Dirty Questions To Ask A Guy To Get To Know Him Deeper

When you’re getting to know someone, it’s important to ask questions that will allow you to get the most out of the conversation. You want to figure out what makes them tick, what makes them happy and sad, and ultimately whether or not they make a good partner for you. To do this effectively and efficiently, we’ve created a list of interesting questions that will get your guy talking about himself without sounding too “interrogative” or “investigatory”. If you want to find out more about him in an organic way (and have some fun while doing it), use these questions as a guide!

Do you ever compare yourself to other guys/girls?

Do you ever compare yourself to other guys/girls?

This question is a little different from the previous one because it focuses on what you think is important in relationships. You can use this to see if he has any regrets or insecurities about his past relationships and get a sense of what he values in people and relationships. If he says yes, then ask him why he feels like that. That will tell you more about his needs, wants, and desires.

What do you think a perfect life is?

What do you think a perfect life is?

Well, to me, a perfect life is one that is free of stress and worry. I like to be able to go out on the weekends with my friends and have fun without having to worry about paying bills or other responsibilities. A perfect life would also be full of adventure. I love being outdoors and seeing new places so I think it would be nice if there was a place in which I could do this for fun. Finally, another quality about my idea of “perfection” would be that there are no worries at all! If we all had everything we wanted (food, shelter etc.), then we wouldn’t have anything else weighing us down on our minds which sounds like heaven!

What has been your worst relationship?

The worst relationship is a great way to get to know a guy’s self-esteem issues. This question will help you understand what he values and what he doesn’t. It also helps you get an idea of how far someone can go for love, so if you’re looking for someone who will stand by your side no matter what, this question could serve as an indicator of that trait in him.

If the relationship ended because he was cheated on or it just didn’t work out, ask him why he stayed with them as long as they did. If they cheated on him multiple times, ask him what made him stay despite all the red flags waving around their heads like flags at a football game.

Do you like me as a friend or something more?

Do you like me as a friend or something more?

How can I tell if a guy likes me?

How do I know if a guy likes me through text?

Why is it so hard to tell if a guy likes me?

Is there any way I can figure out if he likes me body language-wise, without sounding like an insane person when asking how he feels about my body?

Do you prefer making plans or following along with what someone else planned?

This is a good question because it’s not just about how you prefer to plan, but also how you feel about other people planning for you.

If you’re the type of person who likes to make plans in advance, then this question will help you figure out if your partner is the same way. For example, do they have an organized calendar full of scheduled activities? Or are they more spontaneous and prefer going with their gut? If so, that’s great! But if not—if your partner doesn’t like having a schedule planned out for them—it could be a sign that there are some underlying issues that need to be addressed.

Have you ever done or accomplished something you never thought you could?

Have you ever done or accomplished something you never thought you could?

In life, the more we achieve, the more confident we become. When we begin to achieve more things, our confidence increases and we feel like anything is possible. This can be a great feeling! It also means that if we don’t have goals and a plan in place for what we want to accomplish in life, there’s no way for us to reach our full potential. So ask this question on a date if you want him to open up about his aspirations and goals for his future so that he’ll see how much confidence is oozing out of your pores right now because you’re such an achiever!

Do you have a hard time accepting compliments? Why or why not?

Compliments are different from flattery. Compliments are meant to be genuine; they’re a way of saying “I see you and I appreciate what you’re doing.” But when it comes to sharing compliments with men, especially if you’re new acquaintances or just beginning a romantic relationship, it’s important to tread lightly. Asking questions about compliments can help you understand your man’s views on receiving praise—and whether or not he has an issue accepting positive remarks about himself. It’s possible that he was raised in an environment where he felt discouraged from acknowledging his own talents and achievements because that would mean he thought highly of himself—which is often considered taboo. Or maybe he feels like any statements people make about him aren’t true anyway; if so, this question will give him an opportunity for self-reflection about why that might be the case (and how it might be affecting other areas of his life).

If your guy says yes: He might need help understanding how people can get away with giving fake compliments without meaning them at all; if this is something that happens regularly in his life (maybe at work), then think back on some of the things people have said to try and find any patterns between them so they can work towards getting rid of those issues once and for all!

What are some things that sound like compliments but are actually insults?

There are many things that sound like compliments but are actually insults. For example, if someone tells you that you have nice skin, this can be interpreted as a compliment. However, it is also considered an insult because it implies that the person has bad skin and is trying to hide it with makeup. A few examples of other common compliments disguised as insults include:

  • You look so skinny!
  • Your hair looks so healthy!
  • You’re not wearing any makeup today!

How old were you when you had your first kiss and who was it with?

You may be curious to know how old they were when they had their first kiss, and who it was with.

Why do you think you remember it so well? How old were you? Who was it with? Where was it? What was it like? What was your first kiss like? How do you think that person feels about you now?

When was the last time someone checked in on you just to see how you were doing?

You should ask your friend to take action.

If they are not taking action, encourage them to act and ask them what they are doing to improve their situation.

Ask them to follow up on their progress.

If they are taking action, tell them how proud you are of them and encourage more of it.

When have you felt your biggest adrenaline rush?

When have you felt your biggest adrenaline rush?

What was the best thing you ever did that scared you the most?

When driving, when doing an extreme sport, or when doing something you were not supposed to do. What is the most dangerous thing you have ever done?

These questions will help to get to the heart of the matter

These questions will help to get to the heart of the matter:

  • “What do you think about when you’re alone?”
  • “What is one thing that makes you happy?”
  • “When was the last time you cried?”

These questions will not help get to the heart of these matters:


You’ve learned some great questions to ask a guy, but you can also use them as an inspiration for your own. Just remember that the goal is not just to get a funny answer, but to learn about who he really is and what makes him tick.

The main takeaway from this article is that if you’re going to ask someone out on a date or get to know them better, you should do it in person rather than over text messages. If it doesn’t work out then at least there wasn’t any awkwardness between the two of you afterward!

Leave a Comment