100+ Important Questions to Ask Your Boyfriend

Updated September 23, 2022
Couple on a date

Having a great arsenal of questions to ask your boyfriend can keep things interesting in your relationship. If you've had a few dating apps on rotation, then you know what creative conversational burnout really looks like. Unfortunately, just bagging the cute guy doesn't get you off the hook; there are still a ton of things to ask your boyfriend once you start dating. But, we're all blessed to live in the internet age where we don't have to mull over good questions to ask your bf. Rather, you can turn to this assortment of important, serious, and interesting questions to get your boyfriend to open up and reveal his inner self. Whether your relationship is brand-new, or you have been together for a while, the best questions to ask your boyfriend at any stage of the relationship will help the two of you draw meaningful connections.

While sometimes fun couples questions are exactly what you need for your date night, other times it's those deeper things that help you to get to know a potential partner, understand what's important to them, or make decisions about the future. Although you might want to go beyond just the cute topics, it isn't hard to know what to ask your boyfriend with a list of interesting questions like these.

Thought-Provoking Questions to Ask Your Boyfriend

When you start a new relationship, you want to learn everything you possibly can about them, but sometimes you don't know how to start segueing from the sillier stories to the deeper stuff. If you think the relationship might have long-term potential, you shouldn't be afraid to ask your partner the juicy questions about himself. Don't worry about racking your brain for some good questions to ask your boyfriend; use these things as a jumping-off point to get to know him better.

Relaxed couple having a lighthearted conversation
  • Where are you originally from?
  • What was your favorite place to visit and why?
  • What was your parent's relationship like?
  • What was your relationship like with your parents?
  • Do you feel your parents treated you and your siblings the same or was there favoritism?
  • What kind of student were you in school?
  • What are some of your favorite childhood memories?
  • What was your favorite subject in school and why?
  • Do any health problems run in your family?
  • Have you ever had a childhood wish come true?
  • What's the kindest thing you've ever done for someone?
  • What's the kindest thing someone's done for you?
  • Are you close with your extended family?
  • What are some prominent things that have happened in your past that you think have contributed greatly to who you are today?
  • What are some things in your childhood you'd like to improve upon for your child/children?
  • Did you have a lot of friends as a child, or did you have just a few really good ones?
  • How did you spend your summer vacations?
  • Who was your hero when you were growing up?

Serious Questions to Ask Your Boyfriend

Fun questions help get the conversation going, but you'll want to delve into more intimate matters eventually. These deep relationship questions will give you a better idea about your boyfriend's relationship history as well as a hint about how your own relationship might turn out. After all, communication is increasingly important the longer you stay in a relationship, and prioritizing which serious questions to ask your boyfriend about your future can give you a clearer idea of whether your relationship is meant to last. There's no absolute test when it comes to love, but going forward with some of the hard questions to ask your boyfriend can help you know a bit better how compatible you are and where your love might lead.

Young couple talking in coffee shop
  • How did your last relationship end?
  • Are you and your ex still friends?
  • How many sexual partners have you had?
  • How do you cope with stress?
  • Do you have any bad habits I should know about?
  • Are there any habits that get on your nerves?
  • What's the worst thing you've ever done?
  • Have you ever broken the law?
  • How would you handle it if you lost your job?
  • How would you handle it if I lost my job, and we were living together and sharing expenses?
  • What's your relationship to anger? Are you hot-headed or a slow burner?
  • Do you like to travel or would you rather stay home?
  • How do you handle disagreements?
  • What's something you do that's caused problems with relationships in the past?
  • What are some of your ideas for how to keep a relationship strong over time?
  • What do you think of my dream of becoming a ______? (Fill in your own goal, like novelist, karaoke star, or TV personality.)
  • When you break up with someone, how do you normally do it?
  • What's the worst breakup you've ever experienced? Why was it so bad?
  • What are your thoughts on marriage?
  • What are your thoughts on kids?
  • Are you comfortable talking about where our relationship is going?
  • If I were offered a promotion and had to move away, would you move with me?
  • Where do you see us in five years?
  • If one of your friends or family members told you to break up with me because he/she didn't like me, would you?
  • How do you feel about my family and/or friends?
  • How would you deal with a disagreement with one of my family members or friends?
  • How much time do you think we should each spend with our family/friends outside of gatherings that require us both to be there?
  • What do you tell your friends about me when I'm not around?
  • What do your finances look like?
  • Do you have a retirement fund/are you someone who likes to invest?
  • What's the one thing you always splurge your paycheck on?

Good Questions to Ask a Potential Boyfriend

If you're just now re-entering the dating scene after a long time away, weeding out the good picks from the bad will be overwhelming. The last thing you want to do is spend a lot of time with someone where the connection never goes anywhere. Thankfully, there are ways to figure out who's right for you, and one of the best is whittling away at those surface-level conversations with some well-placed, meaningful questions to ask your potential boyfriend. Before you start committing to giving one another romantic nicknames, learn about what's hiding behind those pearly whites of a potential partner with these deeper getting-to-know-you questions.

Couple drinking coffee and talking
  • What was your favorite thing to do with your childhood best friend?
  • What's the scariest thing that's ever happened to you?
  • Have you ever had a falling out with a close friend?
  • Which public figure do you look up to the most?
  • What's the quality about yourself that you admire the most?
  • What's one quality you find yourself drawn to?
  • Who do you wish you could be more like, and why?
  • Where do you see yourself at 50?
  • What does being successful look like to you?
  • What's your biggest pet peeve?
  • What accomplishment are you most proud of?
  • Is there anything you desperately want to do before you settle down?

Interesting Questions to Ask Your Boyfriend

While your relationship is still fresh, it's nice to get to know the silly basics of what makes your man tick. Beyond the simple questions of what's his favorite color, or which food he hates, there's a bevy of interesting questions to ask a new boyfriend that you can use to get him to share some of his deeper thoughts on life, the world, and your relationship. While these topics can be jam-packed with meaning and lead to tons of interesting stories and conversations, some of them are also cute questions to ask your boyfriend that are the perfect foil to the harder-hitting aspects you'll want to learn.

Gay couple looking at Map smartphone
  • How would you describe yourself using only one word?
  • How would you describe me using only one word?
  • Do you think we've met before in a previous life?
  • Can you tell me about your most embarrassing moment?
  • What's the biggest faux pas you've made while traveling?
  • What is your favorite item of clothing?
  • Are you superstitious?
  • If you could be anyone else for a day, who would you choose?
  • What's your dream job?
  • If you're having a bad day, how can I cheer you up?
  • When you're sick, do you like to have someone taking care of you, or do you prefer to be left alone until you're better?
  • If you're lost, do you ask for directions?
  • What would you do if I were suddenly unable to speak your language?
  • What's one household chore you don't know how to do?
  • What's one type of household chore you're unwilling, or at least very resistant, to do?
  • Who's your hero?
  • What's your favorite book?
  • What's your favorite place to go when life can get overwhelming?
  • How do you respond to stress?
  • How much time do you spend on social media in a week?
  • If you won the lottery, what would you do with the money?

Important Things to Ask Your Boyfriend Before Moving in Together

Moving in together is a major step forward in any relationship, so you shouldn't go into it blindly; be prepared with some honest things to ask your boyfriend about habits and lifestyle before you take that leap. Your boyfriend's answers to these revealing questions can help you determine if the two of you have enough basic compatibility to live together on a daily basis. After all, loving someone and living with someone require totally different things, and you should be prepared for any kind of circumstance before signing a lease with someone who can't seem to remember to keep the fridge door closed. So, if you can't stop stressing over what to ask your boyfriend before you move in together, take a deep breath and let these important questions lead the way.

Couple talking while sitting on the couch in the living room
  • Do you want to live together?
  • When do you think you'll be ready to move in together?
  • How will we handle paying the bills?
  • If we were to break up, who would move out?
  • Do you think we'll live in an apartment forever or transition into a house someday?
  • How will we make sure the chores around the house are divided fairly?
  • Are you a neat freak, or do you tend to leave socks and other items lying around everywhere?
  • Do you plan to adopt or purchase a pet in the near future?
  • Would you ever consider having additional roommates to cut costs if we had a place with enough space?
  • How will we make sure we each get to spend time alone when we share the same place?
  • If I have to work really late, will you have a problem with cooking or picking up some dinner for both of us?
  • How do you feel about chore charts?
  • What's the household cleaning task that you actually find a lot of fun?
  • Do you enjoy cooking, or are you horrible in the kitchen?
  • How much furniture do you own?
  • How many alarms do you set in the morning?
  • Do you like your house to stay on the colder or warmer side?

Important Questions to Ask Your Boyfriend Before Settling Down

If you reach the stage where the two of you are talking about marriage, it's time for the really serious questions. You'll need to discuss major life issues before you get engaged - not after. Asking your partner these future questions, or the 100s more at your fingertips, could save you from heartache. Dealing with the hard questions to ask your boyfriend about your relationship and where he stands on certain things might not be easy, but will help you make better decisions and manage expectations as you and your partner move forward.

Couple having a conversation
  • Where do you want to live in the long term? City? Mountains? Country?
  • What are your retirement plans?
  • What is your philosophy on money within a marriage? Is what's yours mine and vice versa, or will you prefer separate accounts and a roommate situation with bill paying?
  • How do you feel about taking in family members during a hard time? Elderly parents?
  • What's your take on getting the housework done if both partners work outside the home?
  • What are your thoughts on how to discipline children?
  • What kind of parent do you want to be?
  • How important do you think date nights are when you have children?
  • Are you open to the idea of marriage counseling?
  • How much time do you expect us each to be able to hang out with our friends once we've had children?
  • Would you be agreeable to staying home with the kids if my career was about to take off or if I made enough at my job to support that arrangement?
  • How will we spend our holidays?
  • Who will be responsible for screening babysitters or a nanny?
  • Are you a spender or a saver?
  • If our spending/saving goals differ, how will we compromise?
  • If you like the idea of marriage, do you want a small wedding, a large one, a visit to the courthouse, an elopement, or do you have no opinion at all?
  • What's your opinion on credit cards?
  • How much debt do you have right now?
  • What are your plans for getting out of debt or staying out of it?
  • What would you say if I told you I have a large amount of debt?
  • Will you support my decision if I want to go back to school one day?
  • Do you think that prenatal tests for certain birth defects or disorders should be done? How would you react to bad news?
  • What do you think each person's role is in a marriage?
  • Would you be willing to take on two jobs temporarily if that's what it took to make ends meet?
  • What is your stance on divorce?
  • If I have a disagreement with one of your family members or friends, will you stand up for me?

Know What to Ask Your Boyfriend

Getting to know your boyfriend on a deeper level is really exciting. There's nothing like peeling back the layers and discovering the things that make him tick, the interesting experiences that shaped who he is today, and the adventures he can't wait to go on with you. But, with the unknown comes the chance that his answers might not vibe with you, and if you find out that his answers aren't compatible with yours more often than not, it could end up in heartbreak. In that case, you should cut your losses early. If you've picked the right one, though, no serious or important question you throw at him will go unanswered.

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100+ Important Questions to Ask Your Boyfriend