21 Questions to Ask Your Boyfriend

What is one memory of us you replay when you miss me?

What was going through your head on our first date?

What is something I do that you find adorable without realizing?

When did you first realize you wanted to be with me?

What is your favorite thing about how we handle disagreements?

What is one thing you want us to do every single week?

If our relationship had a soundtrack, what song opens it?

How have you changed since we started dating?

What is your favorite way I say your name?

What is one thing you brag about me to your friends?

What is the most at home you have ever felt with me?

What is something you want me to always know about you?

What is your favorite outfit I wear?

What holiday tradition do you want us to make our own?

What is the best date we have ever been on, and why?

What is something small I do that means more to you than I know?

What is one thing you would love to hear me say more often?

What is your favorite photo of us and why?

What is something you were afraid to tell me at first?

What do you think is our superpower as a couple?

What is something you are proud of that you rarely mention?

What is a worry you carry that you could share with me?

What is the best decision you made this year?

What is something you used to care about that you have let go of?

What is a compliment that actually changed how you see yourself?

What is something you are better at than you give yourself credit for?

What is one thing that instantly ruins your mood?

What is one thing that instantly fixes your mood?

What is a fear you have conquered, and how?

What is something you believe that most people around you do not?

What is the hardest goodbye you have ever said?

What is one thing you wish your younger self knew?

What is a moment that changed how you see the world?

What is something you are quietly working on improving?

What is the most misunderstood thing about you?

What is something you need more of in your life right now?

What is something you have too much of in your life right now?

What is a small kindness from a stranger you never forgot?

What is the best advice you ignored but later followed?

What is one thing you want to be remembered for?

What is one trip you are determined we take together?

Where would you love to live with me someday?

What is a goal you want us to crush as a team this year?

What does your ideal ordinary Tuesday with me look like?

What is something you want to build with me — a home, a business, a tradition?

What is one milestone you are excited for us to reach?

How do you picture us in ten years?

What is a skill you want us to learn together?

What is one thing you want to teach me?

What is something you want me to show you how to do?

What is a pet name you secretly want me to use?

What is one rule you think every couple should have?

What is something you want to stop doing as a couple?

What is something you want to start doing as a couple?

What is one thing you would defend about our relationship to anyone?

What is the most romantic thing you imagine doing for me someday?

What is one thing you want to apologize for that you never did?

What is one thing you want me to apologize for?

What is a promise you never want to break with me?

What is one thing you hope we never stop doing?

If we had a couple theme song to walk in slow motion to, what would it be?

If we robbed a bank together, what would each of us be in charge of?

If we were stuck at an airport overnight, how would we survive?

If we entered a talent show as a duo, what would our act be?

If we had to eat one meal together every day for a year, what would it be?

If we could adopt any animal together, what would it be?

If our relationship was a reality show, what would it be called?

If we swapped bodies for a day, what would you do first?

If we could instantly master one dance, what would it be?

If you had 24 hours and an unlimited budget for us, what is the plan?

What is the silliest thing you have done to impress me?

What is the weirdest thing you find attractive about me?

What is one guilty pleasure of yours I should know about?

What is the most embarrassing thing your family knows about you?

What is a conspiracy theory you find weirdly entertaining?

What is one value you will never trade away?

What is something you think you were born to do?

What is a hard lesson a past relationship taught you?

What is one thing you want your future family to look like?

What is something you think makes a man a good man?

What is one thing you hope to carry from your family into ours someday?

What is something you think we handle better than most couples?

What is one thing you think we should ask each other more often?

What is a boundary you are glad you set with me?

What is something you forgave me for that I never knew about?

What is something you want to forgive yourself for?

What is one thing money could never buy that we already have?

What is the most generous thing you have ever done?

What is something you want to stand up for, no matter what?

What is one thing you would change about the world if you could?

What is your favorite part of the day to text me?

What is one small routine of mine you secretly love?

What is your favorite meal I have made or ordered for you?

What is one thing you do every day that you think I do not notice?

What is your favorite way to spend a lazy day together?

What is one thing you would add to our weekends?

What is your favorite thing about my cooking — or my takeout orders?

What is one thing you wish we did more of on weeknights?

What is your favorite place to sit next to me?

What is one thing you look forward to when we are apart?

What is the most romantic dream you have had about us?

What is one thing I could text you that would make your whole day?

What is your favorite way to say goodbye to me?

What is one thing you love about holding my hand?

What is one thing you want to whisper to me right now?