Sometimes, I am talking to someone new on im, and I don't know what to talk about. I think lists of questions are always really contrived, but I think if approached correctly, a list of questions can be helpful. I might say to someone; "Hey, because I am really bad at thinking of interesting things to talk about, I created a list of questions for situations just like this; let's have an interrogation session! Only if you want, I mean. I guess it's kind of awkward if I don't really know you. But hey, do you have anything else to talk about?"
Also, a list like this might be more helpful if you admit how ridiculous it is; "So this is really dumb but I made a list of questions for something like this. LET'S ASK EACH OTHER RANDOM QUESTIONS"
Or maybe it would start a conversation about how all these questions suck and you can think of new ones. Then you can tell me what they are and I might add them to the list if I feel like it. But maybe not. At any rate, this is mainly for my benefit:
One disclaimer: many of these came from random websites and thus sound dumb. Some I wrote myself and also sound dumb.
If you knew today was your last day on Earth, how would you spend it and why?
What is the most rewarding experience you have had and what made it so?
Who or what inspires you and why?
Do you have any relatives in jail?
Have you ever gone cow-tipping?
What's your worst pet peeve?
Do you enjoy horror movies? Why?
Do you do dance crazy when no one is looking?
Do you like to sing in the shower?
What is your favorite color? Do you have a reason for it?
At the beach would you rather play in the sand, or play in the water?
Would you rather have your hair be curly or straight? Which do you think is more attractive on someone else?
What's your favorite kind of drink?
What types of things do you enjoy reading?
What is your favorite subject? Why?
What makes you feel really alive, or happy?
Where do you stand on Cake Rights?
Do you have any hobbies? What are they/why do you enjoy them?
How do you think one would know when one is "grown up"?
What age would you like to be and why?
If you could go back in time and talk to yourself at the age of ten, what advice would you give yourself?
How do you feel about infidelity? is it forgivable?
(End. This list is devoid of interesting questions, but I am a little too lazy right now to think of some on my own.)