30 Deep Questions to Ask a Girl You Like
1.       Are you happy with where you are now?

2.       To which point of your life would you come back for some time, if you could or if you had a time machine?

3.       Which experiences don't you like to look back on or what would you like to forget?

4.       Have you ever been involved in any conflicts with law?

5.       Whom can you call your closest friend because he/she understands you without words and is always there for you? Or maybe who is the one who inspires you?

6.       Where can you be truly you?

7.       What was your nickname as a child?

8.       How many children did you want to have?

9.       Do you still have a bone to pick with your parents?

10.   Which flavor does your childhood have?

11.   Whom did you to want marry as a child? And as a teenager? Any movie stars or boy band singers?

12.   Your first time…  How was it? Like you wanted it to be?

13.   Which fashion sins could you confess here and now?

14.   Would you show me your pictures from your teenage years?

15.   What role did you use to have in your clique?

16.   How did you deal with your first lovesickness?

17.   Would you like to to know how many sexual partners I had?

18.   What would that fact change between us if you knew it?

19.   Have you ever done something really crazy because you were in love?

20.   If you could be a man one day long, would you do it? And if yes, what would you try first?
21.   Does a car have to be practical, really fast or just cool for you?

22.   Have you ever really disappointed someone who was really important to you? How did it end?

23.   Would you describe yourself as a reliable person?

24.   Which trip was unforgettable?

25.   What was one of the most embarrassing experiences that ever happened to you?

26.   Do you think that divorced men are always messed up somehow?

27.   What title would a book about you have if it were released today?

28.   Have you ever considered what your funeral would look like and who would come?

29.   Who „hast the permission“ to criticize you? Who doesn’t?

30.   What thoughts/views/values would you like to share with others?