Ask Your BF These Questions to Feel Closer ...

Ask Your BF These Questions to Feel Closer ...
By Holly • Jul 24, 2025

You think you know everything about the person you're dating, but the truth is there's always something new to learn. That's why you should make a point to talk to your man about as many different subjects as you can. Here are a few questions that you should ask your boyfriend the next time you see him in order to feel closer to him:

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1. His Version of How You Met

Everyone experiences the world in a different way. Even though you were in the room the first time your boyfriend saw you and spoke to you, your story about how you met is bound to be different. Ask your boyfriend to explain the first time you met from his point of view. He's bound to point something out that you don't remember, or that you never even knew happened.

2. His Perfect Day

Ask your boyfriend what his perfect day would consist of. You might find out that he would love to live oceanside or that he would love to spend the whole day in front of the television. Even though you think you know everything about him already, a simple question like this could help you learn something new.

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This article suggests asking your boyfriend what his perfect day would look like. This could be a great way to learn something new about him and to feel closer. Examples of answers could include spending the day outdoors, going on a special outing, or spending the day at home with his favorite activities. It is important to remember that everyone's perfect day is different and unique, so be sure to listen to his answer without judgement. This question can be a great way to learn more about each other and to strengthen your relationship.

3. What He's Most Proud of

This sounds like an interview question, but you should ask him what he's the most proud of accomplishing in life. He might tell you about a race he won as a child or the time he helped a little old lady cross the street. Most people don't like to brag, so he might not have mentioned the thing that he's the most proud of about himself.

4. What Would He Want to Know about the Future

If a psychic could tell him the truth about his future, would he want to know what was in store for him, or would he rather be left in the dark? If he says that he'd like to know, then ask him what he's most interested in. Does he want to know who he's going to marry, how many kids he's going to have, or what his job will be? It'll help you see where his priorities lay.

If you're looking to engage your partner in intriguing conversations, why not try some hypothetical questions for couples? These fun queries will not only keep the conversation lively but also stimulate deep thoughts and potentially reveal insights about each other's personality and thought processes.

5. What He Values the Most about You

He compliments you all the time, but do you actually know all the reasons why he loves you? Ask him what he values the most about you. Make sure you answer the question for him too, so it doesn't seem like you're just fishing for compliments.

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6. What He's Most Guilty about

People don't like to talk about their bad traits. That's why you probably don't know what he's most guilty about doing in life. Maybe he pushed a kid on the playground in elementary school. Maybe he broke his ex's heart. It's time to find out what keeps him up at night.

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By understanding the inner workings of his conscience, you can glimpse into the vulnerabilities he rarely exposes. Digging deeper into those moments of regret can be both humbling and healing, allowing space for empathy and connection. Asking about his guilty feelings doesn't just show curiosity, it demonstrates a willingness to accept his imperfections and share in the emotional landscape of his past. Whether it's an innocent childhood mistake or a more profound life misstep, being privy to his contrition can bring you closer, building trust and fostering a deeper emotional intimacy.

7. What He Worries about the Most

Ask him what he worries about the most. Is it his career? Is it his mother's health? Is it his relationship with you? If you just ask him, you'll be surprised what deep secrets he'll open up to you about.

You never know what you'll learn about a person by asking them a few simple questions. What other topics do you think couples should ask each other about to feel closer?

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Feedback Junction

Where Thoughts and Opinions Converge

The first ones really nice. Move done this with my boy friend, helps you to remember things that happened on our first blind date.

@Ashleypaige311 we're on the same page. Guess you're not dying alone after all. :)

Hmm these are good questions. I have been with my boyfriend for a year and i can only answer a few

I've been playing this game with my boyfriend where I ask him questions to get to know him better. It's interesting!

Yes it true

Asking him right now ☺️

It would be fun for the 1st question but leave the rest.

This questions are so good..def will ask them :)

I'm going to ask my boyfriend these questions tomorrow!

Lol that funny 😂

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