Awkward Questions to Ask Your Friends and Partner

20 minutes

Do you want to get to know your friends or partner better? This list of awkward questions will allow you to investigate little-known aspects of the people you love. But, be prepared for some blushes.

Awkward Questions to Ask Your Friends and Partner

Reviewed and approved by the psychologist Valeria Sabater.

Written by Valeria Sabater

Last update: 03 September, 2024

Uncomfortable questions are a good exercise in bonding. They can help us get to know other people better. For example, we’ve all had fun and entertaining times playing Trivial Pursuit, the classic game of questions for challenging our general knowledge. However, it’s a good idea to go a little further and delve into other areas.

We’re referring to those unsuspected nooks and crannies of your partners and friends. Investigating unusual details of the lives and personalities of those who form part of your closest circle is, without a doubt, a great way to discover them in another way. Furthermore, it can be a great exercise in self-awareness.

You can also ask yourself many of these questions. However, you may find yourself face-to-face once more with some of the most uncomfortable moments of your life.

“He who asks a question is a fool for five minutes; he who doesn’t ask a question remains a fool forever.”
-Chinese proverb-

Awkward questions to get to know others better

Let’s face it, there are some people you’d love to ask awkward questions to so you can learn more about them. They’re the kinds of questions that go beyond the ordinary and that uncover territories that usually remain unexplored. As human beings, we’re curious, and bordering on the uncomfortable can sometimes be pleasant and revealing.

It’s rather like compelling the other person to leave their comfort zone and consider certain aspects that they might not even have thought about before. If you’re interested, here are some awkward questions to ask your friends and partner.

Deeply personal questions

There can be few issues as complex as forcing someone else to talk about themselves. Self-knowledge requires effort, even more so when we’re trying to define ourselves by giving opinions of ourselves. The following questions are intended to deepen both the knowledge you have about your friends and that they have about themselves.

What do you think about yourself?
What was your most embarrassing experience?
What do you like the most about yourself?
What’s the worst thing you’ve done for love?
What did you last search on Google?
What’s your most uncomfortable memory?
Who’s the person you hated most in your life?
Name one of your unfulfilled wishes.
Would you tolerate an open relationship?
When was the last time you cried?
What’s the worst lie you ever told your parents?
Have you ever said “I love you” without really meaning it?
Who do you love more, your father or your mother?
Do you regret not having been more daring at some point in your life? If so, when was it?
Do you think everything happens for a reason?
Have you ever stolen anything?
What disgusts you the most?
Did you have a happy adolescence?
Would you die for someone?
When was the last time you were rude and why?
What would you never do again in your life?
Are you insecure?
Have you ever had your heart broken?
What part do you dislike about your physical appearance?
Have you ever betrayed someone?
What’s the most beautiful thing you’ve done for love?
Who do you miss the most from your past?
What do you think of feminism?
What’s the weirdest thing you usually do when you’re alone?
Have you ever been caught doing something you shouldn’t?
In what subject are you hopeless?
Have you ever been stood up?
What’s your biggest fear?
If you could travel in time, what moment would you choose to live again?
What have you yet to experience?
What does human evil mean to you?
What won’t you tolerate in a relationship?
When was the last time you felt envy and why?
What would you prefer, true love or being a millionaire?
How do you see yourself in ten years from now?
Have you been able to satisfy your most bizarre sexual fantasy? What was it?
If a house were about to collapse, who would you save, the young man who lives there or his two-month-old golden retriever?
Do you feel lonely?
Are you childish?
Who would you trade places with? What person close to you or public figure has a life that you’d like to have?
Would you have a relationship with someone of the same sex?
How would you react if the world ended and you were the only survivor?
If you were paid a large amount of money to have sex with someone who you weren’t attracted to, would you do it?
Have you ever fallen in love with a friend’s partner?

Going deeper into these kinds of experiences is a delicate field, sometimes even embarrassing. However, it’s always interesting to put your friends in these kinds of situations and find out how they respond and if they dare to be honest.

Questions about values, experiences, and beliefs

The following questions are formulated to challenge and learn about the experiences and beliefs of your friends, thus generating deep reflection. You’ll see how the answers can broaden their perspectives of themselves.

Do you have any type of debt to settle (personal, emotional, economic)?
Do you have good memories of your first sexual experience?
Do you consider yourself to be intelligent?
What would an ‘ideal world’ look like to you?
Do you love your pet more than some humans?
What’s the worst nightmare you’ve ever had?
Have you ever felt attracted to a relative (a cousin, for example)?
If you were an animal, what would you like to be and why?
Do you have strong political convictions or are you one of those people who don’t even vote?
Do you consider yourself to be a spiritual person?
How often do you change the sheets on your bed?
What do you do when you’re sad?
What would you do to create a fairer society for everyone?
Would you be able to spend a week without the Internet or your cell phone?
Do you believe in reincarnation?
Do you think that the passing of the years is making you a better person?
Finish the sentence: “I find it rude when …”
Do you consider yourself to be a free person or is there something that’s limiting or conditioning you?
Would you welcome an emigrant or refugee from another country into your home?
Would you forgive an infidelity?
Do you believe in revenge or an eye for an eye?
Have you ever had any traumatic experiences?
Do you believe in life on other planets?
If your life were a book, what would it be called?
Do you think animals deserve the same rights as people?
With which actor/actress would you like to spend the night?
What public figure do you distrust and hate?
What do you think happens after death?
What style is your underwear? Is it comfortable or sexy?
Do you regret having fallen in love with someone in particular?
What would you like your funeral to be like?
Do you think we’ll ever be able to travel in time?
What’s the first thing you notice on a first date?
What makes you lose your temper?
Are you scared of getting old?
Is there anyone who doesn’t like you?
Do you have any birthmarks?
What do you think of online porn?
What gives you the most pleasure?
Is there anything you can’t forgive your parents for?
Finish the sentence: “I’m a fabulous person because…”
Have you ever been cruel or mean to someone?
Would you leave your current partner if you were offered a million dollars to do so?
What music are you ashamed to admit that you like?
Have you ever done anything illegal?
What do you think about abortion?
What’s your favorite sexual position?
Do you believe in astrology? Explain why.
Have you ever had a paranormal experience?

We hope that these awkward questions for your friends will give you a deeper insight into their values, experiences, and beliefs. Remember, each question is an opportunity for you to learn and grow together.

Uncomfortable confessions

These questions to make your friends confess are a mixture of curious and hypothetical cases. They’ll allow you to generate greater intimacy with them. But, it’s important to note that there are no bad or wrong answers. After all, everyone has their own experiences and opinions.

Which movie are you ashamed to say made you cry?
What’s the most absurd superstition you believe in?
What’s your grossest habit?
Do you have any kind of addiction that you hide from others?
What things do you do that you think would be socially disapproved of?
Has someone ever outright rejected you because you weren’t attractive?
If you committed a murder, how would you dispose of the body?
What’s the worst thing you’ve ever done to someone else?
What’s your current financial situation?
Have you ever considered a makeover?
If you had the money to have plastic surgery, what would you have done and why?
What’s the biggest lie you’ve ever told me?
What do you think about religion?
What’s the most racist thought you’ve ever had?
And the most racist thing you’ve ever done?
What’s the most pathetic thing you’ve done in a relationship?
What’s your biggest sexual fear?
Do you have a nickname for your genitals?
What’s the strangest thing you’ve ever done in front of a mirror?
Do you masturbate frequently?
What’s the most embarrassing experience you’ve ever had with someone else?
Has anyone ever laughed at you when they saw you naked?
Have you ever had sex while thinking about an ex or someone else?
How far have you gone to have sex with someone?
What’s the first thing you would do if you woke up one day and found you were a member of the opposite sex?
Have you ever peed in a pool?
What’s the weirdest thing you’ve thought of sitting on the toilet?
What would be the worst thing I’d find if I checked your web history?
What’s your most childish undergarment?
Would you marry your current girlfriend or boyfriend?
What’s the weirdest thing you’ve ever tasted from your own body?
Are you comfortable with your genitals? If you could change them, what would you do?
Have you ever been caught looking inappropriately at someone?
What’s the dumbest thing that ever made you cry?
What illegal thing would you like to do and why?
What person do you pretend you like but, deep down, you think is unbearable?
Do you have bad foot odor?
What’s the most unconscious maneuver you’ve done while behind the wheel?
Have you ever tried to bribe a law enforcement officer?
What’s the worst thing you’ve ended up eating because you were too lazy to cook?
What was the worst moment of your life?
If you had to kiss a Disney character, who would it be?
If you had to kiss a family member, who would it be?
If you had to kiss one person in the room, who would it be?
Have you ever used role-play during sex?
What’s the biggest lie you’ve ever told to win someone over?
What are your most embarrassing pajamas?
What’s the stupidest thing you’ve ever bought online?
Would you date someone over 70 for money?
What’s the most embarrassing thing you do when no one is looking?

Each answer is personal and you shouldn’t judge or discriminate against anyone based on what they say. It’s essential that you respect their experiences and don’t invalidate them. They all have their own stories and pasts.

Few issues are as complex as forcing another person to talk about themselves. Self-knowledge requires effort, even more so when they have to define themselves by explaining what they think about themselves.

You might also like to read Intimacy: When Two Souls Meet

Awkward questions for friends and partners

We all hold secrets about our lives and memories that we’re ashamed of or find it uncomfortable to talk about. With these questions, you’ll be able to get closer to those unknown parts of your friends or partner that they don’t usually dare to talk about.

What’s the most ridiculous object that you adore?
Do you have a foot fetish?
Do you lick your plate when you’ve finished eating?
Have you ever been stood up on a date?
Who do you have a crush on?
What’s the worst thing you’ve ever done due to jealousy?
Have you ever done anything scandalous? If so, what was it?
What’s the worst thing you’ve ever done to an animal?
Who wouldn’t you like to see naked?
What have you seen that, for the sake of your mental health, you wish you’d never seen?
Would you kiss your best friend for five minutes for 100 thousand dollars?
What’s the most offensive black humor joke you know?
What do you hate the most about your partner?
Have you ever used someone’s toothbrush?
Have you ever stolen money out of necessity?
Have you ever told someone else’s secret that got the person who told you it in trouble?
What’s the worst thing you’ve ever done to a friend?
What’s the most illegal thing you’ve ever done?
If you could choose, who would you stop being friends with?
If you could exchange one physical characteristic with someone in this room, what would it be?
Who of all those present do you think has the best butt?
Has a friend’s girlfriend or boyfriend ever come on to you?
Would you date two people at once if you could get away with it?
Have you ever sent a hot photo to start a conversation with an unknown person?
Have you ever fallen in love with a teacher?
Who was the last person you stalked on social media?
What do your parents think of your relationship?
Have you ever accidentally heard your parents talk badly about you?
What’s the biggest lie you’ve ever told your partner?
When was the last time you lied about your age?
Which of us do you think would die first in a zombie apocalypse?
What’s the most embarrassing thing you’ve done when drunk?
At what age did you lose your virginity and with whom?
What’s the most embarrassing situation you’ve suffered at work?
If you were invisible for an hour, would you do something perverted?
If it were a choice of life or death, which one of us would you choose to have sex with?
What’s your wildest sexual fantasy?
What’s the most intense homosexual experience you’ve ever had?
What’s the most romantic thing you’ve ever done in your life?
Are you attracted to nudism?
Do you sleep naked?
What’s the most disgusting thing you’ve ever eaten that shouldn’t be eaten?
What’s the cheesiest song you like?
Are you afraid of the dark?
What’s the most embarrassing thing you’ve ever done in front of a friend?
Who would you say is the least attractive in this room?
What’s the weirdest thing you’ve ever done in an elevator?
Have you ever hit someone?
How often do you change your underwear?
If you were to be born again, would you repeat your life in the same way?
What was the worst insult you’ve ever said to someone?
Would you date a porn actor?
What do you think of communism?
What do you think of euthanasia?
Have you ever found someone having sex?
Have you ever been refused a kiss?
What’s the talent that most frustrates you not having?
What do you think about the right to bear arms?
Of all the people you know, who do you find the least trustworthy?
Finish the sentence: “I couldn’t live in a house that didn’t have…”
If you could choose one quality among these three, which one would you choose? To be tall, to be beautiful, or to be successful.
Have you ever recycled a gift you were given by giving it to someone else?

These awkward questions will bring you closer to your friends or partner. Indeed, sharing these experiences allows you to generate a greater connection. So, don’t hesitate to start taking an interest in the lives of your loved ones.

Questions about sensitive moments

No doubt you have some uncomfortable memories in your life. Talking about them with your friends, families, and partners can help you realize that they’ve also gone through difficult moments that are well worth talking about.

What’s the most controversial opinion you have that would cause trouble if you said it out loud?
Have you ever been caught masturbating?
When was the last time you cried over someone?
What was your most humiliating nickname?
What have you done just to look cool?
Who’s the youngest person you’ve ever dated?
Who’s the oldest person you’ve ever dated?
What’s the worst thing you’ve ever said about someone?
Where are your sexual boundaries?
What was the first thing you thought when you first saw me?
What was the worst gift you were ever given?
Have you ever cheated to get better grades?
What annoys you the most about me?
Do you have a secret that you’d never tell your parents?
If you could eliminate one unpleasant experience from your life, what would it be?
Have you ever used any unusual objects for sexual purposes?
Have you ever been unfaithful?
Do you have any suitors at the moment?
Have you ever had sex with someone you met the same day?
What was the most ridiculous costume you’ve ever worn?
Would you tattoo your partner’s name on your body?
What physical characteristics would make you turn down a date with a person?
Is there anyone you regret having slept with?
Are you satisfied with your sex life?
Have you ever had a job that you hated?
Have you ever been hooked on a really bad TV show?
What aspects of your personality do you think others admire about you?
Have you ever feared for your life?
Do you think men and women can be friends?
Would you let me see your WhatsApp chats?
What was your worst binge?
Do you have any hidden tattoos or piercings?
What was the hottest sexual dream you’ve ever had? Who was it about?
What would you most like to have in life that you still don’t?
What’s the longest period you’ve ever gone without showering?
Have you ever farted in public and been caught?
When was the last time you found yourself exposed for thinking you knew enough about a subject but didn’t?
What’s the most embarrassing thing you’ve sent on your phone this past month?
What game based on mental agility are you worse at?
What job would you never do even if you were paid an incredible salary?
What’s the craziest bet you’ve ever made?
What color would you never wear?
If you witnessed a fight in the street, would you be able to try to mediate or would you walk past it?
What urban myth have you believed in for the longest period?
What food do you hate the most?
What do you think of homosexuals?
Do you think everyone should have the right to vote?
What do you think about immigration?
What’s your opinion on prostitution?
Do you think the poor don’t try hard enough?
Up to what age did you wet the bed?
What do you think of the police?
Are you in favor of the death penalty?
Have you ever downloaded porn on your computer?
What kind of porn do you like the most?
Have you ever vomited in a public place?
Have you ever gone out without underwear?
Have you ever tried to contact a famous person through the Internet?
What part of your body do you think has aged or matured less than the rest?
Has someone ever shamelessly flirted with you and you didn’t realize it at the time?

Not everyone shares the same beliefs about sex, and some people are more conservative than others. These questions will allow you to get to know how much openness your friends or partner have regarding this topic.

Awkward questions for your partner

The following questions will allow you to get to know your partner a little more. Bear in mind that the goal is to have fun and find out more about them. Don’t use their answers as an excuse to argue.

You might be interested to read Tips on Spending Quality Time With Your Partner

What’s the weirdest thing that attracts you to me?
What’s your biggest fear in our relationship?
What do you like least about me?
What’s the craziest thing you’ve ever done for love?
What do you most regret doing in a past relationship?
What’s your most secret fantasy?
What’s the most childish thing you still do?
What are you most ashamed of in your past?
Have you ever thought of cheating on me?
What’s the craziest thing you’ve ever done while drunk?
What’s the biggest lie you’ve ever told without getting caught?
What’s your biggest insecurity in our relationship?
Have you ever had an erotic dream about someone I know?
What’s the weirdest thing that turns you on?
What’s the most disgusting thing you’ve ever done when you thought no one was watching?
What’s your biggest fear in life?
Have you ever done something cruel to anyone?
Which of my friends do you think has a bad influence on me and why?
What’s the most embarrassing thing your parents have caught you doing?
Is anyone getting in the way of our relationship?
Is there a friend of mine that you don’t like?
What’s the dumbest thing you’ve ever done to impress someone?
What’s your biggest regret in life?
What’s the weirdest thing you’ve searched for on the Internet?
What disgusting food have you eaten out of courtesy?
Do you think there’s anyone I should distance myself from?
What’s the most awkward situation you’ve found yourself in while on a date?
Have you ever had a fantasy that you’re too embarrassed to share?
What’s the worst lie you’ve ever told in a relationship?
What’s your most embarrassing guilty pleasure?
What’s the worst first impression you’ve ever made?
Have you ever mistaken someone for someone else?
Have you ever pretended to be sick to avoid a date with me?
Is there a song you secretly love but would never admit to liking?
Have you ever had an embarrassing conversation with your parents about us?
Have you ever bought a last-minute gift because you forgot an important date?
Is there a movie, book, or series that you love but you’d be embarrassed to admit it?
Have you ever felt ashamed of something I did in public?
Have you ever had a disturbing dream about me that you didn’t share?
Did you ever lose or break something of mine and didn’t tell me?
What’s the most uncomfortable situation you experienced with your ex-partners?
What’s the most embarrassing moment you’ve ever had at work?
Have you ever sent a message to the wrong chat?
Have you ever felt jealous of a relationship I have with someone else?
Have you ever faked an emergency to get out of an awkward situation?
Have you ever fallen asleep in an inappropriate place?
Have you ever ruined a surprise?
What was your biggest blunder at a family reunion?
What’s the strangest birthday gift you’ve ever received?
Have you ever feigned interest in a topic just to impress someone else?
Have you ever fallen at an awkward moment?
Have you ever cried in public over something you now consider trivial?
What’s your favorite clothing?

Although you’ve shared many moments, there’ll always be certain secrets and undiscovered truths about each other. Encourage your partner to remember those hidden moments. Focus on and value their honesty, and respect them if they decide to keep certain things secret.

You may find that many of these uncomfortable questions for your friends and partners remain unanswered. They may even tell you lies or half-truths. However, forcing them to delve into unusual aspects of their selves can be an enjoyable exercise. Are you daring enough to try it?