The Top Ten Most Difficult Truth or Dare Questions

Truth or Dare

One of the most common party games is “Truth or Dare.” The player has to choose between telling the truth, or completing a dare, and they receive points for one or the other. While there are thousands of truth or dare questions that you can ask players, in this article I will outline the top ten most difficult truth or dare questions, and what they can potentially reveal about the person.

Proceed With Caution

The following truth or dare questions can reveal more about your friends or colleagues than you ever wanted to know. Also, try to be cautious about who is present at the party. If a friend of someone’s current boyfriend is at a party, keep this in mind when you are asking the girlfriend particular “truth” questions. Inevitably, her answers will get back to her boyfriend, and if it’s something that she didn’t want him knowing, it could have a disastrous affect on the relationship.

Question 1: Describe your First Intimate Experience

While this may often result in a fairly tame response, such as the typical intimate experimentation of school kids or younger kids, some people have somewhat traumatic experiences from their childhood. So exercise caution when asking this truth or dare question, because you may get far more than you bargained for.

Question 2: What is the most annoying habit that your girlfriend/boyfriend has?

This question is great to ask the person who is constantly bragging about their boyfriend or girlfriend. It will force them to admit something about them that isn’t “perfect.” Be careful though, the answer to this question can sometimes be fairly disgusting!

Question 3: How well “endowed” is your boyfriend or girlfriend?

This question is much more fun for a party of girlfriends, because with guys it is not quite as obvious which boyfriend is “well-endowed,” and which isn’t. On the other hand, guys will always know which girlfriend is better endowed than others. When girls get together and one of them is asked this very sensitive question, the answer you receive can sometimes be quite surprising!

Question 4: Have you ever not made it to the bathroom in time and had an “accident?”

This question will be very hard for someone to admit if they are a “prude” or very self-conscious. However other people have absolutely no problem answering this question, and will sometimes give you far more information than you bargained for.

Question 5: Have you ever been extremely “intimate” with someone in a public place?

The most common answers to this question, if the person is truthful, can range from in an airplane, an elevator, in a crowded theater, or in the same house (or sometimes the same room!) where parents or siblings are unaware.

Question 6: What is the most embarrassing thing you’ve ever done?

While this is often a fairly tame answer, sometimes people can really get themselves into trouble. If the answer is embarrassing enough, and someone in the room is unscrupulous enough, the answer can be potential ammunition for blackmail. Use this question with caution, and answer it with even greater caution!

Question 7: Have you ever cheated on your boyfriend/girlfriend?

This is a very common truth or dare question, with very common consequences. If the boyfriend or girlfriend is a current one, they **inevitably** discover how this question was answered, and the relationship is destroyed. Avoid this question at all costs, and if you are asked it, and can’t answer with a “no” – chose a dare instead. The embarrassment of the dare will be far less than the damage from sharing such information with friends.

Question 8: If you had only 24 hours to live, what would you do?

While this question isn’t dangerous at all, the answers to it can sometimes be very entertaining and unexpected.

[sociallocker id=”295″]

Question 9: What is the strangest dream you’ve ever had?

Almost everyone has a strange dream, and often it’s a recurring one. Hearing someone else’s dream is sometimes very surreal, and often it can tell a great deal about the person’s deepest fears.

Question 10: If you could make anyone in the room your servant for the day, who would it be and what would you make them do?

The answer to this question runs the gamut from lame, to extremely provocative and sometimes very disturbing! If you are brave enough to ask this question, be prepared for anything.


Ryan Dube


To Top