This article provides readers with 50 awkward questions to ask a guy and embarrass him. These questions are designed to put him in an uncomfortable position and make it difficult for him to answer.
Some of these questions are straightforward, while others are more creative and can lead to some interesting conversations. The goal is not only to make the guy feel embarrassed but also to discover more about his personality and interests.
For those looking for some fun ways to find out more about the man they’re interested in, this article has plenty of ideas that will get you started on an awkward journey toward discovery!
50 Awkward Questions To Ask A Guy
If you are looking for a fun way to tease and embarrass the guy in your life, or just want to make an uncomfortable moment even more uncomfortable, then this list of awkward questions is perfect for you.
1. What was the most embarrassing moment of your life?
Embarrassing moments can be hard to forget, and many people have experienced moments in their lives that still cause them to blush when thinking about them.
2. When was the last time you cried and why?
Crying can be a difficult subject for some people, as it often brings up feelings of vulnerability or shame. Asking someone about their last experience crying is a great way to open up a conversation about emotions and gain insight into their innermost thoughts.
3. Have you ever been caught in an awkward situation with a crush?
Crushes can bring out some of the most awkward moments, and many people have experienced uncomfortable situations when it comes to dealing with their crushes. Asking this question can give you an insight into how someone deals with these situations and how they feel about them.
4. Have you ever sent an inappropriate text message to someone by mistake?
Mistakes happen, and sending an inappropriate message to someone can be an embarrassing experience. Asking this question can give you a better understanding of how someone deals with such mistakes and the consequences they face.
5. Did anyone find out about it, and if so, what happened next?
Once someone finds out about a mistake or embarrassing moment, the situation can become even more awkward. Asking this question gives you an insight into how someone reacts to such situations and how they handle them in the future.
6. Is there any celebrity that you have a secret crush on but would never admit publicly?
A secret crush can be an embarrassing topic to talk about, as it often involves talking about someone who is famous and in the public eye. Asking this question can give you an insight into someone’s feelings and thoughts on celebrities.
7. Who is the most embarrassing person in your life?
Embarrassment can come from many different sources, including family members or friends. Asking this question gives you an insight into how someone views those in their lives and the things that make them feel embarrassed.
8. Are you ever scared of being seen with your parents in public?
Some people may feel embarrassed or ashamed when it comes to being seen with their parents in public, as it can be a reminder of childhood or teenage years. Asking this question gives you an insight into how someone views their family and the feelings they experience when it comes to being around them in public.
9. What was the weirdest dream you’ve had recently?
Dreams can be strange and often reflect our innermost thoughts and feelings. Asking someone about their weirdest dream gives you an insight into what they have been thinking about lately and the things that may be on their mind.
10. Have you ever sent an inappropriate photo to someone by mistake on social media or text messages?
Sending an inappropriate photo to someone can be a very embarrassing experience, as it often involves sending something that was meant for one person to another person who didn’t ask for it. Asking this question gives you an insight into how someone reacts to such mistakes and the consequences they face.
11. Is there anything that makes you feel really awkward when talking to people, like a stutter or something else?
Everyone has something that makes them feel self-conscious or awkward when talking to people, whether it’s a stutter, a nervous laugh, or any other form of physical or verbal tick. Ask your guy if there’s anything that makes him feel uncomfortable when speaking with others.
12. Have you ever had an embarrassing moment while in a public place?
Embarrassing moments in public places can be mortifying and can stick with us for years afterward. Ask the guy if he ever had an embarrassing moment in front of strangers and how he dealt with it.
13. What’s the most awkward thing that ever happened to you on a date?
Dates can be full of awkward moments, so ask the guy about his most awkward date to see what kind of experiences he’s had.
14. Is there something embarrassing about your family that you don’t want anyone to know?
Ask the guy if something is embarrassing about his family that he’d rather keep private, and how he handles conversations when people bring up those topics.
15. Have you ever been caught looking at someone or something inappropriate in public?
We’ve all been caught looking at something inappropriate in public at least once, so find out if it ever happened to your guy and how he managed the situation.
16. Have you ever said the wrong thing and instantly regretted it?
Ask your guy if he ever said something wrong and regretted it instantly, and how he handled the aftermath of his mistake.
17. Are there any topics of conversation that make you really uncomfortable?
Everyone has topics that make them feel awkward or uncomfortable, so ask your guy what topics of conversation make him uneasy and why.
18. What’s the weirdest thing you’ve ever done in public that no one else knows about?
Find out if your guy ever did something weird in public without anyone noticing, and how he kept it a secret afterward.
19. Have you ever been caught doing something embarrassing by someone who was in a position of authority over you?
Many of us have been caught doing something embarrassing by someone in a position of authority, so ask your guy if it ever happened to him and how he reacted to the situation.
20. Are there any embarrassing stories from your childhood that still make you feel uncomfortable when thinking about them?
Ask your guy about any embarrassing stories from his childhood that still make him feel uncomfortable when he thinks about them.
21. Is there a time when you accidentally said or did something awkward and everyone laughed at it?
Everyone has had an awkward moment they wish they could forget, but unfortunately, there are times when even the most embarrassing things can be funny. Have you ever experienced a time when you said or did something awkward and everyone laughed at it?
22. Has anyone ever told you something in private, then later embarrassed you by revealing it to someone else?
It’s never fun to have your secrets revealed to someone else without your permission, especially if it causes embarrassment. Has anyone ever told you something in private, then later embarrassed you by revealing it to someone else?
23. Is there a secret part of your past that would be really embarrassing if it got out?
We all have moments from our past that we would rather forget, and some of them can be embarrassing if they got out. Is there a secret part of your past that would be really embarrassing if it got out?
24. Have you ever been caught checking someone out who was completely inappropriate for your age or social status?
Checking someone out is sometimes seen as inappropriate, especially if it’s someone who is outside of your age or social status range. Have you ever been caught checking someone out who was completely inappropriate for your age or social status?
25. Are there any embarrassing moments from middle school that still make your cheeks flush when thinking about them?
Middle school can be a challenging time when it comes to embarrassment and awkwardness. Are there any embarrassing moments from middle school that still make your cheeks flush when thinking about them?
26. Do people often tease you about something embarrassing that you did in the past?
Sometimes, embarrassing situations can be hard to forget and people might tease you about them. Do people often tease you about something embarrassing that you did in the past?
27. Have you ever been caught doing something naughty or inappropriate in public, and if so, what happened afterward?
Being caught doing something naughty or inappropriate in public can be a mortifying experience, especially if other people were around to witness it. Have you ever been caught doing something naughty or inappropriate in public, and if so, what happened afterward?
28. Is there a person from your past who still makes you feel embarrassed about yourself?
We all have people from our past who have seen us at our worst moments and still haunt us with their memories. Is there a person from your past who still makes you feel embarrassed about yourself?
29. Are there any topics of conversation that make it really hard for you to think of a response without feeling awkward?
Awkwardness can come out of nowhere when talking to someone and it can be hard to think of a response without feeling uncomfortable. Are there any topics of conversation that make it hard for you to think of a response without feeling awkward?
30. Is there anything about your body that makes it difficult for people to look at you without feeling embarrassed?
Everyone has something about their body that they are not comfortable with, and it can be embarrassing when people notice it. Is there anything about your body that makes it difficult for people to look at you without feeling embarrassed?
31. Have you ever been embarrassed by a comment or joke someone made in front of your friends?
Making an inappropriate joke or comment in front of friends can be a humbling experience, especially when everyone is laughing at you. Have you ever been embarrassed by a comment or joke someone made in front of your friends?
32. Are there any embarrassing pictures of yourself that are floating around online for all to see?
Embarrassment can be amplified when it’s documented by a picture or video and shared online for everyone to see. Are there any embarrassing pictures of yourself that are floating around online for all to see?
33. Do people ever tease you about something that happened in the past because it was so awkward or embarrassing?
People can sometimes hold on to embarrassing moments from the past and tease you about them whenever they get the chance. Do people ever tease you about something that happened in the past because it was so awkward or embarrassing?
34. Is there anything from your childhood that still makes you blush when thinking about it now?
Sometimes, memories of embarrassing moments can last a long time and still make us blush when we think about them. Is there anything from your childhood that still makes you blush when thinking about it now?
35. Is there any embarrassing thing that you said to someone when you were younger and still think about it now?
We all have said something to someone in the past that we regret and still feel embarrassed about it now. Is there any embarrassing thing that you said to someone when you were younger and still think about it now?
36. Have you ever been in an awkward situation because of something stupid or silly that happened?
Being put in an awkward situation because of something stupid or silly can be embarrassing, especially when other people are around. Have you ever been in an awkward situation because of something stupid or silly that happened?
37. Is there anything from your past that you wish had never happened, but can’t do anything to change it?
We all have moments in our life that we wish had never happened and are not able to change them. Is there anything from your past that you wish had never happened, but can’t do anything to change it?
38. Are there any embarrassing moments in your life where people might know the truth, but don’t want to talk about them?
Keeping secrets and embarrassing moments private can be difficult when people know the truth about them. Are there any embarrassing moments in your life where people might know the truth, but don’t want to talk about them?
39. Are there any embarrassing secrets that you’ve kept hidden from your family and friends?
Everyone has secrets that they would rather keep hidden from their friends and family, even if it is embarrassing. Are there any embarrassing secrets that you’ve kept hidden from your family and friends?
40. Have you ever had an awkward moment because of something someone else said about you?
Being embarrassed by something someone said about us can be uncomfortable, especially when other people are around. Have you ever had an awkward moment because of something someone else said about you?
41. Have you ever been caught doing something embarrassing in front of a lot of people, and if so, how did it make you feel?
The experience of being embarrassed in public can be an uncomfortable one. It can be difficult to cope with the feelings of embarrassment, shame, and humiliation that come with being put on the spot or caught off-guard in such a situation.
42. Is there anything from your teenage years that still makes it hard for people to talk to or look at without feeling embarrassed?
During our teenage years, we often make mistakes or do things that we feel ashamed about in retrospect. These experiences can leave us feeling vulnerable and exposed, making it hard for others to talk or look at us without feeling awkward.
43. Are there any embarrassing stories from your past that you don’t want anyone to know?
We all have embarrassing stories from our pasts that we would rather keep hidden away. Whether it is a one-time mistake or something that happened over some time, these moments can be filled with shame and embarrassment, making us want to keep them private.
44. Is there anything about yourself that makes it hard for people to look at you without feeling embarrassed?
It is common to feel embarrassed when others look at us or comment on our physical appearance. We might also feel self-conscious if we think we are being judged in any way or if we feel like our appearance doesn’t match up with what society deems “normal”.
45. Have you ever been caught doing something inappropriate in public and if so, what happened next?
Getting caught doing something inappropriate in public can be a humiliating experience. It can be difficult to know how to react in the moment and it can make us feel embarrassed or ashamed of our actions.
46. Are there any topics of conversation that make it really difficult for people to look at or talk about without feeling awkward?
Some topics of conversation can make us feel awkward or embarrassed. These topics might include sensitive or personal matters, opinions on controversial issues, and other topics that can be difficult to discuss without feeling uncomfortable.
47. Is there anything from your past that you wish you could erase, but can’t because it’s too embarrassing?
We all have moments from our pasts that we would like to forget. However, these experiences often remain in our memories and they can be difficult to move on from if they are particularly embarrassing or shameful.
48. Have you ever been in an awkward situation with a crush or someone else and if so, how did it make you feel?
Being in an awkward situation with a crush can be nerve-wracking and uncomfortable. We might feel embarrassed or anxious about the situation, making it hard to act naturally and enjoy ourselves.
49. Are there any embarrassing moments in your life that still make your cheeks flush when thinking about them?
We all have moments from our pasts that make us cringe when we think about them. These experiences can be filled with embarrassment and shame, making it difficult to move on from them and forget about the incident.
50. Have people ever teased you about something awkward or embarrassing that happened to you?
Teasing someone about an awkward or embarrassing experience can be hurtful and uncomfortable for the person being teased. It is important to remember that everyone makes mistakes and no one should have to feel embarrassed or ashamed of their experiences.
What’s the most awkward question to ask over text?
That’s a tough one – it depends on the relationship and context. Some potential awkward questions could include: “What do you think of me?”, “Are you seeing anyone else?”, or “Do you have any feelings for me?”
How do you make a guy embarrassed?
Making a guy embarrassed can be done in a variety of ways. The most obvious way is to make fun of him or tease him in front of others. This could be done by making jokes at his expense, telling embarrassing stories about him, or even just pointing out something he did that was seen as socially awkward. Making a guy embarrassed could also involve bullying or harassing him, which should be avoided at all costs.
Another way to make a guy embarrassed is to put him on the spot, such as asking him a difficult question in front of others or calling him out when he makes a mistake. This could be done with kindness, but it still has the potential to make someone feel embarrassed.
If you want to make a guy embarrassed without saying anything, you can do so by making faces or rolling your eyes when he does something silly or embarrassing. This gesture is often enough for someone to feel uncomfortable in a situation and can lead to embarrassment if done consistently.
Finally, if you want to make a guy embarrassed without having an actual conversation with him, try dressing differently than usual when out together in public. Wearing something that stands out from what everyone else is wearing will draw attention and could cause the person to feel embarrassed about their clothing choices.
What is a juicy question to ask a guy?
A juicy question to ask a guy can be anything from light-hearted to deep and meaningful. It all depends on the type of relationship you have with the guy, as well as your comfort level in discussing certain topics.
If you feel comfortable enough, one juicy question to ask a guy could be: “What are your thoughts on marriage and relationships?” This is an interesting conversation starter because it can provide insight into his ideas about love, commitment, and life-long partnerships.
On the other hand, if you want something more playful, a good juicy question might be: “If you could go anywhere in the world right now where would it be?” This is great for getting him thinking about his passions and dreams for travel or adventure. It can also allow him to talk about bucket list items he’s been dreaming of doing someday.
Another fun – yet still meaningful – juicy question to ask a guy is: “What was your most embarrassing moment?” While this may seem like an awkward topic at first glance, it can open up some humorous conversations and allow both of you to bond over shared experiences or funny stories from each other’s pasts.