Get to Know Him Better: 20 Fun and Insightful Questions to Ask Your Boyfriend



Get to Know Him Better: 20 Fun and Insightful Questions to Ask Your Boyfriend

We’ve all heard the saying “every person is a book waiting to be read”. And it would not be a surprise for us to easily realize this when we talk to someone new. At first glance at someone, it is so easy for us to fall into stereotypes of who that person might be.

But when we engage in a conversation with them, we start to discover new things about them. 

Our perception about them slowly changes as hours and minutes of conversation pass. And at the end of that conversation, our stereotypical view of that person shatters.

You can have this similar experience with your boyfriend, whether you’ve been dating for just a couple of days or if you have been together for years. 

There will always be something new for you to discover about him because as time passes. He will also have had new experiences, realizations, and insights on a couple things that you’ve previously thought you knew about him.

Asking him questions shows him that you care for what he has to say on particular topics. It also tells him that you are still interested in him despite how long you’ve been with each other. (Asking him questions is also a way to get him off too much work or games so you can bond.)

Now, if you’re ready to ask him some questions but don’t know which ones to throw at him and which ones to avoid. We’ve compiled 20 fun and insightful questions that you can use for your fun little interview with your hubby.

Fun Questions to Ask Your Boyfriend

A happy couple sitting

Let’s start it off with some fun questions that tackle some of the nuances in daily life like bonding, relationship traditions, etc. These questions are great conversation starters and can make for some of the most memorable bonding moments with him, and without spending a single dollar.

  1. Where should our next vacation be?
  2. Have you ever slept with stuffed animals?
  3. How do you like to spend a rainy day?
  4. What’s one holiday tradition you think we should start together?
  5. What does your ideal Sunday morning look like?

Deep Questions to Ask Your Boyfriend

A couple sitting and facing  to each other

These questions will touch on some of the more uncomfortable parts of his life. But these are essential as these questions will get you to know him deeper, especially if you’ve only been dating for a short time. 

And if everything goes right, there is a high possibility that he will fall for you deeper than he already is. But do proceed with caution, if he is ever uncomfortable it is best to honor his decision to not talk about that specific area of his life.

  1. What makes you happy?
  2. What’s the biggest misconception people have about you?
  3. What’s the hardest decision you’ve ever had to make?
  4. Who are you closest to in your family?
  5. What do you look for in a friend?

Flirty Questions to Ask Your Boyfriend

A man is looking to his girlfriend

Next, we’ll be letting some butterflies loose. These 20 fun and insightful questions will surely put a smile on his face. And may even grant you both some laughs. These questions are best asked when on a date with him as it is usually during these times that he is thinking about you the most.

  1. What was our first kiss like for you?
  2. How many times did you want to ask me out before you did?
  3. There are eight billion people in the world. Why are you with me?
  4. What gives you butterflies?
  5. What color should I wear more?

Important Questions to Ask Your Boyfriend

A woman is thinking

Let’s end it with some of the more necessary relationship questions, many of these may not be fun for the both of you. But remember that relationships are not just about fun. For your relationship to grow stronger both of you must grow and must plan for your future. 

Ask these when he is not occupied and is on a level head. If there is anything that bothers him or you, it’s best for you to deal with those things first and then ask any of these questions.

  1. Would you speak up if I do something that offends or upsets you?
  2. Do you trust me?
  3. How do you think responsibilities should be divided in a marriage?
  4. Do you expect dinner to be ready for you when you come home from work? What happens when both of us are working?
  5. Can you see yourself getting married to me?

In conclusion…

As we’ve said in many of our blogs, questions are an important tool that must be used in any conversation. It shows to the person who’s receiving these questions that you care about what they have to say and are willing to navigate that conversation with them (Given that your question is not insulting or any negative double-reason for it being asked). 

This tool is all the more important when it comes to romantic relationships. As you as a couple will have to talk things out if you want your relationship to last. 

We hope that we’ve provided you with a solid foundation on what kinds of questions to ask and when to ask them. May you and your boyfriend build a stronger relationship as you each get to know each other with every question you ask.






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