50 Questions You Should Ask Your Valentine

Don't be a victim of awkward silence this weekend.  Here are some questions to help get the conversations rolling.   

By Henry Adeleye on February 13, 2015   


Today is Friday the 13th, fitting for the day before Valentine's Day.  Some people will spend the day gearing up for the forced dates they're going to have to go on this weekend.  Others will be planning a night out with the girls or guys to celebrate non-conformity, pride for being single, or both.  For the rest, there's wine and Netflix.  Regardless of which category you fall in, you'll want to be equipped with good material for the fun-filled water cooler conversations that will happen Monday morning.  And if you do find yourself on a date, you'll want to avoid awkward silences as much as possible.  Because nothing is worse than constantly staring at your plate when there's another human being sitting across from you.  So alas, here are 50 questions to ask your Valentine to make sure the conversations flow like stories from Brian Williams.  Most taken from this tumblr article, and some my own.   


1.  Would you ever marry yourself? 

2.  What are your dreams? 

3.  If you were drunk, would the person you like take care of you? 

4.  What excites you? 

5.  What type of person is your best friend? 

6.  Would you rather be rich or famous? Both is not an acceptable answer. 

7.  What was the last deep conversation you had about? 

8.  Do you love your parents? 

9.  What are your five favorite songs? 

10.  Do you believe in luck? 

11.  Do you think there is life on other planets? 

12.  Do you believe in life after death? 

13.  What are your bad habits? 

14.  Where would you like to travel? 

15.  What do you wish you could spend more time on? 

16.  What part of your body are you most uncomfortable with? 

17.  Have any of your exes ever told you they regret breaking up? 

18.  Can you spell your name with your chin? 

19.  Would you rather live without TV or without music? 

20.  Have you ever liked someone and never told them? 

21.  What do you say during awkward silences? 

22.  Do you believe everyone deserves a second chance? 

23.  If you're being extremely quiet, what does it mean? 

24.  Do you smile at strangers? 

25.  Trip to outer space or bottom of the ocean? 

26.  What makes you get out of bed in the morning? 

27.  What are you paranoid about? 

28.  Have you done anything recently that you hope nobody finds out about? 

29.  What's one thing you wish you could change about yourself? 

30.  How many pillows do you sleep with? 

31.  Is there anyone you want to punch in the face right now? 

32.  What was the last movie you watched? 

33.  Have you ever loved someone so much it hurt? 

34.  Who was the last person you cried in front of? 

35.  What was your childhood nickname? 

36.  What was the last book you read? 

37.  Are you afraid of the dark? 

38.  Can you keep white shoes clean? 

39.  Do you believe in love at first sight? 

40.  Do you believe there's a perfect match for every person? 

41.  What makes you happy? 

42.  Would you change your name? 

43.  Your best friend of the opposite sex likes you, what do you do?

44.  Can you count to one trillion? 

45.  What was the dumbest lie you ever told? 

46.  Do you sleep with the doors open? 

47.  Tea or coffee? 

48.  Was today a good day? 

49.  If you could quit your job today and do something that pays significantly less but is more rewarding, would you do it? 

50.  What’s your favorite quote?