250 Questions to Ask Your Boyfriend That'll Strengthen Your Connection

Don't be shy—these deep thought starters will spark the juiciest conversations.
A couple smiles at each other while lost in a deep conversation.
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sarah hanlon entertainment and celebrity editor the knot
Sarah Hanlon
sarah hanlon entertainment and celebrity editor the knot
Sarah Hanlon
Entertainment & Celebrity Editor
  • Sarah is the Entertainment & Celebrity Editor for The Knot, with special focuses on pop culture and celebrity wedding news.
  • Before joining The Knot Worldwide, Sarah was a contributing writer for Bravo at NBC Universal.
  • Sarah has a degree in journalism and resides in New York City.
Updated Mar 26, 2024

It doesn't matter whether you and your boyfriend have been dating for five days or five years—there is always something new you can learn about each other. There's a good chance you've covered the basic information over your first few dates (like where you're from, how many siblings you have, and what your favorite TV show is, to name a few things). We're of the mindset, though, that there's no such thing as having too many questions to ask your boyfriend. In order for your relationship to flourish and thrive, it's important to know your partner inside and out. After all, understanding their core values and beliefs is a key indicator of how compatible you are. That's why we've compiled the ultimate list of things to ask your boyfriend. Here, you'll find 230 deep, fun and juicy questions to ask your bf, spanning a variety of thought-provoking topics and subjects.

Types of things to ask your boyfriend in this article:

The Top 20 Questions to Ask Your Boyfriend

Looking for a quick-fire list of the top 20 questions to ask your boyfriend? Good news: We've made one for you. Save this handy list to your phone so it's easy to reference the next time you have some quality time to share.

List of 20 questions to ask your boyfriend
Design: Tiana Crispino

Deep Questions to Ask Your Boyfriend

The hard questions to ask your boyfriend are sometimes the most interesting. While it may seem intimidating, one of the best ways to strengthen your emotional intimacy is to simply go there. If you tend to avoid asking the tough Qs, you aren't alone—but we are here to help you get over that fear. Use this list of deep questions to ask your boyfriend to take your connection to the next level.

  • What makes you happy?
  • When do you feel most fulfilled?
  • How would you define success?
  • Do you consider yourself successful?
  • Do you consider yourself happy?
  • Are you proud of your accomplishments thus far?
  • Where do you see yourself in five years?
  • Do you think you've changed a lot since we started dating?
  • What do you look for in a friend?
  • How do your friends make you feel?
  • What was your childhood like?
  • Would you change anything about your upbringing?
  • How did your parents impact your view on love and relationships?
  • What gets you out of bed in the morning?
  • What's your biggest fear? Do you think you could face it?
  • How important is religion do you?
  • What do you think happens after death?
  • Do you believe in a higher power?
  • What's the story behind your middle name?
  • What's the biggest misconception people have about you?
  • How do you deal with personal challenges?
  • Did you ever have to break up with a friend? How did it go?
  • Have you ever had your heart broken?
  • Do you think a relationship can come back from cheating?
  • What's the hardest decision you've ever had to make?
  • What's the biggest risk you've ever taken?
  • What's your favorite quality about yourself?
  • Who are you closest to in your family?
  • What do you think are the most important qualities of a healthy relationship?
  • Who is someone in your life you know you can always count on?
  • What do you love about your mom?
  • What makes me beautiful to you?

Fun Questions to Ask Your Boyfriend

Next time you need a question to ask your boyfriend when the conversation lulls, refer to this section. Not every conversation you have needs to be so serious. In fact, we'd guess one major reason you're dating your boyfriend is because of your shared humor, or his ability to make you laugh. That's why these fun questions to ask your boyfriend are just as important as the hard and serious ones.

  • Where should our next vacation be?
  • When was the time you laughed the hardest?
  • What's your favorite holiday?
  • Would you ever go skydiving?
  • What's your favorite holiday food?
  • What's one holiday tradition you think we should start together?
  • What's your go-to karaoke song?
  • What does self-care look like for you?
  • If you could craft the perfect five-course meal, what would each course be?
  • What was your favorite toy as a child?
  • Did you ever sleep with stuffed animals?
  • How do you like to spend a rainy day?
  • What does your ideal Sunday morning look like?
  • What's one movie you can watch over and over again?
  • What's your favorite time of year?
  • If you could pick a theme song for yourself, what would it be?
  • If there was a movie made about your life, what would the title be?
  • What actor would play you in that movie?
  • How do you feel about tattoos?
  • If you tried a completely new style, what would it be?
  • What was the best Halloween costume you ever had?
  • If you could live in any fictional town or city, which would you pick?
  • When you were a kid, what career did you want to have?
  • Who's your role model?
  • Would you rather time travel or read people's minds?
  • Who's your dream Super Bowl Halftime Show performer?
  • What's your favorite movie theater snack?
  • What are you most passionate about in life?
  • If you could start a non-profit, what cause would you support?
  • What do you like to do after work?
  • Are you a morning person or a night owl?
  • What does your perfect day look like?

Juicy Questions to Ask Your Boyfriend

Who doesn't love a gossip session? When you think you know absolutely everything about each other, come to this list of juicy questions to ask your boyfriend. We bet you'll learn something new about him when you start using these creative conversation starters.

  • What's your most embarrassing moment?
  • Which celebrity would leave you starstruck in real life?
  • What's your guilty pleasure?
  • Do you talk to yourself?
  • Do you sing in the shower?
  • What do you think is more important: an emotional connection or a physical connection?
  • What was the last thing you searched on Google?
  • Do you believe in astrology?
  • Do you believe that every person has one soul mate?
  • Do you think it's possible to fall in love at first sight?
  • If you could go on any reality TV competition show, which would you pick?
  • If you started a podcast, what topic would it be on?
  • What's the last book you read for fun?
  • What's the craziest dare you've ever accepted during Truth or Dare?
  • What's one fact no one else knows about you?
  • Do you believe in ghosts?
  • What's a hidden talent you have that you never get to show off?
  • Who's your favorite person in your life?
  • What's your most memorable experience from high school?
  • Do you ever feel like you lived a past life?
  • If you could go back in time and live in any historical era, which would you pick?
  • If you could host a dinner party with any famous person, who would it be and what would you talk about?
  • Do you think men and women can ever just be friends?
  • What are your relationship deal breakers?
  • What's the craziest thing you've ever gotten the "ick" from?
  • What's your most memorable experience from college?
  • Is there anything you wish you could change about yourself?
  • Is there anything you wish you could change about me?
  • If you could change your name, would you?
  • If there was a book with one page written about every day in your life, would you read the whole thing?
  • What do you think your best attribute as a boyfriend is?
  • Can you list ten authors who aren't men?

Cute Questions to Ask Your Boyfriend

What are good questions to ask your boyfriend? We're so glad you asked. These light-hearted quips will help you two go beyond the surface level. Plus, there's a good chance these cute questions to ask your boyfriend will give both of you butterflies, so have a few of them ready to go for your next date night.

  • What's your favorite memory we've made together?
  • What's one thing we haven't done yet that you're excited to do with me?
  • What's a hobby you think we should try together?
  • Do you like when I cook for you?
  • Do you prefer cooking for me?
  • Have you imagined what our future house would look like?
  • Do you prefer spontaneous or planned date nights?
  • Do you prefer fancy or casual date nights?
  • Do you think we spend enough time together?
  • What's your favorite time of day to go on a date?
  • Do you like getting breakfast in bed?
  • What's been the best year of your life so far?
  • What's something you're passionate about that you never get to discuss?
  • Did you ever have a crush on a fictional character?
  • What was your first kiss like?
  • What's your favorite love song?
  • What are some things I do that make you smile?
  • Have you ever kissed someone under mistletoe?
  • What's the craziest thing you've done to impress someone?
  • Do you like talking on the phone?
  • How do you like to be treated when you're sick?
  • What's the best gift you've ever received?
  • Can you think of two people in your life who have a relationship you look up to?

Romantic Questions to Ask Your Boyfriend

Knowing how your boyfriend expresses (and wants to receive) love is crucial for the longevity of your relationship. Prioritizing these romantic questions to ask your boyfriend will make him feel special and valued, because making the effort to show you care about what makes him happy is priceless.

  • How would you define falling in love?
  • When did you know you were in love with me?
  • What's your love language?
  • How do you like to express love?
  • How do you want me to express love to you?
  • Do you like being surprised by random gifts?
  • Would you like to receive flowers?
  • What does your ideal date night look like?
  • What's your favorite date we've ever been on?
  • If you could plan a date for us anywhere in the world, where would we go and what would we do?
  • What do you think about public proposals?
  • Do you think couples should talk about engagement rings before they get engaged?
  • Have you ever thought about what you want your wedding to look like?
  • Do you like surprises?
  • Do I make you feel heard?
  • Do I make you feel valued?
  • What's your favorite thing about our relationship?
  • Do you see yourself proposing to someone else or being proposed to?
  • What's something I can do to make our relationship better?
  • Do you think we have healthy emotional intimacy?
  • Do I show up in your dreams?
  • Is there anything you've ever wanted to teach me?

Spicy Questions to Ask Your Boyfriend

We've covered fun, cute and serious things to ask your boyfriend—but we'd be remiss if we left out a few spicy Qs too. You might be someone who loves going there with your partner, in which case, you've probably covered these questions already. But for those who find it a little bit awkward to talk about intimacy and sex, you aren't alone. Instead of stressing about what to say, use this list of dirty things to ask your boyfriend when you're in the mood to spice things up.

  • Are you satisfied in the bedroom?
  • What's something we've never tried together that you want to?
  • Do you wish we used more sex toys together?
  • What's a fantasy of yours we've never talked about?
  • Do you like to move fast or take it slow?
  • What's your favorite type of kiss?
  • Do you like PDA?
  • Do you like getting spicy texts?
  • How many times do you think couples should have sex a week?
  • What was I doing the last time you felt turned on by me?
  • What non-sexual act turns you on the most?
  • Do you like when I wear lingerie?
  • Do you like wearing lingerie?
  • Do you wish I was more affectionate?

Serious Questions to Ask Your Boyfriend

While not quite as juicy as the dirty questions for your bf above, these serious ones are just as critical. While they may not be questions you want to whip out on, say, your first date, these topics are important to discuss early in your partnership to evaluate your compatibility.

  • Do you see yourself getting married one day?
  • What qualities do you think are most important in a spouse?
  • Do you envision yourself having kids?
  • What kind of parent do you want to be?
  • Why did your last relationship end?
  • What was your longest relationship?
  • Do you still keep in touch with your exes?
  • What are three things you want to achieve this year?
  • Would you sacrifice your career goals for love?
  • Do I do anything that bothers you?
  • Do you think I'm living up to my potential?
  • How do I make you feel when we hang out with your friends?
  • How do I make you feel when we hang out with my friends?
  • What does your average work day look like?
  • Are you friends with your coworkers?
  • When was the last time you voted?
  • Are you an introvert or an extrovert?
  • How do you handle anger?
  • Do you get jealous?
  • How do you define a committed relationship?
  • What do you do when you feel stressed?
  • What's your favorite part about being an adult?

Flirty Questions to Ask Your Boyfriend

Flirting is essential, especially if you want to maintain the honeymoon phase for weeks, months, and even years into your relationship. Refer back to this roundup of flirty questions to ask your boyfriend when you want to reignite the spark.

  • Do you remember what I wore on our first date?
  • Do you like when I wear perfume/cologne?
  • What color should I wear more?
  • What's your favorite physical attribute of mine?
  • What's your favorite physical attribute of yours?
  • What's your favorite cuddle position?
  • What did you like most about me when we first met?
  • What do you like most about me now?
  • What gives you butterflies?
  • What do I do that makes you laugh?
  • What's your favorite inside joke we have?
  • There are eight billion people in the world. Why are you with me?
  • Will you dance with me right now?
  • What's your favorite way to be greeted by me?
  • How many times did you want to ask me out before you did?
  • What color do you associate me with?
  • Do you think about me during the day?
  • What was our first kiss like for you?
  • If I was sad, how would you make me feel better?

Random Questions to Ask Your Boyfriend

When you think of good questions to ask your boyfriend, your mind probably goes to the serious ideas we've already listed above. We're of the mindset, though, that random questions are just as valuable. (At the very least, they're way more fun than the hard questions.) These obscure and funny things to ask your bf are ideal for when you need something new to talk about. Thank us later.

  • What's the craziest conversation you've ever overheard in public?
  • What's your favorite scent?
  • What candy do you think is overrated?
  • What's the last movie that made you cry?
  • Who's the most surprising musical artist you love?
  • What song could you listen to on repeat forever?
  • What's your biggest pet peeve?
  • If you could pick up and move to an entirely new city, where would you go?
  • If you didn't have to work for an entire year, what would you do with your time?
  • Do you watch the news?
  • If you could have any animal as a pet, what would you choose?
  • What was your favorite subject in school?
  • If you could go back and relive any day of your life, which one would you pick?
  • What food or drink could you never live without?
  • What's your biggest hot take?
  • What's your comfort TV show?
  • What do you think is the weirdest habit you have?
  • Have you ever used a pick up line? Was it successful?
  • Do you believe in aliens?
  • Do you believe there are sea creatures we haven't discovered yet?
  • Would you ever run for President?
  • Do you ever snoop on people's phones in public?
  • If you could adopt any skill without practicing, which would you pick?
  • What's one meal you wish you could make perfectly?
  • What's your favorite amusement park activity?
  • What's your gas station snack combo?
  • What was your favorite school lunch as a kid?
  • Would you go to space if you had the opportunity?
  • What do you think is the best outfit in your closet?
  • Do you make your bed every morning?
  • Would you rather be right or happy?
  • Do you prefer rainy days at home or sunny days at the beach?

Important Questions to Ask Your Boyfriend

We can't complete our list of good questions to ask your boyfriend without highlighting the most significant ones. These questions get to the core of who your boyfriend is—and we'd argue that you don't truly know each other until you talk about these topics. When you're ready, bring up these important questions to ask your boyfriend. You never know what more you'll learn.

  • How do you think responsibilities should be divided in a marriage?
  • How do you identify politically?
  • Do you think it's ever okay to lie? In what circumstances?
  • Would you speak up if I do something that offends or upsets you?
  • What's a relationship mistake you made in the past that you don't want to repeat?
  • Do you think people ever truly change?
  • Does your family have any cultural values or traditions I should know about?
  • Do you think we fight fair?
  • Do you think couples should have shared financial power in a relationship, or should it fall to one person?
  • Would you rather be a stay-at-home parent or a working parent?
  • Do you expect dinner to be ready for you when you come home from work? What happens when both of us are working?
  • Has anyone ever made you feel belittled at work? What about in your personal life?
  • Do you think it's possible to stay in the honeymoon phase forever?
  • Do you think the mental load of our shared responsibilities is equally divided?
  • How do you think couples can keep the spark alive in a long-term relationship?
  • Do you feel like there are gender or societal pressures in our relationship?
  • Would you ever go to couples therapy?
  • Do you trust me?
  • Do you feel safe in our relationship?
  • What do you value most about our relationship?
  • What's something we could change about our relationship to make it stronger?
  • Can you see yourself getting married to me?
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