Comfort Building Questions

A long list of comfort building questions for great conversation

  • What’s your favorite Dr. Seuss book?
  • If you could live in any home on a television series, what would it be?
  • What’s the longest you’ve gone without sleep?
  • What’s your favorite Barry Manilow song?
  • Who’s your favorite Muppet?
  • What’s the habit you’re proudest of breaking?
  • What’s your favorite Web site?
  • What’s your favorite school supply?
  • Who’s your favorite TV attorney?
  • What was your most recent trip of more than 50 miles?
  • What’s the best bargain you’ve ever found at a garage sale or thrift store?
  • Where were you on September 11, 2001?
  • What’s your favorite tree?
  • What’s the most interesting biography you’ve read?
  • What do you order when you eat Chinese food?
  • What’s the best costume you’ve ever worn
  • What’s your least favorite word?
  • If you had to be named after one of the 50 states, which would it be?
  • Who’s your favorite Care Bear?
  • Would you state you were guilty of a crime you didn’t commit to free a loved one?
  • Where is your favorite place to sleep?  Where is the strangest place you’ve ever slept?
  • At the beginning of a relationship, do you trust your new partner unless there is something specific to make you do otherwise, or do you withhold your trust until he or she has earned it?
  • If you ran a hospital, what policy would you set for dealing with emergency patients who arrive without health insurance or money?
  • Who do you think is the most beautiful person alive today?
  • If you could change one day in your life, not a single decision, but one pivotal day, which would it be?
  • Which month of the year do you think would best describe your personality?
  • In selecting a candidate to vote for in an election, would any of these variables influence your decision: the candidate is an alcoholic, the candidate is sexually promiscuous, the candidate has an arrest record.
  • If you could ask God any single question, what would it be?
  • If you could be invisible for one hour, where would you go and what would you do?
  • Your partner, a roommate, or a good friend keeps a private journal that is easily accessible.  Under what circumstances might you read it without permission?
  • If you smoked marijuana as a teenager and were filling out an employment questionnaire asking whether you had ever used drugs, how would you respond? Assume you must sign an affadavit swearing to the truth of your statements.
  • If you could be married anywhere in the world, where would the wedding take place?
  • How many more years do you think you will live?
  • What would you never willingly sacrifice to save a great many people?
  • If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone?  Why haven’t you told them yet?
  • What was your most enjoyable dream? Your worst nightmare?
  • What do you remember about your first day of school?
  • If you could be the house cat or lap dog of any person on earth, whose would you choose to be?
  • What’s the absolute all-time worst movie you’ve ever seen?
  • Would you be able to serve on a jury and sentence the defendant to the death penalty?
  • If you had to name the one thing that most frightens you about growing old, what would it be?
  • If you could have a grand, beautiful front porch with a relaxing porch swing overlooking any place or thing in the world, what would it overlook?
  • What would you like to be famous for?
  • Would you ever consider getting plastic surgery to keep yourself looking young?
  • What was your favorite TV show as a child?  Which TV show is the first you remember watching?
  • If you could suddenly find out that one work of fiction was actually true, what book would you select?
  • Have you given any gifts with messages engraved upon them? What did the inscription say?
  • If you could travel into the future, how far would you want to go?
  • Your child is brain dead and has no chance of recovery. Would you keep that child alive through artificial means? Would your age or the age of the child have a bearing on your decision?
  • A co-worker needs to leave early and asks you to punch her time card when you leave. Do you do it?
  • Do you think that the world will be a better or a worse place 100 years from now?
  • If you could use a voodoo doll to hurt anyone you chose, would you?
  • Who is the most important person in your life? 
  • If you could have had the starring role in one movie already made, which movie would you pick?
  • If you could change anything about the way you were raised, what would it be?
  • Do you feel you have an obligation to spread your religious belief system to others, or do you think religion is a private matter that everyone needs to decide for themselves?
  • What thought or sentiment would you like to put into one million fortune cookies?
  • If, like milk or the newspaper, you could have anything of your choice delivered to your doorstep every morning, what particular item would you want it to be?
  • Would you enjoy an enormous fortune differently if you had inherited it rather than if you had earned it yourself?
  • Describe yourself in one word.
  • If you could have a romance with any fictional character, who would it be?
  • If you discovered that your closest friend at work had for years forged records and stolen from the company, what would you do?  What if you hardly knew the thief?
  • What is the meaning of marriage? 
  • Are you attracted to people whose personalities are similar to yours or very different?
  • If you could undo one thing your parents did, what would it be?
  • Have you ever faked an illness to avoid doing something you didn’t want to do?
  • If you were to name the absolute best gift you ever received as a child, what would it be?
  • What’s your favorite kitchen utensil? Why?
  • If because of intolerance you were going to miss a wonderful chance at a promotion, might you lie to hide your religious beliefs?