Embarrassing Questions to Ask a Guy and Make Him Feel Awkward

400+ Juicy Questions for Truth or Dare

Whether you’re going to a sleepover, a party, or just a little get-together with friends, there’s a good chance you might end up playing Truth or Dare! If it wasn’t in the original plans, then you should totally suggest it because everyone knows it’s always a good time!

How to Play

The rules are simple! One player starts off by asking another player: “Truth or dare?” If the player picks “truth,” they are asked a question that they must answer honestly. If they choose “dare,” they are given a command or some kind of action they need to perform.

Regardless of the choice, it’s a fun game for everyone, and the room is sure to be filled with roaring laughter! To keep the game fun, make sure your truth questions deal with a sore topic that could embarrass them, and make sure the dares don't send anyone to the emergency room or jail!

In this article, you'll find good Truth or Dare questions for:

  • Friends
  • Girls
  • Guys
  • Teens
  • Sleepovers
  • Parties

You'll also find:

  • Funny truth questions
  • Embarrassing questions
  • Flirty questions
  • Dirty questions

They will cover everything from crushes and dirty secrets to school and friendships. Whatever the topic may be, these questions will make even the boldest person at your next slumber party feel awkward and uncomfortable!

Are you willing to share?

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Questions Answers

Question: What questions should I use if I am eleven-years-old?

Answer: You should use the questions from this article:

Dirty Questions To Ask A Guy

This territory is not for the faint-hearted. Especially because you’re a lady. When you’re a lady, you should do everything in a ladylike manner. This includes dirty talking, too. Be colorful and imaginative, but subtle. Make him understand exactly what you mean, but don’t use literal language. Now that he trusts you, you can move a little bit faster, but still with caution.

Being too open and literal leads to him misjudging you for a girl with questionable morale. Sexual desire is something natural, but only when connected to a genuine liking of a person. Contrary to popular belief, men are not animal. They are like us, but take a little bit more time to open up.

Note that dirty questions to ask a guy are a weapon for later dates! If you’re dating for some time now or when you’re close, only then. Earlier attempts lead to miscommunication and misunderstandings. Learn to “sniff out” the situation. If it’s casual, go for it!

  • Whose place do you think has a better interior design? Wanna find out?
  • How do you feel about a nutritious breakfast after a long night?
  • This place is too public, wouldn’t you say?
  • Tell me a fantasy that makes you tremble every time you think about it…
  • Is it true that the lips of a stranger have the taste of excitement?
  • Want to go on a cocktail binge and see where we end up?
  • Let’s put those ears to work… Here’s a fantasy of mine…
  • What’s the sexiest movie you’ve ever watched? Wanna watch it yet again?
  • What’s the most sensitive place on your body?
  • What place on my body do you think is the most sensitive?
  • It’s high time you put those sexy forearms to use?
  • Do you have a map? Because I think I got lost inside of your eyes.
  • How do you feel about us ditching this dinner and heading somewhere else?
  • Sorry, I get carried away by just looking at you.
  • Is it legal to stare as much as I stare at you?
  • What section of your body do you hate the most?
  • I think you might wanna hear this fantasy…
  • I like how you make everything else feel irrelevant…isn’t it?
  • It’s never dull with you, isn’t it?
  • You’re like a walking inspiration for dirty thoughts…

The social rule that girls should be passive is an awful and conservative one. You’re both the same and that notion will bring a smile to his pretty face. With you taking initiative, he might become more liberal himself. By pacing yourself, listening to the signs and choosing the moment, you can strike gold.

Intimacy and going to each other’s places are just about physical contact. You will both become more caring and free with each other. If it doesn’t turn out to be like you’ve dreamt, you gave it your all. And that’s important!

Flirty Questions to Ask Your Boyfriend 

  1. What do my lips taste like?
  2. What is your favorite part of my body?
  3. Would you rather see me in lingerie or nothing at all?
  4. Do you get jealous when other guys check me out?
  5. Do you like it when I pull your hair?
  6. How does it feel when we make out?
  7. Are you thinking about me? Because I am thinking about you.
  8. What times of day do you think about me?
  9. Do I make you nervous?
  10. What would you do if I sent you a dirty picture of me?
  11. Have you ever wanted to tear my clothes off?
  12. Do you think of me when we are apart?
  13. Have you ever had a dream about me?
  14. Do you prefer rough or romantic? 
  15. When was the last time you have a dirty dream? 
  16. If you could choose what I was wearing, what would it be?
  17. What is a sex position you have never tried, but would love to try? 
  18. What is the dirtiest thing you ever thought about me?
  19. Do you prefer eye contact or none during sex?
  20. How high is your sex drive? 

That’s a wrap! This article was all about the best sexy & dirty questions to ask a guy you like. 

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Good Questions To Ask a Guy

Every good conversation is due for a good foundati

Every good conversation is due for a good foundation. Guys may be hesitant at first, but they too love to tell stories. It’s long been a misconception that only us gals like to tell tales. Telling something in the form of a story is a good form of self-expression. Men are no different. They just take a little bit more time, that’s all. The key to asking these “foundational” questions is just to be patient and warm towards your guy.

Like anyone, guys share their true opinions once they trust the person. Even though they might not do so right away, it can come gradually. As they tell their tale, they will free up once they see how carefully you’re listening to them. That’s the only way to reassure your date. Through patience, time and a calming atmosphere, everything is possible! These questions are specific but open-ended. You can modify them, or ask additional ones. By date two, he will be sharing his fantasies with you!

  • I would like to hear about your hometown…
  • What’s your family like?
  • Do you have a nickname? If you do, how did you get it? Do you like it?
  • How would you compare your current town and your hometown? Which one do you like? (If he still lives in his hometown) How did the town change over time?
  • Are you happy with your job? What is your dream job? If you work you dream job, what would you change?
  • Tell me about your friends? What do you value the most in a friendship?
  • What do you value in a movie?
  • What’s your favorite way of traveling a foreign country? Camping? Expensive hotels?
  • If your life was a movie, who would have the lead role and why?
  • What kind of an experience do you have with pets?
  • Do you have an older brother or sister?
  • What was your first drunken experience?
  • What was your first trip abroad? Did you like it?
  • Did you take up any sport when you were a kid?
  • What skill would you say is your best trait?
  • What thing about your childhood do you miss the most?
  • What were you afraid of as a child?
  • What’s your favorite flag and why?
  • What’s your ideal name for a child? What’s your least favorite?
  • Can you juggle?

These questions right here are excellent conversation starters. They can also be asked out of the blue, in order to break the silence. Your man will like that you’ve taken an interest in such topics. His tongue will unravel and you will get to know him a lot better.

Not only are these questions safe, but they also open the door for the next set of questions. By knowing his upbringing and other details, you will know in which way the conversation will go.

These questions are great, but

Regardless of where you are in your relationship, asking questions of one another is a great way to get to know someone and to keep tabs on where you are both at in life.

Even when you’ve been with your guy for a long time, you can continue to build a close relationship with them by staying curious about their likes and dislikes, and check in once in a while to see if things have changed for your guy.

Communication is an important part of a healthy relationship. However, I don’t think it’s always a deal breaker when it comes to the success of one.

In my experience, the missing link in a relationship is failing to understand what your guy is thinking at a deep level.

Because men see the world differently to you and we want different things from a relationship.

Not knowing what men need can make a passionate and long lasting relationship —  something that men crave just as much as women — really difficult to achieve.

While getting your guy to open up and tell you what he’s thinking can feel like an impossible task… there’s a new way to understand what’s driving him.

Embarrassing Questions to Ask a Guy

  1. Have you had a crush on someone from the same sex?
  2. Who is the sexiest girl present here?
  3. Have you masturbated in a public place?
  4. Who is your favorite porn star?
  5. Tell us about one thing that you dream about doing sexually and have not done yet.
  6. Which is the strangest place that you have peed?
  7. What is the most gross thing that has ever come out of your body?
  8. Which sexual activity do you consider to be off limits?
  9. Would you watch your partner have sex with someone else?
  10. What is that one thing that your partner does which makes you cum every time?
  11. Would you want to make a video with your partner making out?
  12. What is the size of your penis?
  13. What article of all the women’s clothing would you like to wear?
  14. Have you ever had a one night stand?
  15. How often do you think about sex?

40 Essential Questions and Follow-up Questions

Here is a list of 40 questions to ask a guy and we’ve thrown in some possible follow-up questions to help you get more out of your conversations.

What has been your proudest moment of your life?

1) What made it so special?

2) What is the funniest thing you’ve ever witnesses?

3) What made it so funny?

4) How do you like to veg out?

5) What’s your favorite Netflix binge show?

6) What is the scariest thing you’ve been through?

7) Did you change anything about your life afterwards?

8) What’s your best memory from growing up?

9) What was your favorite toy?

10) When was the last time you did something nice for someone?

11) What prompted you to do that for that person?

12) What makes life worth living for you?

13) Why is that important to you?

14) What is your favorite kind of animal?

15) What animal would you be?

16) What’s your go-to favorite movie?

17) What makes it your favorite?

18) What’s one thing you have never told anyone?

19) Why haven’t you told anyone that?

20) What are you afraid of in life?

21) Do you think that stems from a previous experience?

22) If you had to leave your house, what is the one thing you couldn’t leave without?

23) What would you definitely leave behind?

24) Who’s your favorite family member?

25) Who’s your least favorite family member?

26) What’s Thanksgiving dinner like in your family?

27) What do you eat at Thanksgiving?

28) What’s the best worst joke you’ve ever heard?

29) Who told it to you?

30) What is your favorite kind of ice cream?

31) What kind of toppings do you like?

32) What do you like about yourself?

33) Why do you like that about yourself?

34) What’s one thing you would change about your life if you could?

35) Have you ever thought about how you might go about making that change?

36) What’s one thing you wouldn’t change about your life?

37) Why is that so special to you?

38) If you had to eat the same food for a month, what would it be?

39) What would be for dessert?

40) What’s your favorite drink and why?

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TRUTH QUESTIONS FOR GUYS

1. If your parents hated your girlfriend, would yo

1. If your parents hated your girlfriend, would you dump her?

2. If your girlfriend hated your best friend, what would you do?

3. Who is your biggest celebrity crush?

4. If you could be invisible, who would you spy on?

5. Who are the top 5 hottest girls you know?

6. Who in this room would you make out with?

7. If you could date one of your bro’s girlf

7. If you could date one of your bro’s girlfriends, who would it be?

8. What’s your favorite body part?

9. When was the last time you flexed in the mirror?

10. Describe your perfect partner.

11. Have you ever been in love?

12. Blonde or brunette?

13. What turns you on the most?

13. What turns you on the most?

14. Have you ever lied about your age?

15. Have you ever fallen in love at first sight?

16. What would you do if you found out your girlfriend liked someone else?

17. If we formed a boy band, who here would make the best lead singer?

18. Would you take steroids?

19. Have you ever had a crush on a friend’s

19. Have you ever had a crush on a friend’s girlfriend?

20. Who are you jealous of?

21. Who do you think is the hottest in our group?

22. What is your biggest turn-off?

23. Have you ever been rejected by someone?

24. If you had to choose between being poor and smart or being rich and dumb, what would you choose?

25. What have you lied to your partner about?

25. What have you lied to your partner about?

26. Have you ever cheated on your partner?

27. Would you go out with an older woman?

28. Boxers or briefs?

29. When was the last time you cried?

30. Have you ever had a crush on a friend’s girlfriend?

31. If you could make out with someone else’s girl, who would it be?

32. If every time you checked out a girl’s body, you would gained 5 pounds, how often would you do it?

17 Personal Questions To Ask A Guy

The questions below are designed to let you peel off the outer layers of his personality and to truly find out who he is.

For example, question #5 will tell you how adventurous he is, and question #9 will reveal to you his inner convictions.

Pick and choose the questions that sound most interesting to you.

1. What did you want to be when you grew up?

2. If you could change anything about your life right now, what would you change?

3. What’s at the top of your bucket list?

4. What are you most afraid of?

5. What’s the most adventurous thing you ever did in your life?

6. What was the biggest mistake of your life?

7. Do you have many acquaintances or just a few close friends?

8. How would you describe your perfect home?

9. What’s something about you that you wish more people knew?

10. What are your 3 best qualities?

11. What is the most expensive thing you ever bought?

12. What is your idea of a perfect vacation?

13. What would you do if you won the lottery?

14. What are some controversial opinions you have?

15. What’s the most spontaneous thing you’ve ever done?

16. What is the biggest personal change you’ve made in your life?

17. What makes you really mad?

Funny Questions to Ask a Guy

Laughter is such a thing that almost everyone is h

Laughter is such a thing that almost everyone is hungry for that. But how difficult or easy is it to think of funny questions to ask a guy? 

It is definitely not an easy task to impress a person with humor. But we strongly believe that we can help you. Here, we have shared some funny questions to ask a guy. Be ready to gift him some hilarious memorable moments.

  1. If a movie is made on your life, then what would be the name of your character?
  2. If suddenly a pie is thrown at you, then which flavor would you love to taste?
  3. In a beautiful morning, if suddenly your crush comes at your doorstep and wants to marry you, how will you react?
  4. How many scores would you give to my humor quotient?
  5. If you ever find yourself on a lonely island on your birthday, then with whom would you celebrate?
  6. Do you remember any situation, where you laughed so hard that you almost peed in your pants?
  7. Would you kiss your bride if she breathes badly on the day of your marriage?
  8. What is the best punch-line you have ever heard of?
  9. If a beautiful lady requests a date night with you, then how would you respond?
  10. If you find a frog with a crown, then which story would come to your mind first?
  11. What is the funniest compliment you have ever received?
  12. Do you find your lady boss attractive?
  13. What is the best adult joke you have ever read?
  14. If you ever participate in a show like Big Brother, then what would be your strategy?
  15. Are you naughty?
  16. Which is the one thing that makes you crazy about a woman?
  17. If suddenly your yawn becomes viral, then what would be your reaction?
  18. Which is the funniest thing you have ever said to a lady?
  19. What is the silliest thing you have done in the hangover stage?
  20. If your wife and mom fight over a trivial issue, then whose side would you take?
  21. What do you do in a boring office meeting?
  22. What is the funniest thing you have done in front of your crush?
  23. Have you ever had a crush on your school teacher?
  24. Coffee with a celeb or coffee with your date – what would you prefer?
  25. Have you got caught while watching an adult movie?
  26. What is the one nickname you have, that everybody laughs at?
  27. A cozy evening with your lady love – what is the first thing would you do to impress her?
  28. Have you ever tried to make a girl crazy by applying sexy perfume, as the advertisements suggest?
  29. If I call you extremely handsome, then would you take that as a hint of a proposal?
  30. Which funniest movie have you watched to date?
  31. How would you introduce your girl to your mother?
  32. Do you turn on easily?
  33. Have you ever sneezed at anyone’s face?
  34. Have you ever been in an embarrassing situation?
  35. What is the silliest thing you believed as a child?
  36. Which food makes you happy, but others mostly find that boring?
  37. If you suddenly find that everyone in the office actually has heard your monologue, then how would you react?
  38. Have you ever had experienced ‘Friends with Benefits’ moments?
  39. Which is the funniest villainous character according to you?
  40. Except for ‘Stone, Paper, Scissor’ game, which is the best game to solve disagreements?
  41. Who can make you laugh really hard among your friends?
  42. Which country would you like to visit as the President of a country?
  43. Which movie scene would you like to recreate on your honeymoon?
  44. How do you enjoy the holidays?
  45. Do you get bored with preaching?
  46. If you ever get a chance, then would you go back to your previous relationship?
  47. What is the funny thing about me?
  48. Do you have any theme song in your life?
  49. What is the one thing you are best at?
  50. Who comes often in your wildest dreams?
  51. What is the funniest prank you have ever made on someone?
  52. Clean shaved or bearded look – which one is your favorite?
  53. If suddenly a bunch of girls becomes crazy for you, then how would you handle them?
  54. If your mom finds you kissing a girl, then what would be your reaction?
  55. Would you ever marry the daughter of a mafia don?
  56. If you find that your girlfriend can fly like Superman, then how surprised would you be?
  57. Have your parents ever caught you doing something really bad-ass?
  58. What is the one food you ask everyone to taste, but they never do?
  59. If the ugliest girl in your office who actually has a golden heart, ever proposes you, then would you accept that?
  60. How long did it take you to understand that Santa never gave you any gifts?
  61. If given a chance, then how differently would you like to live your life?
  62. What was the first slang you learned?
  63. Do you still blush when you see your favorite actress on TV?
  64. Which movie that you went to watch in a theatre with family, turned out to be the worst movie of all-time?
  65. Have you ever met anyone who looks exactly like a Barbie Doll?
  66. In which standard, you finally understood the real meaning of love?
  67. What is your favorite accessory?
  68. One thing that you never leave your house without?
  69. Have you ever fought with a real bad guy?
  70. What is the one thing you dislike about ‘Cinderella’?
  71. Which animation movie did motivate you?
  72. Do you believe in casual dating?
  73. If you suddenly find your office boss in the same restaurant where you are currently dating someone, then would you hide or would you just walk in front of him hand-in-hand with her?
  74. What is the craziest thing you have done on a date night?
  75. Has anyone proposed to you in recent times?
  76. Has anyone ever called you a party pooper?
  77. If in a game, you are asked to kiss a random girl in a shopping mall, then how would you tackle that?
  78. Is there any video that always makes you go ‘rofl’?
  79. What is the silliest thing you have ever been gifted?
  80. If you find two of your best buddies dating each other, then what would be your reaction?

20 weird questions to ask a guy

(Sam Bloomberg-Rissman/Getty)
(Sam Bloomberg-Rissman/Getty)

Unexpected conversations can be so much fun, and sometimes the unexpected can arise out of some super weird prompts. 

These questions to ask a guy might be a little weird at first, but what you find might be an amazing start to a conversation that goes in all directions. You should ask a guy something that taps into humor, his imagination, his nerdy side – whatever you want. There are no rules for this section! 

  1. What do you think another version of you is doing in a parallel universe?
  2. If you could only eat one food for the rest of your life, what would it be?
  3. If all planets in the solar system were inhabitable, which one would you live on?
  4. If you had to play one video game with an historical figure, what game would it be, and who would you play with?
  5. If you could raise any dead celebrity back from the afterlife, who would it be and why?
  6. Which forbidden place on earth would you visit just for fun?
  7. If you were to lose all of your body parts except for one, which one would you want to keep and why?
  8. Have you ever been traveling and gotten completely lost?
  9. Has any horror movie made you paranoid of everyday things in your life?
  10. If future advanced technology could make people immortal, would you volunteer as a test subject?
  11. If you had to plan the most extravagant funeral for yourself, what would it look like and what would be included?
  12. If you had a billion dollars but couldn’t buy things for yourself,  what would be the best way to spend money?
  13. How much money is too much – should there be a legal maximum wealth?
  14. What is the worst superpower to have?
  15. If it were up to you to design heaven, what would it look like?
  16. If you could control people’s minds, how would you change the world?
  17. What is something you wish was real but isn’t?
  18. What is the most unusual thought you’ve had?
  19. If you could make yourself a morning person, would you?
  20. If you were one of the Seven Wonders of the world, which one would you be and why?

EMBARRASSING QUESTIONS THAT WILL TEST YOUR FRIENDSHIP

1. What was your first impression of your best fri

1. What was your first impression of your best friend’s boyfriend?

2. What do you think about him now?

3. Have you ever thought about ditching your friend for a boy?

4. If someone asked you what your best friend is like, how would you describe her?

5. What if your best friend told you that she liked your crush?

6. If you knew your friend’s boyfriend was cheating on her, what would you do?

7. Have you ever told a lie about your best friend

7. Have you ever told a lie about your best friend to make yourself look better?

8. What was your first impression of [fill in the name of a person in the room]?

9. If you had to date someone else’s boyfriend, who would it be?

10. Who’s hotter? You or your friend?

11. Have you ever shared your friend’s secret with someone else?

12. Rate everyone in the room from 1 to 10, with 10 being the hottest.

13. If your crush told you he liked your best frie

13. If your crush told you he liked your best friend, what would you do?

14. Rate everyone in the room from 1 to 10, with 10 being the best personality.

15. Have you ever ignored a friend’s text? Why did you do it?

16. Have you ever lied to your best friend?

17. Would you let a friend cheat on a test?

18. Name one thing you would change about each person in this room.

19. If you had to trade a friend in for the celebr

19. If you had to trade a friend in for the celebrity crush of your dreams, which friend would you choose?

20. You win a trip and are allowed to bring two people. Who do you pick?

21. On an overnight trip, would you rather share a bed with your best friend or her boyfriend?

22. If you could swap one physical feature with your best friend, what would that be?

23. Have you ever told a secret you were told to keep?

24. If your best friend smelled bad, would you tell her/him?

25. What is the most annoying thing about your bes

25. What is the most annoying thing about your best friend?

26. Who do you think your friend should date instead of her current boyfriend?

27. If she doesn’t have a boyfriend, who do you think she should date?

28. Would you share a toothbrush with your best friend?

29. Do you think your friend’s boyfriend is hot?

30. If your friend and your boyfriend were both dying in front of you, who would try to save first?

15 Random Questions To Ask A Guy

Lastly, here are some fun questions that are just kind of…random.

If you hit an awkward pause in a conversation and can’t think of anything else to say, just throw one of these questions at him.

1. What’s your favorite book? Why?

2. Where is the most interesting place you’ve been?

3. What do you hope never changes?

4. What’s your favorite movie? Why?

5. Which of your scars has the best story behind it?

6. If you could have one superpower, which one would it be?

7. What do you think should be taught in school that isn’t already?

8. What is your signature dish?

9. What makes you feel alive?

10. What song defines your life?

11. Pets: yes or no? Why?

12. If you could be one of the first settlers on Mars, would you? Why?

13. Are you the only child in the family?

14. Do you like winter or summer better? Why?

15. What is your zodiac sign?

So there you have it – over 200 questions you can ask a guy to find out more about him and keep the conversation going.

Whew, that was a lot, wasn’t it?

Now what?

I suggest you bookmark this page and write down a couple of questions you can ask your guy the next time you see him.

Then come back and get a few more.

Oh yeah, be prepared to be asked the same question you asked him. So you probably don’t want to ask a guy anything you’re not comfortable answering.

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