The Most Difficult Truth or Dare Questions

Truth or dare is one of those fun games that everyone nevertheless dreads. While it’s great fun to have things coming out about other people, and to see them have to take on all kinds of embarrassing or scary challenges, it is a lot more worrying having to answer the questions and perform the tasks yourself.

Nevertheless it’s the truly cruel and difficult truth or dare questions that really make a great game and that get everyone talking (and talking more about it the next day). Here then, for the sadists and masochists out there, are some of the most difficult truth or dare questions and challenges (designed for groups of friends).

The Most Difficult Truth Questions

What is your most embarrassing memory?

What was your most perverted dream?

Describe your first sexual experience

Describe your worst sexual encounter

What’s your bra size?

How long is your penis?

Who’s your strangest crush?

Do you have any crushes now?

If you had to snog one person in the room, who would it be?

Do you have any fetishes?

Do you have any irrational fears?

What’s the worst thing you’ve ever stolen?

Where was the strangest place you’ve had sex?

Have you ever masturbated anywhere inappropriate? Elaborate…

What’s the strangest porn you’ve ever got off on?

Have you ever had a crush on anyone in the room?

When was the last time you had sex?

Who was your first crush?

Describe your guilty pleasure

What’s the best sex you ever had?

Describe your favourite features

Describe your least favourite features

Have you ever had sex/a crush on someone you shouldn’t have? Who?

The Most Difficult Dare Questions

Remove (any) item of clothing

Prank call a random number

Snog the person to your left

Down a glass of your drink

Down a finger

Let the person next to you text anyone from your phone

Wear an item of women’s clothing (for men)

Wear an item of sexy clothing (for women)

Streak (somewhere safe and not illegal)

Tell the person opposite you you love them

Give a foot massage to the person on your right

Don’t speak until your next go

Spank the person on your left

Text your Mum and tell her you miss her

Take a photo of your ass and e-mail it to someone in the room

Knock on the door next door and run

Play a prank on someone you live with

Put on a strange accent and order a pizza

Buy everyone a round


  1. That was awesome:)

  2. sexyyyyyyyy(;

  3. Kool except the sex's ones.

  4. These make me horny.

  5. They r so good!!! Thanx that will make my life easier and other peoples harder:)

  6. That is super inappropriate I hated it.

  7. Looking at kids view, this doesn't seem right. May need to change some of the questions or add new ones.

  8. Ehh it was alright, some sucked but others were good…

  9. Worst dares ever. Snog like no thanks.

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Adam Sinicki

Adam Sinicki is a full time writer who spends most of his time in the coffee shops of London. Adam has a BSc in psychology and is an amateur bodybuilder with a couple of competition wins to his name. His other interests are self improvement, general health, transhumanism and brain training. As well as writing for websites and magazines, he also runs his own sites and has published several books and apps on these topics.

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