19 Insightful Questions to Ask Your Boyfriend to Learn Everything About Him

Arguably the best part of being in a relationship with someone is getting to learn every bit and detail of them, and getting to connect on a deeper level with someone you love. You want someone to understand you, but your boyfriend does as well. When you find yourself wanting to know more, ask him these 19 questions to know just about everything about him, and then some. They're exactly the type of questions that are perfect for those deep parked car conversations, and will give you the opportunity to do something spontaneous in the car besides having car sex

  1. Favorite childhood memory?

    The things we did as kids and how we enjoyed the most pure and innocent times of our lives have an affect on the people we are today. If you wanna know what your boyfriend was like as a kids, or how he spent his time playing outside or with friends, ask him to tell you a memory he holds dearest from those days. Your boyfriend will most likely love to talk about what he was like back then and why the memory he chose to tell you about is so significant to him.

  2. Worst fear?

    A classic one.

    What people are afraid gives insight to their character, and will show a more vulnerable side to your boyfriend that maybe you haven't seen yet. If you know the thing that makes them scared and what they hope will never happen, it'll bring you two closer because he trusts you with that knowledge. If his worst fear is one that you can do something about, then try. If not, you know when and how to help him get through if it ever does. If it's an irrational fear, you see now to support them even if you think it's a bit silly.

  3. Fetishes? Turn Ons? Turn Offs?

    It's a highly important, but often an overlooked step, in a relationship to talk about what you like in sex and what your preferences are. Ask your boyfriend if he has any fetishes you should know about, that way if they're really creepy you could think twice about your relationship, or if you like it you know what to do next time you're in the bedroom together. Turn ons are also a helpful piece of information when it comes to pleasing your partner because you know what's gonna get them horny and in the mood. It's also good to know what turns your partner off so that you never find yourself killing the vibe just before you get wet and he ends up not feeling it anymore.

    Or maybe when for you're not in the mood you know what to do that'll turn him off instead of saying "I'm tired."

  4. Afraid to die? What Do You Think Death is Like?

    This may seem too morbid, but asking your boyfriend what they think about dying can tell you what they are living for.

    If they're not afraid to die, then that tells you they are living their life as best they can before their time is up. If he's not sure what will happen after death, he's most likely afraid. Maybe he believes in the afterlife, or maybe he just thinks you die and that's it. Stuck in the ground with no memories of your life. Either way, it's good to know how he values life and death, and how he wants to spend the inbetween.

  5. Favorite Song?

    Picking a favorite song is hard. I, myself, can never pick just one, so I say I don't have a favorite song. But if your boo happens to have one, you should really take the time to listen to it. Music taste is a defining trait in people, and what their favorite songs are can tell you more than you think.

  6. Favorite Movie?

    Similarly to a favorite song, your favorite movie is a crucial piece to your identity. It's what you see on every ice breaker sheet of paper to fill out with info about yourself because it's just that important to who you are.

    Knowing your boyfriend's favorite movie, and possibly watching it together, will give you guys a bonding opportunity to share something that he loves with you.

  7. Something You Wish You'd Learned Earlier?

    We all go through those moments in life where we're taught a lesson we really wish we would've known sooner. More often than not, if you ask someone this question, the experience they choose to tell you is the one they most think about and had the most affect on them. Your boyfriend telling you about something he wishes he knew in his life earlier is something he probably doesn't tell most people.

  8. What Is Your Biggest Insecurity?

    Ah, insecurities.

    We all have them no matter how secure in yourself you think you are. They're the things no one likes to talk about or admit to. Insecurities can sometimes eat away at people and cause for deep wounds. But knowing what your boyfriend is insecure about himself can help both of you get closer because sharing your vulnerabilities with someone means you trust them enough to know.

  9. First Kiss?

    This question is meant to be a lighter one that could potentially make you both laugh if his story of his first kiss is kinda funny. It's always interesting to know when someone's first kiss was, with who, and how it happened because it usually happens when we're young, and most likely don't know what we're doing. Or maybe it happens at an age most people don't expect it to, or when you're a bit older, and makes for a sweet story. Either way, being enlightened of your boyfriend's first kiss is one way of getting to know how he handles awkwardness (because let's face it, most first kisses are) and see a time of innocence in your partner.

  10. First Serious Relationship?

    If you're not this person for your boyfriend, then asking about his first serious relationship could provide some helpful insight into how your boyfriend works in relationships that could maybe help the two of you. Nobody likes hearing about their partner's ex, but sometimes it could be useful, and showing that you can hear about a person in your boyfriend's life that he once held a serious relationship with displays maturity. Listen as your boyfriend tells you the good parts, but also the bad, and what worked and what didn't, and ultimately why they broke up and consider it for your relationship, but not heavily.

    After all, you are not his ex and your relationship is not the same as theirs.

  11. A Time You Were Happiest?

    Recollecting the happiest moments in your life so far, or when you felt happiest, is a sweet memory that is pleasant to share and pleasant to hear. Knowing what's made your boyfriend happy or when he felt the happiest in his life will make you cherish those memories as much as he does.

  12. A Time You Were Saddest?

    As much as we all love talking about the highest points in our lives, we also have to talk about the lowest. And if you're in a relationship with somebody, sharing the low points in your life is a unique bonding experience. Being able to expose yourself as a person with insecurities and open up about them is a hard thing for most people. Sometimes only reserved for the most special and important people in our lives, and if your boyfriend shares these with you, you're definitely one of them.

  13. Tell Me About Your Family

    Usually, the most important people in your boyfriend's life, besides you, of course, is his family. The people that are closest to him, and know him better than you do in some cases. At least for the time being while you're trying to get to know everything about him. Learning about the people closest to him and sharing fond memories he has with them is one way to get closer and dig deeper into the person you're dating, because after all, family is an extension of you.

  14. Tell Me About Someone You've Lost

    Going through loss and mourn changes people. Finding out which person in your boyfriend's life that he's lost, and how it changed him and made him feel, will bring you two together even more and make you close-knit.

  15. Biggest Fight With Somebody?

    If you and your boyfriend have yet to have argued, him telling you about the biggest fight he's had with somebody and how he handled it will show how he handles arguments. It's important to know what type of person your boyfriend is when it comes to arguing, and if he properly argues, when it comes to future disagreements you guys may have.

    Did he yell at this person he fought with? Say mean things? Or did he handle it calmly? Be the bigger person? Ask this question and you'll find out how your boyfriend likes to fight.

  16. Tell Me About Your Friends/Best Friend

    Another important person/people in your boyfriend's life are their friends, or best friend. You may have met their friends already, or have not, or maybe are even in the same circle of friends as your boyfriend, but you may not know them as well as your boyfriend does. Showing an interest in your boyfriend's friends will make him happy, and actually wanting to know about them and listen to him talk about all the fun times he's had with them will get him to feel more comfortable with you and adds to the friendship aspect of your relationship.

  17. Do You Believe in Aliens?

    What better way to get to know someone than to converse about the existence of extraterrestrial life?

    Time to find out if he believes. If you're a firm believer in alien life out in the universe, discussing why with your boyfriend will share your views of life with them. Also, if you're not and he is, he can tell you why and vice versa. It's a trip to think about if we're truly the only ones in this universe, or if we're not and share this space with another life form we've never seen. This topic will make for an interesting conversation between the two of you.

    And who knows, maybe it will also spark up a Hulu and Hump (no, not "Netflix and Chill") date watching The X-Files.

  18. Dream Goal in Life?

    A person's biggest goals and aspirations in life are a piece of identity to who they are, and what they're about. What's most important to accomplish in life for your boyfriend and hearing his reasons for it, is yet another bonding experience, that you too can participate in by sharing yours.

  19. What is One Thing That Can Destroy a Relationship and Never Be Forgiven?

    Setting boundaries and identifying what is, and what is not, acceptable in your relationship for both parties is crucial for any successful relationship. You must know what your boyfriend is, and he must know what you are, okay with in your relationship. Asking this question will ignite a meaningful conversation between you two where you can discuss what you wouldn't like your boyfriend to do, and what he wouldn't like you to do, and build from there. Knowing what you could do that your boyfriend would deem as a breakup factor will help build your relationship stronger so that you don't do these things to each other.