A Casual 150 (!!) Questions to Ask Your Boyfriend
Have you ever sat down to dinner with your partner and realized that you have absolutely nothing to say to each other? Sure, it could be because this is your hundredth dinner together, and the topics have naturally waned. But it could also be that you might not be asking the right questions.
“I believe deep questions open up layers of emotional intimacy that might otherwise stay hidden,” explains dating and relationship expert at Flirtini, Anastasiya Pochotna. Not only does asking deep questions allow you to get some insight into what your partner’s thinking, but it can also help break down walls and create a sense of trust and understanding, says Pochotna. Plus, it shows your partner that you’re genuinely interested in learning and growing together—not just focused on surface-level conversations.
Need some help getting started? Tell them you want to plan a “deep date night,” where you spend some time getting to know each other better. “There shouldn't be hard ‘off-limits’ topics, but be mindful of timing,” suggests Pochotna. “Sometimes, certain questions might need more emotional prep or aren't right for that moment. Let it flow naturally and keep the focus on deepening your connection, not stirring up conflict."
Once the mood is set, defer to this list of the best deep questions to ask your boyfriend. These cover everything from future hopes and dreams, to how they feel about family, how they grew up, and what kind of partner they want to be. We’re betting that after asking each other a few of these, you’ll feel closer than ever. Whether you’re out on the town or cozy at home, use these conversation starters to spice up any date night.
Deep Questions About Their Life
What part of your childhood would you like to recreate if you have kids?
What brought you pure, unfiltered joy when you were a kid?
What is your best childhood memory?
How did your parents make you feel when you were a child?
How did you discover your passion for (*insert favorite hobby here*)?
Do you believe that everything happens for a reason, or that we build our own futures?
What is one thing your mother did growing up that you’d never want to repeat for your kids?
What is one thing your father did growing up that you’d never want to repeat for your kids?
Tell me about your first heartbreak. How did you recover from it?
What is one thing you thought happened to everyone growing up, only to realize that it was unique to you?
What’s your most embarrassing memory from childhood?
Why do you think that memory still sticks with you to this day?
What was your dynamic like with your siblings when you were growing up?
Do you think you fit the role of a typical (younger, older, middle) child?
How did you learn to handle fear when you were a child?
What is your favorite birthday memory?
Why do you think that memory sticks out so powerfully to you today?
Tell me about a time your siblings hurt your feelings?
Tell me about a time you hurt someone’s feelings when you were a child?
What TV show or movie influenced your life when you were a child?
Do you want to let your kids watch TV/have screens if you are/become a parent?
What is the worst thing that ever happened to you?
What is the best thing that ever happened to you?
Have you ever bullied someone or been bullied yourself?
What is one thing you wish you knew about life now when you were a kid?
If you could go back in time and comfort your inner child, what would you say to them?
What smells, if any, stick out to you from your childhood?
What is a time that you remember being truly frightened from childhood?
What did you think your life would look like now when you were a child?
Did you ever think about finding a partner when you were younger?
Deep Questions About Your Relationship
Did you think you were ready for a relationship when we first met?
What do you remember about our first date?
When do you find yourself having the most fun when we’re together?
Where is your favorite place to go with me?
What did you learn about love from your first relationship that you think influences you in our current relationship?
Do you want to get married one day?
Do you want to have children one day?
How do you think your friends see our relationship?
What is the most interesting thing your parents have ever said about our relationship?
What is the most interesting thing your friends have ever said about our relationship?
When did you know you wanted to make our relationship official?
What do you think makes you a great partner?
What do you think makes me a great partner?
What do you think you could improve on in our relationship?
What would you like to see me improve on in our relationship?
Where would you like to see our relationship headed in the next year?
What about in the next five years?
Do you have any fears when it comes to our relationship?
Do you think growing up seeing your parents’ relationship influenced the way you see our relationship now?
How do you go about problem solving in our relationship?
What is the worst thing about fighting with me?
What is the best thing about fighting with me?
What have you learned about yourself during the time we’ve been together?
What do you wish I would open up about more in our relationship?
Is there any part of me that confuses you/is a mystery to you?
What do you think is the key ingredient for a long-lasting relationship?
What qualities do you think make for a healthy relationship?
Who is the best couple you know? Why do you think so?
What is something about our relationship that you’re proud of?
Did you think you’d be the type of partner that you are now?
Deep Questions About Sex
What was your ultimate sexual fantasy when you were younger?
What did you think about your first sexual experience?
What were you most excited about the first time we had sex?
What do you remember about the first time we had sex?
Have you ever had to use a safe word during sex?
What’s your favorite safe word?
Did anything about having sex with me make you nervous when we first met?
What is something you’ve always wanted to try in the bedroom, but haven’t yet?
What’s your biggest fear when it comes to trying that new thing?
What is something I do that turns you on when we have sex?
What is something you feel like you’re really good at during sex?
What is your favorite sex position?
What position do you wish we had sex more in?
Would you ever be interested in introducing food into the bedroom?
What about sex toys?
What is your favorite accessory (ex: toys, lubes) to use in the bedroom?
What is the sexiest thing I could wear in the bedroom?
What song do you think best describes our current sex life?
What song do you want to describe our future sex life?
Are we having sex as much as you’d like to?
What do you think is my favorite thing that you do during sex?
If you were to have a video/TV show/movie playing in the background when we had sex, what would it be?
What is something most people like in the bedroom that you don’t really care for?
What is your ultimate sexual fantasy that you actually don’t want to do in real life?
What is the most embarrassing thing that’s ever happened to you in the bedroom?
What is something that you never want to try/do in the bedroom?
What smells turn you on?
What type of lighting turns you on?
What is your idea of the perfect foreplay?
What is the sexiest text message you’ve ever gotten?
Deep Questions About Their Goals and Dreams
Where did you think your life would be now when you were 10 years younger?
What would you be truly disappointed in having not happened by the time your life is over?
What do you think is the formula for a happy life?
What does success look like to you?
What do you think scares you the most about the future?
What is one of your biggest dreams?
What are you doing now to make that dream a reality?
How can I be more supportive of you and your dreams?
If money wasn’t an object, what would your dream job be?
Do you have milestones that you want to reach in your life?
What do you think holds most people back from achieving their dreams?
What accomplishment are you most proud of?
If you could go back to school, would you?
If yes, what would you study?
Do you think it’s possible to be successful in your career and be a great parent? Why?
What do you like about living here?
Do you see yourself staying here forever?
Where do you want to retire?
At what age do you want to retire?
What is your dream vacation?
If you could have a second house anywhere, where would it be?
What country is number one to visit on your bucket list?
At what age would you like to visit that country?
What is your dream car?
What would be your dream band/artist to see in concert?
If you could play any instrument, what would it be?
What does a dream day in your life look like?
Is there a certain amount of money you want to make by a certain age?
If you were giving a TED Talk, what would it be on?
Whose career inspires you the most and why?
Deep Questions About Your Future Together
If you want to get married, when do you see us taking that step?
If you want to have kids, do you see yourself with a son or daughter?
Do you have any concerns over politics and how they can impact us in the future?
Is owning a home one of your goals?
If you want to have kids, what type of parent do you want to be?
What type of parent do you see me being in the future?
Do you think two people can be in love for most of their lives?
What is one thing you need from me to build a successful future together?
What is one thing that scares you when it comes to building a future together?
How do you think we will handle disappointments in the future together?
Do you think we're emotionally compatible?
Do you think divorce is sometimes necessary, or should a relationship always be fought for?
What do you think is unforgivable in a relationship?
When you picture us in our future home, what are we doing on a Saturday night?
What do you picture the holidays looking like for us in five years?
How would you handle it if you didn’t get along with one of my family members?
Does any member of my family concern you when it comes to spending forever together?
How do you think we should handle taking care of our parents/family members in their elder years?
How do you think we should handle childcare in our family if we have children one day?
What do you want our legacy to be as a couple?
Would you ever want to live half the year in one location and another half somewhere else?
Do you believe that going to bed angry is a big deal?
Do you think it’s okay to fight in front of our friends or family members?
What scares you about committing to me for the next few years?
What excites you about committing to me for the next few years?
In what way do I make you happy in our current life?
What is one thing you never want us to fight over in our future?
What is one thing you never want me to be afraid to talk to you about?
Do you think fighting can sometimes be healthy?
Does the idea of our future excite you, or does it make you nervous?
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