Here are 50 questions that are designed to be awkward and embarrassing. All though not everyone will be embarrassed by every questions it is guaranteed that every one will find some of the questions embarrassing. Remember as you make your friends uncomfortable they will see to return the favor.
Truth or Dare Questions: 50 questions guaranteed to embarrass any adult.
What was the last lie you told?
When was the last time you where caught in a lie?
Have you ever been unfaithful to a boyfriend/girl friend?
When you lie about your income do you lie round up or down? By how much?
What was the most painful break up you ever had?
When have you been fired from a job?
When have you had to walk away in shame?
If you could go out on a date with anyone in this room who would it be?
If you could kiss anyone one in this room who would it be?
What celebrity do you have a crush on?
Who was your first crush with?
When have you loved some one who has not loved you back?
When have you broken your mothers heart?
What feature of yours are you self-conscious about?
What is the first physical feature you look for in someone you are attracted to?
When you are trying to impress people what personality trait do you hide?
Would you sill love your significant other if he or she gained 100 pounds?
What things are you shallow about?
How much money did you make last year?
What makes you feel insecure?
What is the worst sin you ever committed?
What action from you past would put you in jail if law enforcement ever found out?
If you were the opposite sex for one day, what would you look like and what would you do?
Why did you break up with your first girlfriend/boyfriend?
What music are you embarrassed about listing too?
What is your guilty pleasure?
What TV show are you embarrassed about watching?
What is the worst thing about being a grown-up?
What is the longest you have gone without taking a bath?
If you and someone else were the only people alive on earth, who would you pick the other person to be?
Who in this room would be the worst to be trapped in an elevator with?
What are you afraid of?
What fear keeps you up at night?
In what way are you inadequate?
When have you lost you dignity?
Assuming every man/woman has their price, what is yours?
What talent do you have that is embarrassing to share?
Who in the room do you think would be a bad date?
What is your best physical attribute?
What do you do to let someone that you are interested in know that you like him/her?
For men: What article of women’s clothing would you like to ware?
What is something you stole?
When where you embarrassed getting caught in the middle of something?
How do you think you are most likely to die?
Who in this room do you most trust?
What prejudice do you harbor?
If you had only 24 hours left to live, what would you do?
If you significant other said it was ok would you cheat on them?
If you will be given a chance to become invisible for one day, what would do with this ability?
If you had another player to be your slave for the next fifteen minutes what would you have them do? (The other player must then accept or reject the offer to become your slave.)
What to talk about on a first date, 
