30 Deep Questions To Ask If You Really Want To Get To Know Someone

30 Deep Questions To Ask If You Really Want To Get To Know Someone

For all of those conversations that go until 4 a.m.


We've all been there at some point. You're up late, on the phone with the person you're crushing on/talking to/S.O./friends, etc. and suddenly the conversation comes to a halt and there's silence on both ends. (This has happened to me a few times.)

What do you do?

Well, chances are, that's how you found this article (or maybe not). So if you really want to get to know someone (crush or otherwise) on a deeper level, here are 30 deep questions that you could ask in order to really get to know someone.

1. What's one thing you would change about yourself?

Is it good? Is it bad?

2. Have you made any decision(s) you regret?


What were they? Why do you regret them?

3. Do you consider yourself more of an Introvert? Extrovert? Ambivert?


Shy and quiet? Outgoing? A bit of both?

4. Who is the one person you can talk to about anything?

For me its my best friend.

5. Would you ever take back someone who cheated?


And if so why? Would you have a hard time trusting them again?

6. What kind of parent do you think you'll be?

Like your parents?

7. If your in a bad mood, would you rather be left alone or talk to someone?

THis question could help you with future conversations.

8. What would be an ideal date for you?

For those who are talking to their crush, S.O., etc.

9. Are you confrontational?

Do you hate conflict?

10. Do you believe in second chances?

If not, why?

11. What's one thing that you learned from a past relationship?

How did it affect you/make you who you are today?

12. What did you want to be when you were younger?

model career

Do you still want to be that thing?

13.  What was your biggest mistake so far in life?


What did you learn from it? Why do you consider it your biggest mistake?

14. How would you describe your best friend?

Funny? Smart? Kind? Caring?

15. What's your biggest pet peeve?

pet peeves


16. If you could live anywhere in the world, where would it be?

world map

17. What are the three most important things you value in a person?

why do you value them? What happens if someone doesn't have theM

18. What is one of your biggest accomplishments?

mission accomplished

Why do you think it is?

19. Who was your favorite teacher growing up?

Why? What do you remember the most about them?

20. What is one thing you learned when you were younger that has stuck with you since?


Why did it stick with you?

21. What is the greatest risk you've ever taken?

take risk

How did it turn out?

22. If asked to say one fact about yourself, what would it be?


This is also one of those questions that we see a lot in big groups.

23. What would you consider your deepest fear?


Note: This can say a lot about a person.

24. Do you have a favorite book(s)? Genre?


What is it? Why do you like it/them?

25. Have you ever been in love?


Tell me about it. What happened? Why did you fall out of love?

26. Is home for you a place or feeling?


Maybe it's a person. Tell me about it.

27. Where does happiness come from?


What does it mean to you?

28. Have you ever been unable to sleep?


Why? What did you do with your time?

29. What is the most adventurous thing(s) you've ever done?

For me, I'd say it was a tie between cave zip lining and repelling down the side of a castle.

30. And one of the most important yet, Cats or Dogs?

You can tell a lot about a person by their preference.

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To The Guy Who Told Me Not To Be Me, Nice Try

He will not silence me.


He told me to never cut my hair short because it would make me look too masculine.

So, I sent him pictures of three different pixie cuts and asked him which one I should get.

He told me not to wear red lipstick because it made me look like a slut.

So, I bought every shade from blush rose to maroon.

He told me not to buy heels taller than one and a half inches tall because it's unattractive for a girl to be taller then the guy she is with.

My favorite shop was having a sell on a beautiful pair of three-inch stilettos. I bought them.

He told me that I was putting on a few extra pounds and that I shouldn't order dessert on our next dinner date.

Did he honestly think I would say no to the red velvet cake that our waitress offered?

He flirted with the waitress, saying that I should "look more like her."

I wrote down his number on our receipt before we left the restaurant.

He told me not to leave my "feminine products" on the counter because it's embarrassing.

When his friends came over for guys night, I organized my tampons and pads nicely on the bathroom shelf.

He told me that I couldn't talk to my best friend of 12 years because he was a guy.

I invited him to watch a movie with us at the local cinema the following week.

He told me not to order wine at the bar with him and his work friends because he didn't want me to seem "trashy."

I ordered jack and coke instead.

He told me not to be a feminist because it meant that I thought I was better than him.

My new "GIRL PWR" shirt is my favorite.

He told me to be silent.

He told me that I think too much and that I speak what I think too often.

He told me nobody cares about what I have to say.

He told me that the things I say don't matter.

So, I wrote a poem about him.

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A Well-Deserved And Long Overdue Thank You To My Boyfriend

I know it's cliché, but he deserves it.


Thank you for choosing me and loving me unconditionally every day. I do not deserve the love that you radiate, but I am beyond thankful for it. Thank you for showing me kindness in every action and for listening to every pointless story I have. Thank you for being the person I can go to 24/7 with any piece of news. Thank you for being the only person who can make me laugh when I am not in the mood at all. Thank you for picking up all of my pieces and wiping all of my tears. Thank you for making sure I always feel loved.

Thank you for believing in pinky promises just as much as I do and for making sure you never break them. Thank you for always reassuring me even though it gets annoying. Thank you for believing in me and pushing me out of my comfort zone. Thank you for knowing when I need a confidence boost, when I need a push, or when I just need a shoulder to cry on. Thank you for taking the time to learn everything about me.

Thank you for never giving up on me no matter how grumpy I get or how hard our week has been. Thank you for never going to sleep mad and always saying "I love you" before we leave. Thank you for the tight squeezes and play fights. Thank you for the deep belly laughs and jam sessions in the car. Thank you for the late-night phone calls when I can't sleep and for doing everything you can to make me better when I'm sick. Thank you for loving me no matter what and no matter when. Thank you for all of the memories. Thank you for holding on tight and never letting go.

Thank you for being everything I could ever want and for showing me what love really is.

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