Entertainment Love and Romance 21 Questions to Ask a Guy to Get to Know Him Share PINTEREST Email Print Westend61/Westend61/Getty Images Love and Romance Relationships Divorce Teens LGBTQ Friendship By Stacey Laura Lloyd Stacey Laura Lloyd Writer B.A., Art History and Creative Writing, University of Pennsylvania Stacey Laura Lloyd is an author with a passion for helping others find happiness and success in their dating lives as well as in their relationships. Learn about our Editorial Process Updated on 04/07/19 If you want to get to know a guy a bit better, it can be hard to figure out exactly what to say to him in order to strengthen your bond. The good news is that there are 21 key questions to ask a guy in order to get to know him better while also laying the foundation for a meaningful and long-lasting connection with one another. 1. What’s Your Family Like? Knowing more about his family can help clue you in not only about how he grew up, but how his relationship is with his family today. If you want to learn more about him that goes past the superficial, this is a key question to ask. 2. What’s Your Favorite Childhood Memory? Childhood experiences often shape the person that you are today, and in order to know more about your guy and what's important to him, this question can let you know more about what he truly values. Whether it's time with his grandmother or going on a trip to France, this question can enable you to know about what he treasures. 3. What’s Your Favorite Song? A guy's taste in music can give you more insights into his likes and dislikes, and by asking about his favorite music, you're creating an opportunity to not only bond over shared favorite bands but also discover new types of music. 4. Where Do You See Yourself in Five Years? A question about his future goals, hopes, and dreams is something that can not only make you closer but can also let you know if you want the same things. 5. Do You Want Children? Inquiring about his desire to have children in the future is a must if you want to have children one day. If this is a must-have for you, it's better to know now. 6. If You Could Have One Superpower, What Would It Be? If you want to unlock a guy's playful side, this question is a great way to break the ice and see where he falls on the superhero spectrum. Whether he chooses the ability to fly, super strength, or super speed, this is a super question that will likely guarantee you some laughs and playful banter. 7. What Do You Enjoy Most About Your Job? Asking this question about work can not only bring you closer together by revealing more about his day-to-day life, but it can also let you know more about his priorities. No matter what part of the job he enjoys the most, this can help you to learn what he's most passionate about in his career. 8. If You Could Travel Anywhere, Where Would You Go? Travel questions are not only great in terms of generating a fun conversation, but it's possible that discussions about travel and vacations could lead to a couple's trip down the road. 9. What Are You Looking for in a Relationship? This is an imperative question to ask a guy in order to figure out if you're both on the same page. If you're looking for a serious relationship while he's mostly interested in friends with benefits, it's best to discuss that openly and honestly so that you're not wasting your time. 10. What’s Your Favorite Movie? Is he an action fan? Horror? Drama? If you want to get to know him better, knowing the types of movies he's into can not only tell you more about his interests and passions, but it can also help you for planning potential movie dates in the future. 11. What’s the Best Gift You’ve Ever Received? If you want to know what your guy truly values, this question is a great way to learn more about what he finds meaningful and noteworthy. 12. What’s on Your Bucket List? Does he want to go skydiving, visit Greece, or win a Pulitzer? A question about his bucket list is a fun way to learn more about what he wants to accomplish one day and if the two of you have shared goals. 13. Do You Believe in Love at First Sight? If you're wondering if your guy has a romantic side, this question can be a terrific way to see what he thinks of falling in love. Does he have a more cynical outlook on love or is he an optimist? It's time to find out. 14. What’s Your Favorite Book? Learning more about what a guy reads is also a great way to learn more about his interests and hobbies and see what you have in common. 15. What’s Your Favorite Food? Discussing food preferences with a guy can be a fun way to help you pick out restaurants for future dates while also letting you know more about him and his taste. 16. How Would Your Best Friend Describe You? This question can be a great way to learn more about a man's personality and the traits of which he's most proud. 17. What’s Something That Not Many People Know About You? This question can be a great way for you to know something about your guy that he only reveals to people who are important to him. 18. What’s Your Definition of a Perfect Date? This is a terrific way to know what he enjoys doing while also giving you inspiration for a date in the future! 19. What Are You Most Afraid Of? If you want to learn more about him that goes past the superficial, inquiring about his fears can be an interesting way to get to know him better. 20. If You Could Change One Thing About Yourself, What Would It Be? Being self-aware is a great trait in a man, and this question can help let you see how he actually sees himself. 21. What Makes You Happy? If you truly want to know more about your guy, finding out what truly makes him smile will help to strengthen your relationship and pave the way for even more smiles to come.