Fun Questions To Ask Your Boyfriend To Get To Know Him Better

Whether you've been together for a short while or a long time, there's always an opportunity to discover something new about your significant other. However, relying on natural occurrences alone won't always lead to new insights. Sometimes, asking specific questions during conversations is necessary to deepen your connection. Below are some enjoyable questions you can ask your boyfriend to spice up your chat or alleviate boredom.

Why You Should Ask Your Boyfriend More Questions

Even if you believe you have a deep understanding of your partner, there is always room for new discoveries. Even couples who have spent years together can amaze each other. By asking questions, no matter how trivial, you can enhance your relationship.

1. You discover new things about him

You may believe that you have complete knowledge of your boyfriend, but the truth is, there is always more to discover. By posing interesting questions to your partner, you can unveil fresh facets of his personality, which can be quite exciting.

2. You strengthen your bond

The more you discover about your boyfriend, the more intimately connected you'll feel with him. This closer bond between you two enhances the level of intimacy in your relationship, which is a win-win outcome.

3. You find new things to talk about

Contrary to popular belief, you don't necessarily have to ask your boyfriend profound or philosophical questions to improve your relationship. Ultimately, it's about having enjoyable conversations. Over time, many couples may exhaust their conversational topics, and this exercise is an excellent way to provide new topics to discuss.

4. You can uncover new hobbies and passions

Your boyfriend's response to your question may unveil a new hobby or interest that you never knew existed, which can be particularly useful in generating new date night ideas. You will never be short of novel and exciting things to explore together!

5. You show him that you're interested and engaged

It's natural to become overly comfortable in a long-term relationship, which can lead to complacency. While your boyfriend may be aware of your affection, asking enjoyable questions is an excellent way to demonstrate it. He deserves to know that you care about his everyday experiences. So, don't hesitate, start asking those questions.

6. You make him feel appreciated

Undoubtedly, you don't intend to take your boyfriend for granted, but at times, he may feel that way. Posing enjoyable, light-hearted questions that delve into his personality can help mitigate these feelings. By being actively engaged, you can demonstrate how much you value and appreciate him.

Fun Questions To Ask Your Boyfriend

1. If you won a multi-million dollar lottery, what would you do with the money?

You can learn about your boyfriend's financial profile by asking questions such as, would he travel the world, quit his job, chase his secret dreams, buy a house, or donate money to charity, research, or start a scholarship fund. His responses can offer insights into his financial priorities and preferences.

2. What would success look like for you?

Perhaps your boyfriend envisions a life well-lived as one with substantial wealth, the ability to purchase private islands, and indulge in life's luxuries. Alternatively, he may prioritize comfort, taking care of his loved ones, and making a positive impact on the world. There is no correct or incorrect answer, but his response can provide insight into whether your goals and values are compatible.

3. What's the most embarrassed you've ever been?

Asking such questions could lead to an intimate conversation that might make you feel sorry for him, or the encounter might be shocking. It could even turn into a humorous discussion. You will also learn what makes your boyfriend feel overwhelmed or want to withdraw from the situation.

4. What can you talk about for 2 hours nonstop?

This question is an excellent way to gain insight into your boyfriend's hobbies and interests. You will have the opportunity to hear about the things he is passionate about and can easily talk about for an extended period, given the chance.

5. If money wasn't a question, what would you do?

Your boyfriend's response to this question can provide insights into his values and how he likes to relax or spend his free time. You could discover his favorite hobbies and what he enjoys doing the most.

6. What are your guilty pleasures?

Your boyfriend might admit to enjoying a guilty pleasure, like staying in all day and playing video games, hate-watching cheesy TV shows, or indulging in unusual food combinations. His answer to this question can provide insight into what brings him comfort and how compatible your interests are.

7. Which movie or book have you lied about seeing or reading?

Most people have a few TV shows, movies, or books they pretend to have watched or read. For example, I haven't read the Harry Potter books, but many people who know me think I have because I've let them believe this. You could even turn your boyfriend's answer into a bonding activity by reading the book or watching the movie with him.

8. If you could have a superpower, what would it be?

This lighthearted question can help you uncover your boyfriend's playful and quirky side. Whether he chooses the ability to fly, read minds, or become invisible, his answer is likely to spark some fun banter and laughter between you both.

9. What were you like in high school?

Learning about your boyfriend's high school experience can offer insights into his formative years and help you understand how he became the person he is today. Was he popular, a misfit, a promising athlete, a drama enthusiast, or a huge nerd who loved magic, Dungeons and Dragons, and fantasy novels? High school is a pivotal moment in people's lives, and asking about his experiences can help you get to know him better.

10. How do you most prefer to spend date night?

Your boyfriend's preferred date night activity can reveal what he values and enjoys. He may prefer a romantic evening at home, fine dining at a fancy restaurant, or an active date like bowling or cooking classes. By learning his preference, you can get some great ideas for future dates.

11. What did you think of me when we first met?

It's possible that your boyfriend's first impression of you could be unexpected. He may have noticed something about you that others tend to overlook, or something that you're frequently criticized for. Whatever the case may be, it can be an enjoyable experience to see yourself from his perspective.

12. If you could be a color, what color would you be?

The task may appear straightforward, but his response could catch you off guard. Would his personality align more with the dark and mysterious vibe of the color black, or the cheerful and lively energy of the color pink? It's tempting to make assumptions, but it's more entertaining to inquire since you never know what his answer may be!

13. What kind of conspiracy theory can you make up on the fly?

Asking your boyfriend this question can be incredibly entertaining. If he's a fan of true crime or is passionate about reading thrillers, he's bound to be intrigued. However, be ready for a lengthy and potentially convoluted response that could be difficult to track.

14. What's the funniest story someone has drunkenly told you?

Whether he attended college or spends time with his friends at a local bar, there are bound to be amusing stories he can share about those experiences. However, if he struggles to think of any, don't worry. You could also ask if any strangers have ever approached him with funny or random anecdotes.

15. If any animal could be your pet, what would you choose and why?

Encourage him to expand his imagination beyond the typical household pets like dogs and cats, as well as their larger counterparts. Would he prefer a mythical creature like a dragon or a shark? Alternatively, perhaps he'd opt for something more whimsical, like a unicorn.

16. You're on a desert island and can only take five movies with you, what would they be?

If he's inclined to think too logically, reassure him that the TV has some magical powers that can stream movies for him. Moreover, this question can provide insight into his cinematic and television tastes.

17. What's your go-to dad joke?

You could also swap out "pickup line" or "knock-knock joke" for "dad joke." Based on his response, you could then search for appropriate jokes or pickup lines to gauge his reaction.

18. If you changed your name, what's the most epic name you could choose?

This query isn't intended to be taken seriously, so don't be afraid to press him for answers. You could inquire whether he'd prefer monikers like "Super Awesome Dude" or "Ultimate Party" to get the conversation flowing.

19. How curious are you?

Discover more about him by posing this question. You'll gain insight into his inquisitiveness and which areas of knowledge pique his interest.

20. What movie best resembles your life?

If he offers an answer, you could consider watching the movie together and then assessing if it aligns with his initial response.

21. What song always puts you in a good mood?

He may be able to identify a single song or offer to share a playlist. If he has a playlist prepared, consider asking if you could listen to it together as a way to strengthen your bond.

22. If you don't hear music, would you dance anyway?

Asking this question can be fascinating since it can reveal his level of shyness. Is he comfortable with the idea of appearing foolish in public? Or does he see it as a chance to be impromptu and romantic?

23. As a kid, what did you imagine adulthood to be like?

During our childhood, we all had various perceptions about the activities that adults engaged in. Additionally, you could ask him to reflect on his answer and compare it to his current life.

24. What's your go-to karaoke song?

If he hasn't done karaoke before or has no interest in it, you could inquire about his favorite song that he knows all the lyrics to. If he appears willing, you could even request that he give you a small performance of it.

25. Ice cream or milkshake?

Who knows, this question could be a decisive moment for your relationship! (Just joking!) It's a playful query that may not have an apparent answer. From a technical standpoint, milkshakes are basically ice cream mixed with milk. However, don't let him off the hook too quickly.

26. What is your most useless skill?

Perhaps he possesses a talent for cleaning fish tanks or can recite all the presidents in order. The skill or hidden talent should be something that has no practical or monetary worth. You could also substitute "useless skills" with "hidden talents" while adhering to the same standards.

27. What was the worst job you ever had?

The intention isn't to dwell on unpleasant memories but rather to extract humor from them. He may have a comical anecdote or two to accompany the experience. Ideally, he isn't still in his worst job now!

28. What would you do if you were stuck in the mall overnight?

Would he tour all the stores and test out expensive outfits? Or would he panic and try to flee? Perhaps he would go to the mattress store and enjoy a comfortable night's rest on one of those memory foam beds? This is unquestionably one of the most entertaining questions to pose to your boyfriend. Plus, experiencing it firsthand would be a lot of fun!

29. What's the worst purchase you've made?

In the era of online ordering and shipping, he's sure to have a story about purchasing something that was different from what he expected, or he may have forgotten why he even wanted the item in the first place.

To Sum Up

Spice up your conversations with your boyfriend by asking fun questions like the examples listed above. Not only will you learn more about each other, but it will also add a new level of excitement to your relationship. Don't stress about coming up with the perfect question, the more lighthearted and humorous, the better. Remember how enjoyable it was to get to know each other when you first met? There's still so much more to discover, just put in a little effort and have fun!