What is your legacy? Could you live with yourself if your legacy was that you were a small minded, unkind person who was never happy?
If you were given $1 million, what would you do with it?
Is the glass half-empty or half-full?
What's the best present she has ever received?
What's been her proudest accomplishment in life so far and why does she think it's her proudest achievement so far?
Where would she rather be right now than where she is now, physically speaking (if possible to answer)?
Do you have any regrets about anything in life that doesn't really matter much anymore but still bothers her for some reason or another even though it.
What is your greatest fear?
Is there any dream more important to you that you have yet to pursue?
What's your favorite kind of music?
On average how many hours does she spend on social media per day? How often does she feel she needs to check her phone for a message from her significant other?
Has she ever gone on dates with men who were really bad for her and if yes, how do they compare to the ones that she might be better off without and what was it about them that turned out bad for her or did it really matter much at all in the end?
Has he ever taken advantage of a secret she holds close to the vest or something else about her life that he wouldn't know.
Why does she always feel like he is stalking her?
Do you have any illness or medical condition that you are still dealing with or did but went away?
What is the most foolish thing he has ever done?
How long does it take him to get home from work on typical nights, days, and weekends? Does he need help getting there from his job, from friends, or from her house? If he's going to a bar or club where will they go once they arrive (if you know)?
Does she feel like she's living in a prison more often than not sometimes? If so why and how much prison is she willing to accept before taking action to move out of prison land if possible.
Does he still have friends from high school or college that she doesn't know?
What's her favorite season to be in, winter, spring, summer, or fall?
What was her first job like and what did she learn from that experience? Who was the first person she ever dated and why did they break up (if they did)? What kind of food is best served at a wedding? Has she ever had an out-of-body experience? What are some of the most common regrets of the dying as reported from hospice nurses and other medical professionals who care for people in hospitals when they are on death's door.
Does he like to be kissed on the first date? What questions does she ask herself during an interview for a potential new job? Has she ever been in love with another man besides the one that she is with now, and if so how did things work out for her in the end? Does she have a favorite sport and if so why?
What's her favorite thing to do together as a couple and why. Which ethical standards matters the most to her above all else?
Who was her first crush back when she was in elementary school, middle school, high school, and college or whatever other time periods that you can think of.
What's been the biggest obstacle that she has encountered during her lifetime and how did she overcome it?
What are three of her favorite movies (and why)?
Has she ever felt like the best in school, at work, or in any other capacity during her life?
What are some of the most common traits shared by the people that she feels most sorry for in life?
What are some of the things that he is doing right now to make himself better than he was before and what do you appreciate about it? How does she feel about you not talking about all your feelings with her at least sometimes, if not most of the time? What was his childhood like as a whole and what kind of family did he grow up knowing.