440 Questions to Ask Your Boyfriend (2024)

Questions to Ask | Conversation Starters | Dating

By Bea Mariel Saulo

Updated on December 1, 2023

About You

What’s the first thing that attracted you to me?
How did you feel when we first met?
What’s your favorite memory of us together?
When did you realize you were in love with me?
What makes you happy when you’re with me?
What’s one thing you wish I knew about you?
How would you describe me to your friends?
What’s your favorite thing about our relationship?
What do you think is my best quality?
What’s your favorite way to spend time with me?
Do I make you laugh? What’s the funniest moment between us?
What’s a small thing I do that you really appreciate?
How do you feel when we’re apart?
Do you think I understand you well?
How do you feel when I’m upset?
What do you think is something I’m really good at?
What’s a dream or goal you think we can achieve together?
How would you handle it if we had to be long-distance for a while?
What’s something new you’d like to try with me?
How do you feel when I surprise you?
How do you feel about meeting my family?
How do you want to celebrate our anniversaries?
Do you feel like I support your passions and interests?
How do you feel when I talk about my own dreams and goals?
Do you get jealous if other guys talk to me? How do you handle it?
How do you feel when I make sacrifices for you?
What are some things you wish I would do more often?
Do you think I listen to you well?
How do you feel when we disagree on something?
What’s the most important thing you’ve learned from our relationship?
Do you think we make a good team? Why?
What’s your favorite thing for us to talk about?
How would you feel if I had to move away for work?
What do you think is my biggest challenge, and how can you help me overcome it?
Do you feel like you can be your true self around me?
How do you feel when we make plans for the future?
What do you think I find most attractive about you?
Do you think I make you a better person? How?
How would you feel if we had to spend some time apart?
How do you know when I’m really happy?

About His Views on Love and Romance

What does love mean to you?
Do you believe in love at first sight?
How do you know you’re in love with someone?
What do you think is the most romantic thing ever?
Do you believe soulmates exist?
What’s your love language?
How important is romance in a relationship for you?
How do you show someone you love them?
What’s your idea of a perfect date?
Do you think a relationship can last without love?
What romantic movie best describes your view of love?
How important is physical attraction in a relationship?
Do you believe in ‘the one‘?
Do you think love can conquer all obstacles?
What’s a romantic gesture you’ve always wanted to try?
How do you keep the spark alive in a relationship?
What’s your favorite love song and why?
Do you think it’s important to say “I love you” often?
What’s the most romantic place you’d like to visit?
How do you feel about public displays of affection?
Do you think love changes over time? How?
What qualities make someone “marriage material” for you?
How would you handle love in a long-distance relationship?
How important are anniversaries to you?
What do you think is the key to a happy relationship?
Do you believe opposites attract?
How do you feel about love letters?
What’s the biggest sacrifice you’d make for love?
Would you move to a different place for love?
What’s your opinion on online dating?
How do you feel about couple’s vacations?
Do you believe in taking breaks in a relationship?
What’s your view on flirting when you’re in a relationship?
Do you think it’s okay to keep secrets in a relationship?
What’s your take on open relationships?
How important is it for you to hear romantic words?
Do you think love should be easy or a challenge?
What’s a relationship deal-breaker for you?
How would you handle disagreements in love?
Do you think love needs to be “tested” to be true?

About His Goals and Dreams

What’s your biggest dream in life?
Where do you see yourself in 5 years?
What job would make you the happiest?
Do you have any goals for this year?
What’s one thing you want to achieve before you turn 30 (or any other age)?
What’s on your bucket list?
How important is money to you?
Do you have a ‘dream’ place you’d like to live?
What skills do you want to learn in the next few years?
Is there a cause or charity that you feel passionate about?
Do you have any travel goals?
What’s your dream car or mode of transportation?
Is there a specific path you want your career to take?
Do you have any health and fitness goals?
Is there a hobby you’ve always wanted to pick up?
How important is family to you in the future?
Do you have plans for further education or courses?
Are you interested in starting your own business someday?
How do you want to grow as a person?
What’s something you’ve always wanted to do but haven’t yet?
Do you have any role models or people who inspire you?
How do you want to make a difference in the world?
Do you want to write a book, make a movie, or create something?
Do you have any financial goals like buying a house?
How do you deal with setbacks or failures?
What’s your philosophy on work-life balance?
What are some milestones you want to reach in your career?
How do you measure success for yourself?
Is there a particular industry you want to excel in?
Do you have any plans for retirement?
What would you like to be remembered for?
Do you believe in having a “five-year plan“?
Is fame or recognition important to you?
How do you handle stress or pressure to achieve your goals?
Do you have any artistic or creative dreams?
Is there a particular challenge or adventure you want to take on?
Do you have any spiritual or personal development goals?
How do you prioritize your goals?
What are you willing to sacrifice to achieve your dreams?
How do you plan to achieve these goals and dreams?

About His Family

How close are you to your parents?
Do you have any siblings? What’s your relationship like with them?
What’s your favorite family tradition?
Who in your family are you most like?
What was your childhood like?
What’s the most important lesson your family taught you?
What’s your favorite memory with your family?
How often do you see or talk to your family?
What’s the funniest thing that ever happened at a family gathering?
Who’s the ‘black sheep’ in your family, if there is one?
What’s a typical family dinner like at your home?
Do you have any family secrets you can share?
Who is the peacemaker in your family?
What’s the best advice a family member has given you?
Do you have any famous or highly accomplished relatives?
What’s something you admire about your parents?
Are there any family heirlooms that are special to you?
What do family holidays look like in your home?
Who are the storytellers in your family?
Do you have a favorite cousin, aunt, or uncle? Why are they your favorite?
How do your family members handle conflict?
What was the hardest thing your family has gone through?
What values do you share with your family?
Is there a family member you wish you were closer to?
How did your parents meet?
What are some family sayings or mottos?
How does your family celebrate birthdays?
Are there any traits that run in your family?
Is there a family business?
How many generations of your family can you trace?
How would you describe your family in three words?
Do any of your family members have special talents?
What’s something your family doesn’t know about you?
Is there a ‘favorite’ child in your family?
What’s the most important thing your family has done for you?
How does your family handle money and finances?
Does your family have any yearly trips or outings?
Is religion a big part of your family’s life?
How do your family members show their love for each other?
What are your parents’ hopes for you?

About His Fears and Worries

What’s your biggest fear in life?
Are you afraid of losing someone close to you?
What keeps you up at night?
Have you ever been really scared for your safety?
What’s a fear you’ve overcome?
What worries you most about our relationship?
Are you afraid of getting old?
Do you worry about your health?
What’s a financial worry you have?
What scares you about the future?
Do you have any phobias?
What were you scared of as a child?
Do you worry about what others think of you?
Are you afraid of failing in your career?
Do you have any fears about becoming a parent someday?
What scares you about commitment?
What’s something you’re hesitant to tell me?
Do you worry about natural disasters or events out of your control?
Do you have fears about our long-term compatibility?
What would you do if you weren’t afraid of failing?
Do you ever worry about our communication?
Are there fears you’ve never told anyone about?
What worries you most about your loved ones?
Are you afraid of being alone?
Do you get anxious about social situations?
What would be your ‘worst-case scenario‘?
Do you worry about missing out on things (FOMO)?
Are you afraid of not being good enough?
What’s a recent worry you’ve had?
What scares you about love?
Do you worry about losing your freedom?
What’s a fear you hope to conquer?
Are you afraid of having regrets?
Do you worry about not making a difference?
What scares you about vulnerability?
Do you have any travel-related fears?
Are you afraid of being misunderstood?
Do you worry about your family’s health?
What would you like to change but are afraid to?
What’s a worry you’d like us to solve together?

About His Friends

Who’s your best friend, and how did you meet?
What do you usually do when you hang out with your friends?
Have you ever traveled with your friends?
Do any of your friends know me well? What do they think?
Are there friends from your past you miss?
How do you solve conflicts with your friends?
What’s the most fun you’ve ever had with your friends?
Do you have a friend who’s the complete opposite of you?
How do you support your friends when they’re going through tough times?
Have you ever had to end a friendship? Why?
What qualities do you look for in a good friend?
What’s a tradition you have with your friends?
Do you have any friends who have known you since childhood?
Are there things you only share with your friends and not me?
Have you ever been jealous of a friend? Why?
What do your friends tease you about?
Is there something your friends do that annoys you?
How do you feel about my friends?
How have your friends influenced your life choices?
Do you have any friends that you admire? What for?
How often do you catch up with your friends?
Are there friends you wish you were closer to?
What’s a funny story involving you and your friends?
How do you feel about lending money to friends?
What’s something you only do with your friends?
Have your friends ever given you relationship advice?
Is there a friend you have a lot in common with? What are those things?
Do you have friends from different stages of your life?
Have you ever worked on a project or hobby with your friends?
Do your friends come to you for advice? What kind?
How did your last birthday celebration with friends go?
Have your friends ever surprised you? How?
What’s something you learned from your friends?
How do your friends react when you’re going through hard times?
Do you have friends from diverse backgrounds? How has that enriched you?
Do you keep in touch with friends who moved away?
What’s a skill or trait you admire in one of your friends?
Do you have any group chats with your friends? What’s it like?
Are you the planner in your group of friends, or someone else?
How important is it for you that I get along with your friends?

About His Hobbies and Interests

What’s your favorite hobby right now?
How did you get into your main hobby?
Is there a hobby you’ve always wanted to pick up but haven’t?
What’s a hobby you loved as a kid?
Do you have a go-to way to relax and unwind?
What’s your favorite type of music?
Do you have a favorite artist or band?
What’s the last book you read and enjoyed?
Are you into any sports?
What’s your favorite thing to do on weekends?
Do you like video games? What’s your favorite?
Are you a movie buff? What’s your favorite genre?
Is there an activity or hobby you think we should do together?
Do you have any artistic talents like drawing or playing an instrument?
What’s a skill you want to learn?
What’s your favorite way to get some exercise?
Do you enjoy cooking? What’s your best dish?
Do you like the outdoors? Hiking, camping, or something else?
What TV shows are you into right now?
Are you a podcast fan? Any recommendations?
Do you follow any blogs or YouTube channels closely?
What’s your favorite type of food?
Do you enjoy going to concerts or live shows?
Are you interested in history or museums?
Do you have any collections, like stamps, coins, or something else?
What’s your favorite board game or card game?
Do you enjoy doing puzzles or brain teasers?
Are you into photography?
Do you like to write, maybe a journal or stories?
What’s your favorite thing to do at the beach?
Do you have a dream travel destination?
Are you a fan of any particular sports team?
Do you like to garden or take care of plants?
Are you into fashion or style?
What’s your favorite way to spend time in nature?
Do you like to dance?
What’s your go-to karaoke song?
Are you into any niche hobbies that most people haven’t heard of?
Do you enjoy going to the gym or working out?
What’s something you’re really passionate about?

About His Job and Career

Do you enjoy your job? Why or why not?
What’s your typical workday like?
Who’s the most interesting person you’ve met through work?
What’s the most challenging part of your job?
Is this the job you thought you’d be doing when you were younger?
What’s the most rewarding part of your work?
Do you have a work best friend?
Are there any skills you’ve picked up at your job that you’re proud of?
What’s a project you’ve worked on that you’re really proud of?
Do you feel like you have a good work-life balance?
What are your career goals for the next few years?
Do you see yourself staying at your current job long-term?
What’s something you wish you could change about your job?
Do you have any mentors or people who’ve really helped you in your career?
What was your first job ever?
Is there another career you’d want to try if you had the chance?
What’s the best career advice you’ve received?
How do you handle stress at work?
Do you like working in a team or alone better?
How do you deal with difficult coworkers?
Are there any company perks you really enjoy?
Have you ever considered starting your own business?
What’s a typical meeting like at your workplace?
Do you have to travel for work? Do you enjoy it?
How important is job satisfaction for you?
Do you ever have to bring work home?
What’s your morning routine before work?
How do you unwind after a tough day at work?
Are you a part of any work-related organizations or networks?
Do you think your job makes a difference in people’s lives?
What’s the most important quality for success in your field?
Have you ever thought about going back to school for further career development?
How do you keep up-to-date with your industry?
Do you have a ‘dream job’?
How do you handle office politics?
What’s one thing you’d like to accomplish in your career?
Have you ever had to make an ethical decision at work?
How do you feel about your career progress so far?
Is your job what you thought it would be like?
What’s the first job you ever wanted as a kid?

About His Past

Have you had a long-term relationship before?
How long ago was your last relationship?
What did you learn from your last relationship?
What caused your last relationship to end?
Were you ever engaged or close to getting engaged?
How do you handle breakups?
Did you remain friends with any of your exes?
Do you believe in staying in touch with exes?
Was trust an issue in any of your past relationships?
Have you ever been in a long-distance relationship?
What’s something you regret about a past relationship?
Have you changed anything about yourself after a past relationship?
Were your past relationships more casual or serious?
Did you ever live with a previous partner?
How did your family feel about your exes?
Have you ever had to deal with a difficult breakup?
Have you ever had your heart broken?
What’s the longest relationship you’ve been in?
What’s a deal-breaker for you in a relationship?
Were you ever in a relationship that you knew wasn’t right?
How do you handle arguments in a relationship?
Have you ever been in a relationship where you felt you had to change yourself?
Have any of your past relationships impacted your career?
Did you ever date someone your friends didn’t like?
Were any of your past relationships during a turbulent time in your life?
How long do you usually wait before introducing someone you’re dating to your family?
Have you ever had a ‘rebound’ relationship?
What’s a relationship pattern you don’t want to repeat?
How long do you usually wait before getting into a new relationship?
Have you ever gone back to an ex?
Do you think any of your past relationships affected your self-esteem?
Were you ever in a relationship where you felt taken for granted?
Did you ever date someone who was very different from you?
Have you dated someone from a different cultural background?
How did you meet most of your exes?
Have you ever stayed in a relationship out of convenience?
Were pets ever an issue in your past relationships?
Have you ever been cheated on?
What’s something you wish you’d done differently in a past relationship?
Do you believe that ‘once a cheater, always a cheater‘?

Romantic Questions

What was your first thought when we met?
When did you know you were falling for me?
What’s your favorite memory of us so far?
How would you describe our relationship in three words?
What’s the most romantic thing you’ve ever done for someone?
What’s one thing that always makes you think of me?
How do you feel when we’re apart?
What’s your dream date night with me?
What’s your favorite way I show you love?
Do you believe in soulmates?
What’s your favorite physical feature of mine?
What’s your favorite personality trait of mine?
What song makes you think of me?
Do you ever have dreams about me?
What’s the most meaningful gift you’ve ever received?
How would you feel about writing love letters to each other?
What’s a small thing I do that you absolutely love?
What was your favorite date that we’ve been on?
What’s something you want to do with me that we haven’t done yet?
How do you picture us 10 years from now?
What’s the most romantic place you’d like to visit with me?
What’s the best way to show you that I love you?
Do you remember our first kiss?
What’s your favorite thing about our relationship?
What do you think is the strongest part of our relationship?
What’s a romantic movie you’d want to watch with me?
Would you ever write a poem about me?
What’s the most romantic thing I’ve done for you?
What’s your favorite way to be close to me?
Do you like it when I surprise you?
What’s your favorite thing for us to do on a rainy day?
Do you like star-gazing? Would you do it with me?
What’s a romantic gesture that would melt your heart?
Do you like cuddling while we sleep?
What’s a couple you admire and why?
Do you like holding hands in public?
What’s your favorite romantic quote?
How do you feel when you read my messages?
What’s something that would make our relationship even better?
How much do you love me?

Deep Questions

What’s a life lesson you learned the hard way?
What do you value most in your closest friendships?
Do you have any regrets? What would you change if you could?
What do you consider your greatest accomplishment?
What’s something you wish people understood about you?
What are you most afraid of losing?
How do you cope with stress or sadness?
What’s your biggest fear about our relationship?
How do you define a successful life?
What’s your philosophy on life?
What does love mean to you?
What are your thoughts on faith and spirituality?
How do you feel about money and its role in your life?
What would you do if you found out you only had a short time to live?
What’s your stance on forgiveness?
What’s something you’ve never told anyone?
What’s the most challenging experience you’ve been through?
What’s one thing that changed your outlook on life?
How do you handle anger or resentment?
What’s something you struggle with in your personal life?
What’s a dream you have that you haven’t pursued? Why?
What’s your biggest insecurity?
What do you think happens after death?
Is there anything you wish you could say to someone who isn’t in your life anymore?
Do you ever feel lonely? What makes you feel that way?
What’s something you wish you could change about yourself?
What are your thoughts on marriage and starting a family?
How do you feel about gender roles in relationships?
What do you think is the hardest part of being in a relationship?
How do you deal with conflict?
What’s your idea of true happiness?
Is there a cause or issue that you’re passionate about?
What are your thoughts on social media and its impact on relationships?
What’s the worst piece of advice you’ve ever received?
How would you like to be remembered?
Do you ever think about your own mortality?
What do you think is your biggest character flaw?
Is there anything you consider unforgivable?
What’s the most difficult decision you’ve ever had to make?
How do you want to grow as a person?

Frequently Asked Questions

What if my boyfriend is shy or introverted? How should I approach asking questions?

Gentle and Non-Intrusive.

If your boyfriend is shy or introverted, the key is to ease into deeper conversations. Start with lighter, non-probing questions and gradually build up to more intimate topics as he becomes comfortable. The idea is to make the conversation feel natural, not like an interview.

What if my boyfriend asks me the same questions back? Should I be prepared to answer?

Reciprocity is Key.

Absolutely, be prepared to answer any questions you ask. Conversations are a two-way street, and being open with your answers can set the tone for a more open and honest relationship.

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