10 Questions To Ask A Guy To Get Closer To Him

Building an emotional connection with someone is a great way to strengthen your relationship. If you’re hoping to learn more about your boyfriend or crush, asking him questions about his life is one of the best ways to do so. That said, it can be hard knowing where to start. Make sure your delivery is sincere and ask at a time he won’t be afraid to be a little vulnerable. Here are some questions you can ask a guy to get closer to him than ever.

  1. What was your childhood like? This question can be as detailed or basic as your guy wants it to be. He can say he had a nice childhood and talk about the activities he did, or he might mention early tension with his family or siblings. No matter what he chooses to share, you should make sure to listen and ask follow-up questions. In answering this, he may be getting some stuff off his chest. So, monopolizing the conversation isn’t the best move.
  2. Tell me about your first pet. Whether it was a rock or a rottweiler, hopefully he’ll have nothing but fond (or funny) memories of his first pet. It can also help you get to quietly know him on a more emotional level. Maybe he has fond memories of when he found his childhood best friend at the shelter, or maybe his first pet was a carnival goldfish that also unfortunately taught him about loss at an early age.
  3. Are you a dog or a cat person? This is similarly related. Both of them are great pets, but they’re attractive to two different personality types. A cat guy might like activities like reading, hiking, and solitude. A dog guy might be more into sports and family. Of course, it’s not always the case — but it can be a good indicator. It’s also good to know if he’s simply not into pets. Maybe he isn’t into the additional responsibility.
  4. What’s your morning routine like? This is a question that’s a little out-of-the-box, but think about it — we all have a routine of some sort. Figure out if he’s the kind of guy who hits snooze on his alarm clock three times every morning or the kind of guy who bravely goes out for a run first thing, regardless of the weather. This is also good information if you’re thinking about moving in with him someday. Will you have compatible mornings?
  5. What was your first real heartbreak? A sad question, yes — but if you guys are on the track towards marriage, it may feel natural to ask him about his past. It might not even have been a romantic heartbreak. Maybe a friend broke his trust, or perhaps he lost a pet. Being a strong couple means being there for each other through the good times and the bad, and having some insight into his life before you can be incredibly helpful. This is one of those questions that a guy might feel hesitant to talk about but will bring you so much closer.
  6. What’s your favorite home-cooked meal? This could be a nostalgic meal that his mom or dad made, or maybe a holiday tradition. Keep note of what he says. Someday, maybe the two of you can try to recreate it at home for a fun date night.
  7. Where have you always wanted to go on vacation? This is another one worth listening to, especially if you think this guy has the potential of being your husband someday. You might want to incorporate his idea into the honeymoon. Or, if you happen to love travel, you can start making that dream a reality by surprising him with plane tickets.
  8. Do you believe in astrology? It’s a fun question, and his answer isn’t just about yes or no — it can indicate whether or not he believes that our personalities may be driven by factors outside of just genetics. Astrology can be a lot of fun for many, but upsetting to few. Learning his opinions on it now will help you learn more about his overall character.
  9. What’s the scariest situation you’ve ever found yourself in? Looking for an entertaining story? Then, this might be the question to ask. Even the bravest of individuals have had moments where they were scared. Did your guy get dangerously lost in the woods? Did he survive a scary car accident? Was he ever on a rollercoaster that broke down midway through the ride? His answer will tell you a lot about him.
  10. What are your best snowed-in activities? If you live in an area with a lot of snow, this is an important question. You might get snowed in with him at some point and should know what to expect. Is he the kind of guy to run outside and build a snow fort, or is he inside staying warm with a glass of whiskey by the fireplace? Learning about his snowy day prep will help you figure out how he relaxes and how he enjoys his free time.
Karen Belz is a New Jersey native who is currently living in Maryland. She has a Bachelor’s Degree in Speech Communication with a focus in Broadcasting and Print Media Studies from Millersville University of Pennsylvania. Since graduating, she has written for sites like LittleThings, HelloGiggles, and Scary Mommy and is currently an e-commerce editor at Bustle.

When she's not writing, she enjoys making her phone run out of memory after taking too many photos of her dog. You can find her on Twitter @karenebelz or on Instagram @karenbelz.