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50 Embarrassing Truth Or Dare Questions To Ask Your Friends

Discover a fun list of 50 embarrassing questions to ask your friends, your significant other, or even your ex

Embarrassing questions are usually a bad idea as we are taught not to make anyone feel ashamed  or put on the spot. There are, however, situations when awkward questions can offer valuable information about your friends and significant other (and even your ex).


Feel free to use these questions in a game of "Would you rather" and " Never have I ever" as they fit these categories perfectly. We have compiled  a list of the 50 most embarrassing questions to ask your friends, family, and even people you don't know that well but you want to make uncomfortable.


50 embarrassing truth or dare questions

This list of awkward questions is ideal if you want to spend some quality time with your friends, have fun, and learn some controversial things about one another.  Just for fun, these are without a doubt the 50 of the most embarrassing questions EVER.



1. How many sexual partners have you had?

What better question to ask when you want to uncover someone's sexual past.


2. Have you ever been attracted to the opposite sex?

This can be a very embarrassing question if the person we're asking is straight, but it could also offer valuable information about them. 


3. Are you happy?

This may not seem like such a difficult question but it can lead to some sticky situation, and it might not be so easy to say a simple "yes" or "no." 


4. What is your least favorite thing about me?

One tricky question for the most direct ones. Which d they think is our biggest flaw? Will they answer?


5. Have you ever cheated on your partner?

This one goes out to all the couples; we can gather some spicy information about them and put them on the spot. 


6. What turns you on the most in bed?

A dirty question, perfect for revealing what we're interested in, and offer some insight into the other person's sexual preferences. 


Some friends laughing after a nice or embarrassing joke
Asking embarrassing questions can make any party much more fun and exciting | PixaBay


7. Have you ever been attracted to one of your partner's friends?

Answering this embarrassing question could be even more difficult if your partner or ex-partner is present. 



8. What was the most embarrassing situation of your life?

This problematic question will provide entertainment for a while as you're bound to get some funny answers. 


9. Have you ever peed in the pool?

Let's see who is up to answer this doozy! Ask all your friends and find out who you should never go to the pool with. 


10. What do you think of me?

Honesty is required in high doses for this one, will the other person dare tell you the truth?


11. Would you have sex with me?

This is the ideal sexy question to ask if you want to put the other person on the spot. Who knows, maybe you'll be the one blushing. 


12. Would you be in a relationship with me?

This is the next level of the previous question, depending on what they say we can ask for more explanations as to why. 


13. Why are you still single?

Definitely, an embarrassing question that might spark some controversy. 



14. How would you define our relationship?

The million dollar question for most couples -  What are we? Depending on where you are in the relationship this problematic question could be more or less embarrassing. 


15. Who of the people present interest you more than just platonically?

An ideal naughty question that you can ask your friends. We suggest introducing a new challenge by taking this to the next level and kissing the person they're interested in. 


16. Have you ever sent someone a sexy picture of yourself?

Although there are some exceptions, this is one of the most embarrassing questions we can receive. 


18. Who is your least favorite person in the room and why?

This is indeed a difficult question that not many will want to answer. Ask this in a group of friends or colleagues and watch all hell break loose. 


19. Have you ever been/are you addicted to anything?

This is a tricky one to answer as the person might not want to admit it publicly or perhaps they're not even aware of it. Even so, this is one of the most embarrassing questions that you can make. 


20. What grade would you give yourself in bed?

Will they tell the truth? You can double down and ask them what criteria have they used when deciding on the grade.


21. How well endowed are you?

The most embarrassing sexy question there is. Remember, however, that size is not just about the length but also girth. 



22. Have you ever fantasized about anyone in this room?

Discover if someone in your group has had wet dreams about you. Follow it up with a question about the details of the fantasy. 


23. Did you ever regret hooking up with someone?

We've all, at some point in our lives, hooked up with someone we didn't really like that much. What will their answer be? 


24. How often do you masturbate a week?

Although it is something completely natural, admitting how many times a week one masturbates could pose somewhat of an embarrassment. Let us say this loud and clear:  masturbating is healthy, and we shouldn't be ashamed to talk about it. 


25. What's the strangest place you've had sex in?

One more sexy question to test your friend's honesty with. Discover funny stories and perhaps get some ideas for your sexual escapades. 


26. Have you ever had/do you have an STD?

This is a very uncomfortable question, seeing how diseases are a complicated topic and often it carries a stigma attached to it. Tread carefully with this one, and only ask it if you are close to the person you're asking this. 


27. Which three animals would you choose to describe your sexual style?

People sometimes associate sexual behavior with that of animals. Discover if your friend or significant other considers themselves a lion or a sloth in bed. Some may prefer to choose cartoon characters or game characters such as the ones from Pokemon. 


28. What is your deepest secret?

We all have secrets we want to hide. What dark secrets is this person hiding  and will they divulge it to us?


29. What's the last thing you searched for on Google?

It seems like an innocuous question, but depending on the moment and the person, it could give some hilarious answers. An interesting variation would be to go around the group and  see what everyone's last search was. 


30. Have you ever done dirty things in bed? 

A truly embarrassing question especially if the person in question has already started their sex life. If that is the case, we will notice a smile on their face as soon as they hear this. 



31. Who is your secret crush?

Lying is quite uncomfortable to admit to but confessing that you like someone can be even more embarrassing. 


People celebrating with wine during a party
Embarrasing questions for every moment | Healthy Way Mag

32. Have you ever lied to me?

An uncomfortable question for friends as well as romantic partners. Learning that you were lied to is never a pleasant thing. 


33. What would be in your web history that you’d be embarrassed if someone saw?

Unrequited love interests, fantasies, dark curiosities - the list could go on and on and so can the level of embarrassment of the person answering. 


34. What's the worst thing you've ever done to someone?

Ask this difficult question and discover what's the worst a person can do. 


35. Who would you kill if you knew there were no consequences?

Admitting that you would be capable of murder is not an easy task. Discover if you have a potential assassin sitting next to you. 


36. Who in this room would you save from a burning building?

A perfect question for a large group of friends, see who would be willing to risk their own lives to save yours. 


37. Have you ever fantasized about a teacher?

This is always an embarrassing question, and not many dare own up to it. It's entertaining to ask this if your former classmates are in the room - lots of giggles guaranteed. 


38. Who's the last person you looked up on Facebook or Instagram?

It could be particularly uncomfortable if you ask this question to your significant partner: it could be a good way of finding out what they're up to online. 



39. How old were you when you started masturbating?

This tends to be a very embarrassing question for many, so expect some blushing from the people in the room. 


40. Who do you hate?

Many people have a hard time admitting that they have negative feelings towards others. Imagine if, on top of that, the person they detest is in the room! Awkwardness ensues.  


41. Who is the sexiest person in this room?

This could spark some controversy as the "sexiest" person could already have a significant other. Beware of jealousy!



42. Have you ever stolen anything?

Maybe a piece of candy or some face creams, stealing is frowned upon although many of us have gone through a rebellious stage in our formative years. Will the person come clean?


43. Have you ever ran away without paying for something?

Although fleeing a restaurant without paying is not such a capital crime, many would be ashamed to admit it. 


44. What is your most extraordinary sexual episode?

This steamy question could pull out the juiciest stories about someone's sexual adventures; you may be in for a treat!


45. What is the most illegal thing you have ever done?

This is one of the most private questions one can ask, and not many will be willing to answer truthfully. 


46. For how long have you worn the same pair of underwear?

Hygiene is a basic human requirement which is why some may find this question very embarrassing, especially if they're guilty of spending a few days in the same frock. 


47. Who in the room has fewer chances of succeeding professionally?

This question will bring out the pettiness in your friends, or their brutally honest side. Expect killing looks and sharp comments. 


48. Have you ever been caught having sex?

Although it may have been unpleasant when it happened, talking about it should be less stressful and why not, perhaps even amusing. 


49. What's your favorite type of porn?

"Tell me what porn you like to watch, and I'll tell you who you are," goes the saying. Porn has always been a tabu subject which is why this particular question will be even more embarrassing. 


50. Would you leave your significant other/friend for 10 million euros?

Imagine if the person in question is sitting right there when you ask the question. Sparks might fly, and not the good ones either!



Check out the original article: 50 preguntas incómodas (para jugar con amigos o parejas) at viviendolasalud.com