18 Deep (But Deceptively Simple) Questions To Ask A Guy Before You Get Too Serious

It might be challenging to know what to say to a man to deepen your connection if you want to learn

smiling man with curly hair and freckles

It might be challenging to know what to say to a man to deepen your connection. After all, what seems like friendly conversation to one person might feel like an inquisition to another. 

However, there are specific essential questions to ask a man if you want to learn more about him and his values and to establish a strong basis for a long-term relationship. This is a crucial part of getting to know if someone is right for you  before you get serious.


Please note that your tone matters greatly in how he will interpret these questions, so be sure to smile and keep it friendly and relaxed when asking these questions so he knows you are curious because you are interested, not because you are judging him.

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18 questions to ask a man before getting serious — so you know who he truly is, inside. 

1. What is your relationship like with your family?

You may learn a lot about his upbringing and current family dynamics by learning more about his parents and siblings. You should ask this question if you want to understand more about him beyond the surface.


2. What is the happiest memory from your childhood?

This inquiry may help you learn more about your boyfriend and his values, and it's a great way to get to know him better. To find out what he cherishes, you may ask this question about his time with his grandma or a vacation to France.

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3. What is your favorite song about love?

It's possible to learn a lot about a person by inquiring about his favorite music. This may lead to a deeper connection via a mutual love of bands and new musical discoveries.

4. In five years, where do you see yourself?

How can you know whether you desire the same things as he does? By asking him about his plans, ambitions, and dreams.


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5. Have you thought much about having a family?

Whether or not you want to have children in the future, you must find out if he is interested in having children someday. It's best to know this up front if it's a must-have.

6. What superpower would you choose if you could have any?

This inquiry is an excellent approach to understanding a guy's sense of humor and discovering where he stands on the superhero spectrum. It will elicit laughter and lively banter, regardless of whether he picks the power to fly, super strength, or super speed.

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7. In what ways do you get satisfaction in your work?

Asking him about his job might help you get to know him better by shedding light on his daily routine and showing his priorities.

No matter what aspect of the work he appreciates, you may learn about his professional interests by asking him about it.

8. Which place would you most like to visit?

It's conceivable that a chat about travel and vacations might lead to a couple's trip in the future.

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9. What do you desire in a relationship, and how do imagine that happens?

Whether you want to know if you and a man are on the same page, ask him this question. To avoid wasting your time, it's essential to openly and honestly address whether you're searching for a long-term relationship or just friends with benefits.


10. What is your favorite gift you've ever received?

If you're curious about what your boyfriend genuinely values, this question is a fantastic place to begin your exploration. Was it hand-made, thoughtful, or simply expensive? 

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11. What is on your lifetime to-do list?

Do you want to go skydiving, visit Greece, or get a Pulitzer? That's the question. It's great to ask him about his bucket list and see whether the two of you have similar aspirations for the future.

12. What do you think about first impressions?

This is a great approach to find out whether your boyfriend has a romantic side by asking him this question. Is he a pessimist or a pessimist when it comes to love? Find out for yourself.


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13. What is your favorite book?

Knowing what a person reads is a terrific approach to get a better sense of his interests and see if you have anything in common with him.

14. How do you think your friends would describe you?

This question might reveal more about their personalities and the attributes they are most proud of.

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15. What don't people know about you?

With this inquiry, you can learn something about your boyfriend that you wouldn't otherwise know. It may even be something he normally wouldn't tell you until later, when you're already committed.


16. What scares you the most?

The more you know about someone, the more intriguing it might be to find out how he deals with his worries.

Men are too often told they cannot speak about being afraid, and this is an opportunity for him to confide in you. 

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17. What one thing would you change about yourself?

Self-consciousness is an admirable quality in men, and this inquiry might help you learn more about him.


18. Are you content with your life?

Finding out what makes your boyfriend happy can assist in enhancing your connection and open the road for even more smiles to come.

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After some time together, you may want to get to know your partner better to determine whether he's the right guy, but asking too many questions may be helpful or irritating. Make him feel more at ease by asking some of the most common questions to ask a man, such as, "How would you describe your relationship with this person?"

We are all so distracted by the technology intended to bring us closer together that it has made it more challenging than ever to get to know someone.


Asking these kinds of questions to men will help you learn more about a man and determine whether he is the perfect one for you, since it takes more work to establish a deeper connection with men.

It's up to you whether or not he says what you want to hear, but you may use your inquiries to your advantage.

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Sidhharrth S. Kumaar is the Founder of NumroVani and a registered pharmacist-turned-Astro-Numerologist. For more information, visit his website.