Want to figure out what’s going on in a guy’s head? Whether it’s a new romance or a long-time friendship, asking the right questions can help you understand his real plans. Let’s dive into some questions that can clear the air!
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About the Relationship
- What are you looking for in a relationship?
- Do you want something serious or casual?
- What’s your idea of a perfect date?
- How long was your longest relationship?
- Why did your last relationship end?
- Are you close to your family?
- Do you see yourself getting married one day?
- What do you think is the most important part of a relationship?
- How do you handle conflict in a relationship?
- Are you looking to date multiple people or focus on one person?
- How often do you want to see each other?
- What are your thoughts on moving in together?
- How soon do you want to meet each other’s families?
- How do you feel about public displays of affection?
- What’s a deal-breaker for you in a relationship?
- How do you feel about long-distance relationships?
- What’s your opinion on sharing passwords?
- Do you want to have kids?
- How important is religion in a relationship to you?
- How do you show love?
- How do you like to receive love?
- What are your goals for the next 5 years?
- How would you handle financial matters in a relationship?
- How do you feel about your partner having close friends of the opposite sex?
- Do you have any relationship deal-makers?
- How would you handle jealousy in a relationship?
- What are your thoughts on taking trips together?
- How important is quality time to you?
- How often do you want to communicate when we’re not together?
- Do you like to plan dates or be spontaneous?
- How do you feel about pet names?
- Do you have any relationship fears?
- How do you feel about social media and relationships?
- What’s your comfort food after a bad day?
- How do you handle stress in your life?
- What’s your dream job?
- How important is physical attraction to you?
- Do you believe in relationship breaks or time apart?
- How important is it for your partner to get along with your friends?
- What’s your favorite way to spend a weekend?
About Commitment
- Do you believe in monogamy?
- What does commitment mean to you?
- How long do you think people should date before making it official?
- Have you ever been engaged or close to it?
- How do you feel about joint bank accounts?
- Would you consider premarital counseling?
- Do you think it’s important to have the same life goals?
- What role does trust play in your idea of a committed relationship?
- What makes you ready to commit to someone?
- Do you think it’s okay to keep secrets in a committed relationship?
- How would you introduce me to your friends?
- Do you believe love is enough to make a relationship last?
- How do you know you’re in love?
- Would you be willing to compromise your lifestyle for a committed relationship?
- What’s your outlook on work-life balance in a committed relationship?
- Are you a fan of grand romantic gestures?
- How do you feel about discussing future plans?
- Would you ever consider couples therapy?
- Do you think it’s okay to have a “Plan B” in a committed relationship?
- What are your thoughts on renewing vows?
- How do you feel about telling each other our deepest fears?
- How would you want to spend holidays as a couple?
- What’s your idea of a romantic anniversary celebration?
- How do you feel about matching outfits or jewelry to show commitment?
- What are your views on co-parenting if kids are in the picture?
- Would you put the relationship first, or are there other priorities?
- How do you feel about spending time apart for work or family?
- What are your thoughts on gift-giving in a relationship?
- How do you handle relationship stress?
- What are your thoughts on “taking a break” in a committed relationship?
- How would you handle it if we disagreed about a big life decision?
- What’s your comfort level with discussing past relationships?
- How would you handle it if one of us got a job offer in another city?
- What would make you end a committed relationship?
- How do you feel about relationship roles?
- Do you think date nights are important in a committed relationship?
- How often should a committed couple have serious talks?
- How do you handle disagreements?
- How much personal space do you need in a committed relationship?
- What’s your philosophy on open and honest communication?
About the Future
- Where do you see yourself in 10 years?
- Do you plan on staying in your current job, or are you aiming for something else?
- How important is it for you to own a home one day?
- Do you see yourself living in this city long-term?
- What’s your dream vacation destination?
- Would you ever want to live abroad?
- Are you open to changing religions or belief systems for someone?
- How would you feel about supporting a family?
- How important is retirement planning to you?
- Would you ever go back to school for more education?
- What’s your opinion on long-term health care planning?
- Do you want to be involved in community or social causes in the future?
- How would you feel if a future job required lots of travel?
- Do you plan on pursuing any other life dreams or ambitions?
- How do you feel about aging and getting older?
- Would you take care of your parents as they age?
- How would you handle it if one of us had to move for family reasons?
- Do you have a plan for your career growth?
- Would you join your family business if asked?
- What kind of legacy do you want to leave behind?
- Are you open to adopting kids if we can’t have our own?
- How would you handle a long-term illness in the family?
- How do you feel about long-term investments like stocks or real estate?
- What’s your plan for staying healthy as you age?
- Are you into sustainable living or planning for a greener future?
- Would you be open to relationship check-ins every year to talk about our future?
- Do you have any bucket list items you want to cross off in the next few years?
- How would you feel about taking a year off to travel or try something new?
- How do you plan to balance work and family life?
- How involved do you want grandparents to be in our future family?
- Do you see us spending most holidays with family or traveling?
- How would you handle unexpected financial difficulties?
- Would you be willing to do couples activities like dancing or cooking classes?
- How would you feel about taking adult education classes together?
- How involved do you want to be in our kids’ education?
- Do you see us living a busy life, or a more relaxed one?
- How often would you want to visit your hometown in the future?
- What are your thoughts on writing wills or future planning documents?
- How would you feel if I wanted a career change that required going back to school?
- How important are yearly traditions, like anniversaries or family reunions, to you?
About Trust and Honesty
- What does trust mean to you?
- Have you ever lied in a relationship?
- How would you handle it if you caught me lying?
- What’s your opinion on keeping secrets from your partner?
- How do you feel about transparency in finances?
- How would you handle a situation where you’re attracted to someone else?
- Do you think it’s okay to have private conversations with an ex?
- How would you feel about me reading your text messages?
- Would you lie to protect someone’s feelings?
- How do you feel about spying or snooping in a relationship?
- What would you consider a betrayal of trust?
- How do you rebuild trust once it’s broken?
- Do you think it’s okay to tell white lies?
- How would you feel if I had trust issues from a past relationship?
- What would make you lose trust in me?
- Do you believe in giving second chances after trust is broken?
- How do you feel about sharing personal or sensitive information?
- Would you keep something from me if you thought it would make me angry?
- How honest are you with yourself?
- How do you approach conflicts to keep the trust intact?
- Do you trust easily, or does it take time for you to trust someone?
- How do you feel about me having close guy friends?
- Do you think emotional cheating is as bad as physical cheating?
- Would you ever go through my phone without asking?
- Do you think honesty is always the best policy?
- What’s the hardest truth you’ve had to tell someone you care about?
- Do you think jealousy has a role in trust issues?
- What do you expect from me in terms of honesty?
- How transparent should we be about our past relationships?
- How would you handle it if a friend flirted with me?
- Do you think trust can be one-sided, or does it have to be mutual?
- What are your thoughts on having mutual friends of the opposite sex?
- How would you feel if I kept a private journal?
- Would you tell me if you didn’t like one of my friends or family members?
- How important is self-trust to you?
- Would you ever keep a health issue from me?
- How do you handle gossip or rumors?
- What’s your take on trust in an online relationship?
- Would you trust me to make big decisions for us?
- How do you feel about trusting someone with your emotional vulnerabilities?
About Family
- Do you want to have kids? If so, how many?
- How close are you to your family?
- What are your family traditions?
- How do you feel about meeting my family?
- How important is it for you that our families get along?
- What are your views on parenting?
- Would you be okay if I wanted to be a stay-at-home parent?
- What’s your opinion on family vacations?
- How do you handle family conflicts?
- What role do you see grandparents playing in our family?
- How do you feel about pets being part of the family?
- Would you move away from your family for a job opportunity?
- How do you feel about homeschooling kids?
- Would you be open to couples therapy for the sake of the family?
- How do you feel about family involvement in our life?
- Would you ever live with your parents again or have them live with us?
- How do you plan to balance work and family time?
- What’s your idea of quality family time?
- How do you feel about gender roles in family responsibilities?
- What are your expectations for holidays and family gatherings?
- Would you support my career, even if it meant less family time?
- How do you feel about financial support to family members?
- Would you be open to adoption or foster care?
- What are your thoughts on having a family immediately after marriage?
- How do you feel about blended families?
- Would you be open to family counseling?
- How would you approach family traditions, like religion and culture?
- What do you think about kids participating in extracurricular activities?
- How do you handle stress in the family?
- What are your thoughts on having family dinners?
- How do you feel about splitting time between both families during holidays?
- Would you be okay with me being the primary breadwinner?
- How do you plan to teach kids about money and responsibility?
- What’s your view on discipline and setting boundaries for kids?
- How would you handle it if our kid wanted to follow a non-traditional career path?
- What role do you think extended family should play in our lives?
- How do you feel about family members borrowing money?
- What are your thoughts on family reunions?
- How do you feel about having family photos and keepsakes around the house?
- How would you approach disagreements on family values?
About Work and Career
- What’s your dream job?
- Do you see yourself sticking with your current job long-term?
- How important is career growth to you?
- How would you handle job loss or setbacks?
- Would you ever consider becoming an entrepreneur?
- Do you believe in having a “work-life balance“?
- How many hours a week do you think is okay to work?
- Would you ever take a pay cut for a job you love?
- How do you deal with stress or pressure at work?
- Do you bring work home often?
- Would you relocate for a job?
- How do you feel about working on weekends or holidays?
- Do you think it’s important for both of us to work?
- How would you feel if I made more money than you?
- What’s your plan B if your current career doesn’t work out?
- How do you approach networking and building professional relationships?
- How would you handle it if we both had demanding jobs?
- What’s more important: job satisfaction or salary?
- How do you handle criticism at work?
- Would you ever go back to school to further your career?
- What’s your 5-year career plan?
- How do you handle office politics?
- How important is your job title to you?
- What would you do if your job asked you to do something against your values?
- Do you like to take work trips?
- How do you feel about me having a career that involves travel?
- Would you consider early retirement if it was an option?
- How do you feel about freelance or gig work?
- What are your views on job security?
- How important is it for you to have a job you’re passionate about?
- Would you ever work with family or friends?
- How do you continue to learn and grow in your career?
- Would you be okay with me being the primary earner?
- How do you feel about working from home?
- How do you approach job interviews and job changes?
- What’s your idea of professional success?
- Do you believe in taking sabbaticals or career breaks?
- How do you feel about workplace relationships?
- How do you separate work stress from home life?
- Would you ever work in a job you dislike to support the family?
About Finances
- What’s your philosophy on saving money?
- How do you feel about debt?
- Do you have a budget, and how strict are you with it?
- How would you handle a big, unexpected expense?
- What’s your credit score?
- Do you invest your money? If so, how?
- Do you think it’s important to have separate bank accounts?
- How do you feel about splitting bills?
- Are you okay with a prenuptial agreement?
- How would we decide on big purchases like a car or house?
- Do you give money to charity or believe in tithing?
- How would you handle it if one of us lost our job?
- What’s your financial goal for the next 5 years?
- How would you prioritize spending: experiences or material things?
- Would you consult me on all financial decisions?
- How do you feel about lending money to friends or family?
- Do you have an emergency fund?
- How do you plan for retirement?
- How much do you think we’d need to live comfortably?
- How would you teach our kids about money?
- How do you feel about coupons and bargain shopping?
- What’s your view on financial transparency in a relationship?
- Do you have any financial deal-breakers?
- Would you be willing to see a financial advisor?
- How do you feel about student loans, if applicable?
- What’s more important to you, income level or job satisfaction?
- Do you believe in joint financial goals?
- How do you feel about vacations and their costs?
- Would you ever take a job just for the money?
- Do you pay your bills on time?
- How much debt are you comfortable with?
- Would you ever consider going back to school, knowing it’s a financial investment?
- What are your thoughts on luxury items?
- How would you handle financial difficulties in a business, if you owned one?
- Would you support me if I wanted to go back to school?
- How do you feel about gambling?
- What’s your spending weakness?
- Do you think it’s okay to hide small purchases?
- How would you handle an inheritance or a large sum of money?
- What’s your view on financially supporting aging parents?
About Personal Growth
- What are your life goals?
- What does personal growth mean to you?
- How do you work on bettering yourself?
- Do you read self-help books or follow any motivational speakers?
- What skill do you want to learn in the next year?
- How do you handle failure?
- Do you believe in setting New Year’s resolutions?
- What’s something you’ve always wanted to do but haven’t yet?
- How do you keep yourself motivated?
- Do you meditate or have any mindfulness practices?
- What would you like to improve about yourself?
- How do you approach learning from your mistakes?
- Are you open to therapy or counseling?
- How do you keep a healthy mind and body?
- What’s a challenge you set for yourself recently?
- How do you handle criticism and feedback?
- What are you doing to achieve your career goals?
- How do you manage stress and burnout?
- Are you willing to step out of your comfort zone?
- How do you maintain a work-life balance for personal growth?
- How do you nurture your emotional well-being?
- What’s a fear you’re working on overcoming?
- How do you prioritize your time for self-improvement?
- What are your views on lifelong learning?
- How would you handle it if I wanted to take time off for personal growth?
- Do you have a mentor or someone you look up to?
- What role does spirituality play in your personal growth?
- Do you believe in the importance of emotional intelligence?
- Are you okay with being alone sometimes for personal growth?
- How do you deal with negative thoughts or self-doubt?
- How do you ensure you’re always growing in a relationship?
- What impact has your upbringing had on your personal growth?
- Are you a risk-taker?
- How do you handle conflict, and what do you learn from it?
- Do you believe in the power of positive thinking?
- What’s a piece of advice you’ve received that has helped you grow?
- How do you approach making major life decisions?
- Do you believe in second chances?
- How important is it for you to have a partner who also values personal growth?
- How do you celebrate your achievements, big or small?
About Social Life
- How often do you like to go out with friends?
- What does a perfect weekend look like for you?
- Are you more of an introvert or an extrovert?
- How do you feel about me hanging out with my friends without you?
- Do you like big social gatherings or smaller, more intimate groups?
- How important is it for you to have “guy time”?
- What’s your take on social media? Do you use it a lot?
- Do you like to host parties or get-togethers?
- How would you feel about going to events or parties where you don’t know anyone?
- How do you handle conflicts within your friend group?
- What kinds of activities do you enjoy with friends?
- Are you open to making new friends, or is your social circle set?
- Do you keep in touch with friends from the past?
- How often do you like to be social in a week?
- How do you feel about a couple of friends? Is it important for you to have them?
- Would you mind if I didn’t want to participate in some of your social activities?
- What’s your comfort level with public displays of affection in social settings?
- How do you feel about friendships with the opposite sex?
- What’s your policy on inviting friends over to our place?
- Do you like traveling with friends?
- How do you feel about work friends hanging out outside of work?
- What’s your approach to networking events?
- How would you handle it if one of your friends didn’t like me?
- Do you like your alone time?
- How do you feel about group vacations?
- What are your thoughts on friendship and loyalty?
- How would you handle a friend who starts to become a bad influence?
- Do you talk about your relationship with your friends?
- How do you deal with social anxiety or awkward situations?
- Are you a planner or more spontaneous when it comes to social activities?
- What are your favorite kinds of social outings?
- How do you feel about going to events like weddings or functions without me?
- How often do you communicate with your closest friends?
- Do you have any friendship deal-breakers?
- Are you open to being friends with my friends?
- How do you feel about social drinking?
- Do you believe that your friends reflect who you are?
- How much time do you spend on social media each day?
- How would you handle it if I wanted a quiet or introverted weekend?
- What role do your friends play in your life?
About Friendship
- What qualities do you look for in a friend?
- How long have you been friends with your closest buddies?
- How do you handle disagreements with friends?
- Do you believe in the concept of a “best friend“?
- What would cause you to end a friendship?
- Do you like to keep a wide circle of friends or a tight-knit group?
- How do you support your friends when they’re going through tough times?
- What’s the most meaningful thing a friend has ever done for you?
- Do you like making new friends or sticking with old ones?
- How often do you catch up with friends you don’t see regularly?
- What activities do you enjoy the most with friends?
- How do you feel about friends borrowing money?
- Would you help a friend move house?
- How would you handle it if you didn’t get along with a friend’s significant other?
- Are most of your friends from work, school, or other areas of your life?
- Do you think friendships change when people get into romantic relationships?
- What’s your opinion on maintaining friendships with exes?
- How do you feel about friends dropping by unannounced?
- What do you value more: long-term friendships or new exciting ones?
- Do you keep secrets for your friends?
- How do you feel about gossip within a friend group?
- Would you cancel plans with a friend for a romantic date?
- Do you ever outgrow friends, and how do you handle it?
- What role does trust play in your friendships?
- Do you think men and women can just be friends?
- How do you celebrate your friends’ successes?
- Would you take a trip just with your buddies?
- What do you think of friends who communicate mostly through social media?
- How do you handle a friend who talks behind your back?
- Do you have any friendships you regret ending?
- Would you stand up for a friend even if it caused you inconvenience?
- How do you feel about friends sharing personal problems with you?
- Do you have any friendships that are mostly online?
- Would you consider yourself a good friend?
- How would you handle it if you and a friend liked the same person romantically?
- Do you ever compete with your friends?
- Would you lie for a friend?
- How important is it for your significant other and your friends to get along?
- How would you handle a friend who becomes too clingy or demanding?
- What do you think is the right balance between friendship and a romantic relationship?
Frequently Asked Questions
Should I prepare for any negative reactions?
Be prepared for all kinds of responses. If he becomes defensive or irritated, it might indicate that he’s not ready for this kind of conversation or perhaps not serious about the relationship.
Is it wrong to ask about intentions early on to avoid wasting time?
It’s not wrong, especially if you know what you want. Just be aware that asking too early might make some guys uneasy, so gauge the situation carefully.