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100 questions to ask your boyfriend

Learn more about your sweetheart with these insightful prompts.

You’ve made it past the first date. And the second. And the third. Each time, you dazzled this guy with your personality, impressed him with your intelligence and probably make him laugh, too. Now that you’ve taken your relationship to the next level and he’s officially your boyfriend, open, honest communication is more important than ever.

One way to facilitate such dialogues is by asking good questions. Curiosity, after all, has the power to make or break a relationship. “Good, meaningful, foundationally-secure relationships with partners who are lovingly, vulnerably invested in the continuation of that relationship are so often tanked or ended by a lack of curiosity in both or one partner,” says psychotherapist Taylor Orlandoni, M.A., M.Ed., LMHC in New York City. “As soon as we stop being curious about our partner and their internal world, their desires, their hopes — we are at risk of simply assuming we know what our partner wants or means.” 

That’s why Oralndoni says so much of a couple’s work is in the reinstallation of curiosity. “You and your partner are constantly evolving and there is always more to learn,” she says, adding that questions can range from deep (“What’s something I do that makes you feel loved and safe?”) to playful (“If someone asked you to write a blurb about me, like the ones for authors on the jackets of their books, what would it say?”).

Ahead, there are 100 more questions to ask your boyfriend — whether you want to deepen your relationship or simply want a few conversation starters for long car ride.

Questions to ask your boyfriend anytime

  • What’s a food you’ve been craving recently that you want to cook together this weekend?
  • What’s your favorite movie or TV character from childhood?
  • What’s an interesting podcast you listen to that you think I would like too?
  • What’s the best piece of advice you’ve gotten this week?
  • If you could be any video game character, who would you pick?
  • If you could invent a new ice cream flavor, what would you call it?
  • Is there anything new you’re passionate about lately?
  • If you won $1 million but could only spend it on an experience, what would it be?
  • If you could attend any sports game in history, what would it be?
  • If you could have any super power for the rest of your life, what would you choose?
  • What’s an athletic challenge that’s a dream of yours to complete?
  • If you could live during any era but this one, which would you pick?
  • What’s your favorite thing to do after work?
  • What do you get complimented on the most?
  • If money were no issue, where would we go on vacation?
  • What’s the funniest thing to happen to you all month?
  • Do the holidays stress you out or do they make you happy?
  • What’s a collection you wish you started years ago?
  • What does your perfect day with friends look like?
  • What’s your favorite place to visit in your neighborhood?

Serious questions to ask your boyfriend 

  • Do you have any regrets about our relationship?
  • What do you see for our future?
  • Do you think we’ll move in together?
  • What’s your biggest fear about our relationship?
  • What could I do to support you better in our relationship?
  • What’s your attachment style?
  • What’s your love language?
  • Do you think we handled [XYZ] fight well?
  • How could we communicate better as a couple?
  • When you’re in a bad mood, what should I do?
  • Do you hope to get married one day?
  • Do you hope to have a child or children one day?
  • Would you ever relocate for our relationship if I had to move somewhere else?
  • Could you be in a long-distance relationship?
  • When did you know you wanted to be my boyfriend?
  • How would you describe our relationship to others?
  • Do you feel like we spend the right amount of time together?
  • Do you see us as compatible long-term?
  • What do your closest loved ones think about our relationship?
  • Do you feel like we’re putting in equal effort into our relationship?

Reflective questions to ask your boyfriend

  • What’s your favorite thing about our relationship?
  • What’s an area for improvement in our relationship?
  • Do you have a favorite memory of us?
  • When I’m having a tough time, how does that make you feel?
  • Is our relationship moving at the right pace?
  • Is there anything you wish we had done differently so far in our relationship?
  • What are you most proud of when you think about our relationship?
  • Do you think we both trust each other fully?
  • How is this relationship different from your previous ones?
  • When you’re upset with me, how do you think you handle it?
  • What do you value most about our bond?
  • What’s the most important lesson our relationship has taught you?
  • What’s the ideal amount of time for you to date before getting engaged?
  • Am I different with you in groups than I am alone?
  • Are there any goals you’d like for us to achieve together?
  • How do you think our relationship has evolved?
  • Has your outlook on love changed since we started dating?
  • Do any areas of our relationship need more attention?
  • How do you prioritize our relationship in your life in ways I may not know?
  • What’s something we could regularly do together to strengthen our relationship?

Sweet questions to ask your boyfriend

  • Do you have a favorite ritual that we do together?
  • Are there any love stories that remind you of us?
  • What do you think your loved ones who are no longer with us would say about our relationship?
  • Are there ways I can step up to help you this week?
  • What errand of yours can I run to make your life easier?
  • What’s the nicest thing I’ve ever done for you?
  • What’s a memory of us that always makes you smile?
  • What’s a song that always reminds you of us?
  • Can I share with your family and friends that you did [XYZ] for me?
  • What ways do you think we complement each other best?
  • How many days can you go without missing me too much?
  • What’s a new way that I can show you I love you?
  • Are there any ways I’ve influenced you for the better?
  • What words come to mind when I ask you to describe having me in your life?
  • What lesson do you think could help others from our relationship?
  • Are there any small things I’ve done for you that made you feel extra loved?
  • What’s your favorite gift you've received from me?
  • Do you think we might stay in the honeymoon phase forever?
  • Do you think about me when we’re apart?
  • Do I show up in your dreams?

Random questions to ask your boyfriend

  • Sweet or savory?
  • Snow sports or water sports?
  • What’s your favorite Broadway show?
  • What do you think of horoscopes?
  • What’s one talent I’d be surprised to learn you have?
  • What’s your favorite kitchen tool?
  • What actor would play you in a feature film biopic?
  • How long could you stay indoors without going stir-crazy?
  • Are there any musicians you’d love to see live for the first time?
  • What’s your favorite time of day?
  • Glamping or camping?
  • What’s the best newsletter in your inbox?
  • Have you ever seen a psychic?
  • Fresh flowers or houseplants?
  • Hot sauce or barbecue sauce?
  • Beach or lake?
  • Physical books or e-books?
  • Cold shower or hot shower?
  • Plain water or sparkling water?
  • Do you make New Year’s resolutions?