Personal and Deep Questions to Ask a Lady on a First Date

Are you wondering how and what questions to ask a lady to know more about her? Here we’ve provided a must-read list of Personal and Deep Questions to ask a lady that will help you know her on a more up, close and personal level.

With the right questions, you’ll show her how interesting you find her. The right personal questions perfectly used will make her feel valued and help you truly get to know her.

These questions aim to bring you to a place of better understanding of the lady and how to go about your relationship with her.

In so doing, you’ll get to find out what interests her as an individual and also get to hear more secrets about her that many people around her don’t know. This will make your first date with her a memorable experience.

Whether you want something nice to open up a meaningful conversation with her on a date or through an online chat, this compilation will help you. All you need do is read through, copy and edit these prototype questions to fit your personality and the occasion.

Use these collections of personal and deep questions to ask a lady to your advantage.

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What are Juicy Questions to Ask a Girl?

First impression matters. Asking a lady some juicy questions on your first date or through a chat will make her see you as an interesting person to be with. Thereby increasing your chances…

Here are the top juicy questions to ask a lady:

1. What are the things that interest you about life?

Everyone living on earth has one thing that forms the core of their interests.

And just as we all have different mindsets and opinions about things in life, the things that interest us are formed from our perceptions, ideas and experiences about life.

So getting to know this about a lady helps you align your thoughts and subsequent questions in that regard.

2. What are you most passionate about?

As it is said, “different strokes for different folks“. This is true for the question of passion.

What drives one might not be what drives the other. However, there may be similarities in some areas.

So be sure to ask her this very vital question. It will help you know what she is living for and, in some cases, what she can die for.

3. How do you define friendship? What does that term really mean in your mind?

The definition of friendship, most time, depends on the person being asked. This means we don’t have a particular answer to that question, but the end result remains almost the same.

So please get to know her perspective and opinion about the subject matter and the roles her friends play in her life.

This could also help you know what role(s) to play in her life.

4. What fun activities made your childhood fun?

A flashback down memory lane is one activity that rekindles happiness and brings smiles to people’s faces, especially as you advance in age.

Who doesn’t love reliving a beloved childhood memory? I don’t know any.

At some point, We all wish for those days to come by. Days when you had little, or no worries and all you did was live your life free of concerns.

You will surely enjoy her responses.

5. What is the strangest habit you have?

Everyone has some quirky things they do regularly. As much as it’s not exactly a deep dark secret, it’s often something that they haven’t opened up to tell a lot of people.

And so sharing something as small as nose-picking though slightly embarrassing, is a great way to build mutual trust for one another.

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6. What is your worst date story?

As much as we enjoy telling stories about the past, especially those ones that make us laugh, we could derive more fun from telling stories about dating disasters.

The chances are that she has some good stories to share about dates that turned into train wrecks.

You’ve probably had a fair share as well, so feel free to share yours, too; it’s all part of what makes your conversation interesting.

7. What was the dumbest thing you believed for a very long time?

Myths, beliefs and notions about some things in life can be a bit embarrassing for one to admit.

Especially when you discover that what you have believed in for a very long time was a lie, plus, it can also be good for a laugh.

Try to have one of your embarrassing things you believed ready after her answer so she can laugh at your expense as well.

8. What movie did make you cry the most?

By asking this question, you’ll get to discover what type of things constitutes the basis of emotionality for her and possibly how often she cries at movies.

And if you’ve seen the same movie, you can talk about it, or if you haven’t, you can ask what she found so touching about it.

9. What is the scariest thing you have ever done?

In a bid to make inquiries, be careful with this particular question. It must be approached with utmost care and sensitivity as it could open up old wounds if there are.

Be quick to let her know that you don’t mind skipping the question, and the reason is that, while most of the time, her answer will be something normal and can lead to a good conversation, it can also dig up some traumatic memories.

Just be aware that this possibility exists. All the same, it is a worthy question to ask.

10. What things make you happy the most in life?

Happiness is one thing that we all want to experience always. So when the question about the things that make us happy is asked, a lot comes to mind.

In this context, we could say it’s the perfect question for finding out what she loves most in this world.

Be ready to do a lot of listening as a good number of what she has to say are more of the things that she is passionate about, and so you’re in for an all interesting conversation.

11. What are your hobbies?

Most times, we spend our time on either our jobs or businesses, and these things don’t afford us the time to do the things we’re passionate about.

So asking her this question will help you know the activities that bring fun and help her unwind from the many things that crave her attention.

12. What is a goal you have, and how will you achieve it?

Goals are the objects of a person’s ambition or effort. We can also say that it’s an aim or desired result.

A goal gives a glimpse of the future or desired result that a person envisions.

In this context, knowing her goals, aspirations, and dreams helps you know what role(s) to play in her life.


You will surely open up a great conversation with the twelve questions outlined above. You must also note the personality of the lady involved, just to be on the safe side.

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Personal and Deep Questions to Ask a Lady.

Beyond asking a lady some vital questions that help you know her better, there are some other questions that can stir up in-depth conversations.

Though not really gender-based, these questions are really for anyone who enjoys a good conversation about deep topics.

Don’t forget to make it comprehensive with many details and ensure to ask follow-up questions to find out more.

You’ll find that many of these questions will lead to in-depth conversations about broad topics.

Here are deep questions to ask a girl:

  1. What's the most vital thing in a relationship?
  2. What do you think is the reason why people are lonely?
  3. Can you sacrifice your career for someone you love?
  4. What lies do you most often tell yourself?
  5. What keeps you up late at night?
  6. How do you know when you are in love?
  7. What have you learnt from your past relationships?
  8. How do love and affection play a role in your life?
  9. What is something you've never done that you've always wanted to do?
  10. Have you ever had an unrequited love?

Flirty Questions to Ask a Lady.

There’s always this really exciting feeling that comes with chatting with a girl you’ve got your eyes on.

Whether you are trying to get to know her better or create amazing chemistry in a relationship, there are some flirty and fun conversation starters that will come in handy when the need arises.

Here, we’ve compiled a few of these flirty questions to ask a girl. Try some of these out when texting or talking in person, and before you know it, sparks will be flying.

  1. What physical feature attracts you most in a guy?
  2. What vital qualities do you look out for in a guy?
  3. What do you think is the most attractive quality in a person?
  4. Do you prefer to make the first move?
  5. When will I get to kiss you for the first time?
  6. What was your first kiss like?
  7. What are your biggest turn-on and turn-offs?
  8. What physical attributes do you like most about yourself?
  9. What are your views about sex?
  10. What's your view of "love at first sight"?

Having read and understood these points we have outlined for your consumption, we can confidently say that your outing with your date will be well remembered. All that is required is that you use one of these personal and deep questions to ask a lady. You will be amazed at the magic!

Use them. Copy them. Edit them. And enjoy your friendship.

Let us know if you have any questions or comments.

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