A comprehensive list with questions a good conversationalist might ask.
What would you do differently if you knew no one would judge you?
If you could visit anywhere where would you go?
If you could be anyone in history who would it be? Why?
If you could be any fictional character who would it be?
If the world was going to end and you knew it, what 3 things would you do?
Top 3 visited websites
Toilet paper over or under? (IMPORTANT)
best/worst gift you ever got?
What's something's the concerns you right now? Anything you are worried about?
When have you been the most proud of someone else/yourself
Something you wish you were better at
Something you learned today
Favorite thing you did today
Favorite lyric from a song
What song/cd impacted you the most or helped you thru something?
Where do you want to go on your honeymoon
Is there anyone you haven't forgiven?
What is your dream car or vehicle if price didn't matter?
Who was your favorite teacher in high school and what did they teach?
Have you met anyone famous?
What is something you can't help but spend money on?
If you could change something about the world, what would it be and why?
What is the craziest thing you've done?
If your job made you move, but you could choose which country you would be living in, which country would you choose and why?
What is your favorite TV show?
What is your worst habit?
How would you describe yourself if you could only use five words?
Do you have any phobias?
What is your favorite day of the week?
What are your pet peeves?
What website would you say you never go a single day without viewing it?
Would you rather regret doing something, or not doing it?
What do you think your best characteristic is?
If you were given the day off from all of your everyday responsibilities, how would you spend it?