Already Know Everything About Your Man? Ask Him These 35 Surprising Questions
If you’ve already talked about everything, this one's for you.
After years of being together, sometimes it can feel like you're having the same five conversations on repeat. Thankfully, this list of questions is designed to spark new insights between couples who already know each other inside and out.
These aren’t surface-level prompts, but since you’ve already been through a lot together, I’m guessing you can handle what comes up. They’re designed to stretch you past your usual default answers, remind you of who you are as individuals, and see what else is still left to discover together.
Be playful and honest, and try a few tonight. Once one person answers, let the other take a turn. You might be surprised at what unfolds.
The Questions
Fun & Flirty
Questions to spark connection, memories, and intimacy
What’s one thing I do that makes you feel really loved?
What’s a sexy memory of us that you still go back to in your mind?
If we wrote our relationship like a novel, what would the current chapter be called?
What movie, show, or book most reminds you of us as a couple?
What do you miss about our early days that you wish we’d bring back?
If we could make our sex life 10% better with just one small change, what would you suggest?
When are you most in your “flow” state?
What Lights You Up
Questions to uncover what stirs up each other's passion and inspiration
What’s a quote, lyric, or phrase that’s shaped the way you think about life or love?
What’s a piece of art (music, painting, poem, etc.) that is most memorable to you?
Who’s a historical figure you’ve always admired and why?
If you could master any creative skill, what would it be?
What kind of beauty (natural, architectural, fashion, etc.) do you find most interesting?
Reflect & Repair
Questions to explore emotions and deepen trust
Do you feel like there’s anything we’ve swept under the rug and never truly talked about?
Is there a part of you that you’ve changed to make our relationship work?
When did you last feel emotionally distant from me, and why?
Is there something you’ve forgiven me for without bringing it up?
Are there any boundaries you want us to make stronger?
Do you think we’ve changed in the same direction over time, or in different ways?
What would you like to hear more often from me?
What’s something you used to believe about love, but no longer do?
What’s one thing you’ve never fully understood about me?
Which of your friendships do you think have influenced our relationship, for better or worse?
Beneath the Surface
Questions for personal reflection and mutual understanding
What do you think we handled really well as a couple?
What change in yourself are you most proud of?
What is something about yourself you’d like to keep improving?
What’s a belief you’ve developed because of our relationship?
If you could relive one day of your life, what day would it be?
Dream & Build
Questions to help you imagine the future, realign, and grow together
What would we be doing if we quit everything and reinvented our lives tomorrow?
What’s one dream you still hope we’ll chase together someday?
What kind of legacy do you want our relationship to leave?
If you could totally revamp your schedule, what changes would you make?
How can I help you make progress toward your most important goals?
If we made a spiritual habit part of our weekly rhythm, like praying, meditating, or reading, what would you want it to look like?
What role do you think fate, timing, or faith played in bringing us together?
When you imagine us in old age, what scene comes to mind first?