117 Questions to Ask Your Boyfriend

How well do you know your boyfriend? ☕

Last updated: May 12, 2025 by Michelle

When you’ve got those new relationship jitters, it can be easy to overlook things. There comes a day in every relationship when you have to sit down and ask the hard (and fun) questions. That’s why we put together these 117 questions to ask your boyfriend. Some are deep, some are illuminating, some are juicy, but all of them will get you and your beau talking.

Questions to Ask Your Boyfriend Couple Having Coffee

Dive into questions to ask your boyfriend so you can get to know your special person in an even more intimate way. Jump to the questions that pique your interest, or simply keep scrolling to see all our questions to ask your boyfriend. Then, keep reading to learn how these questions can actually help strengthen your relationship.

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Need a quick question to get the conversation moving?

Questions to Ask Your Boyfriend - What was your dream career?

Best Questions to Ask Your Boyfriend

If you want to cut to the chase, here’s our very best questions to ask your boyfriend. They span a range of topics and categories, but all of them will get you talking.

How do you manage your finances?

What is the biggest challenge you’ve overcome recently?

What qualities do you seek out in a friend?

When’s the last time I made you laugh?

What was your dream career as a kid?

What was the first moment when you knew you were attracted to me?

Kiss, marry, kill…

Have you ever lived with a partner?

Have you ever been in a long-term relationship?

Where did you grow up? Did you like it?

What would you change about yourself?

What’s something you’d like to tell your younger self?

How many people have you kissed?

Are you happy?

Do you prefer fancy dates or casual dates?

What are some of your pet peeves?

Tell me about your most memorable childhood
experience.

How do you feel about pets?

If we swapped bodies for a day, what would you do first?

Do you play any instruments?

Questions to Ask Your Boyfriend - Who would you get coffee with?

Interesting Questions to Ask Your Boyfriend

These are some real head-scratchers. Check out our most interesting questions to ask your boyfriend.

What was your first impression of me?

What values guide your decisions in life?

Which countries would you like to visit?

Tell me about your childhood.

What is one of your core beliefs?

Would you change your name if you could?

Do you have any holiday traditions?

What was your last Google search?

Which actor would you choose to play you in a movie?

What’s the first album you bought?

Who’s your favorite relative?

Have you ever done something purely out of jealousy?

Do you think we have free will or do you believe in fate?

What’s your favorite season?

What is your perfect weekend morning?

What is something you’re super passionate about?

If you could get coffee with one famous person, who would you pick?

What is the worst present anyone ever gave you?

Questions to Ask Your Boyfriend - What's your spirit animal?

Fun Questions to Ask Your Boyfriend

Keep it light with these fun questions to ask your boyfriend. Fair warning: Some of them get really silly.

What’s your theme song?

Do you have a role model? Who is it?

Have you ever gone skydiving? Would you?

Which do you prefer: Morning or night?

Do you have a weird food that you secretly love?

What’s your spirit animal?

What’s my spirit animal, in your opinion?

If you could choose a superpower, what would it be?

What’s your favorite thing to do after work?

Do you believe in anything supernatural?

If you got to be any cartoon character ever, which would you choose?

Did you have a favorite childhood toy?

What’s your position on tattoos and piercings?

Where would you like us to go on vacation?

If you had infinite money, what is the first thing you’d buy?

Do you have any hidden talents?

What’s your favorite way to spend a rainy day?

Do you have any stuffed animals?

What do you do to feel better when you’re having a bad day?

What’s your favorite holiday food?

Do you talk to yourself?

Questions to Ask Your Boyfriend - What's something you learned from a relationship?

Deep Questions to Ask Your Boyfriend

Let’s get deep. These questions to ask your boyfriend touch on some deep topics you might not otherwise bring up.

Did you ever have a “friend breakup?”

Tell me about a time you were totally out of your comfort zone.

What role does religion have in your life?

What’s most important to you in a friend or partner?

How many serious relationships have you had?

What do you think happens when we die?

Do you see yourself becoming a parent someday?

What does success mean to you?

Where do you find happiness in life?

What is the last thing that made you cry?

Who is your favorite author?

What’s something valuable you learned from a past relationship?

Who can you count on no matter what?

What is the hardest decision you’ve ever made?

How do you deal with setbacks and challenges?

What are you most proud of so far in your life?

What is your biggest fear?

What do you think is your best trait as a partner?

Who is your favorite person?

What’s your guilty pleasure?

Questions to Ask Your Boyfriend - What's your dream romantic getaway?

Romantic Questions to Ask Your Boyfriend

Relationships are all about romance. Find out how your boyfriend feels about matters of the heart.

What is your preferred love language?

How do you balance your personal goals with your relationship goals?

What do you see as the hallmarks of a healthy relationship?

What’s something romantic you did for someone in the past?

How do you feel about marriage?

What are three things we have in common?

What are three things we don’t have in common?

How do you like to show love to others?

What are some deal breakers for you?

What’s your dream romantic getaway?

Do you know your attachment style (anxious, avoidant, etc.)?

Do you believe in soulmates?

When do you think it’s time to say “I love you?”

What are your favorite little tokens of love that a partner can do for you?

What do you like most about our relationship?

Show me your favorite picture of me.

What’s your perfect date night?

What lessons have you learned about relationships over time?

What is a romantic relationship that you admire?

Questions to Ask Your Boyfriend - What's the most adventurous thing you've done?

Juicy Questions to Ask Your Boyfriend

These questions turn up the heat a little. Make sure you’re alone for these juicy questions to ask your boyfriend.

What are your thoughts on PDA?

Do you like making out?

What do you think about when you miss me?

What’s the most adventurous thing you’ve ever done?

Do you like spicy text messages?

What is our most memorable intimate moment in your mind?

Have you ever crushed on a friend?

Would you kiss someone on a first date?

What’s something you learned from a past relationship?

Describe a time a partner did something that turned you off.

How much do you like cuddling?

Do you have any recurring spicy dreams?

Have you ever snuck around to be with a partner?

What makes you want to make the first move?

When did you have your first kiss?

What is something I do that does it for you?

What is the dirtiest thing someone’s ever said to you?

Where do you most like to be kissed?

Give me your best pick-up line.

How These Questions Can Help Your Relationship

Questions to ask your boyfriend can be a fun thing to do on a rainy day, but they could also serve as a great way to strengthen your relationship. These questions are more than idle curiosity. They get at some really crucial topics. Here are some ways these questions can help your relationship.

Open Up Deeper Conversation

Many of the questions to ask your boyfriend can lead the way to a far deeper conversation. It isn’t always the deep questions, either. A question about a favorite hobby can lead to learning a lot more about your boyfriend’s interests and passions. A silly question about pick up lines could lead to a discussion about past relationships. As long as you keep the conversation flowing, any of these questions to ask your boyfriend could result in so much more.

Learn Things You Wouldn’t Otherwise Know

When looking through our list of questions to ask your boyfriend, think about what you might not otherwise know about your partner. Maybe you know all his favorite foods, but not where he grew up. You could use these questions to learn things that might not come up naturally in everyday conversation. This is a great opportunity to learn more while doing a fun, low-pressure activity.

Practice Deep Listening

This can also be a chance for you to practice skills such as deep listening. This isn’t simply a nice skill to have. It can also strengthen your relationship.

An intimate relationship is about more than just talking and telling him about you. You also have to know how and when to listen, as this can make your partner feel valued and important. So as you go through these questions, pay attention to how well you do when listening to the answers. Eye contact and nodding or other forms of confirmation can show your boyfriend that you are listening and really care about his answers.

Identify Shared Values and Miscommunications Early

These questions to ask your boyfriend can also help you find pitfalls early on in the relationship. You might discover you’re a cat person and he’s a dog person. You may also discover shared values, however. Maybe you both place a lot of emphasis on family and can bond over that via some of these questions. Don’t feel like you need to stick to the script. If you discover a difficult area or point of commonality, leave these questions behind and go explore that!

More Fun Activities for You and Your Boyfriend

Questions are great, but we have more activities you can share with your boyfriend. Check out these similar pages you might enjoy: