Whether you're in a new relationship or years-deep into love, there's always something new to uncover about your partner. That’s where the right questions come in: fun ones, flirty ones, even deep, thought-provoking prompts that spark real connection. Before you know it, a simple question can lead to a meaningful conversation that helps you better understand your significant other—be it your boyfriend, girlfriend, or long-term love.
From lighthearted icebreakers to conversation starters that go way beyond small talk, we’ve compiled 100 questions to ask your partner—designed to help couples learn more, laugh more, and maybe even fall a little harder. Because the best conversations often start with the simplest prompts.
Firsts & Milestones
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What’s your first memory of me?
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What was our first date like for you?
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When did you first feel totally comfortable around me?
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When was the last time you felt truly proud of yourself?
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Do you remember your first big risk? Would you take it again?
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When did you first move out of home, and what was it like for you?
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What was your first big purchase, and did you regret it?
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What was a milestone in your life that completely changed you?
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What was your first love, and your first heartbreak?
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What’s a “first” you still want to experience with me?
Darren McDonald, Ivanka Smilenko
Trust & Boundaries
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What does trust look like to you?
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What boundaries are essential for you in a healthy relationship?
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What’s one value you’ll never compromise on, no matter what?
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What’s a dealbreaker for you when it comes to a partnership?
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Is it easy or hard for you to be vulnerable, and why?
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When do you feel most emotionally safe with me?
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How do you like to be supported when you’re going through something?
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What does loyalty mean to you, and how do you show it?
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What’s something you need in a relationship that can often be overlooked?
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Do you tend to be more idealistic or realistic in love and life?
Sergei Nasonov, Grach Photography
Sex & Intimacy
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What are your love languages? And what do you think mine are?
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What makes you feel most desired?
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When do you feel closest to me?
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What’s something small I do that turns you on?
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What’s something you’ve always wanted to try together?
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What’s a fantasy you’ve never shared before?
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What’s one of your favorite intimate memories with me?
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How do you feel about spontaneous vs. planned intimacy?
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How do you feel about talking openly about sex?
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What other ways do you bring intimacy into a relationship, beyond sex?
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How do you feel about public displays of affection?
Pavel Golubnichy, Melissa Jane Tarling
Career & Financial Mindsets
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What does balance look like to you between work, love, and rest?
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What’s your relationship to money: stressful, strategic, or chill?
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Do you see yourself as more of a saver or a spender?
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Would you rather have a lot of money or a lot of free time?
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How do you define success, and what does “making it” mean to you?
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What’s your dream lifestyle, and what would it take to get there?
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If you could switch careers or be in your dream role tomorrow, what would you do?
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How do you feel about financial transparency in a relationship?
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What are your expectations around finances within a relationship?
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What role do you think each partner should play in contributing to household and shared finances?
Conflict & Resolution Styles
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How do you usually deal with conflict?
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Are there any patterns or topics that tend to push your buttons or trigger a disagreement for you?
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When you're upset, what's your default verbal response: quiet, snappy, or something in between?
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What’s your biggest pet peeve during disagreements?
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Do you prefer to talk things out right away or take time to cool off first?
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What’s one thing that helps you feel heard and understood during an argument?
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What does a real apology look like to you, and how do you say “I’m sorry”?
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Do you believe all fights need resolution, or can you agree to disagree?
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How do you know when an issue is truly resolved?
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What’s something I can do better during conflict?
Personality & Daily Habits
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Are you more routine-driven or spontaneous?
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Are you more of a morning person or a night owl?
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What’s your favorite way to start the day? Do you have any morning rituals?
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What’s your favorite way to unwind after a long day or work week?
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What does an ideal weekend look like for you?
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Do you have any hobbies, passions or side-projects?
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How do you usually respond to stress?
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Do you process things out loud or in your head?
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Do you have any bad habits you'd like to change, or notice any bad habits in me?
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What’s a weird little quirk or habit you have that love about yourself, and about me?
Family Dynamics
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What was your relationship like with your parents growing up?
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What’s one family memory that always makes you laugh?
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How do you handle holidays with family: excited or overwhelmed?
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What role do you usually play in your family?
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How close are you with your siblings (if you have any)?
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How did your family express love?
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What's the biggest lesson you've learned from your family?
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Do you want kids someday, and if so, how many?
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Is there a family tradition you cherish that you’d like to continue?
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What’s something from your upbringing you want to do differently?
Dias De Vinos Y Rosas, Sarah Lazaro
Dreams & Bucket Lists
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What’s a dream you have that you’ve never shared with anyone?
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If money and time weren’t an issue, what would you do tomorrow?
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What’s one thing on your bucket list you hope to accomplish in the next five years?
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What’s something totally out of your comfort zone you still want to try one day?
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What's your dream date?
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If we could plan the most epic vacation, where would we go?
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If you could drop everything and start a new chapter anywhere, where would it be and what would you do?
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Would you ever want to live in another country? If so, where?
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What's your dream house look like to you, and where would it be?
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What kind of legacy or impact would you like to leave behind?
Pet Peeves & Unpopular Opinions
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What’s a “hot take” you stand by no matter what?
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What’s a trend you wish would disappear forever?
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What’s a small thing that irrationally drives you nuts?
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What’s your biggest pet peeve in relationships?
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Do you have a “weird ick” that feels silly but is very real for you?
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What’s something I do that annoys you — but you haven’t told me yet?
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What’s one of your own habits that you know is annoying for others?
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What’s your least favorite chore, and do you ever secretly avoid it?
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What’s one of my quirks that drives you a little crazy?
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What’s a TV show or movie everyone loves, but you just don’t ge the hypet?
Favorites & Fixations
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What's your all time favorite meal, and who made it best?
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What’s your ultimate comfort food, no matter how basic or weird?
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Do you have any guilty pleasures?
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What’s a TV show or movie you’ll never get tired of rewatching?
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What’s your favourite song, and what memory does it recall?
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What is your favorite book, and why?
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If you could only buy your clothes from one store, which would it be?
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What’s your favorite annual holiday, and how do you like to celebrate it?
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What’s one thing that always and instantly lifts your mood?
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What’s your favorite compliment you’ve ever received — and why did it stick with you?
