(would you rather) 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 have your left arm amputated at the elbow or your right leg amputated above the knee?
Would you rather be able to play the guitar like a rock star or Dance like Mikhail Baryshnikov?
Would you rather do without toilet paper or tooth paste?
Would you rather have $50,000 free and clear or $150,000 that is illegal?
Would you accept a life as a successful artist making 4 times your current annual pay if it meant that your art was considered offensive by one of the worlds major religions making you unwelcome in many countries and attracting unwelcome, often hostile, attention from people in your own county?
Would you rather be unable to see for one day or unable to use your phone for one month?
Would you rather have the respect of your child or your boss?
Would you rather publicly embarrass your mother or be the reason why your best friend breaks up with their girlfriend/boyfriend?
Would you rather lose your sense of taste and smell or lose your ability to distinguish colors?
Would you rather spend 48 straight in a public restroom or spend the next two month taking only public transportation.
Would you rather be ''just friends'' with someone you love or marry an attractive person who does not love you?
Would you rather shave your eyebrows or accidently send a nasty computer virus to 1000 of your friends, classmates and colleagues?
Would you rather have every detail of your love life made public or have the details of you finances made public?
Would you rather have a boring repetitive job that paid $90,000/year or an engaging job that you really enjoy but it pays $45,000/year?
Would you rather live the freegan lifestyle for a month or give money to anyone who ask for the 3 months?
Would you rather be able to paint like an renaissance master or be able to put anyone at ease in a conversation?
Would you rather have many causal friends or one close one?
Would you rather spend 2 months living in a nursing home or spend a 2 weeks eating only from Taco Bell?
Would you rather receive a life time supply of meals from your favorite restaurant or a life time supply of gasoline?
Would you rather cook like a gourmet chef or sing like an opera virtuoso?
Would you rather be rich of famous?
Would you rather marry someone who is attractive or rich?
Would you rather have an extra finger or lose a finger?
Would you rather go 30 days without refined sugar or 90 days without caffeine?
The best humorous and funny questions, 
