Perplex and confound your friends with random would you rahter questions. Classic dilemmas where you have to chose between two alternatives. All thought there is value in the answer to each of the questions the greater value is in why a given option was chosen. This format tends to appeal to guys.
Random Would You Rather Questions
Would you accept $1,000,000 if it meant that a every computer you touched for the rest of your life would crash?
Would you rather receive a sincere complement from a stranger or from your sibling?
Would you rather get a speeding ticket or two flat tires?
Would you rather go on vacation any where in the world for on week or spend 24 hours with anyone in the world but be unable to leave your house during that time?
Would you rather have your left arm amputated at the elbow or your right leg amputated above the knee?
Would you rather spend one month living without using any money or spend 3 months in a wheelchair?
Would you rather spend a year teaching at an inner-city school or spend one month as a beat cop in the same neighborhood?
Would you rather, Work your current job for the next year at double your current rate of pay, or have the next year off at full pay?
Would you rather spend the next week sleeping more than 12 hours per night or less than 4 hours per night?
Would you rather have to wear adult diapers for one year or have any computer you touch over the next two months crash?
Would you want to be forever 21 years old physically if it meant that you were also forever 21 financially?
Would you rather be the star player on a losing basketball team or ride the bench on a winning one?
Would you rather have an ugly scare across your face or lose 15 points of intelligence?
Would you rather be extremely attractive or be married to some one who is extremely attractive?
Would you rather eat one and a half pounds of icecream in under 60 seconds or run 5 miles?
Would you rather survive the apocalypse or be instantly and painlessly killed by it?
Would you rather have an ordinary home in an extraordinary location or an extraordinary home in an ordinary location?
Would you rather never be able to travel more than 50 miles from where you now live or live in hotels never staying in the same city for more than 3 nights?
Would you rather have all of your emails, for the next two months, be sent out "reply all" or have your jaw wired shut for a week?
Would you rather have nine children or never be able to have any children of your own?
Would you rather spend a week adrift at sea in a life raft or spend on month in Milwaukee County Jail?
Would you rather win the Nobel Peace Prize or have the $1.2 Million that comes with the prize?
Would you rather have two tickets to this year's super bowl or two seasons tickets to the NFL team of your choice?
Would you rather have a vending machine eat your money and give you nothing in return or get stopped at every red light on your way into work?
When was your first time, 
