36 Questions to Fall In Love With Yourself

Singapore Feb 13, 2021

Inspired by the 36 questions to fall in love shared on The New York Times, here are 36 questions to ask yourself this Valentine’s day as you embark on your journey of self love.

Every human being is an ever evolving person with hopes and desires that may change throughout the years. But one thing remains – the love for yourself will always be the foundation that determines your relationships with others. RuPaul said it best, “If you can’t love yourself, how in the hell you gonna love somebody else?” And that’s on period.

The same way the original 36 questions are structured, these introspective questions are broken into three sets with each set getting progressively more intimate. These questions are relevant to everyone. You can be married, single, or in a phase of self-rediscovery, the point is to check in with yourself using these questions in hopes that you’ll know yourself better and in turn, love yourself better. If you’re someone who has explored every corner of your mind, heart and soul, we hope these questions help remind you of how amazing you truly are.

In the original study, after the questions are asked and answered between two people, they have a final task – stare into each other’s eyes for four minutes. For the purpose of this exercise, we suggest that you look at yourself in the mirror for four minutes and practice self love affirmations out loud. Ready? All you need is some time, a safe space and an open heart. Good luck!

Set I

  1. If your loved ones were to use one word to describe you, what would it be?
  2. What’s the first thing you’ll do if fame and fortune came to you overnight?
  3. Before making a telephone call, do you ever rehearse what you are going to say? Why?
  4. What would constitute a “perfect” day for you?
  5. Do you ever find yourself singing more often while you’re around any particular person?
  6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want? Ask yourself why.
  7. Would you rather die before your loved ones or be the last? Why?
  8. Can you name your top two love languages?
  9. For what in your life do you feel most grateful?
  10. If you could change anything about the way you were raised, what would it be?
  11. Name four people that you can’t picture your life without.
  12. If you could wake up tomorrow having gained any one quality or ability, what would it be?

    Set II
  13. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know? Why?
  14. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
  15. What is the greatest accomplishment of your life?
  16. What do you value most in a friendship?
  17. What is your most treasured memory?
  18. What is your most terrible memory? How do you feel about it now?
  19. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
  20. What are the top three qualities you look for in a friendship?
  21. What roles do love and affection play in your life?
  22. Name five positive characteristics about yourself.
  23. How close and warm is your family? Do you feel your childhood was happier than most other people’s?
  24. How do you feel about your relationship with your mother?

    Set III
  25. Name three non-negotiables that you look for in a life partner.
  26. In times of conflict, what is your first reaction?
  27. Complete this sentence: “I wish I had someone with whom I could share ... “
  28. How good are you with verbalising and enforcing your boundaries?
  29. Is there anything that you’ve never told anyone but you really want to?
  30. What characteristics do you dislike most about yourself? Why?
  31. What’s the most embarrassing moment in your life? How do you feel about it now?
  32. How would you like someone to comfort you when you’re crying? If not, why do you feel you don’t need comforting?
  33. What, if anything, is too serious to be joked about?
  34. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
  35. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?
  36. Of all the people in your family, whose death would you find most disturbing? Why?

Knowing what self care looks like for you is also important to continue loving yourself holistically. Some people indulge in exercise, others volunteer, and some add journaling to their self care routine. If you’re feeling up for it, you can also try these icebreaker questions with your housemates to get to know them better.


Fizah Hatman

Marketing Manager at Hmlet. Keeping up with pop culture, the news and TikTok.