Childhood & Family Questions
• What’s your happiest childhood memory? Who was there and what made it so special?
• If you could have had any other name growing up, what would you have picked?
• What were you irrationally afraid of or obsessed with as a little kid?
• How would you describe your personality and role in your family growing up?
• What family traditions, meals, or inside jokes do you look back on most fondly?
• Which relatives had the biggest impact or influence on your life and values?
• If your childhood self could see you now, what would she think or feel?
Looking Back on Relationship Firsts
• What were your first impressions or thoughts when we met initially? Be honest!
• What moment, outing, or conversation do you remember first making you see me in a romantic way?
• Which “firsts” do you reminisce over most from our early dating days?
• What’s the most daring, spontaneous thing we did in our relationship’s early stages?
• If you had one chance for a re-do on our first date, what would you have done differently?
• What initial trait or quality of mine first made you realize I could be “the one”?
• How has your impression, perspective, or feelings about me and our relationship evolved?
Learning Her Personality
• What are some of your favorite little-known facts, skills or talents that might surprise me?
• If you had to describe your personality in five words, which would you pick?
• What irrational fears, phobias, or quirks do you have that are unique to you?
• What’s one uncommon belief, opinion or principle you hold stubbornly?
• Which personal strengths or traits are you most proud of? Which could you work on?
• If you could take a break from reality and “be someone else” for a week, who would you want to be?
• If you had an entire day free with no obligations, how would you spend your ideal day start to finish?
Reminiscing Together
• What are some of your fondest memories you look back on from our adventures together so far?
• What little moments or inside jokes make you smile or nostalgic when you remember them?
• If you could re-live or re-experience one memorable day or night of our relationship again, which would you choose?
• What’s one thing I used to do or say when we were first dating that you wish I still did now?
• If you had to choose one time, place and circumstance where you felt the most romantic spark or intimacy with me, what comes to mind?
• Do you remember the last time you felt exceptionally appreciated, cared for or cherished by me? What did I do to make you feel that way?
• Is there a wish, dream or goal you’ve achieved with my love and support that you’re especially grateful for?
Flirting & Intimacy
• What first drew you to find me physically attractive before we got to know each other?
• Which aspects of my personality and romantic efforts still give you butterflies?
• Do you remember the last time I gave an unexpected gesture, gift or romantic surprise that swept you off your feet? What was it?
• If you could plan an ideal romantic fantasy date with no limitations or boundaries, what would you choose for us?
• What are some of your favorite quirky idiosyncrasies, habits or unconscious gestures I have?
• What’s your favorite non-sexual way we share intimacy and closeness together?
• Where’s your favorite overlooked place or way we’ve snuck in spontaneous physical affection?
• What seductive or steamy memory can you not stop daydreaming or reminiscing about these days?
Her Dreams & Aspirations
• If you could achieve any dream or milestone, what would mean the most to you?
• What are some adventures, travels or experiences still on your bucket list?
• What’s a cause, issue or personal belief that you are most passionate about?
• Where do you imagine your life’s journey taking you 5, 10 or 20 years from now?
• If you could pursue any career or endeavor regardless of money or stability, what would it be?
• What personal development goals or skills would you like to acquire?
• How might you want to have a greater positive influence or impact in the world?
Future Visioning
• Based on our dreams and goals, where could you see us living our ideal life together down the road?
• In an ideal world, how many kids would you want to have someday and why?
• If we could develop any unique, unconventional traditions for our future family, what would you want them to be?
• What hopes, dreams or expectations did you have for your life as a kid that you could share with our future kids?
• How important is marriage and would you envision an elaborate or simple wedding someday?
• If you could achieve and conquer any one major life milestone before starting a family, what would mean the most?
• When you envision us as an old, elderly couple, what quirky traits do you hope we’d still share?
Just getting the conversational ball rolling with a few intriguing romantic questions can quickly rekindle feelings of mystery, appreciation, intimacy and chemistry between both of you. Her responses will open your eyes to new angles of her personality, memories, and ambitions. You’ll mine deeper into her heart and soul while affirming her value.
Best of all, these types of curious, affectionate questions will make her feel seen, heard, understood, and adored. She’ll bask in the romantic attentiveness you devote to truly knowing her wants and needs. Before you know it, those nostalgic sparks and pangs of early courtship will come rushing back full force.
The key is to sprinkle these thoughtful questions into your daily doldrum, pose them in the right setting and context, then be an engaged listener as her fascinating commentary unspools. You’ll break the monotony of routine conversations while creating the ideal atmosphere for vulnerability, flirtation and falling in love with her most authentic self all over again. Suddenly, the boredom and conversational ruts will be the furthest thing from both of your minds.
So the next time you find yourselves struggling to chat beyond the day-to-day minimum, get ready with these romantic inquiry starters. You’ll turn any dull moment into an enlightening reminiscence, steamy appreciation, or heartfelt examination of your past, present and future together. That constant curiosity, pursuit of deeper intimacy, and adoration for her stories will keep the spark forever ablaze between you both.
