113 Awkward Questions to Ask a Guy to Make Him Embarrassing

Embarking on the uncharted territory of awkward questions to ask a guy is like entering a realm of unexpected revelations and amusing discomfort.

Unveil the intriguing world of human interactions with a curated collection of over 100 weird questions to ask a guy, designed to elicit unexpected responses and ignite laughter.

From curiosity-driven inquiries to playful provocations, these questions hold the power to unravel layers of personality and foster connections in the most unconventional ways.

As you navigate through various categories, each question becomes a stepping stone towards breaking barriers, sharing laughter, and strengthening relationships.

Awkward Questions to Ask a Guy to Make Him Uncomfortable

Step into the realm of discomfort with weird questions to ask a guy to make him uncomfortable that are guaranteed to make a guy squirm and reveal sides he never expected.

1. Have you ever, at any point, been attracted to a guy?

2. Have you ever sent someone nudes?

3. Did you ever have any addiction?

4. What’s your favorite physical feature in a woman?

5. Would you want to experience childbirth if you could?

6. Would you want to sleep or date a virgin girl?

7. What do you think about starring in an OnlyFans video?

8. Did you stalk your last girlfriend on social media?

9. Have you ever gone to therapy?

10. Do you care about your partner’s body count?

11. Have you ever ghosted anyone?

12. When did you lose your virginity?

13. Would you choose love over a career?

14. Have you ever had a one-night stand?

15. Is it intimidating if a woman makes more money than you?

Awkward Questions to Ask a Guy over Text

Elevate your digital dialogues with awkward questions to ask a guy via text that invite discomfort and foster playful exchanges even through text conversations.

1. Do you have secret fantasies?

2. When are you most comfortable talking?

3. What do you think about dating someone who is a parent?

4. What is the one thing that turns you off the most?

5. Have you felt butterflies in your stomach before?

6. What do you think of hickies?

7. How big are you?

8. Do you prefer flirty texts or face-to-face chats?

9. When do you think girls look most beautiful?

10. What is the most sensitive part of your body?

11. Has anyone seen you naked accidentally?

12. What would you undo from the past if given a chance?

13. Guess what I am wearing right now?

14. Do you have dirty pictures on your phone?

Awkward Truth or Dare Questions to Ask a Guy

Uncover truths and dare him to face uncomfortable and awkward questions to ask a guy in truth or dare, adding a twist of awkwardness to your truth or dare games.

1. Have you ever practiced kissing in a mirror?

2. What was your most embarrassing moment in public?

3. Have you ever peed in the pool?

4. If you had to choose between going naked or having your thoughts appear in thought bubbles above your head for everyone to read, which would you choose?

5. What is your guilty pleasure?

6. What color underwear are you wearing right now?

7. Have you ever walked in on your parents doing it?

8. Google the dirtiest thing you can think of and show it to the person next to you.

9. Write your name on the floor with your tongue.

10. Put one ice cube inside your pants.

11. Send your ex a message saying you miss them.

12. Pick up the nearest object to you and demonstrate how to put on protection.

13. Show the most embarrassing message on your phone.

14. Perform a seductive dance in front of the group.

Awkward Relationship Questions to Ask a Guy

Navigate the intricacies of relationships with awkward questions that encourage candid conversations about feelings, preferences, and expectations.

1. What are the things you enjoy the most about the relationship?

2. What do you fear in romantic relationships?

3. Have you been unfaithful in past relationships?

4. Should people keep secrets in relationships?

5. Do you think the idea of having children? How many?

6. How long did your previous relationship last?

7. What have you learned from your past relationships?

8. Money or love, what would you choose?

9. What matters to you most in a relationship?

10. Do you want to get married one day?

11. Do you have plans outside of the relationship?

12. What makes you feel insecure?

13. Have you ever lived with someone before?

14. What would be the limits that you would establish in a relationship?

Awkward Questions to Ask a Guy You Like

Bridge the gap between curiosity and attraction with awkward questions that create unique moments of connection with someone you’re interested in. let’s dig right into them.

1. What’s your idea of the perfect first date?

2. If you wanted us to have our first kiss, how would you plan it?

3. Have you ever taken a sexy picture of yourself?

4. How sexually experienced are you?

5. Do you talk in your sleep?

6. Would you give me a massage?

7. What score would you give me out of 10?

8. Do you have a recent STI test?

9. What would I be shocked to find in your room?

10. What are your kinks?

11. If you could spend a romantic night with a celebrity, who would it be?

12. What do you think about ethical non-monogamy?

13. What’s the most embarrassing thing to happen to you in public?

14. What is your favorite body part in a girl?

Awkward Questions to Ask a Guy You Are Dating

Navigate the journey of dating with awkward questions to ask your boyfriend that dive into deeper realms, sparking candid discussions that pave the way for a genuine connection.

1. When was the last time you lied to me?

2. How many girls are you talking to apart from me?

3. How would you react if a girl made the first move?

4. What if I cheated on you?

5. What would you say if I told you I am pregnant?

6. Who pays on the first date?

7. Would you leave me for a more beautiful girl?

8. What’s the first thing you noticed about me?

9. How many times do you masturbate in a day?

10. Do you have a weird fetish?

11. What specific thing do you like about me?

12. Do you see your future with me?

13. What do you feel for your ex-girlfriend now?

14. Who do you care about most, me or your best friend?

Awkward Questions to Ask a Guy Best Friend

Unveil the uncharted facets of your friendship with awkward questions to ask your guy best friend that push boundaries and create unforgettable moments with your guy best friend.

1. Have you ever had a man crush?

2. What is the worst thing about being a guy?

3. What’s the dirtiest thought you’ve ever had?

4. What video game would you most like to be transported into?

5. What was the strangest thing you liked to eat as a child?

6. Have I ever done something to you that pissed you off, but you didn’t mention it?

7. What’s one app you couldn’t live with?

8. What’s the most creative insult you can come up with?

9. What joke would it be if you had to tell one joke to save your life?

10. Have you ever drooled in your sleep?

11. What’s your favorite rom-com movie?

12. What part of your body do you wish you could change?

13. What’s your worst secret?

14. Who do you regret kissing?

Awkward Questions Girls Are Afraid to Ask a Guy

Conquer fears and unveil the unspoken with awkward questions girls are afraid to ask guys, fostering open conversations and shared understanding.

1. What’s the worst thing you’ve done for love?

2. Tell me about your most awkward date.

3. Do you think there is a difference between making love and sex?

4. What is your most disgusting habit?

5. How many girls have you had sex with?

6. Which is your most embarrassing moment with a girl?

7. What is the real reason you and your ex broke up?

8. What’s the most insane thing you’ve ever done?

9. If you were the opposite sex for the day, what would you do first?

10. Do you think aging alters how attracted you are to someone?

11. What was the worst situation you were ever naked in?

12. How many times do you change your boxers in a week?

13. Have you ever shared a toothbrush with someone?

14. What’s the longest you’ve been without sex?

Final Thoughts

We hope you enjoyed going through these awkward questions to ask a guy.

Whether you’re exploring unspoken curiosities, or simply looking to spice up conversations, these awkward questions are your ticket to intriguing and unforgettable interactions.

Embrace the power of unpredictability, laughter, and understanding as you venture into the world of embarrassing questions to ask a guy.

We encourage you to share your favorite questions, and the laughter-filled moments they’ve ignited in the comments below.
Thank you so much.