40 Fun Questions to Ask Your Crush

We all know the joy and desperation of being attracted…

We all know the joy and desperation of being attracted to someone.

The feeling of yearning often comes with a sense of fear and uncertainty. When it comes to matters of the heart, it can be difficult to resist the pull of attraction. This is why you need juicy questions to ask your crush.

We want our crush to notice us and hopefully develop an interest in us. But before we even get there, most people want to first gauge their compatibility with their crush. It’s only normal and wise for people to test the waters before investing time, money, and emotion into a person.

Learning this information takes some finesse. You don’t want to take a straightforward approach because you could come off as unfriendly or rude. Going for a subtle approach would be ideal, and it allows both of you to ease into a mood (if there’s mutual attraction).

Conversations are a great starting point for determining your compatibility. If you’re unsure of what to ask, you can start with these questions.

woman and man wearing white shirt while sitting near green trees during daytime
Photo by Clay Banks on Unsplash

Conversational Questions to Ask Your Crush

Conversational questions are ideal starters because they are mostly general questions. They are perfect because they don’t reveal too much about your intentions.

At the same time, they give you valuable information on the type of personality your crush has. They’re a simple way to get to know your crush without making things awkward.

  • What’s something you’re looking forward to?
  • What’s the best compliment you’ve ever received?
  • Which things do you think we have in common?
  • What’s something you think everyone could benefit from trying?
  • What’s your favorite meal to eat?
  • Whom did you vote for in the last election?
  • What’s your favorite meal to cook?
  • What would you rather be doing if you weren’t working as (job)?
  • What’s the most memorable place you’ve visited?
  • Where are the next five places you want to visit?
  • How do you recharge? Do you do it on your own or around other people?
  • Who’s your favorite author?
  • You’re playing hooky for a day. How are you spending it?
  • What’s your favorite childhood memory?
  • What is something you like that might surprise other people?
  • Do you have any tattoos?
  • What’s the best new song you’ve discovered recently?
  • How did you meet your best friend?
  • What’s the first album you ever bought?
  • What’s the first blockbuster movie you remember seeing in theaters?

Juicy Questions to Ask Your Crush

Once you’ve determined that there’s a chance for a deep connection, you can shift the tone of your questions. You can go from conversational to fun, deep, or even flirty.

Depending on how your crush responded to your previous questions, you may want to flip things up a notch. Think about what your crush likes to talk about and ask questions that will spark different kinds of connections. You can choose from this list of flirty and deep questions.

  • Do you believe in monogamy?
  • Have you been in love before? Who was your first love?
  • When was your most recent relationship, and how did it end?
  • Have you ever been to therapy?
  • What’s the kindest gesture anyone has ever done for you?
  • Do you believe in soulmates?
  • Have you ever had your heart broken?
  • Have you ever broken someone else’s heart?
  • What’s your love language?
  • Do you have any phobias?
  • What’s your biggest fear?
  • Does the approval from others matter to you?
  • When was the last time you felt inspired to create something? What’d you create?
  • How do you like people to comfort you when you’re sad or upset?
  • Who in life do you look up to most?
  • What’s something you’d like to learn more about?
  • Do people trust you to keep secrets?
  • How did your parents meet?
  • How would you describe your approach to conflict resolution style?
  • Do you think it matters more what we achieve or who we surround ourselves with?

In Summary

The main purpose of asking questions is to learn about a person. Their answers can tell a lot about their thought process, emotional maturity, and other important aspects. Nobody wants to go all-in before they’re sure about someone. Moving too rashly can leave you in an embarrassing situation.

Remember to choose the right tone for your questions. Make sure you ease your conversation to a certain mood. Let your questions come naturally. Make sure to come prepared with conversational and juicy questions to ask your crush. Good luck, Casanova!

Frequently asked questions

40 Fun Questions to Ask Your Crush

Abir is a data analyst and researcher. Among her interests are artificial intelligence, machine learning, and natural language processing. As a humanitarian and educator, she actively supports women in tech and promotes diversity.

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