Asking your girlfriend open-ended, thoughtful questions fosters deeper conversation and intimacy in your relationship. While it’s easy to stick to small talk about school, friends and hobbies, purposefully asking more probing questions shows her you want to truly know and understand her on a deeper level.
The right questions inspire vulnerable sharing as you provide a safe space for authentic self-expression. This builds trust and fondness between you. But it can be tricky thinking of which questions to ask that feel meaningful rather than interrogating.
The following questions touch on many dimensions of her inner world like goals, memories, emotions, opinions and dreams to take your conversations beyond surface-levels into more insightful territory. There’s no need to rapid-fire all these questions in one sitting! Integrate a few at a time naturally when texting or talking in person so she feels comfortable opening up at her own pace. Deepen your connection through the power of intentional, thoughtful questions.
Childhood & Family
• What traditions did your family have when you were young that you loved the most?
• Who would you say has been the most influential person in your life so far and why?
• What is your best memory from grade school? And your most embarrassing?
• Which family member are you closest with and why?
Personality & Self-Image
• How would your friends describe your personality? Would you describe yourself differently?
• What are some of your best and worst personality traits?
• What is your biggest insecurity? Know I am here to provide reassurance if you want to talk through it at all.
• What personal accomplishments make you most proud when you look back?
• Do you consider yourself more of an introvert or extrovert? How is that aspect of your personality apparent in your life?
Life Outlook & Goals
• What would you say is your life’s purpose or mission?
• Where do you see yourself in 5 years? 10 years?
• What are you most excited about or looking forward to in the near future?
• What’s on your bucket list for things to do over your lifetime?
• If you knew you couldn’t fail and money was no object, what dream would you pursue?
Core Values &Beliefs
• What principles or causes are most important to you?
• Which of your values come from your upbringing versus values you’ve chosen for yourself?
• What’s one thing you would never compromise your ethics on?
• What social issues or politics are you passionate about?
Hopes & Dreams
• If a genie granted you three wishes right now, what would you wish for?
• What are your secret superpowers or hidden talents? Share one with me!
• What would your dream house look like if you could design it however you wanted? Walk me through the details!
• Where’s your dream travel destination and what about this place appeals to you?
Favorite Things
• What’s your favorite book? Why did it impact you?
• What movie comforts you every time you watch it and why?
• What music inspires you, pumps you up or matches your moods?
• What’s been your best concert experience seeing a favorite band live?
• Which fictional character or celebrity do you relate to the most?
Emotions & Fears
• What makes you feel most loved/appreciated?
• What never fails to make you happy, even on stressful days?
• What irrational fear have you never quite shaken?
• What’s something that comforts you instantly when you’re sad?
• What bad habit are you trying to break right now? How can I help?
Our Relationship
• What first attracted you to me when we met?
• What do you think is the key to maintaining a healthy relationship long-term?
• What dating “green flags” have you noticed about me so far? 😉 Share a few so I know what you value!
• How do you typically prefer to handle disagreements?
• What dating experiences or qualities are important to avoid repeating from past relationships you’ve had?
Hypothetical Scenarios
• If you won the lottery tomorrow, what causes would you support or how would you help others?
• Where would we go and what would we do if we could take a whole year off to travel together?
• What would your reaction be if aliens made first contact with Earth? Would you try communicating?
• If you could live in any alternate reality scenario (fictional world, period in history, etc), which would you choose?
Fun “This or That” Questions:
• Mountains or beach vacation?
• Marvel or DC movies?
• Sweet or salty snacks?
• Hot or cold weather?
• Apple or Spotify playlists?
• Online or in-person classes?
• Super strength or ability to fly?
In final analysis
Asking thoughtful questions—from playful this-or-that’s to vulnerable shares about values, dreams and fears—deepens intimacy and understanding between partners. Keep these suggestions handy for taking any conversation to a more meaningful place. Prioritizing quality conversations guarantees you’ll grow closer through ever-richer understanding of each other’s inner worlds.
