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18 Epic Awkward Questions to Ask A Guy - Begin A Really Cheerful Talk

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Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Dai ...
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by | | October 21, 2021


Do you want to know the most awkward questions to ask a guy? Look no further because we've got you covered with all the best questions to ask.

I'm the resident expert on conversation starters here. I love writing funny questions for our blogs. No doubt that this list of questions to ask a guy will definitely help you start some awesome conversations.

Let's get started!

Contents

Ultimate List of Awkward Questions to Ask a Guy

When starting a conversation with someone, it's always a good idea to ask questions. Since we provide all kinds of questions for you, maybe it's time to start with something a little different. Asking an awkward question may be counterintuitive, but it might lead you to some interesting conversations.

3 Best Awkward Questions to Ask a Guy

Sometimes, uncomfortable questions are just what you need to break the tension. They'll let the other person open up to you in ways you never expected. If you want a good conversation starter, ditch the small talk and ask a juicy question to get the exchange flowing.

Here are 3 of the best awkward questions to ask a guy:

1. Did you ever pass out in a public place?

Asking this may take the other person aback, but don't worry. It might lead to a funny story. Passing out in a public place may be the craziest thing for some people, but a medical condition or a wild event may cause this to happen spontaneously.

2. If technology advances, would you try and give birth, if that became possible?

I know this may be the weirdest thing to think about for some guys. But, if you're with a man who loves to imagine the impossible, this funny question just might work for you. You can also ask him if he'd like to experience the pain of giving birth, just to see if he can handle it. He may play it all macho, but we all know he'll avoid the pain if he can.

3. What is the stupidest situation you almost got killed in?

This is an interesting question to ask because he'll get to tell you a crazy story. Men are almost always getting themselves into trouble, so this will definitely lead to a great conversation. Find out if your guy friend has done something that you'll be talking about for a long time. If there is something he's done, it may probably be his biggest regret.

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3 Quite Unpleasant But Funny Things To Talk About With Him

Making a man laugh is one of the best ways to connect with him. To do this, you're going to need great funny questions to ask a guy. He'll laugh with you and solidify that bond. These may make him like you back!

Here are 3 awkward questions that will make him laugh:

4. Did you ever get caught skipping classes?

This embarrassing question is a great one to ask when you want to know a little bit about how he was as a student. Getting caught skipping classes is definitely an awkward situation. Ask him why he thought that was a good idea and find out what happened to him when he got caught.

5. What's the funniest thing you ever did while drunk?

This is a fun question to ask because he'll get to talk about what he does when he doesn't know what he's doing. He might tell you about the time he danced on a counter or getting caught peeing on a policeman's bike. Whatever it is, it will eliminate any awkward silence you have between you two. It will definitely get him laughing and talking.

6. Do you have a habit of laughing when being scolded?

This is an interesting question to ask because you'll get to find out if he can handle owning up to his mistakes. It's good to be that girl who pays attention to the signs of whether or not he's a good fit. If he can't handle the truth about his faults, then maybe it's time to find another male friend to entertain.

3 Random Things To Talk About With Him To Break The Awkwardness

Have you ever needed to break the awkward tension with a guy? Maybe you need these random questions to ask a guy and see if you can make him feel more comfortable talking to you. Find out if there is a great question here that you can ask the man you're with.

Here are 3 random questions to ask a guy to break the awkwardness:

7. What's your favorite outdoor activity?

This is a great question to ask because here you'll know if he's an outdoorsy person. He may even turn this into one of those surprise dare questions and challenge you to do his favorite activity. Whether it's hiking, jogging, or even outdoor yoga, try it out and see if you also enjoy the things he likes to do.

8. What superpower would you have and why?

This is a good question to ask because you'll find out what he wants to happen with his life. If he wants to fly anywhere, it means he likes to travel and see the world. If he wants to grant wishes like a genie, it means he wants to help people achieve their goals. Asking an open-ended question like this helps you know him on a deeper level.

9. Your favorite breakfast to have in the morning?

Asking this will let you know what he likes to have when he starts the day. For some people, it's their biggest pet peeve when they are served a heavy breakfast. So, find out if he's someone who enjoys pancakes, bacon, and eggs when he wakes up. Or, maybe he's the type to drink a cup of coffee and a piece of bread in the morning. This way, you'll know what to offer him when the day begins.

3 Awkwardly Interesting Topic To Know About Him

My favorite thing about asking questions is the response I anticipate. So, I know that these interesting questions to ask a guy will elicit some controversial reactions from the guys you'll ask. Make sure to listen carefully as these will show his character.

Here are 3 interesting questions you want to ask, but guys find it awkward to answer:

10. Who should pay for the first date?

Have you ever experienced not having cash on a date? Some women consider it the worst thing to happen on a first date. Find out if he's the kind of man to take the initiative and pay on a first date. If his biggest fear is to turn off a woman, he'll definitely say that he will pay on all dates.

11. When did the saying "looks can be deceiving" really hit home?

This weird question is something that will show you a different side to him. It will reveal how attached he is to appearances. He might even tell the dirty truth and say that he is more into looks than anything else. Pay attention to what he answers because it will tell you a lot about what he values. And if he answers something out of the ordinary, then maybe you'll know it's true love.

12. Have you ever experienced a major heartbreak in a romantic relationship? Details?

A deep question like this will open up a great personal exchange between the two of you. Hopefully, with this question, he will talk about a past relationship that was very meaningful to him. You will know about what broke them up. It will guide you in the future when you do end up together.

3 Awkwardly Sexy Things To Ask Shy Men

Did you ever think about using some flirty questions to ask a guy, but you thought sexy questions were too awkward to ask? Maybe this will be the push of confidence you need. Check out our list and see if any of these work for you.

Here are 3 sexy questions but are awkward to ask shy guys:

13. What's your favorite part of my body?

A dirty question doesn't always have to be a bad thing. It may even lead to a seriously sexy conversation. Asking this personal question will tell you what he appreciates most about you. It's a strange conversation topic, but it will take you to another level with him.

14. If you could choose what I was wearing right now, what would you choose?

Dirty talk can be a good place to start when starting a talk with a guy you like. Just make sure to strike a good balance between being flirty and being serious. You don't want him to think you're into him just for that. Plus, if you ask this question to a shy guy, it will help him open up to you about these taboo things.

15. Whose place do you think has a better interior design? Wanna find out?

If your guy's favorite place is home, this is a good question to prompt him to take you there. Planning to go all the way may be a thing of anxiety for some men, so if he's a little shy, it's okay to initiate it. Let him know that you're open to the idea and see if he wants the same.

3 Embarrassing Things That Are Too Awkward To Ask Men

Once you've established a little comfort in your relationship with a guy, maybe it's time to bring out these embarrassing questions and see if you can peel that shell a little bit more. He may feel a little shy and hesitant to answer, but try it out and see if it makes you or breaks you.

Here are 3 embarrassing questions that are too awkward to ask men:

16. What would you do if I tell you that I am pregnant?

Asking this will tell you a lot about what he will do when faced with a sticky situation. Obviously, you'll be asking this before you're married to the guy. So, be wary of his answer. He'll either be so thrilled or so freaked out that you're having a baby with him. See how he reacts, and with that, you'll know if he's in this for the long haul.

17. Do you think we will end up getting married?

This is another great question to ask if you want to know his commitment to you. If he ends up saying, "Yes, and let's use my favorite song for our first dance!" then you've got a catch. But, if he looks uneasy and worried when you ask this, it's probably a good time to talk about it. No better time than the present, right?

18. Have you ever regretted an affair or a relationship?

Probably everyone has had a relationship they regret, and most of them happened during our childhood. Sometimes, being too attached to a person occurs when it's your first time getting attention and affection. So, let him tell you about that time when he was too invested in a relationship that wasn't really worth it.

All Relationships Are Awkward In The Beginning - Don't Worry It's Normal

It's true. There's a learning curve in all relationships. It's a matter of time and effort. You have to get to know each other deeper for the awkwardness to subside. Little by little, you'll start to shed those hesitations and insecurities. You'll be able to show who you really are and let your guard down.

In the beginning, you'll see each other, and you make it a point to look your best. But then, it will come to a point that you will be fine going out in your sweatpants and flip-flops when you're just out for a drive together. It goes the same with your conversations. At the start, you'll feel the need to use these conversation starters so you'll have something to talk about. You'll need them to fill those awkward silences. But, once you get into the groove of talking to them, it will seem like second nature.

So, don't worry if it's a little tense and awkward in the beginning. You already have a handy list of awkward questions to ask to get to know each other a little better. Plus, asking awkward questions opens up those little hesitations you might have because they poke at the things you may be embarrassed about. Talking about them with your partner builds trust and honesty. Not only will you have learned something new about each other, but you will have also deepened your relationship.

Downloadable and Printable List of Awkward Questions To Ask A Guy

Here is a downloadable and printable jpg/pdf list of awkward questions to ask a guy (right-click the image and select Save Image As…):

Frequently Asked Questions

Do you still have some questions about awkward questions to ask a guy? See if these frequently asked questions can clear some things up.

What are the benefits of asking awkward questions?

Asking awkward questions will make him feel more comfortable talking to you about unusual things. When you ask him these questions, it lets him know that you're open to talking about these things. It will make him feel more open to sharing taboo issues with you and eventually build trust and honesty for both of you.

How can I be less shy in asking embarrassing questions?

You can start with a disclaimer. Say something like, "Hey, I'm about to ask an embarrassing question, and it's totally fine if you don't want to answer." This way, he'll be a little prepared for the question. You will have some time to prepare too.

What should I do to survive an awkward conversation?

Keep thinking of topics to talk about. This list can definitely help you out with that. Also, you can try sharing your ideas and answers to the questions you're asking. It will keep the discussion going. No matter how awkward the conversation is, as long as you're actually talking about something, you'll be just fine.

How do you start a good conversation from an uncomfortable one?

An uncomfortable discussion can actually start good conversations once you both start laughing at what you're saying. Awkward topics can also be sources for interesting discussions. Talking about your preferences, past relationships, and unique ideas can all start great conversations. Just keep it light and casual, so your partner doesn't feel too uncomfortable.

How can I ask a guy awkward questions over text?

Texting is sometimes the easiest thing to start something with a guy. Having some questions to ask a guy over text can also help you create some good conversations. When asking these over text, be sure to add some emojis to keep the exchange fun and light.

How To Make Any Awkward Conversations Fun and Memorable

Are you having trouble making awkward conversations fun? Check out these tips and tricks and see if they can help you out!

Here's how to make any awkward conversations fun and memorable:

1. Always ask the question with good intentions.

Your man will know if you're asking just to make fun of him. But, asking these questions are ways to get to know each other better, so be nice and genuine when you ask them.

2. Offer your answers as well.

Just because you're the one asking doesn't mean that he wouldn't like your input as well. Of course, he'd want to hear your side. Plus, he'll feel a lot better about answering these awkward questions when he knows that you're open to sharing your responses to them as well.

3. Don't push if he doesn't want to answer.

Given that these questions are a little invasive and controversial, don't force him to answer them. Sometimes, there are things that he doesn't feel comfortable talking about, so just let him be. Move on to the next topic or question if he doesn't feel okay talking about them.

More Questions to Ask A Guy

Now that you know all about how to make it less awkward with your guy, you should try out these other questions to ask to have some variety in your conversations.

  1. Once you've made it official, these fun questions to ask your boyfriend are the next ones to try. You'll have a good laugh with them!
  2. When it gets a little dull, these funny random questions can help you start a funny conversation with your man.
  3. If you're having trouble approaching the man you like, these questions to ask your crush may just be what you need.

In Conclusion

Didn't I tell you that these awkward questions to ask a guy are the absolute best? You'll have a great time talking with your guy when you have all the excellent questions to ask.

You no longer need to worry about conversation starters when it gets a little awkward or boring. These funny questions are all about getting to know your partner a little better in a fun and memorable way. Plus, these questions to ask a guy will get him to open up to you a little more. They will deepen your relationship and build your trust in each other.

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