Deep questions to ask your boyfriend: 40 that go somewhere
Deep questions to ask your boyfriend are the ones he has to think about before answering: about what shaped him, what he is afraid of, what he hopes for and how he sees the two of you. Ask one at a time, in a quiet hour, and answer it yourself as well. Forty follow, in four groups.
When and how to ask
Depth needs time and no audience. A long walk, a drive or the last hour of the evening works better than a restaurant. Ask one question and let it take as long as it takes. Silence after a deep question means he is thinking, so do not fill it.
About where he comes from
The past explains more than opinions do.
- What was the mood in your home when you were ten?
- Who believed in you first?
- What did you have to learn alone?
- Which moment changed the direction of your life?
- What do you miss about who you were at twenty?
- What did your parents never say that you wish they had?
- Which loss shaped you?
- When did you first feel like an adult?
- What were you told about men that you no longer believe?
- Whose approval did you spend too long chasing?
About what goes on inside him
Ask these gently. They are an invitation, not a test.
- What are you afraid people will find out about you?
- When do you feel most like yourself?
- What do you do when you are overwhelmed, and does it help?
- What is hard for you to ask for?
- What would you do if you were not worried about failing?
- What are you still angry about?
- Where do you go in your head when you cannot sleep?
- What makes you feel respected?
- What do you wish you were better at saying?
- When did you last cry, and why?
About what he wants
Hopes are easier to talk about than plans.
- What does a good ordinary day look like in ten years?
- What would you regret not having tried?
- What does enough look like for you?
- What kind of old man do you want to be?
- What would you like to be known for among the people close to you?
- Where would you live if nothing held you?
- What are you working towards that nobody sees?
- What do you want to learn before you are fifty?
- What would you do with a year off?
- What does home mean to you?
About the two of you
Keep your tone curious. You are asking, not auditing.
- When did you first feel safe with me?
- What do I not know about how you love?
- What do you need from me when you go quiet?
- What are we avoiding talking about?
- What have I changed in you?
- When do you feel far from me?
- What is one thing we should protect, whatever happens?
- What do you wish I understood without being told?
- What does commitment mean to you?
- What are you grateful for in us?
Questions and answers
- What are deep questions to ask your boyfriend?
- Questions about his past, fears, hopes and the relationship that need reflection, such as "When do you feel most like yourself?"
- What if he does not want to answer?
- Leave it and answer the question yourself. People often come back to a question hours later, once they have had time.
- How soon is too soon for deep questions?
- Match the question to the closeness. Early on, ask about what shaped him. Save questions about the relationship for when there is one.