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25 questions to ask your crush to see if you should be with them

Relationship Rules Editorial Team Relationship Rules Editorial Team | September 20, 2015 | 3 min read

I was talking to a friend of mine and how she completely rejected a guy on the first date because he asked her a silly question. First dates are hard, they set the stage for what’s to come (or not to) and a lot is riding on them. I’ve been to one bad first date in my life, and I still can’t forget how horrible it felt when it wasn’t going in the right direction, when you see a lot of hope just fading away as time goes by. The same goes for someone you have a crush on, you can easily mess it up if you act a little too stupid or upfront with them, it can easily scare them away before they even get to know you. So I made a list of questions, questions you can use on your first date or during your first serious conversation with each other. These questions can also lessen the awkwardness between you two and will pave the way towards finding chemistry together. Let’s begin.

1. When was the last time you cried and what was the reason?

2. What scares you the most?

3. Who is the most important person to you?

4. What do you hate about yourself?

5. What’s your favourite book and why?

6.В When was the last time when you felt extremely happy?

7. What’s your dream job?

8. What do you dislike about yourself the most?

9. If you could go back in time, what would you tell yourself in the past?

10. What’s your favourite TV show?

11. Who knows you inside out?

12. What’s that one thing you badly want to do in your life?

13. Who’s that one friend you can call your "closest friend"?

14. What do you regret doing the most in life?

15. Unlimited money or infinite happiness?

16. If you see your ex somewhere, what would you do?

17. Are you happy with the person you are or do you aspire to be someone else?

18. Do you have faith in karma?

19. Do you believe in hope?

20. What are you superstitious about?

21. What’s the biggest lesson you’ve learnt in life so far?

22. Who are you closer to, your mother or your father?

23. What would make you the happiest person in the world?

24. If you could trade lives with someone for a day, who would it be?

25. What do you hate the most in others?

Add to the list, folks

Add your own questions to the list by commenting below. And as always, stay blessed and keep the love alive! Consider the important questions to consider before dating, as they can help you better understand your own needs and expectations. Reflecting on your values and desires can lead to more meaningful connections. Remember, taking the time to evaluate these aspects can set a strong foundation for a relationship. As you navigate these considerations, you might also want to explore some flirting tips for texting your crush to keep the conversation lively and engaging. Crafting sincere compliments or playful messages can create a fun dynamic and spark their interest. Always be authentic and let your personality shine through to foster a genuine connection.


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Evelyn Wingate · January 22, 2023

Are you an honest person?

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Relationship Rules Editorial Team
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Relationship Rules Editorial Team

The Relationship Rules Editorial Team is made up of writers, researchers, and relationship enthusiasts who have been covering love, connection, and personal growth since 2012. Based in Singapore, the team draws on real-world observation, reader experiences, and established relationship psychology to create content that is honest, practical, and grounded. All articles are reviewed for accuracy, tone, and balance before publication. Learn more about how we work on our Editorial Standards page.