

133. Have you ever lost someone close to you?

This question could be triggering but is a nice way to bond with someone if you've been through something similar.

134. Do you stay friends with your exes?

Do you keep your own exes in your life? This answer could matter a lot.

135. Who is that one person you can talk to about just anything?

Who do they value most in their life? This is a great way to find out.

136. What do you think of having best friends of the opposite sex?

This question will help you understand what their boundaries would be if you have a best friend of the same gender.

137. When was the last time you broke someone's heart?

Hopefully they don't have a very long answer for this one!

138. Would you relocate for love?

This is a good way to find out how far they would go (literally) for their significant other if things got serious.

139. Do you believe in second chances?

This question can help you figure out if they hold grudges, or if they are more the easygoing type.

140. What are you most thankful for?

This can really show you someone's priorities in life, and if they line up with yours.

141. What is the craziest thing you've ever done and would you do it again?

This is a great conversation starter, which will definitely lead to some funny stories!

142. What's the one thing that people always misunderstand about you?

This question gives them the chance to tell you something about themself that they may feel very passionately about.

143. If you were given 3 wishes from a genie, what would you wish for?

Hopefully they can come up with an answer better than "three more wishes", you may find out they want to save the world!

144. Who was your favorite teacher?

While they're answering a question about someone else, their answer gives you the opportunity to understand their learning style and see what they value in a mentor.

145. What do you think about when you are alone?

This could lead to a conversation where you share your interests. Definitely a great question if you're looking to get to know someone on a deeper level.

146. Why did your last relationship end?

It's good to get the hard questions out of the way first. Watch out for red flags if they start trash talking!

147. What's your biggest mistake in life and what did you learn from it?

This question is a good way to find out if they value growth and if they learn their lessons the first time.

148. What's something you cannot go a day without doing?

This is a good way to find out what they spend most of their time doing, which is really important!

149. What's the craziest thing you have done for love?

A great question, and you can find out if they would do something even crazier for you.

150. What is your biggest pet peeve?

This is a good way to find out what makes them annoyed, maybe you can bond over hating the same thing!

151. Do you work to live or live to work?

This gives you insight into what someone values in life. While we all need to work, someone who is a workaholic might not be emotionally available for a relationship. On the other hand, if you love working, you might not mesh with someone who only does the bare minimum.

152. What is the greatest and hardest struggle you have overcome?

This question will allow you to get to know your partner on a deeper level and understand what may be sensitive topics to them.

153. What’s the worst job you’ve ever had?

Don't forget to ask what about the job made it so bad to see what's important to them.

154. What's your best quality?

Having someone tell you what they feel is their best quality makes them feel good, and you get to learn good things about them.

155. What's the weirdest thing about you?

This can give you a good idea of what they consider to be "weird." This will also let you know more about your compatibility with them.

156. If you could change one thing in the world, what would it be?

If making a difference in the world is important to you, this question could be super helpful to learn more about their values.

157. Why did you go to the school you went to?

This will let you know if someone is a risk-taker, and how they want to spend the milestones in their life.

158. What food could you not live without?

If you love to cook, this could be something you can make for them in the future!

159. What food could you live without?

For the foodies out there, you can talk about what foods you do and don't like the most.

160. If you could get away with anything, what would you do?

This will let you know someone's secret desires, and how adventurous they are.

RELATED: 100 Deep Questions To Ask Before Your Relationship Gets Too Serious

Questions to bare your soul

Next, it can be hard for you to get the information you want from your partner or someone in your life. So, sometimes you have to find the list of questions that you can ask and find out so much more information about a person's personality than anything else. 

161. What is the greatest risk you've ever taken?

This will give you an idea of this person's comfort zone, and how willing they may be to leave it.

162. Do you believe in fate?

If you believe in fate, this may give away some hints of your compatibility!

163. How do you think people see you?

This question can let you know how they see themselves from another perspective, which is important when you're getting to know someone.

164. What's your biggest insecurity?

There's no better way to make someone feel better about themselves than to learn their insecurities so you can help them overcome them.

165. What fictional character do you relate to the most?

This fun questions can also lead to some interesting conversations about your favorite movies and books.

166. If you could erase something that you did in the past, what would it be?

This question will give you a look inside the chapters of this person's life.

167. When will you know you've "made it?"

Find out what this person considers success. Are they more money-oriented or happiness-oriented?

168. Have you ever experienced something you cannot explain?

This question will aid in discovering how much skepticism this person holds in their life.

169. If past lives are real, what was yours?

Asking this will tell you their character and whether or not they are an old soul. You can also try digging into your past lives together!

170. When were you the happiest in life?

This will give enlightenment on the level of happiness they have in their life currently.

171. If you could do one thing without suffering the consequences, what would you do?

Asking this question will tell you how far this person is willing to bend the rules.

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

Dreams are a window to the soul and our deepest thoughts and concerns. Asking this can show you a person's most hidden stresses and desires.

173. What calms you the quickest?

If you're thinking long term, it is important to know how to be there for your partner in a time of need and quickly be able to help them in stressful events.

174. What is the darkest thought you have ever had?

This question will show you a person's deepest and darkest fears. 

175. What makes you feel uneasy, anxious, and overwhelmed?

Finding out what makes your partner feel the most uneasy and overwhelmed will shed light on their triggers and tell you what to avoid when communicating.

176. When have you felt the lowest in your life?

This will show you a time in your partner's life that was a terrible time for them and try to prevent that from happening again.

177. What is the first secret you ever kept from anybody?

This will give you a good idea of what they felt was worth lying about as a child.

178. Where do you find meaning in life?

Ensuring that your values are in alignment is the key to a healthy relationship. Asking this will help make sure you're on the same page.

179. When have you caused the most harm to yourself?

This question will help you know things to look out for when your partner is feeling down and out.

180. Have you cried tears of joy before?

Asking this will show you how your partner experiences happiness. 

181. When was the last time you cried?

This can let you know how emotional they are.

182. When has someone broken your heart?

This allows you to be an open book with one another about your past relationships. 

183. What did you do when you hurt someone the most?

The answer to this question will help you understand how your partner would reconcile with you after a fight. Their answer can be a red flag or a green light!

184. Is home a place or a feeling? Why?

Asking this will help you learn where your partner feels safe and what their home life is like. 

185. Do you ever have imposter syndrome?

Unfortunately, a lot of people deal with imposter syndrome. Find out how this person views their own success. 

186. What do you think happens after death?

If religion has prominence in your life, this is an important question. Your beliefs have to be aligned for a healthy and long-lasting relationship.

187. How do you define beauty?

This will let you know if your partner is a surface-level person or if they look into the soul.

188. Do you believe in deja-vu?

This question can let you know if this person has recurring thoughts and feelings which could indicate an important part of their life.

189. What does happiness mean to you?

This can let you now the level of happiness in their life and what it takes to get there.

190. How do you deal with stress?

We all process and deal with stress differently — some people healthier than others. 

RELATED: 50 Deep Questions To Ask Your Mom (To Get To Know Her Better)

Unconventional questions to ask

When you are just trying to find something to talk about, using unconventional questions can make you get to know someone better than any other form of a question. So, if you can make the person you are talking to laugh, then you are doing a good job so far. Why not have an interesting, weird conversation? 

191. If you were a brand, what would be your tagline?

If you get a creative answer, you may start a great conversation! You can learn their life motto.

192. What is the toughest decision you have ever had to make?

This will let you know how they may make tough desicions and could spark conversation on a hardship they have encountered.

193. What's your superpower?

This is a fun question to find out how creative they are and what they feel confident about.

194. What would you do in the event of a zombie apocalypse?

With the way 2020 is going, you may end up relying on them for this so take notes on their answer.

195. What advice would you give your previous boss?

This will let you know about what they have done previously for a living, and if they have burned their bridge or not.

196. Are you a lucky person?

This question can let you know how someone feels about themselves and whether or not they make their own luck.

197. If you could be any fruit, what fruit would you be?

The fruit that someone likes says a lot about them. Are they sweet or sour?

198. What was the weirdest conversation you have overheard?

We have all been in the wrong place at the wrong time and heard the most ridiculous. This will spark a fun conversation with loads of humor.

199. When was the last time you stopped and smelled the flowers?

Asking this question can give some insights on if they are the type to stop and admire the small thing in life.

200. What are some things that you've never bought and will never buy?

This question can help you see if they value material items, and what they consider useful.

RELATED: 40 Get-To-Know-You Questions To Ask A Guy To See If You’re Compatible

This or that questions about food

Food questions can lead to some awesome conversations or some awkward ones. But this is something you really need to know when you are dating someone or spending time with new people in your life. So much about life revolves around food, so it's understandably a major discussion that you should have at some point in your relationship.

201. Do you eat beef?

This is one way to figure out if they're vegan or not.

202. Do you ever skip breakfast? If so, how often?

Breakfast is the most important meal of the day. This can help to see if you have similar eating habits.

203. Are you a vegetarian?

If you're a meat-eater, this could be a turn off for you.

204. How many different colored foods did you eat for dinner last night?

How adventurous is their food palette? This is one way to find out.

205. Do you have a favorite cafe or restaurant?

Asking this can give you the perfect idea for your next date!

206. Do you prefer takeout or cooking?

This may give you some insight into how they feel about mental health issues.

207. How often do you eat out?

Not only do you get a preview of what your future dates will look like, but you can also learn more about where they like to spend their money and time.

208. Do you read the nutritional information on the foods you buy?

This will let you know if they are health conscious or go with the flow.

209. Do you take vitamins? 

Asking this question can let you know if your partner has any deficiencies.

210. What foods do you really dislike?

This will let you know where to never take them on a date.

211. How often do you go shopping for food?

If this person snacks a lot during the day, you can learn more about their shopping habits. 

212. What food can you cook the best?

Asking this is the perfect way to figure out what you are going to cook for them on your first night in together.

213. What's the most unusual thing you've ever eaten?

This is a great way to find out how bold someone is when it comes to trying new foods.

214. What is the most expensive restaurant you have ever eaten at?

Everyone has a different opinion of what is luxurious, this will show you exactly what they think!

215. What's your favorite fast-food restaurant?

Get this answer and you've got the perfect late-night date planned.

216. What's your favorite fruit?

This will show you how much sweetness they like in their life.

217. What's your favorite vegetable?

Finding out how often they eat vegetables can give you an idea of how healthy they are and if they are getting enough vitamins and nutrients.

218. What would be your last meal?

If you think it sounds good, you can make it for them and have dinner together.

219. Do the utensils we use to eat affect the kind or way we prepare the foods we eat?

This is a thought-provoking question and will show you how cultural they are.

220. How does your etiquette differ from other countries? 

This question will show you how they see other countries and how they compare themselves to them.

221. Are there any foods that bring back special memories for you?

Food is symbolic of many things in our life. Asking this question can help you further understand what they value.

222. What is your favorite food?

This is a quick, no-pressure question to ask that can be used as a date idea further down the road. 

223. Have you ever tried a traditional English breakfast?

If the answer is no, maybe you can try it together! Breakfast in bed?

224. Do you think that you eat a balanced diet?

Does this person feel that they are a healthy eater? If nutrition is important to you, this could be a dealbreaker.

225. Do you try and reduce your salt intake?

This can let you know if this person may have any underlying conditions that may require them to monitor their salt intake.

226. Are you allergic to any foods?

Well now you know what not to cook for them!

227. What do you consider junk food?

This one is super important if you love to snack. What if they consider broccoli junk food? Run!

228. Do you prefer, salty, savory, or sweet?

Now you know what movie snacks to pick up for hitting the cinemas.

229. How much sugar do you add to your tea or coffee?

Now you will know how to prepare their coffee in the morning as a nice gesture. 

230. How does the color of the place you are eating affect how we like something?

This question will show you how much symbolism plays a role in their life.

RELATED: 24 Questions To Ask A Guy That Will Help You Find Out If You're Really Compatible

Questions to break the ice

It can be uncomfortable or weird when you meet someone for the first time. Here are some great ice breakers for you to talk about if you are at a loss as to what to talk about.

231. How much does a polar bear weigh?

Enough to break the ice — this one is sure to make them chuckle.

232. Have you ever gotten super lost? If so, where?

This will provoke an interesting story without asking too many questions.

233. Do you have any crazy roommate stories?

Asking this question can help you find out if this person has been involved with a lot of conflicts in their life.

234. What words could you not pronounce as a child?

Heading down memory lane is always a great way to get to know someone, especially learning more about their childhood.

235. What's the most embarrassing thing you have ever done?

This is another question that coud lead to a funny and entertaining conversation.

236. What's the worst haircut you ever had?

This can give you an idea of any hilarious phases they had while growing up.

237. What TV family most reminds you of your own?

Asking this question will help you learn more about the way they grew up.

238. Who is your craziest/most interesting relative?

The relationship they have with their family is important, asking this can spark an interesting conversation!

239. What nickname did you have growing up?

This gives you some insight into their personality and childhood.

240. What's your zodiac sign?

If you believe in astrology, finding out someone's zodiac sign can give you some idea about your potential compatibility!

241. Which celebrity do you shamelessly follow in the news?

You can get an idea of how much they follow pop culture and if you have any similar interests.

242. Which Disney character's story does your life most resemble?

Do they choose a heartwarming and fun character or a sad and lonely character? This can tell you a lot about them.

243. What's a funny pick up line that works for you?

Now that you know this one, you'll have to come up with something funnier to really knock their socks off.

244. What's a weird fact you happen to know?

This can give you a look into what they find the most interesting, and any topics they may enjoy exploring in their free time.

245. What commercial jingle gets stuck in your head frequently?

Asking this question can help you see if this person has a musical brain and if you are compatible in that way.

246. What is the most random thing in your purse/wallet?

You can compare it with something random that you have in your own bag and start a great conversation!

247. What's a nickname someone actually calls you?

This will let you know what to call them once you are closer.

248. Who is your celebrity look alike?

If they choose someone good looking, they must have a pretty good sense of self-confidence. That is important in a relationship!

249. If all your clothes had to be one color forever, what color would you pick?

This can let you know what color they think looks best on them, so you know what to buy them as a gift!

250. If you were a type of jeans, what type would you be?

This can let you see if they have a flare for life, or if things are just distressed.

RELATED: How To Talk To Someone New, By Zodiac Sign

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Emily Francos is a writer who covers astrology, pop culture, and relationship topics.