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202 Embarrassing Questions to Ask a Guy to Make Him Uncomfortable

It’s normal to be curious about a man you are dating. It doesn't matter if a relationship will come out of it or not; there are a couple of things you should know. For one, you need to know his sexual past, as the last thing anyone wants is STDs. 

Curating a list of embarrassing questions to ask your guy can be a great way to get an unfiltered response from him. This way, you see behind all the polite demeanor to honestly know what type of guy he is.

Creating a list of awkward and embarrassing questions can be pretty tricky, especially if you need help figuring out where to start. Fortunately, I have created a list of awkward questions to ask a guy. You can read the questions on this list to make your own list or simply co-opt it to know if that guy is your dream guy. 

These are weird questions you can share with all your friends too, to make your evening time together entertaining. 

A tip to remember when trying to ask the most awkward questions is that you can break the ice by highlighting something equally embarrassing about yourself. Doing this helps to make him more comfortable and open about sharing some truly personal things. And asking awkward and uncomfortable questions can lead to the most interesting conversations. 

Either you become vulnerable with one other and discover that you are closer, or your soon-to-be relationship with this guy won't simply work out. If the latter is the case, you can amicably split before things get too messy.

100+ Embarrassing Questions to Ask a Guy

You shouldn't make a big deal out of it when asking the opposite sex these awkward questions. Such awkward and embarrassing questions can be tricky at first since you want to make a great impression. 

Nevertheless, you must be candid with each other, especially if you want to build a relationship with them—no relationship is complete without honesty.

When asking these questions, ensure you give him enough space if he begins to look uncomfortable. He should always have the option of skipping a question—you can always come back to the question once you feel you both are closer.

With that in mind, here are 100+ embarrassing questions to ask a guy!

  • Would you give me a massage?
  • What turns you off in a woman?
  • Who pays on the first date?
  • How would you react if a girl made the first move?
  • Would you want to sleep or date a virgin girl?
  • Do you care about your partner’s body count?
  • Did you stalk your last girlfriend on social media?
  • What’s your favorite physical feature in a woman?
  • Would you choose love over a career?
  • Is it intimidating if a woman makes more money than you?
  • How many girls are you talking to apart from me?
  • Have you ever ghosted anyone?
have you ever ghosted anyone
  • What do you think about starring in an OnlyFans video?
  • Have you ever sent someone nudes?
  • Would you want to experience childbirth if you could?
  • What if I cheated on you?
  • What’s the first thing you noticed about me?
  • Have you ever, at any point, been attracted to a guy?
  • What would you say if I told you I am pregnant?
  • Did you ever have any addiction?
  • Have you ever gone to therapy?
  • When did you lose your virginity?
  • Have you ever had a one-night stand?
  • What specific thing do you like about me?
  • How many times do you masturbate in a day?
  • What do you think about dating someone who is a parent?
  • Would you date someone that doesn’t have children?
  • Where do you see us in the future?
  • When was the last time you cried?
  • How big are you?
  • How sexually experienced are you?
  • What are your kinks?
  • Do you have a recent STI test?
  • What do you think about ethical non-monogamy?
  • Have you been unfaithful in past relationships?
  • Tell me the sweetest thing you have noticed about me.
  • Tell me the worst gift you have ever received.
  • Do you have a crush on someone in your workplace?
  • Have I ever done something to you that pissed you off, but you didn't mention it?
  • When would you like to get married?
  • What is the first thing about me that attracted you?
  • If you could spend a romantic night with a celebrity, who would it be?
  • How long did your previous relationship last?
  • What is the thing you want from your life partner other than sex?
  • When was the last time you peed in your bed?
  • Would you leave me for a more beautiful girl?
  • What is your most disgusting habit?
  • What is the real reason you and your ex broke up?
  • Do you see your future with me?
  • Tell me about your most awkward date.
  • When was the last time you lied to me?
  • Have you ever stalked anyone on social media?
  • What is your biggest fear?
  • Have you ever thought of marrying someone else?
  • What was your first impression of me?
  • What do you feel for your ex-girlfriend now?
  • Who do you care about most, me or your best friend?
  • Which is your most embarrassing moment with a girl?
  • When was the ultimate moment you realized that you were in love with me?
  • What is the worst thing about being a guy?
  • Have you ever drooled in your sleep?
  • What’s your worst secret?
what's your worst secret
  • What would be your best weekend getaway?
  • What’s your favorite rom-com movie?
  • What has been the most significant waste of money you've spent?
  • What’s one app you couldn’t live with?
  • What’s the dirtiest thought you’ve ever had?
  • What joke would it be if you had to tell one joke to save your life?
  • Have you ever tasted ear wax?
  • What’s your biggest fashion faux pas?
  • What video game would you most like to be transported into?
  • How many weeks could you last without your smartphone?
  • What’s the worst thing you’ve done for love?
  • What’s your idea of the perfect first date?
  • Do you talk in your sleep?
  • If you held a world record for something, what would it be for and why?
  • What score would you give me out of 10?
  • How many girls have you had sex with?
  • What was the strangest thing you liked to eat as a child?
  • Have you ever taken a sexy picture of yourself?
  • What’s the most embarrassing thing to happen to you in public?
  • Do your work colleagues/friends have any nicknames for you?
  • Have you ever lied to me?
  • Have you ever had an STD?
  • Can I give you a makeover?
  • Do you enjoy having a beer belly?
  • What’s the most creative insult you can come up with?
  • Have you ever had a man crush?
  • What part of your body do you wish you could change?
  • What’s the worst smell you’ve ever smelt?
  • What is the earliest memory you have?
  • Who is your best friend, and why?
  • What would you do with the money if you won the lottery today?
  • Who is your favorite movie character? What is the thing you like about them?
  • Do you think there is a difference between making love and sex?
  • Do you think aging alters how attracted you are to someone?
  • What’s your biggest accomplishment?
  • Have you ever been non-monogamous?
  • Who is your favorite designer?
  • If you wanted us to have our first kiss, how would you plan it?
  • How many girls' numbers have you collected?
  • Will you betray your own country?

100 Awkward Questions to Ask a Guy Via Text

100 awkward questions to ask a guy via text

Texting is an integral part of our lives today. We use it to keep in touch with loved ones, get the lowdown from friends, and sometimes to fuel our interest after a chance meeting. This list of extremely awkward questions to ask your boyfriend over text can be pretty challenging. 

However, they can be an excellent way to gauge his personality to see if it matches yours. This is especially important at the beginning of any relationship. The last thing you want is to get close and serious with someone only to discover that their personality doesn’t match yours.

Another fascinating thing about this list is that these questions are interesting conversation starters. You ask him one question, and he provides an answer that lets you ask another that delves deeper into his psyche

It also helps that you can ask these questions via text, so you don't have to deal with the awkwardness that typically happens when you ask these awkward questions in person. With that in mind, here are 100 awkward questions to ask a guy over text.

  • What would you undo from the past if given a chance?
  • How would you know if someone was the right person for you?
  • What reveals a person’s character most when dating?
  • What is your favorite memory of us?
  • Which scent do you like on a woman?
  • Are birthdays special to you?
  • What do you do when angry?
  • How do you express love?
  • When do you think girls look most beautiful?
  • What do you like in a girl but are shy to admit?
  • Do you prefer flirty texts or face-to-face chats?
  • Have you felt butterflies in your stomach before?
  • Do you like it when a girl makes the first move?
  • When are you most comfortable talking?
  • What is your ideal first date?
  • Do you have secret fantasies?
  • What is your idea of a perfect girlfriend?
  • What is the one thing that turns you off the most?
  • What is the most sensitive part of your body?
  • Guess what I am wearing right now?
  • Could you forgive someone that cheated on you?
  • Should people keep secrets in relationships?
  • What does a healthy relationship look like to you?
  • Money or love, what would you choose?
  • What would you sacrifice life for?
  • What brings you the most joy in life?
  • What would you never tell your crush?
  • What do you fear in romantic relationships?
  • What kind of father will you like to be to your kids in the future?
  • Have you ever cried in front of someone?
have you ever cried in front of someone
  • What makes you trust someone?
  • Are you scared of commitment?
  • How far away would you live?
  • What is the one thing you would hire someone for?
  • What is the weirdest thing you have received in the mail?
  • Have you ever sent a love letter?
  • What is the craziest thing you have done for a friend?
  • What is your go-to dinner meal?
  • Who do you talk to the most?
  • Who was the last person you called?
  • What physical quality do you compliment people on?
  • What is the craziest thing you have done to seek attention?
  • What do you daydream about when bored?
  • What do you like to drink often?
  • What makes you smile the most?
  • What kind of compliments do you like to hear?
  • Have you been caught staring at a girl?
  • What would you do if you had a day with your crush?
  • Can girls and guys be friends without catching feelings?
  • What kind of clothing looks best on a woman?
  • What lesson about men would you teach girls?
  • How do you start small talk with strangers?
  • Do you believe in love at first sight?
  • What do you wear when alone?
  • Who did you last try to impress?
  • What is the funniest pickup line you’ve heard?
  • What is your top guilty pleasure?
  • What do most people get wrong about you?
  • What would you do if you were a girl for a day?
  • What is your favorite quote?
  • Which joke do you say the most?
  • Which is your favorite movie of all time?
  • Which song has the best intro?
  • What is your go-to video for laughs?
  • Have you been caught snooping on someone’s phone?
  • Do you sing in the shower?
  • Do you dance by yourself?
  • What do you think of hickies?
  • Has anyone seen you naked accidentally?
  • Have you skinny-dipped?
  • Have you ever been stood up by a date?
  • Do you have dirty pictures on your phone?
  • What would I be shocked to find in your room?
  • What name would you give your first child?
  • What have you gotten away with in the past?
  • What is your biggest insecurity?
  • Have you been cheated on before?
  • When was the last time you cried?
  • Have you had a crush on an older girl?
  • What is your favorite body part in a girl?
  • Do you have a weird fetish?
  • What is on your nightstand?
  • What would you do if I gave you $100?
  • Have you ever shared a toothbrush with someone?
  • Did you ever stalk someone?
  • What is the worst gift you have gotten?
  • Who do you regret kissing?
who do you regret kissing
  • Have you ever flashed someone?
  • When was the last time you got furious?
  • What accents can you make?
  • Would you rather live in a world without sport or a world without women?
  • If you were the opposite sex for the day, what would you do first?
  • What’s the longest you’ve been without sex?
  • What’s the strangest thing you’ve been to the hospital for?
  • Where’s the strangest place you’ve been on a date?
  • If you could have a drink with anyone from history, who would it be and why?
  • What do you dislike most about being a man?
  • What would your last meal on death row be?
  • What strange phobias do you have?
  • What celebrity would you love to be stuck on a desert island with?


If you only recently started talking to a guy or have been in a relationship with him for a while, these interesting questions can be a great and fun way to delve deeper into who they are. The great thing about these awkward questions is that there is no limit to the type of answers you get.

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