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    Questions to Ask Your Crush: 113 Great Ways to Kickstart a Conversation
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Questions to Ask Your Crush: 113 Great Ways to Kickstart a Conversation

Striking up a conversation with your crush is essential. Not saying it’s easy, though. But we’re here to help with this collection of the best questions to ask your crush to strike up a friendship and even romance!

Great Questions to Ask Your Crush

Is that puppy love we smell in the air?

We get it. You want to talk with your crush. Maybe ask them questions, get to know them better, and hopefully discover if they like you back, but you don’t know how. Don’t fret because we have the answer.

It’s easy to get tongue-tied in front of your crush. However, with this handy list of potential questions in your back pocket, you’ll be a conversation champion in no time. 

Finding the Right Way to Talk to Your Crush

We have the list of the best questions to ask your crush to get the conversation started! From simple conversation starters to get you into the game subtly to funny questions to highlight your unmistakable wit or flirty digs to let him know your intentions (without downright saying it). 

What’s left for you to do is muster some courage to approach your crush. The next step will be easy. Take note from this questions list and spark a conversation with your crush that’s filled with curiosity, hilarity, and hopefully, fingers crossed, romance!

20 Simple Questions to Ask Your Crush?

Their hobbies and interests are a safe topic. These questions are laid-back and straightforward but will help you learn a lot about your crush. It’s also a great way to find out if you have things in common. 

Ask Your Crush Anything

Try some of these awesomely simple questions the next time you try and start a conversation with your crush!

1. What kind of music do you enjoy listening to right now?

2. Are you undoubtedly a cat person or absolutely a dog person?

3. Which activities do you prefer on a typical Saturday, huge parties or a night in with a good pizza and your favorite movie or sports on television?

4. Can you tell me when your birthday is? What about your zodiac sign?

5. What do you say was the best gift you’ve ever given someone? Received? And from whom?

6. Would you say you’re a morning or night person?

7. What do you say is the most impressive skill that you’re most proud of?

8. In a group setting, would you be hanging in a small group, alone, or at the center of everything being the life of the party?

Make Sure to Ask Your Crush About Them

You can also ask your crush about their dreams and aspirations in life. While some of these random questions are hypothetical, they will give you an insight into their perspective and desires about certain things. 

Talking is a Great Way to Get to Know Your Crush

9. What is your dream job?

10. If you received a lot of money, what would you spend it on?

11. If you could plan your ideal fake sick day, how would you spend it?

12. What are the top three things you find attractive about the opposite sex?

13. What is usually the last thing on your mind when you fall asleep?

14. If a genie gives you a chance to have three wishes, what would you wish for?

15. What is your favorite word?

Family Life Makes for Interesting Question Opportunities

16. How would you describe your family life? Are you close to your parents? Siblings? Any extended family?

17. Who do you say is the smartest of all your siblings? The goofiest? The most likely to get arrested?

18. What do you say is your favorite childhood memory?

19. Do you have any idea how your parents’ relationship or love story started?

20. What was the most embarrassing moment you can remember about your childhood?

22 Funny Questions to Ask Your Crush?

So, you’ve started a conversation with your crush without hyperventilating. Thumbs up! Now, seize the moment and ignite a more lively convo that can help bring you and your crush to the next step. 

Chatting with your crush about funny things is a great way to find some common ground while getting a few good laughs. And if you’re still nervous in front of your crush (because who isn’t?), touching on some light-hearted topics will hopefully take away those nerves. 

Make Your Crush Smile With These Funny Questions

These fun questions will make for amusing conversations. If the questions themselves aren’t funny, they’re designed to inspire funny answers and stories from your crush!

21. What was the worst lie you’ve ever had to come up with to get out of a date?

22. What are your favorite comedy movies or shows?

23. Would you try singing your go-to karaoke song?

24. What is the most foolish purchase you’ve ever bought in your life?

25. What do you say is your favorite meme?

26. How would you describe your first kiss?

27. If you could date your celebrity crush, dead or alive, who would it be, and how would you plan your dream date night?

28. What’s the worst job interview you have ever had?

29. What would you pick if you were granted a rare chance to be incredibly skilled at something?

30. What is your excuse for existing in this world?

31. Can you still remember the wildest thing you’ve ever done in your life? What was it?

32. If you can call peanut butter any name, what would you call it?

33. What is the funniest fact about you that you think not many people would believe is the truth?

34. Would you let me see the funniest photo you have on your phone?

35. I have way too much money, how would you spend it?

Flirty Questions to Ask When You’re Feeling Confident

You will never go wrong with adding a little bit of teasing into your conversation with your crush. 

36. What is your go-to emoji when flirting with your crush?

37. What do you say was the most bizarre thing that happened to you on a date?

38. Okay, you have to spill the beans. What was the craziest thing that you’ve ever done to get a guy or a girl’s attention?

39. Have you ever mistaken someone’s goodness and friendliness for affection and love?

40. On a scale of one to ten, how crushable do you think you are?f

41. Have you ever stolen something (or maybe someone) in your life?

42. Would you say you’re guilty of lame excuses whenever you want to spend time with a guy or girl?

17 Cute Questions to Ask Your Crush?

Okay, you’ve unleashed your funny and witty to get their attention and most likely got a chuckle or two and a few good stories from your crush. Now, it’s time to lay on the charm. 

Cute Questions Are Great For Talking to Your Crush

Because you can’t simply dive right into the deep end, you might want to start with asking your crush some cutesy questions first. Consider this as the hair flip (if you’re a girl) and the your-hands-at-the-back-of-her-chair (if you’re a guy) step in the flirting with your crush guide

This list is a mixture of questions about your crush and about you. 

43. What do you think makes someone attractive? 

44. Would you consider tattoos sexy?

45. Asking for a friend, where’s a good place to go for a dinner date around here?

46. What do you say is the weirdest thing about you?

47. What do you think is something that sets me apart from your celebrity crush?

48. Would you consider yourself the romantic one in a relationship?

49. So, where do you work out?

50. what do you think was my first impression of you?

51. What kind of flower do you think fits me the most?

52. Do you dig my outfit? I love yours!

53. What do you think is the cheekiest pickup line that would make me laugh?

54. There’s just something about you, but I can’t put my finger on it. Have any clue what it is?

55. You have the most amazing eyes. What color are they exactly?

56. Would you consider yourself a funny guy or girl? Tell me a good joke, and I’ll be the judge!

57. Are you a heartbreak girl/guy?

58. Seriously, why on Earth is someone like you still single?

59. Would you rather dance in a club or in the rain?

16 Awesome Saucy Questions to Ask Your Crush?

Don’t overlook well-crafted flirty questions to ask your crush to strengthen your connection. The flirtiness might be subtle initially, but like everything else, things progress, and intentions become more obvious. Plus, these flirty questions will give you useful information about who they are or if you’re on the same page. 

Flirting is Fun!

These questions to ask your crush are a little cheeky. And if you’re game (and got the courage), go right ahead!

60. Would you prefer dating someone intelligent or someone hot? Under which category do you think you belong?

61. What are your go-to makeout moves?

62. What was the first thing that pops into your mind whenever you meet someone you’re attracted to?

63. Would you know if someone is into you? How can you tell?

64. How would you want to know if someone fancies you?

65. What would make you go crazy over a guy or girl?

66. Is there any question you’re nervous about asking me?

67. Would you consider yourself a blanket hog?

68. Which one do you think you are most of the time, the big spoon or the little spoon?

69. What excites you about being in a relationship?

70. Have you ever felt shy telling your crush you like them, or are you good at telling people how you feel? wink

71. What do you usually want to do whenever you feel lonely?

72. Would you prefer cuddling oversleeping alone?

73. What kind of thoughts keeps you up at night?

74. Do you like whipped cream?

75. Would you rather be called sexy or hot stuff?

8 Spicy Questions for When You’re Ready to Turn Things Up a Notch

This is level two of flirty questions to ask your crush. They are probably more seductive and bold than just flirty. And this can only go two ways – your crush gets open and free with you, and sparks are flying, or they get uncomfortable. 

Naughty Questions to Bring You Out of Your Comfort Zone

It is why we have this one essential tip to keep in mind – ask these questions playfully (and somewhat dismissively). If they answer and even strive to discuss the subject, there’s a great chance your crush is into you too! If not, you’ll know it. 

76. Would you say you are ticklish? Do you want to play a game where I try to find out where your tickle spots are?

77. If I have to answer truthfully, what’s one thing you would ask me?

78. I’ve always wanted to try painting. Would you be into body paint?

79. If I am the last person on Earth, besides you, of course, would you consider going out with me? 

80. If you could pick what I’m wearing right now, what would it be?

81. So, are we going on a date or what? (This one is reserved for those with  a bold heart.)

82. So, what are your plans for this Saturday? 

83. Apart from your name, what other name would you like me to call you?

6 Naughty Questions For Those Brave Enough to Try

These flirty questions for your special guy/gal are on the top of the food chain – sexy and sexual and a little more intimate. This takes guts, but remember, if you’re interested to know your crush’s opinion on intimate matters, you just have to ask them. 

Spicy Questions When You're Read to Have Some Fun

But just a tip, you might be better off asking these questions to your crush when you have some privacy. You don’t want someone to put you on the spot, so avoid putting your crush on the spot. 

And without further ado, here are some flirty, sexy, intimate questions for your crush with a balanced playfulness and sexiness. 

84. Do you consider dirty talk as foreplay? 

85. Would you prefer to be a starter, main, or dessert?

86. Would you ever consider doing a nudie run (for a good cause!)?

87. Do you even wear anything to bed?

88. Would you like to be naughty together?

89. No holds barred, what is your biggest guilty pleasure?

11 Deep Questions to Ask Your Crush

If you want to know your crush on a deeper, the secret is to ask the right questions that can open up to deeper conversations.

Deep Questions For Your Crush

From deep and thought-provoking questions about life and values to their past and lessons learned, these questions to ask your crush will surely start meaningful conversations. 

90. Would you say that your younger self would be very proud of your life today?

91. What do you say is your number one red flag and biggest deal-breaker when it comes to a serious relationship?

92. Have you found your life’s purpose? Care to share all about it?

93. If you were given a chance to do one thing differently, knowing that it will change what and who you are now, would you do it? If yes, what would you change about the past and why?

94. What is the most memorable moment when you were scared to step out of your comfort zone but did, and it paid off?

95. What do you think makes you a better person than you were ten years ago?

96. What is the most embarrassing thing to happen to you?

97. Can you sum up your life philosophy in a single sentence?

98. Has any past heartbreak shaped your life right now?

99. Would you consider yourself someone living their life to the fullest?

100. How do you deal with anger? Disappointment?

13 Interesting Conversation Starters

Since you aim to know your crush a little deeper and maybe foster a new relationship, friendship, or otherwise, you can also ask about their past relationships and their overall perspective about love and relationships.

Interesting Questions Breed Deeper Conversations

These interesting questions for your crush may also give you plenty of intel whether they are in for a committed relationship or not. 

101. What is your opinion about love and first sight? Do you believe in it? How about soul mates?

102. Have you ever been in love? Have you broken someone’s heart or trust?

103. What do you say was wrong about your past relationship that led to the breakup? (But be sure that you know for sure they have an ex-boyfriend/girlfriend before asking this question.)

104. What are your three biggest pet peeves when it comes to being in a relationship?

105. For right now, do you prefer casual dating, or are you looking for long-term relationships?

106. What do you say is your biggest relationship fear?

107. If you don’t mind me asking, how did your last relationship end?

108. Do you believe it’s important to know your love language in a relationship?

109. Why do you think your last relationship ran its course?

110. What do you think makes most relationships turn toxic?

111. Do you believe that exes can really become just friends and not have things get awkward?

112. Is there ever a part in a relationship where it’s okay to lie to your partner?

113. What do you say would be the biggest risk or the sappiest, most romantic thing in the whole world you’re willing to do to make a relationship work?

Teasing Your Crush with Questions

Getting to know your crush doesn’t have to be so serious. Tease them a little bit.

Adding a little teasing to your chat simply makes things lighter and more interesting. Not to mention, you don’t really want to put your new crush on the spot by digging right into their deepest, darkest secrets. 

When it comes to teasing your crush with questions, you want to go for topics that will get them smiling and thinking and just put the seed of interest in there too. 

Final Thoughts on Questions to Ask Your Crush

Hopefully, these questions to ask your crush will help you start a few meaningful and engaging conversations with the person you like. They are perfect to put you at ease while chatting with your crush and learn more about them too. 

While it’s not the best idea to bombard your crush with all these questions in one sitting, you can pick a few and table the rest later.  So, what are you waiting for? Armed with the best questions to ask your crush no matter the occasion, grab your courage and start chatting with your favorite guy or gal!

The comments are open, so let us know how it goes. Or, if you think we’ve