There have been a number of times, most often on AIM but occasionally on the phone or in person, when somebody, be it a new romance interest or an old friend (and once even a co-worker!), in the course of flirting or just trying to keep the conversation interesting, has challenged me to “ask her anything, no matter how private or personal” … usually either one of two things happens - I ask something, and then she asks me something and then it leads to a “lets see who can top each other” contest, or I find out that she actually does have a limit to how personal a question can be and quickly changes the subject. Based on the multiple occurance of this with multiple people, I doubt I’m the only one lucky enough to land in this position from time to time.
What are some good questions to keep on the tip of your tongue?
a couple that I’ve used that have been noted as getting what they asked for, but have still been answered at least once:
Who was the WORST person you’ve slept with?
How, how often and for how long do you masturbate?
What is your weight? What is your bra size? What do you wish your bra size was?
Do you shave down there? Or if it’s a blonde or redhead - Are you blonde all over?
What is your salary?
What is your email password? (yes, somebody actually answered this once)
and no matter what, the questions I always eventually get asked are:
are you circumcised?..followed by Would you circumcise your children?
what MALE celebrities would you most like to sleep with?
does being tied up turn you on? (strangely, nobody has ever actually offered to do it for real, even if I say yes)
If I’m hittin’ you from the back with my strap-on, do you expect a reach-around? I need to know these things because my arms are short and it can be a little uncomfortable with taller guys.
This seems tame by comparison. Dick Cavett, when he was having trouble prying answers out of a guest on his show, asked, “What kind of toothpaste do you use?” It was just absurd enough to loosen up the flow.
Some people are unpreturable. Like the guy who offered to sent me naked pictures of himself and merely answered “no” to the question “Are you doing anything to farm animals in them?” I don’t know if anything would have shaken him. Maybe “Do you eat babies?[pause for “no”] No, I mean live ones.” but I didn’t think of that.
What do you really look like naked?
Are you into fisting? Can you fit two fists into any orifice?
What kind of pancakes do you like - strawberry or blueberry?
