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 rather spend 2 months living in a nursing home or spend a 2 weeks eating only from Taco Bell?
Would you rather give someone a gift that is a truly bad gift or give no gift at all?
Would you rather write a best-selling novel or be an expert at picking stocks?
Would you rather get married in an arranged marriage or spending the rest of your life single without dating anyone.
Would you rather lose you sense of taste and smell or lose all of your hair?
Would you rather have a photographic memory or be able to forget anything you wanted?
Would you rather have your own action figure or a wildly popular YouTube video?
Would you rather do without toilet paper or tooth paste?
Would you rather spend a night with no money on the streets of Pittsburgh or spend the same night in a house that is reported to be haunted?
Would you rather be able to travel to the 3 most amazing places on earth or have ever meal you eat for the rest of your life prepared by a gourmet chef?
Would you rather have to leave the country you now live in and be unable to return or spend the rest of your life being unable to make more than minimum wage?
Would you rather communicate only by text message for the next four days or eat nothing but Mac & Cheese for the next three weeks?
Would you rather be able to lie without being caught or always be able to tell when someone is lying?
Would you rather be able to visit 100 years in the past or 100 years in the future?
Would you rather be able to stop time at will of age at half the normal human rate?
Would you rather have an ordinary home in an extraordinary location or an extraordinary home in an ordinary location?
Would you rather have one year off at your current rate of pay or work your current job for a year at double your current rate of pay?
Would you rather be able to eat anything and any quantity of food with no negative health effects, or be refreshed and well rested after only three hours of sleep?
Would you rather have a mob boss owe you a really big favor or have a low interest credit card with a $1,000,000 limit?
Would you rather find a parking space and discover that the parking meter has plenty of time left on it or have someone genuinely laugh at one of your jokes?
Would you rather be extremely attractive or be married to some one who is extremely attractive?
Would you rather be 100 percent debt free or have good health guaranteed for the next 10 years?
Would you rather shave your eyebrows or accidently send a nasty computer virus to 1000 of your friends, classmates and colleagues?
Would you rather cook like a gourmet chef or sing like an opera virtuoso?
user favorite questions, 
