90 Questions to Ask Your Long Distance Boyfriend

If long-distance relationships come with a handbook, page one would probably say, “Prepare to miss them like crazy.” They’re filled with late-night calls, cheesy texts, and way too many “I wish you were here” moments.

Who said love was easy, anyway?

But here’s the thing—distance doesn’t have to mean disconnect. Asking the right questions can make your calls and texts more than just updates about your day. They can be moments to laugh, dream, and get even closer to the person you love.

So, if you’re ready to strengthen your bond and make your boyfriend smile, this list of questions is here to help.

Daily Life and Routine

  1. What’s the first thing you usually do when you wake up?
  2. How do you spend your evenings after work or school?
  3. What’s your favorite part of your daily routine?
  4. Is there something you do every day that makes you feel productive?
  5. What does your ideal weekend look like?
  6. What’s one thing you wish you had more time for during the day?
  7. How do you usually relax after a stressful day?
  8. Are there any new habits you’re trying to form?
  9. What do you usually have for breakfast, lunch, and dinner?
  10. Do you prefer a structured day or a more spontaneous schedule?
  11. What’s the most interesting thing that happened to you today?
  12. What music or podcasts have you been listening to lately?
  13. Do you enjoy your commute, or do you find it tiring?
  14. Is there a part of your daily routine you’d like to change?
  15. How do you usually spend your lunch breaks?

Getting to Know Him on a Deeper Level

  1. What’s the most valuable lesson you’ve learned so far in life?
  2. How do you typically handle failure or setbacks?
  3. What’s a memory from your childhood that shaped who you are today?
  4. Who has been the most influential person in your life?
  5. What’s something you’ve always wanted to try but haven’t yet?
  6. How do you define happiness in your life?
  7. What role does family play in your life and decisions?
  8. Do you believe people can change, or do you think they stay the same?
  9. What’s the one thing you’re most passionate about?
  10. How do you usually approach difficult decisions?
  11. What’s a secret dream or goal you’ve never shared with anyone before?
  12. What does success mean to you?
  13. How do you deal with criticism?
  14. What are your thoughts on forgiveness and second chances?
  15. If you could relive one moment in your life, what would it be?

Strengthening Emotional Connection

  1. What’s one thing you miss most about being together in person?
  2. How can I make you feel more loved and appreciated?
  3. What’s your favorite memory of us so far?
  4. When was the last time you felt truly happy, and what made you feel that way?
  5. What do you think makes our relationship special?
  6. How do you prefer to express love—through words, actions, gifts, or something else?
  7. Is there anything you’ve been wanting to share with me but haven’t?
  8. What’s the most thoughtful thing someone has ever done for you?
  9. How do you usually cope when you’re feeling down?
  10. Is there a specific way I can support you during tough times?
  11. What’s one thing about me that always makes you smile?
  12. How do you feel about the way we communicate with each other?
  13. What’s a fear you’ve been able to overcome recently?
  14. What’s something you’ve learned about love from being with me?
  15. What are some small gestures I can do to make your day better?

Dreams, Goals, and Future Plans

  1. Where do you see yourself in five years?
  2. What’s one big goal you’re working towards right now?
  3. Do you have any travel destinations on your bucket list?
  4. How do you envision your dream home?
  5. What motivates you to keep pushing forward in life?
  6. Are there any skills or hobbies you want to develop in the future?
  7. What kind of legacy do you want to leave behind?
  8. Do you see yourself living in the city, suburbs, or countryside in the future?
  9. How do you balance short-term goals with long-term dreams?
  10. What’s your dream career, and why?
  11. What’s one thing you’d like to achieve before turning 40?
  12. How do you feel about the idea of us living together someday?
  13. Do you want to have pets in the future, and if so, what kind?
  14. How do you stay motivated when your goals feel far away?
  15. What’s one goal you think we can work towards as a couple?

Handling Challenges in the Relationship

  1. How do you usually handle conflicts in a relationship?
  2. Is there something I do that unintentionally bothers you?
  3. What’s your biggest fear about being in a long-distance relationship?
  4. How can we make sure we both feel heard during disagreements?
  5. What’s the hardest part about being apart for you?
  6. Is there anything you’d like me to do differently to support you better?
  7. How do you cope with feelings of loneliness or frustration?
  8. What’s a small habit we can build to make our communication even better?
  9. Do you feel comfortable expressing your emotions to me?
  10. How do you want us to handle disagreements in the future?
  11. Is there a specific time when you felt our relationship was tested? How did you feel?
  12. What’s one thing you think we can work on as a couple?
  13. How do you handle jealousy or insecurity in a relationship?
  14. Do you think our expectations for this relationship are aligned?
  15. What’s a challenge you’ve overcome in the past that makes you feel more prepared for ours?

Romantic and Intimate Topics

  1. What’s one romantic thing you’ve always wanted us to do together?
  2. How do you define romance in a relationship?
  3. What’s your favorite memory of a date we’ve had?
  4. How do you like to show affection when we’re apart?
  5. What’s a small romantic gesture that would make your day?
  6. What’s something you love about our relationship that feels unique?
  7. How do you feel about writing letters or notes to each other?
  8. What’s one song that always reminds you of me?
  9. What’s your idea of the perfect date?
  10. How do you feel about surprising each other with small gifts?
  11. What’s the most romantic thing you’ve ever experienced?
  12. Is there a movie or book that reminds you of our love story?
  13. How do you feel about celebrating anniversaries in a long-distance relationship?
  14. What’s one thing I do that makes you feel truly loved?
  15. What’s your favorite compliment I’ve ever given you?

Final Thoughts

Long-distance relationships aren’t easy, but they’re a chance to prove that love can grow no matter the miles.

Don’t stress about making every conversation profound or perfect. The key is consistency, care, and a willingness to share and listen. These small steps make a big difference over time and remind you both why your relationship is worth it.

Distance isn’t forever, but your connection can be. Keep showing up, stay patient, and make time to truly connect—you’re creating something strong and lasting.

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Bea is an editor and writer with a passion for literature and self-improvement. Her ability to combine these two interests enables her to write informative and thought-provoking articles that positively impact society. She enjoys reading stories and listening to music in her spare time.