42 Weirdly Awkward Questions To Ask A Guy or Your Boyfriend

You might have probably been a good conversationalist all your life and have always had your way, be it in debates or negotiating different things with your family or friends; however, starting a conversation with your dream guy or boyfriend on your ideal first date can be somewhat of a wonderful feeling and nightmare at the same time. You could think that things might become so perfect if you had everything that could keep the conversation going planned out, including knowing some awkward questions to avoid. Still, the chances are that things may go in the wrong direction for a while before you start enjoying each other’s company. For instance, bringing up a good conversation and knowing how to sustain it is vital, and the only way to ace it is to be yourself. When you know what to say, it helps boost your confidence and enhance your creativity because you are where you want to be, and your goal is to make the best out of it.

While asking weirdly awkward questions is not bad, you must keep in mind that every guy is different. What works for one may not necessarily work for the other. Therefore, it is pertinent to know which questions will work best for your guy. Also, keep in mind some of the questions that need to be avoided not to ruin your chances of having a good outing.

On the other hand, relationships could be somehow boring and uninteresting over time, especially when you seem to have gotten used to a particular routine. At this point, spicing up things a little bit might be all you need to reignite the spark between you and your partner. And, while there are many ways to go about this, asking some weirdly awkward questions can do the magic for you.

That being said, below are some weirdly awkward questions to ask a guy or your boyfriend in your next outing to keep the conversation going. You can also check out flirty questions to ask a girl or your girlfriend.

A Collection Of Weirdly Awkward Questions To Ask A Guy

questions to ask a guy or boyfriend

1. Have you ever starred in an amateur or professional video?

Probably, he may have good looks and smart appearances like that of a celebrity or dancer. You may never know; this question could make them tell you more about their craft or what they have done.

2. Do you have any old friends you wish you could meet up with again?

Everyone has one or two friends they wish they could meet up with some time in life and asking a guy this question could end up taking him on a journey down memory lane.

3. What do you consider is the most important piece of furniture in a house?

This has to do with individual personalities, and whatever his answer might be may trigger off uncontrollable laughter because this is really an awkward question to ask a guy.

4. Do you lick the spoon clean after making something sweet?

Some people have the habit of licking even the plate after eating something sweet and don’t be surprised he might be on that lane too.

5. Which would you rather have if you had to, a broken leg or a broken arm?

To some people, having a broken arm can be much easier to cope with than a broken leg because, with a broken arm, you’d have the opportunity to move around, but with a broken leg, one can be lying down for a long time. Asking this question can get you to know how smart and articulate one is.

6. When it’s your birthday, do you always wear an age badge?

What a funny question! It’s not out of place to wear a badge on your birthday. While some wear badges with write-ups like, “It’s my birthday, don’t ask my age,” others would prefer to boldly write their age. This question will also help you find out their preferences.

7. Who would you say are more attractive, English or Europeans?

Opinions may differ in this regard. While some say Brits are more attractive than Europeans, others may have a different opinion. However, it all depends on personal encounters one might have had with people from these two parts of the world.

8. Could you go out with someone who had a child from a previous relationship?

Dating someone who has a child from a previous relationship isn’t impossible, but it’s somewhat challenging. Depending on what answer he might give, his reasons may or may not justify such an answer. If they see things differently, don’t feel bad but try to respect it because it’s their opinion.

9. If you had to describe yourself as an animal, what would it be?

Sometimes, the best way one can express who they are and what they want to be in life can be through animals. For instance, one can say a monkey because monkeys are great problem solvers and are very intelligent. Although the animal may be strange compared to humans, they have lots of characteristics that can suit anyone applying such in his life.

10. What is the one thing you have done that you would try to discourage anyone from doing?

Some guys might feel embarrassed at this question because they may feel ashamed that you’d laugh at incredibly stupid things they have done. To make it more fun, also try to tell him some of the stupid things you have done as well.

11. How many valentine’s cards did you receive this/last year?

Although not everyone is prone to receiving cards on valentine’s day, you might be surprised if he’s among those who get lots of gifts and cards on such occasions, and be sure that occasions will always be memorable between you two.

12. What potential talents do you think you might have if you worked at them?

While talent is one’s natural ability to do and perform and potential refers to the possibility of doing something but the abilities are not there. To some, it could be music or acting, while to others it could be a comedy and other performances.

13. What’s your favorite musical instrument beginning with the letter H?

Asking someone who loves music or perhaps who knows how to play different musical instruments can lead to very creative and interesting answers. For such people, it would be quite easy to flow when it comes to their field of passion, and if you also share the same passion, then it might just be the beginning of a rollercoaster of love between you two.

14. What is the name of the board game that always ends badly?

You may not anticipate the kind of answer you’d get when you ask your guy this question, especially if he is good at various board games like cheese and the likes. He might just be someone who brings everyone together and tear them apart.

15. Would you rather be the world’s greatest football player or lover?

This is, no doubt, one of the best questions to ask your boyfriend or a guy you are just meeting for the first time. His answer might lead to some more romantic questions. However, it could just end up as just a normal question.
wierd questions to ask your guy16. What’s the most expensive thing you’ve ever broken?

He may have broken something very expensive, be it electronics or personal items, either accidentally or intentionally. Perhaps, asking him this question might give you more insight into their comportment and how careful they can be.

17. If you could change your name to anything, what would your new name be?

Although this is one of the weirdly awkward questions to ask your guy, it is also a very interesting question. As children, one may have had one or two superhero characters as role models, and in this situation, you’d get to hear funny and interesting names that would leave you with laughter.

18. In your lifetime, what piece of tech would you want to be invented?

Absolutely a fun topic to be discussed. There are so many technological advancements in the world, and everyone must have thought of something they wished were invented. Sharing such ideas can be quite incredible, and what’s more? when you both share the same view, it can be really exciting.

19. If your life was a movie, who would play the lead role and why?

Here, you’d be expecting to hear about his celebrity role models, especially movie stars they admire a lot. To some, it may be the actor’s apt portrayal of a movie character that gets them inspired to choose him as a role model. More so, if you both like the same kind of film genre, you might be surprised that his answer won’t be far from your ideal actor.

20. Have you ever had a paranormal encounter? Are you sure they are real or not?

It is not everyone that believes in ghosts and paranormal activities, but for those who do, chances are that they might have encountered one in their lives. Learning about their experience could go along way to enlighten you, especially when you’re too scared and don’t believe that they exist.

21. If you could be trained up in any profession of your choice by top professionals, what profession would you choose?

Choosing a career can be somewhat a herculean task, especially when you have no idea what you want to do. He might have chosen a different career part, but asking this question will take you guys back to when it all started, and how you decided on your future career and goals.

22. Have you ever walked out of a cinema before the film was done?

This may be hardly something no one would be proud of, “walking out of a cinema before a film was done.” Although there may be a couple of reasons that would lead to this, it is not everyone that can be comfortable with it. You can go further to share your own experience if you have had a similar one.

23. What is the most sumptuous meal you can prepare?

Some people are food lovers but are not good at cooking. By asking this question, it creates an avenue for you to find out if he can cook delicious meals, and see if you can convince him to cook you his favorite food.

24. If you had to describe yourself as a flavor, what would it be?

It will be quite funny and interesting to find out how creative they can be. The answer you’d get can make you laugh and roll on the floor as there are different flavors but his choice may not be the commonest of them all.

25. If you could invent brand new baby names, what would they be?

Picking the perfect name for your baby can be one of the most difficult decisions parents have to make. To someone who isn’t a parent yet or about to be a parent, you may get answers that might leave you with rib-cracking laughter.

26. What part of your body would you replace with an improved mechanical version?

Guys love tech stuff a lot, and asking this question will leave you stunned. From cyborgs to robots, you will hear all kinds of stuff, and this will make your conversation worthwhile.

27. If you were the ruler of your own country what would you call it and what title would you give yourself?

Time to find out what a world of his own can be like and how he can make things happen if he had the opportunity. Such a question can also show you if he watches too many fairytale movies and fantasizes a lot.

28. If you win a lottery of $10 million, what would you do with it?

Quite a creative question. We all like winning, but not too many people can outrightly say what they can invest their money on. Asking him this question will help you understand how smart and creative he can be when it comes to investment.

29. If there’s one meal you could eat for the rest of your life, what would it be?

Someone’s love for food can influence any answer you’d get by asking this question. Finding out about his best meal isn’t such a bad idea, though the answers may be insanely funny because there are foods that one can eat for the rest of life, which would result in vitamin deficiency.

30. Do you have a list of things to do before your ‘x’ years old?

While asking this question, bear in mind that you can replace the x years old to a specific age you have in mind; for example, 50 years old. There are a million fun things one would wish and want to do before getting to a particular age and they differ from person to person. To one, it might be to travel around the world, and to another, to attain a particular height in their profession.questions to ask a guy 31. What’s your favorite actress beginning with the letter J?

This question can either be right or wrong. If his favorite actress’s name starts with the letter J, then it would be sweet; otherwise, you won’t get an answer for it. However, some people do have more than one favorite; who knows? he might be one of them.

32. If you were comfortably rich, would you work hard for more or rest on your laurels?

Some people can become too lazy to work when they feel they’ve had enough. Hence there’s no need to do anything else. This question can trigger off wonderful answers and would also help you find out if he is such a person, and match it with your own views.

33. What fact do you wish you had never learned?

When one learns something, it will be hard to unlearn them, except in some cases. However, asking this question would definitely fetch some surprisingly creative answers.

34. I am a born sinner; do you wish to risk the fiery depths of hell with me by ordering that chocolate cake?

This might be the height of asking weirdly awards questions to your guy or boyfriend because this question is not just flirty but can easily be misunderstood. Either way, your primary aim is to keep the conversation going and have fun in the process. So it won’t be out of place to ask him such a question.

35. Have you ever made your own orange juice?

Nothing could beat the taste of a freshly made juice. This question would help you understand his favorite fruits and why he loves them. You’d also get to share yours and ask him to prepare his best juice probably on your next date.

36. What is the most insane thing you have ever done?

Everyone has done one or more insane things at some point in their lives, and while he may be ashamed of some of those things, don’t hesitate to follow up with your own experiences. That would make the conversation more interesting.

37. If you could have any celebrity hair, whose would it be?

As far hairs are concerned, it means a lot to the guys, and asking questions about hair and looks could make your outing more fun. We all know that some celebrities have nice looking hairs, which have become talking points over the decades, and what could be more soothing than to find out that your boyfriend or crush appreciates such nice looks.

38. If you could see any band, which would you like to see?

There are several musical arts one might have seen when they are young and would wish to see them now if they have the opportunity. Depending on their choice of music genre, who knows? You might find yourselves liking the same band.

39. Do you prefer Honey or Jam?

This has to do with choices; you might find out what you both share in common. For instance, you may like honey and he like jam, which would give you more insight into their personality. If it’s your crush or your dream man, try to be open. It’s not bad if you both don’t like the same thing.

40. Do you believe in destiny, fate, or free will?

Fate is the destiny that is pre-planned for you, but it’s up to you to do something with it. One’s free will determines whether or not they take them while fate brings opportunities. Discussing such a topic may lead to a more interesting conversation between you two.

41. What is the fantasy that makes you tremble every time you think about it?

We all have different experiences, and for some, when you remember them, it will leave you frightened. Recounting such fantasies, one may need someone to assure and encourage them. More so, telling them that you understand, will go a long way in reducing their fear.

42. What is the craziest idea you have ever had?

When you ask this question, if he is not a shy person, he will go deeper into dishing out all his fantasy ideas and things you might not have expected. However, you should be nice to also tell him your craziest ideas too.

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Alexander
Alexander
Alexander Hamilton is a fun-loving, seasoned writer, and researcher. He holds a masters degree in communication and hopes to get his doctorate soon. His passion is to share his knowlege through writing.

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