40 Good and Cute Questions to Ask a Guy You Like

I was the leader of the Scout Team in school and there was this newcomer guy who I was supposed to give instructions to. I’d be lying if I said he wasn’t cute. He was amazingly cute and every girl in the scout team laid her eyes on him.

Initially, I was nervous about how to initiate a conversation in order to give him the instructions. I mistook him for a shy one at the first instant. He turned out to be quite the opposite of a typical shy guy.

He proposed to play the game of 20 Questions first saying that he wanted us to be friends before me being his Scout leader. I fancied the idea and the other girls were burning out of jealousy. LOL!

So, yeah! That happened and since he was pretty darn interesting right from the beginning, I fell for him and he fell for me somehow, and we are the “It Couple” of high-school now. Thank you lady luck for smiling upon me.

Anyways, playing the game of questions is an insanely amazing idea to spice things up and get to know someone better.

I bet you want to get on the game. Are you in short of questions? I have a sea, in fact an entire ocean of them.

Here’s my share of 40 cute questions that you could ask your crush while texting or while hanging out, or whilst you are boarded on the same bus as him. Sounds fun? Let’s begin!


1. If you were stranded on a marooned island, who would you want to be with ? (Celebrities don’t count)

2. What’s your deepest fear?

3. If I was down in the dumps, what would you do to cheer me up?

4. Do you think I’m cute or sexy?

5. What is something you want to know about me?

6. Have you been in love before? If yes, I want to know the number.

7. If I asked you to describe yourself in 5 words, what would the words be?

8. What is your idea of an ideal date?

9. Which physical feature of me do you find the most appealing and why?

10. What’s your wildest fantasy?

11. Would you give away playing your favorite video game to spend a day with me?

12. Have you ever written a piece of an art for anybody?

13. Can you fake a British accent?

14. Do you like cuddling and snuggling? If yes, would you want to do it with me?

15. Does your heart get filled with joy when I’m with you?

16. Would it make you feel any better if I admired your beauty?

17. Do you have a pet? If so, what’s its name?

18. What are your pet-peeves?

19. What is the craziest thing you’ve ever done in your life till date?

20. Which celebrity are you head over heels for?

21. If a genie ever came to you and asked you to make 3 wishes, what would they be?

22. If you found a 100 million dollars legit cheque in your bag one day, would you encash it? If yes, what would you do with it?

23. What’s your favorite movie of all times?

24. If you had to spend the rest of the lifetime wearing one attire, what would it be?

25. If i were to serenade you right now, what song would you want it to be?

26. Who is your favorite artist and what’s your favorite song?

27. What’s your favorite food?

28. Do you like a sculpted body that has starved to get into shape or a petite one that belongs to the one who is happy with their body image?

29. If you could turn back time and amend one thing from the past, what would it be?

30. Who is the most important person in your life?

31. Ice-cream or milkshake?

32. Would you take me for an adventurous day out for a date or stay in the couch snuggling all day long?

33. What are the best memories of your life?

34. If you got an opportunity for a renowned publishing house to get your autobiography published, would you do so?

35. Who’s your best friend? What are they like?

36. When was the moment in your life that you were brutally hurt?

37. What does love mean to you?

38. Would you fancy us as a couple?

39. How committed can you be in a relationship?

40. If I told you that I loved you more than you could ever imagine, what would your answer be?


I’m sure you’ll have known him 100 folds better by now, after asking a series of a row of questions.

But remember that you aren’t interviewing him. It’s a game and you’d want to make it fun.

Give him his turn and a tad bit of your insight.

You’ll have all your answers and he’ll have all the things he needs to know about you by the end of this game.

Have fun! Cheers!

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