145 Questions To Ask Your Crush That Will Keep The Conversation Flowing

Oh, that lovey-dovey feeling and the butterflies… Having butterflies in your stomach feels like you are on top of the world, doesn’t it? Or that you are about to throw up. Either of the two. Especially when you are prepping to go on a first date with that special someone. What do I ask them? What if I say something stupid? While it would be ideal for the conversation to just flow and for there to be no awkward silent pauses, that only happens in movies. In reality, it’s not all smooth like butter. Well, unless you have crazy chemistry going on. But assuming you are on the lookout for questions to ask your crush, you need a little prep me up ahead of your date. 

However, doing a little homework beforehand ain’t never hurt nobody. There are many foolproof questions to ask to get to know someone that will liven up the conversation. After all, questions are always good conversation starters as you show interest in the person you are talking to. Yet, starting off with flirty questions to ask your crush might not be the best way to strike up the conversation, as you might appear too pushy. Yes, by that, I mean asking whether they would like to Netflix and chill at your place. That’s a no-go.

However, there are plenty of conversation starters and good questions to ask your crush that will keep the conversation going. To put in my twopence from the journalistic experience, the best way to get the dialogue flowing is to ask open-ended questions. That’s a foolproof way not to run into a brick wall. And another good way to prevent the conversation from coming to a dead end is to simply ask: why? Pluck up details you learned from the conversation and the answers they gave you and expand on them.

Below, we’ve compiled some interesting questions to ask and deep conversation starters for when you really want to get to know the person. And don’t worry, “What’s your favorite color” is not one of them. Nevertheless, if the chemistry is just not there and you feel you have to push through the conversation, maybe they are not the one. Remember that the effort must come from both sides. And hey, good luck! We are rooting for you!

Is there a tried-and-tested question to ask your crush that has worked like a charm for you? Share it with others!

#1

Who do you listen to more, your heart or your brain?

#2

What’s the worst advice you’ve ever given someone?

#3

How do you think you would fare in the Hunger Games?

#4

When was the last time you cried?

#5

Do you have any phobias?

#6

What’s the best thing you’ve done for someone?

#7

What is the one thing you fear the most?

#8

What songs do you usually sing in the shower?

#9

What’s the one thing that you’re too tired of explaining to people?

#10

If you were arrested for something, what would your family and friends assume it would be?

#11

What question do you hate being asked?

#12

What would you do if you knew that no one would judge you for it?

#13

What’s the quality you admire the most in the person that you dislike the most?

#14

What’s the last thing you did for the first time?

#15

What food do you want to be served as your very last meal?

#16

What is something that people usually misunderstand about you?

#17

What’s your love language?

#18

What popular personality from the past do you think would be Instagram famous today?

#19

If you could find out how you would die, would you want to know?

#20

Do you believe in second chances? Why or why not?

#21

Funniest lie you told as a kid?

#22

Where would you like to live if you could choose to live anywhere in the world?

#23

What do you hate most about people?

#24

What are you proud of but never get the chance to talk about?

#25

Have you murdered anyone recently?

#26

What are the funny things that you believed as a child?

#27

How would you spend an ideal fake sick day?

#28

What’s a relationship dealbreaker for you?

#29

What is one thing that you swore you’d never do again?

#30

Would you rather choose love or money?

#31

What’s the worst thing you have experienced so far?

#32

If you could go back in time, what would you do differently?

#33

What’s the craziest thing you’ve ever done?

#34

Do you like adventure?

#35

What do you do for fun?

#36

Do you have a bucket list?

#37

What’s the one thing you can’t live without?

#38

What were you like when you were a child?

#39

Would you rather live in the city or in nature?

#40

If there was one thing you could save from a burning house, what would it be?

#41

If you had a time machine, would you go back to the past or travel to the future?

#42

Who do you think is the best actor/actress to play as you in a movie about your life?

#43

What’s the most foolish purchase you’ve ever made?

#44

If peanut butter wasn’t called peanut butter, what would it be called?

#45

How funny was your first-ever email address or username? Do you mind telling it to me?

#46

If money wasn’t an issue, what would you do with your life?

#47

What’s the worst date you’ve ever had?

#48

The world is ending in 24 hours. How do you spend the rest of your time in this world?

#49

Which website do you waste most of your time in?

#50

If you were to write a book, what would it be about?

#51

If you could pick a day to relive over and over, what day would it be and why?

#52

Who is your nemesis?

#53

What are you proud of right now?

#54

What’s something you wish would go out of style forever?

#55

What’s your go-to karaoke song?

#56

What’s something you consider a guilty pleasure?

#57

If your life was a TV show, what would the theme song be?

#58

What’s something weird that you find attractive?

#59

Do you know how your parents met?

#60

What is the worst possible name you might give your child?

#61

What are some of your favorite places to be with your partner?

#62

What is the best gift you’ve ever received?

#63

What do you think about open relationships?

#64

What’s the first thing that came to your mind when you first saw me?

#65

Do you have any ambitions?

#66

Is there anything you would like to change about yourself?

#67

If you were an animal, what would you choose to be?

#68

What’s your favorite TV show?

#69

Do you like small meet-ups or big parties?

#70

Do you like to spend time in nature?

#71

What is the one thing you spend money on even though you know you shouldn’t?

#72

Do you believe in soulmates?

#73

Do you have a crush?

#74

What’s your favorite thing to do on the Internet?

#75

What do you do when you’re feeling sad?

#76

Have you ever had your heart broken?

#77

How do you deal with break-ups?

#78

What does “fun” look like to you?

#79

How vivid are you dreams?

#80

How do you usually react when you’re crush is nearby?

#81

How do you position a roll of toilet paper, over or under?

#82

If you have to sit on a person for the rest of your life, who would it be and why?

#83

What’s something that you think I wouldn’t believe about you?

#84

What’s your most bizarre pet peeve?

#85

If you had a plane ticket that can take you anywhere you want in the world, where would you go?

#86

If real life was like a video game, what level are you now?

#87

If you were an inanimate object, what would you be and why?

#88

What’s the pettiest thing you’ve ever done in your life?

#89

If you could jump into a pool of anything, what would it be?

#90

What is your favorite childhood memory?

#91

Do you believe in the paranormal and would you go ghost hunting?

#92

Could you go for a week without your cell/smart phone?

#93

Do you volunteer anywhere?

#94

What does your name mean, and why did your parents give it to you?

#95

What makes for a perfect date, in your opinion?

#96

If you could only eat three foods for the rest of your life, what would they be?

#97

What is one rule you really enjoy breaking?

#98

What’s something you’re really looking forward to?

#99

What’s one rule to live by?

#100

On a scale of 1 to 10, how weird are you?

#101

If you could live in another era, what era would it be?

#102

Which is more important to you: platonic friendships or romantic relationships?

#103

Do you judge a book by its cover?

#104

Which app on your phone do you use the most?

#105

Do you believe in magic?

#106

Is your best friend male or female?

#107

What’s the first thing you would do if you had lots of money?

#108

What’s your opinion about cheating in a relationship?

#109

Do you think about the future?

#110

Do you believe in karma?

#111

How many times did you look at a mirror today?

#112

What is the most normal thing about you as a person?

#113

Would you rather be able to fly or teleport?

#114

What takes most of your time in your everyday life?

#115

What do people usually get wrong about you?

#116

What’s the most horrifying thing you could think of?

#117

How many ducks can you defeat if they all came at you at once?

#118

What would be the title of the book/movie about your life?

#119

Which historical person would you like to have lunch/dinner with if it was possible?

#120

What’s the place you would definitely not go to and why?

#121

Which celebrity do you think will be president next?

#122

Which do you value more: honesty or loyalty?

#123

Have you ever broken someone’s heart?

#124

Have you ever been caught cheating on a test?

#125

If Donkey Kong is a monkey, not a donkey, why was he given that name?

#126

What is your weirdest quirk?

#127

What is your favorite song?

#128

Are you superstitious?

#129

What are the things that you find exceedingly laughable but other people don’t?

#130

What’s the most hilarious nickname anyone has ever given to you?

#131

Who would you eat first if you suddenly turned into a zombie?

#132

If you could change your name, what would you like it to be?

#133

What’s the most interesting question you can ask someone in order to get to know them?

#134

Would you rather be a cat or a dog?

#135

What’s the weirdest animal you would want as a pet?

#136

What’s the weirdest thing you find attractive in a person?

#137

Do you ever wonder why we’re here?

#138

Choose one: Bulbasaur, Squirtle, or Charmander?

#139

What do you think you’ll be like in old age?

#140

Do you like huge parties or would you rather spend time in a small group/alone?

#141

Would you rather your loved ones always be truthful with you or tell you lies to protect your feelings?

#142

What’s your philosophy on life?

#143

Have you ever tried talking to your dog?

#144

Do you think penguins have knees?