22 Questions To Ask Your Boyfriend To Get Closer Than Ever

You and your boyfriend might be dating, but that doesn’t mean the effort and learning should stop. You should still be getting to know each other and building a strong bond. One of the best ways to do that is to communicate, but not just about how your day at work was or what you want to do in the next five years. I’m talking about questions that will help you to get a deeper knowledge of each other. Here are 22 questions to ask your boyfriend that will take your connection to a higher level.

  1. What’s been your most embarrassing moment? With loads of cringe, this question is filled with greater intimacy. When we see our partner’s vulnerability, it makes us feel closer to them. It’s like peeling back the curtain on their deepest moments. Of all the questions you ask your boyfriend, this one offers one of the best chances to bond. Just be willing to share your own as well!
  2. When do you feel your weakest? Again, this question is all about vulnerability. It’s especially great to ask your boyfriend questions like this if he’s always acting tough and like nothing can hurt him. Does he feel weakest when he’s at a work meeting and has no clue about what’s going on? Or when someone he loves is sick and he doesn’t have the power to help them?
  3. Have you ever been cheated on? If you don’t know much about his previous relationships, ladies, now’s the time to get in there. You can open with this question to suss out what he’s been through. Being cheated on hurts like hell, but people respond to it differently, so this question will give you insights into what he’s like as a man in love.
  4. What’s the best gift anyone’s ever given you? This might sound tame, but it’s a fun question ’cause it can go in any direction. Was the best gift the edible underwear his ex gave him? Was it a letter his sixth-grade student wrote him? Or, was it the Beemer his parents got him for his 18th birthday? See, this will show you some of his deeper layers and what he prioritizes in life.
  5. Do you prefer to cook or wash dishes? This is one of the best questions to ask your boyfriend because hey, chores need to be split fairly. Okay, so hopefully his answer is compatible with yours. If you love cooking but hate doing the dishes, you’d want him to choose washing dishes. Ha! But seriously, this will also show you the type of person he is. Does he love to cook because he’s so creative and imaginative or does he like to do the dishes because it’s the time of day when he can clear his mind? Also, you’d want to hope that he does at least one of those chores to ensure he’s the type of person to pull his weight when living with someone.
  6. What’s your fighting style in relationships? Maybe you’ve already seen glimpses of how he likes to argue, but it’s always good to scratch a bit deeper under the surface. Is he a walk-away-and-slam-doors kind of fighter? Or the type to foster peace and talk it through until 3 a.m. if need be?
  7. If you could meet one celebrity, who’d you pick? This is another one of those fun, light-hearted questions to ask your boyfriend, but it will reveal a lot about him and who he looks up to. Ask him why he’d choose that famous person to learn even more. For example, would he fanboy over his favorite football player ’cause he had dreams to be one himself?
  8. What would you do if your ex texted you? Ooh. Okay, so maybe you know he’s still in contact with some of his exes and they’re mates and you’re fine with it. But, even so, it’s interesting to ask him this question. Would he reply to the text because he’s a cool guy who doesn’t want any enemies, or would he totally ignore it ’cause he’s all about that clean break?
  9. What would you break up with me over? This might feel like a heavy question, but it’s a juicy one. It’s sometimes interesting to step back from your relationship and see what it’s like from your partner’s perspective. It’s also good to know where his boundaries lie.
  10. What do you like the most about me? It’s always good to know what your partner values about you, especially if you haven’t really exchanged “I love you” statements yet. Is it how your butt looks in your sexy jeans? Or is it how you can always make him laugh no matter what? Kudos if he says, “Can I choose more than one thing?”
  11. Would you rather be a working parent or stay-at-home parent? I love this question because it challenges gender roles in our society and shows you where he’s at. It also sneakily brings up the kid question and if he sees himself being a father someday. This is one of those questions you should only ask your boyfriend if you’ve been comfortably dating for a little while.

More questions to ask your boyfriend

  1. If you could have a secret superpower, what would it be? Hmm. Does he want to be invisible? Does he want to be able to hear everyone’s thoughts? Or, does he want enough strength to be able to carry all the grocery shopping in one trip?
  2. What do you like most about yourself? This will show you how he perceives himself. Does he love his toned body (that he works super-hard for at the gym)? Or, does he love how he’s always up for a challenge? Remember, what he values about himself is probably what he wants others to value about him.
  3. Do you believe in soulmates? This question is good to ask at some point because it will show you if you’re on similar relationship road maps. Does he believe in one person he’ll settle down with, or does he think it’s a stupid idea? What else about relationships and love does he find silly?
  4. If you hadn’t dated me, who would you have dated? Okay, so you might have to proceed with caution when asking him this question because it might freak you out to hear that he’d have asked the woman who works at Starbucks and who gives him coffee every morning on a date. But it can show you what his girlfriend type is and what he finds attractive in a woman.
  5. If you got fired from (or quit) your job, what would you do? If he wasn’t constrained to his current job or career, what would he be inspired to do with his life? This is one of those questions you should ask your boyfriend to reveal things about his desires, ambitions, and where he’s headed in life.
  6. What are you most proud of achieving in your llife? It’s good for him to know his talents, skills, and goals. His answer to this question will also show you how seriously he takes himself. Is he most proud of the prank he pulled on his eighth-grade teacher in school? Is he most proud of looking after his sick mom before she died? Is he most proud of working his way up in his company?
  7. What do you do when you’re stressed? If you haven’t been dating each other for a long time, you might not know what he’s like when he’s really stressed out, so this should be illuminating. Does he hit the gym? Does he phone his best mate for advice? Does he turn to booze?
  8. Who understands you the most in the world, besides me? Without you in the equation, who is it that he feels he can open up to without judgment? Who is always there for him? Is it a parent, sibling, friend, or ex?
  9. What’s your favorite way for someone to show you love? This will give you greater insight into his love language and how he likes to receive love. Does he like being told that he’s valued? Or does he like physical touch? On the other hand, maybe he’s all about acts of service?
  10. If your house is on fire, what would you go get (besides me and your pets)? This will give you a clear indication of what’s most important to him. Would he rush back into the fire for his expensive gaming laptop or his Kindle? Or perhaps he’d want to get his favorite jeans. The answer to this question might show you if and how materialistic he is.
  11. What would you want to do when you retire? It’s one thing to have a five-year plan but what about the distant future? Would he want to be lying on a beach somewhere when he’s 70, shooting the breeze and drinking margaritas? Or would he want to retire at 50 so he can travel the world?
Giulia Simolo is a writer from Johannesburg, South Africa with a degree in English Language and Literature. She has been working as a journalist for more than a decade, writing for sites including AskMen, Native Interiors, and Live Eco. You can find out more about her on Facebook and LinkedIn, or follow her on Twitter @GiuliaSimolo.