282 awkward questions (love, friends, women, men)

1344
Charles McCarthy

I leave you the best uncomfortable questions to ask your friends, your partner or your crush. These questions are ideal to get people out of their comfort zone and into difficult situations and those that do not feel completely comfortable..

If they dare to play they will have to deal with issues such as love, intimacy, oddities, politically incorrect, betrayals, infidelities, self-esteem and social pressure.

Uncomfortable question that makes the girl sweat. Source: pixabay.com

Article index

  • 1 Awkward Questions for Friends
  • 2 Uncomfortable Questions for Boyfriends 
  • 3 Uncomfortable Questions for Women
  • 4 Uncomfortable Questions for Men
  • 5 awkward love questions
  • 6 awkward questions for my crush 
  • 7 Topics of interest

Awkward questions for friends

-Have you ever betrayed a friend? As was?

-Do you have any prejudice or are not very adept at a certain cultural group or region of the world?

-What is the strongest thing you have done in a challenge?

-Mention a rumor you started about someone.

-What do you do when you are alone and nobody is watching you?

-Have you ever shared the secret of a friend of yours with someone else?

-What's the biggest lie you've ever told that they haven't caught telling it?

-Who in this room would be the worst person as a couple and why?

-If you could erase some negative experience from your life, what would it be??

-If you were stranded on a desert island, who would you like to be there with from your companions?

-Tell one time that you pretended to be sick to get rid of something.

-Tell your most unpleasant anecdote.

-Would you have sex with a relative of yours?

-What is the cruelest thing you have done to a friend?

-Name three adjectives that describe how you are in bed.

-Tell me about your biggest failure in life.

-In what way do you think you are better than others?

-What animal do you consider is similar to you in the style in which you eat?

-If you had to kill someone, marry someone, or have sex with people in this room, who would they be??

-Describe the strangest dream you've ever had.

-What is the worst crime you have ever committed?

-Why would you be more likely to be expelled from your school or fired from your job??

-If someone in this room had to see you naked, who would you choose?

-If you knew that your friend's boyfriend is cheating on her, what would you do?

-If you had to swim naked with someone in this room, who would you choose?

-Tell me one time when you think you've gotten away with it big..

-Tell one time that you accidentally crashed into something (wall, window, door), and the reaction of the people around you.

-Would you share your toothbrush with your best friend?

-Have you ever lied to your best friend? Was it to protect him?

-What would you do if your best friend tells you that he likes your partner?

-What is the weirdest thing you've done alone?

-Who do you think of your peer group is the best kissing?

-Mention one thing you would never do in front of the person you like..

-Have you had a job that you hated too much?

-Who did you tell your last lie to?

-What do you think it takes to be an influential person in life?

-Who is the person you like the worst in this room and why?

-Have you ever got into debt with someone or an entity and it was difficult for you to pay? For what amount?

-What was the longest time you've stayed in a bathroom and why did you do it??

-When was the last time you cried and why?

-What is the most expensive thing that you have stolen?

-Have you ever tested positive for an anti-doping test?

-What would you do if you won the lottery tomorrow?

-What's the grossest thing you've ever done?

-What is the most sexually suggestive thing you've ever done?

-What would you do with a million dollars?

-What food makes you very disgust to eat?

-What position does your pet have in your family?

-If you could say something to someone in your life without any consequence, what would you say??

-What is the most embarrassing thing your parents have caught you doing?

-Who is the last person you were stalking on social media?

-What is your favorite song to sing in the shower?

-What is it that you can't stand about yourself?

-What is your guilty pleasure?

-When was the last time you brushed your teeth?

-With whom would you like to exchange lives of those present here?

-Say one positive and one negative about everyone in this room.

-Mention the worst time you've treated someone you know.

-Which adjective best describes you?

-What doesn't your family know about you?

-Do you think it is possible to continue being friends with your ex-partners?

-What do you think when you are sitting in the bathroom?

-What would be in your browser search history that would make you feel ashamed that someone saw it?

-Have you ever been caught doing something you shouldn't have?

-If you had to choose between the death of your brother / a and that of your best friend of all life, what would it be??

-Have you fallen asleep at school / work and gotten in trouble for it?

-How many years do you think it takes to work to get rich?

-What has been the longest period of time you have spent without bathing?

-Tell a time that you have thrown a gas in a public place and the reaction of people. Did they know it was you?

-Have you lied to a police officer? What did you say to him?

-Mention a post that you regretted putting on your social networks.

-Who did you vote for in the last elections?

-Have you ever fallen or made a fool of yourself dancing?

-Have you ever put on dirty clothes because you didn't have a spare?

Uncomfortable Questions for Boyfriends 

-Do you think your best friend's boyfriend / girlfriend is handsome??

-(For men) If you suddenly got someone pregnant and you don't consider yourself ready to be a father, what would you do??

-If you were given a choice between love or money, which would you choose?

-Describe your worst sexual experience.

-With which two people would you like to have a threesome?

-When was the last time you had sex?

-What is your favorite part of your partner's body?

-What is the strangest thing that you have been asked to do in bed?

-Which person do you need the most in your life right now?

-Do you think you are macho?

-Do you usually flirt even if you have a partner?

-What would you do if your ex suddenly wants to get back with you and you are already in another relationship?

-If your partner tells you that they like your best friend, what would you do?

-What is your biggest regret?

-Have you ever had or have a significantly shorter or taller partner than you??

-Who is the person you most regret having kissed?

-Have you ever been infected with a sexually transmitted disease?

-If your girlfriend likes your best friend very badly, what would you do?

-What do you consider to have been the worst gift you have ever received?

-What would you do if I went with someone else?

-What skill have you worked hard to develop but never succeeded in it??

-You want to have children?

-What has been the most impressive site you've ever had sex on?

-If you could spend all your waking time with your partner, would you?

-Mention the most embarrassing or ridiculous reason you've been through with me.

-What do you like to do the most and have them done to you in bed?

-What was your first impression of me?

-Have you ever lied to me?

-What's the worst thing you've done when you've been drunk?

-Do you believe or want to marry me?

-If you knew that you cannot get anyone pregnant / get pregnant or get venereal diseases, how would your sex life change??

-Have you ever been attracted to a friend of your partner?

-If both your best friend and your boyfriend / girlfriend are in front of you, who would you save first??

-Have you ever been unfaithful to someone or have they been unfaithful to you?

-Who did you lose your virginity with?

-Would you like to have or have you ever had a threesome?

-What do you consider the sexiest in a man / woman?

-What would you do if you found your partner cheating on you?

-What would you improve in your sex life?

-What is it that you can't stand about me?

-Do you think we would function better as friends or as boyfriends?

-Would you accept that my mother came to live with us at home?

Awkward questions for women

-What's the most illegal thing you've ever done?

-Have you ever stolen money from someone close to you without them noticing?

-Have you ever married or thought about getting married in a crazy moment?

-What is the time when you have felt the most physical pain in your life?

-Mention one time you had to lie about your identity and why.

-Have you waxed or would you consider waxing your intimate area?

-What physical characteristic would make you not want to go out with someone on a date?

-Do you think you are a self centered person?

-What was the last 21+ movie you saw??

-If you could choose between never sweating and never having to go to the bathroom for the rest of your life, which would you choose??

-How many times do you masturbate a week?

-Would you go to a nude beach?

-What is the most embarrassing thing you have ever done in front of someone you like?

-What has been the worst time you have been ridiculed?

-What would you do if someone is constantly harassing you to go out with him / her, but you are not interested?

-What people have seen you without your clothes on?

-Would you or do you have any cosmetic surgery?

-Are you still a virgin?

-If you had to rate your appearance from 1 to 10, how much would you give?

-Have you had any erotic dreams lately?

-Your feet stink?

-Would you rather live without internet or without air conditioning / heating?

-If your date was a disaster, how would you escape from it?

-What is the most ridiculous costume you have ever worn?

-Would you keep looking at a naked person you've accidentally seen if they don't already know?

-Tell how your strangest date was.

-What is the worst grade you have obtained in an exam?

-Have you ever wished someone death? Who and why?

-What has been the most days in a row that you have slept with different people?

-Have your parents discovered you in bed with someone?

-Would you stop using your cell phone forever if it implies that you can marry the person of your dreams?

-Have you ever pretended that you like a gift? Tell details and if you were able to convince the person of it.

-If your partner allowed you to have sex with another person, would you?

-What secret have you confided to someone and then those people ended up telling many other people?

-Have you ever received a photo of someone naked? Whose was it?

-Have you ever practiced kissing in a mirror?

-What part of your body do you hate and why?

-Would you consider having a friend with rights?

-What would you do if you were in the bathroom and there was no toilet paper?

-What is the most extravagant thing that you have done in bed?

-Describe your worst jealousy attack.

-Size Matters?

-If you had to choose between a pretty face or a good body in your partner, what would you choose?

-Tell me once you have drunk and done things that you have regretted.

-Do you think that you can only alleviate your physiological needs in the bathroom at home??

-With whom would you not dare to discuss politics?

-Have you ever had to ask for the morning after pill?

-Have you ever been caught criticizing another woman?

Awkward questions for men

-Would you rather be thin and hairy or fat and hairless?

-What has been the most inappropriate moment in which you have thrown a gas?

-Do you pick your nose in public?

-Have you ever dressed in your partner's clothes?

-What was the biggest lie you ever told?

-What was the worst fight you have participated in and why did you participate?

-Who of your friends do you think is the one you can trust the least?

-If every time you stared at a girl's body, you gained 2 kilos in weight, how often would you do it compared to how you do now?

-Have you ever done drugs?

-What has been the craziest event you have attended?

-What do you consider to be the most important folder or file on your computer?

-What is the first thing you would do if you woke up being someone of the opposite sex?

-What is the last lie that you told?

-Have you slept with someone with a specific interest involved? Which?

-If you could change one part of your body, what would it be and how?

-What is your biggest sexual fantasy?

-What is your worst memory of your childhood?

-What is the most childish thing that you still do?

-If you wanted to kill me, how would you do it?

-In which sport are you worse?

-Have you used any object for sexual purposes despite not being your objective?

-What's the dirtiest thought you've ever had?

-Would you rather lose your sexual organs forever (you can still urinate), or gain 200 kilos of weight that you can never get rid of?

-How many people have you slept with?

-What is your goal in life?

-What adjectives best define your private parts?

-Describe what you consider to be your worst habit.

-What's the most wicked thing you've ever done?

-What categories of erotic movies are you looking for?

-What has been the largest amount of food you have consumed in the same sitting? How was it and why?

-Who would you like to see naked from the people you know?

-If you had a managerial position or were a senior executive, how would you be a boss??

-Have you declared to someone who did not correspond to you?

-If you had to describe your best friend, what would you say?

-What excites you the most?

-Have you ever become addicted to an activity, habit, thing, game, or substance?

-Have you been expelled from school or fired from work for arriving drunk?

-What would you do if your son / daughter was homosexual?

-How often do you lie, and why?

-How much do you earn per month?

-What is the most embarrassing thing that has happened to you this year?

-If you were told that you would not be able to have sex for the rest of your days, what would you do??

-Have you felt lonely even having people around you?

-Would you help a friend in need in the middle of a test or exam?

-What is the size of your member?

-Tell me a disturbing fact that I should know about you.

-Have you ever been caught peeing in the street?

-Do you know how to put a washing machine?

Awkward love questions

-What are the three things that make you?

-Have you played with someone's feelings?

-What do you usually do when you like a person? Do you approach it or do you get more shy?

-You feel lonely?

-How important is intimacy in a romantic relationship for you??

-Do you prefer a wild and hot relationship or a calm and stable one?

-What was the worst lie you've ever told to impress someone?

-What has been your shortest love interest relationship?

-Would you have a poly love relationship?

-How long do you think a person must be in a relationship to be ready to get married??

-Tell me how was your first kiss.

-Have you thought about another person while having sex with your partner?

-Tell the worst time you've ever been rejected by someone.

-What has been the worst disappointment you have suffered from someone?

-What was it that made you end your last relationship?

-If you had to choose between going out with someone who was ugly but who was good in bed, and going out with someone who was handsome who was bad in bed, what would you choose??

-How was your first kiss?

-How was your first time?

-What do you consider to be your worst flaw?

-If you had to go out with someone else's boyfriend, whose would it be??

-Do you regret meeting someone? To who?

-Describe what your ideal partner would be like.

-Have you ever broken someone's heart?

-Have you made love somewhere forbidden?

-What is the craziest thing you've done for love?

-What is your favorite sexual position?

-If you could travel back in time to erase one thing you've done, what would it be??

-What is your biggest fear in a relationship?

-Have you ever called your father-in-law on the phone thinking that you were calling your partner?

-Do you ever think about your ex?

Awkward questions for my crush 

-Would you rather be of the opposite sex? Why?

-What is the first thing you thought when you saw me?

-Are you for or against abortion? Why?

-Have you ever had a secret affair, relationship or romance?

-Report a problem you had because of a spicy message.

-At what age did you give your first kiss?

-With which celebrity would you like to spend a crazy night?

-Which of the things you have in your room do you consider to be the most embarrassing?

-What has been the worst nickname that you have been given throughout your life?

-How was your worst date?

-Why are you still single?

-Would you rather go a whole month without being able to wash your hair, or a whole month without being able to wear underwear?

-What singer, band or song do you like but are embarrassed to admit it??

-What would you do if you were the opposite sex for a month?

-Do you consider yourself to be more, less or just as intelligent than the average?

-If you could be invisible, who would you spy on?

-Would you date someone shorter than you? Argues.

-Describe the underwear you are wearing at the moment.

-What do you think others admire about you?

-How much do you care about the image that others have of you?

-How far would you go to try to conquer someone?

-Would you kill someone if you could? To who?

-If you could choose between being poor and smart or being rich and dumb, what would you choose??

-What's the worst thing you've ever said to someone?

-Have you ever gotten revenge on someone? How has it been?

-Would you trade someone in your family or your best friend for $ 1 million?

-What is your worst phobia?

-Have you ever been attracted to someone much older than you?

-What was your worst subject in school?

-Describe your worst kiss and who gave it to you.

-What is the most important thing you treasure on your cell phone?

-Mention a time that you had to lie about your age.

-Who were you thinking of the last time you touched?

-Do you have any fear that you have not told anyone?

-What would you be willing to do to have a determined life?

-From one to ten, what score do you think I have?

-Have you ever had a scare thinking that you could get someone pregnant or get pregnant?

-What is the silliest thing to which you have an emotional attachment?

-If you saw me on the street with my parents, would you greet me?

-If I had a stain on my teeth or lips, would you tell me?

Themes of interest

Games for whatsapp.

Challenges for facebook.

Questions for conversation.

Truth or dare questions.

Love questions.

Interesting questions for men and women.

Fun questions.

Questions to meet someone.

Yes or no questions.

Questions of me never.

Leading questions.

Stupid questions to laugh at.

Hot and daring questions.

Questions of what do you prefer.

Conversation topics.


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