50 Important Questions To Ask The Guy You're Dating
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50 Questions To Ask Someone You Want To Get To Know On A Deeper Level

Dig a little deeper.

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Just like travel is good for the soul, so is good conversation. Consider getting to know another human being a form of exploration. Similar to wandering through the wilderness, exploring another soul is full of unknowns. You really don't know what you might uncover, or what surprises may lie ahead.

This is not something that can be sufficiently accomplished in minutes, it takes time to fully explore someone's depths and peel back their many layers. All human beings are complex, some more so than others, holding more baggage, trauma, secrets, and stories. But, make no mistake, we do all have baggage.

So be kind and gracious before you make judgments about someone else. The task of uncovering someone's truth, learning their mysteries, their stories, and hidden treasures, is anything but an easy effort. It's one that requires patience and care. Not everyone is open.

Most of us have built up high, sturdy walls to protect ourselves from getting hurt by others. Therefore, it isn't easy to then break them down and there truly is no such thing as an open book. Even the most open people have things they don't like to share or things that are difficult to talk about. One has to take the time, effort, and care to open the cover, turn the pages, and discover the mysteries carefully embedded within them. Keep this in mind before you take off on your journey. Word to the wise, I hope you packed lots of water and a snack because there's a long journey ahead of you!

Whether talking to a complete stranger, a new friend, someone you're interested in dating, your current partner, or someone else special in your life, here are 50 questions and conversation starters to spark deeper and more meaningful conversations. You might just be surprised at what you find!

Would you consider yourself more of an introvert or an extrovert?

Do you believe humans are inherently good or bad?

What was your childhood like? Do you have a favorite childhood memory?

Do you believe in luck, miracles, or fate? Why or why not?

How did you meet your best friend? What are they like and how long have you been friends?

What would you say is your best quality and why?

Name one weakness and one strength of yours.

What is your biggest challenge on a daily basis?

What is something most people don't know about you?

What is something that can always put a smile on your face? What makes you happy?

Do you consider yourself an optimist, a pessimist, or a realist? Explain.

What is one of the best compliments you've ever received?

What inspires you?

When you were younger, what did you want to be when you grew up?

What is your dream job? Are you finding it or creating it?

Where do you see yourself in 5 years? How about in 10 years?

How often do you set goals for yourself? Would you consider yourself driven and/or goal-oriented?

What role does family play in your life? What does family mean to you?

What does an average day in your life look like? Walk me through it.

What are five things you couldn't possibly live without?

After a bad day, how do you like to be comforted? What is your go-to comfort food?

Would you live in another country? If so, which one?

What is your biggest pet peeve?

What is something you are proud of?

Do you believe people can change?

What are your thoughts on love and marriage?

Do you want a family of your own someday? If so, what does this look like?

Describe your dream vacation.

Describe a role model in your life. Who is this person and what do they mean to you?

What is your favorite holiday? How do you like to celebrate it? Do you have a favorite tradition?

In your opinion, what are the key components to a happy life?

What is one thing you would change about our society?

At this moment, what are three things you are grateful for?

Is there a quote or saying that you live by?

Tell me something that's happened in your life that's made you a stronger, better person. Has there been a time where something has truly tested you?

What is one lesson in life that you've had to learn the hard way?

What is your biggest fear?

What are your guilty pleasures or favorite pastimes?

If your life was a novel, what would the title be?

Describe yourself in just five words. If your friends and family had to describe you in one word, what would it be?

What is the first thing you notice about the opposite sex?

If you could have a superpower, what would it be? Explain.

Where do you want to travel? What places do you desire to see?

Name three things on your bucket list.

What is the wildest thing you've ever done?

Where do you go when you feel like escaping, need to be alone with your thoughts, or find peace?

Where is one place you feel most like yourself?

Would you rather time travel to the future or the past?

In your opinion, what is the true meaning of life? For what purpose were we put on this Earth for?

When you leave this life, how do you want to be remembered?

Be curious, explore people, see how far the connections in your life can go, as well as what meaning they hold. I hope this was helpful for you... from wherever you may be reading this.

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