Romantic Gup Shup: playful conversations for your Valentine

Valentine's Day Conversations

It’s Valentine’s Day – possibly the most romantic, playful day for singles. The focus is on having fun with your partner and discovering more about each other. Happy couples talk about their childhoods, laugh at inside jokes, share feelings and more.

But sometimes, the conversation comes to a halt. If you really want to know your Valentine, here is a playful way forward. In fact, there are 39 ways to get the conversation going. Check them out and let us know if you have more questions that a couple could ask to get to know each other better!

Try these for starters.

“If someone handed you a magic lamp and gave you three wishes, what would they be?”

“If you won the lottery, what are the first three things you would do and which are the five things you’ve been most longing for, that you would buy?”

And, here are 36 more. Share the list with your Valentine so that both of you can take part in this fun game!

  1. What was your first impression of me? 
  2. How accurate do you now think it was? On which counts do you think you were totally wrong and on which were you right?
  3. What is your idea of a truly romantic evening?
  4. If I promise not to get upset, can you tell me something that you’d like to change in me but don’t have the nerve to tell me?
  5. If you weren’t in the profession you are, what would be your other dream profession and why?
  6. Apart from the most obvious one, which other two areas of your body are the most sensitive and responsive?
  7. Which three parts of my body are your personal favourites and why?
  8. Can you name three qualities that attracted you when you met me/got to know me?
  9. Which is your dream destination and why?
  10. Which is your favourite movie of all time and favourite scene in it? (If the other hasn’t seen it, narrate in detail.)
  11. Which fruit/vegetable do you think I resemble and why?
  12. Can you remember your earliest childhood memory of happiness and that of fear?
  13. Your favourite aunt/uncle/cousin and why?
  14. What are the qualities that draw you to people that you can base a friendship on?
  15. Can you give me a mock session of how you would discuss sex education when you have a child?
  16. Your first crush – what drew you to her/him?
  17. Your first date – where did you go, what did you do and how long did the relationship last?
  18. How have you coped with break-ups in the past?
  19. What has been your scariest dream? Which has been your most frequently recurring one?
  20. Which has been the best decision you ever made?
  21. Which is the decision you regret the most?
  22. Can you narrate to me your proudest moment?
  23. If your house was on fire and you had a chance to grab only five things before leaving, they would be…
  24. If you were asked who you would like to be born again as, the answer would be…
  25. Which is your favourite flavour of ice cream, your favourite junk food and your favourite dessert?
  26. Whose wardrobe would you most like to possess and why?
  27. The one argument your parents had, that you would try and avoid with your partner, would be over…
  28. Which is your favourite asset/body part on a man/woman and why?
  29. The most embarrassing thing that ever happened to you was…
  30. Your most wicked fantasy has got to be… (Be open to this one, if you react adversely, he/she will never feel free to confide in you again.)
  31. If our relationship doesn’t work out, do you think we can remain friends? If no, why not?
  32. Who are you closer to – your mum/dad – and why?
  33. Your favourite song of all times and why – is it because of the lyrics, because of the memories associated with it or just the whole package?
  34. What upsets you most in a relationship and what makes you the happiest?
  35. What is your perception of how people see you?
  36. If someone told you they saw me with another guy, what would your first reaction be – she’s cheating on me, he’s probably an old friend or I need to get to the bottom of this?
  37. Can you think of something you craved for when you were young and were denied?

Have fun and let us know how your date went!