Deep questions to ask your boyfriend
The ones that get past the surface and into who he really is.
Guys do not always get asked the deep stuff. Give him the space and the right question, and you will be surprised what he tells you.
These go past how-was-your-day into who he really is, what he carries, and where he wants to go.
Deep questions for him / About who he really is1 / 72
What do you carry that nobody else knows about?
About who he really is
- 1What do you carry that nobody else knows about?
- 2When do you feel the most pressure to have it together?
- 3What does strength actually cost you?
- 4Who taught you it was not okay to cry?
- 5What do you think about in the moments you go quiet?
- 6What part of yourself do you think I have never seen?
- 7What is something you are quietly ashamed of?
- 8Who are you when nobody is depending on you?
- 9What do you pretend to have figured out?
- 10What do you wish you were allowed to feel out loud?
- 11What do other men see in you that I might not?
- 12What feels heavier than you let on?
- 13Where does your anger go when you do not let it out?
- 14What do you do the moment you feel like you are losing control?
- 15What are you most afraid people would think if they knew you?
- 16What do you need that you never learned how to ask for?
About us
- 17What do you hide from me to protect how you look?
- 18When do you feel like less of a man around me?
- 19What pressure do you feel providing for us that you never say out loud?
- 20When are you most free to just be yourself with me?
- 21What do you think I expect from you that I have never said?
- 22What is something you are scared to disappoint me with?
- 23Do you ever feel like you have to earn being loved by me?
- 24What do you wish I understood about the weight you carry for us?
- 25When have you felt the most unseen by me?
- 26What do you think would happen if you leaned on me instead?
- 27What do you need from me most when you are struggling?
- 28What do you compare our relationship to that scares you?
- 29What do I do that makes you feel most like a man?
- 30How much of your effort do I actually see?
About his past
- 31When did you first learn to hide how you felt?
- 32What did you need as a boy that nobody gave you?
- 33Who told you to toughen up, and did you believe them?
- 34What is a time you needed comfort and did not get it?
- 35When did you first feel like you had let someone down?
- 36What did your father teach you about being needed?
- 37What is a version of you that you are still trying to forgive?
- 38When did being the strong one start to feel like a role for you?
- 39What did an old relationship teach you to protect yourself from?
- 40What is the first time you remember feeling truly alone?
- 41What did you learn about love before you were ready to hear it?
- 42What is a moment from your past you have never fully told me about?
- 43What did you promise yourself as a kid that you have broken since?
- 44Who was the first person who made you feel like enough?
About the future
- 45What are you most afraid you will not become?
- 46What does enough look like to you right now?
- 47What part of your father are you most scared of repeating?
- 48What is something you fear passing on to your kids one day?
- 49What would you have to give up to feel like you have made it?
- 50What are you quietly worried you are running out of time for?
- 51What does winning even mean to you these days?
- 52What do you worry you are sacrificing for success?
- 53What do you think happens to men who stop trying?
- 54How would you define security these days?
- 55What happens if you stop needing to prove anything?
- 56What is a version of success you have let go of?
- 57Do you worry what I would think if you slowed down?
- 58What would it take for you to finally feel like enough?
The ones that take courage
- 59What is something you have never told your own father?
- 60What do you resent that you have never said out loud?
- 61What is the loneliest you have felt since we got together?
- 62What do you doubt about yourself that you have never admitted to me?
- 63Have you ever wanted to give up on us, quietly, and not told me?
- 64What are you most jealous of in other men?
- 65What do you go quiet about when we are fighting?
- 66What kind of help are you too ashamed to ask for?
- 67What do you wish I would just notice without you asking?
- 68What is a fear about becoming your father that you have never said?
- 69What is something about yourself you are still hiding from me?
- 70What do you think would happen if I saw you break down?
- 71What are you too proud to admit, even to me?
- 72When did you last feel like you were not enough for me?
