50 Personal Questions to Ask a Guy (That Really Open Him Up!) post image

50 Personal Questions to Ask a Guy (That Really Open Him Up!)


In the age of texting as a main mode of communication and using emojis and memes to express how we feel, it’s getting harder to build a deep connection. A lot of us are afraid of vulnerability and there are certain places we just won’t go … and few realize that this is the reason so many people have a hard time building genuine connections.

Asking the right questions can push past someone’s walls and get them to open up. You can learn a lot about one another and really form a deep bond and really get to know someone.

MORE: 225 Questions to Ask a Guy- The Ultimate List 

The following list includes all types of personal questions. Some are fairly mild and others really get in there. Pick and choose what you feel comfortable with, and what you think your guy will be comfortable with. The most important rule is to not push too hard. Know when to back off and let it go when he doesn’t feel comfortable answering something, even if you might really, really want to know the answer.

And with that, here are 50 personal questions to ask a guy to get him to open up:

In what area of life do things never seem to go your way?

When was the last time you cried?

What is your number 1 biggest dealbreaker?

What behavior is always unacceptable?

What is the worst thing one person can do to another (aside from murder or other serious crimes!)?

What is one thing you would change about your childhood?

Do you get overwhelmed often?

Who do you look up to in life?

What was your biggest fear as a child?

What is the worst thing you’ve ever done to someone?

Do you have a good relationship with your parents?

What do you wish you had more of in your childhood?

How do you pick yourself up when everything seems to be going wrong?

Have you ever had your heart broken?

Have you ever broken someone’s heart?

What was the worst day of your life?

What was the best day or your life?

Have you ever lost someone close to you?

Have you ever been addicted to something?

What is the worst lie you’ve ever told?

What is something you always procrastinate on?

Do you believe in soulmates?

Do you think everything happens for a reason?

What is your proudest accomplishment?

What always makes you angry?

What always makes you choked up?

If you could re-live one moment of your life, which would it be?

Describe your perfect day.

What do you like most about yourself?

What do you dislike most about yourself?

What is your biggest irrational fear?

What is one thing no one realizes about you?

What has been your biggest blessing in disguise?

Do your parents have a happy marriage?

Is there anything you wish you could change about your family?

What are you most ashamed of?

Have you ever been arrested?

Have you ever told a big lie and gotten away with it?

Have you ever made a decision that changed the course of your life?

What keeps you up at night?

What is something you wish you were better at?

What keeps people in unhappy/toxic relationships?

What’s something you’re glad you’ll never have to do again?

What will you never allow someone else to do to you?

What is something you appreciate, but often take for granted?

What do people always get wrong about you?

What is the nicest thing anyone has ever said to you?

What lesson do you wish you learned earlier in life?

What makes you different from everyone else?

MORE: 300 Rejection-Proof Conversation Starters 

Conversation Tips

There is more to building a connection than asking the right questions. You also have to be the right kind of listener, this is actually the most important element of being a brilliant conversationalist.

Listen without judgment. Listen without thinking about what you want to say next to make yourself seem charming and hilarious. Take yourself out of the equation entirely and just enter his world and learn what he’s about. Most people don’t do that at all and that’s why people are more self-absorbed than ever.

Being a good listener is a rare and valuable skill. When you can do it right, you will be unlike any other woman he’s ever met, or unlike any other person he’s ever met.

It’s so hard to find people we can be our true, authentic selves with. When you give him that freedom, you become a rare find and he won’t want to let you go.

What if you don’t agree with what he has to say?

That’s totally fine. Just don’t make him feel like a bad person for thinking or feeling a certain way. If you really find it so abhorrent, then maybe he’s just not the right guy for you.

It’s about coming from a place of openness and empathy. Of being able to listen without judgment and express opinions without making the other person feel attacked or ashamed.

Want more questions? Check out these articles:

Amazing Questions to Ask a Guy 

20 Questions to Ask a Guy to Get Closer

Interesting Questions to Ask a Guy

Questions to Ask a Guy [Best Dirty, Funny, Interesting, Awkward, Flirty]

Fun Questions to Get to Know Him Better

I hope this article gave you some good ideas for personal questions to ask a guy to really open him up and form a strong connection. Now I have a question for you. Do you know what inspires a man to commit to a woman? Do you know what makes him see you as a rare gem that he can’t let go of, a woman he wants to be with forever? If not, read this next: The #1 Things Men Desire in a Woman

And now another question. Do you feel like he might be losing interest? Does he seem to be pulling away? If so, you need to read this too: If He’s Pulling Away, Do This...

Take The Quiz: Does He Like You?

Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out once and for all if he likes you...

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