Courtship is that sweet spot where you’re still getting to know each other but starting to dig a bit deeper. Get this chance to ask the questions that really matter—the ones that reveal their values, dreams, and maybe a few quirks, too.
Yes, it can feel a bit intimidating, but these conversations are what help you both decide if you’re building something that could go the distance.
This list of questions will guide you through every topic that counts, from lifestyle habits to family and future goals. Think of it as a gentle roadmap to help you both open up without feeling like you’re diving in too deep, too fast.
Just keep it light, be yourself, and don’t shy away from being curious. After all, courtship is all about finding out if you’re truly a match—one question at a time.
Table of Contents
About Personal Values and Beliefs
- What values would you never compromise on, no matter what?
- How do you define success, and what would make you feel fulfilled?
- What does loyalty mean to you, especially in a relationship?
- What’s one thing you think everyone should strive for in life?
- How important is it for you to give back to your community, and in what ways do you hope to?
- What role does religion or spirituality play in your life?
- What do you believe makes a person “good”?
- How do you feel about honesty, even when the truth is hard to hear?
- Do you think people should follow a set path in life, or is it better to go with the flow?
- How important is it to you to stand up for what you believe in, even if it’s unpopular?
- What do you think about forgiveness—is it easy or difficult for you?
- Do you believe people can change, or do you think we all have a set nature?
- What’s your perspective on work-life balance and what would your ideal balance look like?
About Future Goals and Aspirations
- Where do you see yourself in the next five years, and do you have a plan to get there?
- What’s something you’ve always wanted to achieve but haven’t started yet?
- Do you dream of living in a particular place or city someday?
- How do you feel about taking risks to achieve your goals?
- Is there a skill or talent you’d like to develop in the future?
- What’s your ultimate dream job or career path?
- Do you have any goals related to family or personal life?
- What motivates you to keep working toward your dreams?
- What’s your bucket list item you’re most excited about checking off?
- How do you feel about constantly pursuing self-improvement?
- What’s your ideal work-life balance, and do you think it’s achievable?
- Are there any charities or causes you’d love to contribute to someday?
- How do you feel about retirement?
- What’s one thing you would never give up on, no matter how hard it got?
- Would you consider moving for a job or personal opportunity?
About Lifestyle and Habits
- How do you usually spend your weekends?
- Are you more of a morning person or a night owl?
- What’s your idea of a perfect day off?
- How important is health and fitness in your daily routine?
- Do you prefer quiet nights in or going out and socializing?
- What’s your take on drinking or partying?
- How do you feel about traveling—do you like to go often or just once in a while?
- Do you enjoy cooking, or are you more into dining out?
- How much alone time do you need to feel recharged?
- What kind of hobbies do you enjoy doing in your free time?
- Are you more comfortable in a city, a suburb, or the countryside?
- Do you have any habits or routines that are non-negotiable?
- How do you feel about pets—are you an animal person?
- What’s your favorite way to relax and unwind?
- How do you typically handle stress or anxiety?
- What’s one daily habit you can’t go without?
- How do you feel about spending time alone?
- What are your sleeping habits like?
- What’s your view on spending vs. saving money?
- How often do you try new things or explore new hobbies?
About Communication Styles
- How comfortable are you with expressing your feelings?
- Do you believe in addressing issues right away, or do you prefer to wait and cool off?
- How do you usually express affection?
- What’s your preferred way to receive feedback?
- How comfortable are you with silence in conversations?
- Do you like to talk things out, or do you prefer to think about it alone first?
- How do you handle misunderstandings in a conversation?
- How do you prefer to communicate (in person, by phone calls, or by text)?
- How often do you check in with people you care about?
- What’s one thing you wish people understood about the way you communicate?
About Conflict Resolution
- How do you usually handle disagreements in a relationship?
- Do you believe in “taking a break” during a heated argument?
- What’s your approach to conflict—talk it out or give it time?
- How do you feel about compromise in a relationship?
- How important is it to you to find a resolution immediately?
- How do you feel about “agreeing to disagree” on certain issues?
- What role do you believe forgiveness plays in conflict resolution?
- How comfortable are you with admitting when you’re wrong?
- What’s your biggest pet peeve in arguments?
- Do you think there’s always a “winner” in disagreements?
- What’s something that helps you feel heard in an argument?
- Do you believe in following up on a discussion after some time has passed?
- How do you handle situations where you strongly disagree with someone?
About Hobbies and Interests
- What’s your favorite way to spend a weekend?
- Do you have a hobby you’re really passionate about?
- What’s one hobby you’ve always wanted to try?
- Do you prefer outdoor activities or staying in?
- Are you a book lover, and if so, what genres do you like?
- How do you feel about board games or puzzles?
- What’s your favorite way to stay active or fit?
- Do you enjoy exploring new places and traveling?
- Are you a movie buff, and if so, what genres do you love?
- Do you enjoy attending events, like fairs or festivals?
- Are there any artistic pursuits you enjoy, like music or dance?
- What’s something you could do for hours without getting bored?
- Do you prefer solo hobbies or activities with others?
About Finances
- Do you budget regularly, or do you go with the flow financially?
- What’s your approach to handling debt or loans?
- How important is it to you to achieve financial independence?
- Do you believe in combining finances in a committed relationship?
- How comfortable are you discussing finances with a partner?
- What’s your view on credit cards and credit scores?
- How do you feel about investing, and are you interested in learning more about it?
- How much financial security do you need to feel comfortable?
- Do you believe in planning for retirement early, or do you take it as it comes?
- Are there any purchases you believe are worth spending more on?
- How do you feel about saving for big life events, like a house or a wedding?
About Family and Friends
- How close are you to your family, and how often do you see them?
- Do you think family involvement is essential in a relationship?
- How do you feel about spending holidays with extended family?
- What kind of relationship do you want your partner to have with your family?
- How important is it to have friends outside the relationship?
- How often do you catch up with your closest friends?
- Do you enjoy social gatherings, or are you more of a homebody?
- How do you handle conflicts within family or friend groups?
- What’s your view on introducing a partner to family early on?
- How important is it to you that your family likes your partner?
- How much influence do you think family should have on life decisions?
- What are your thoughts on family vacations or reunions?
About Past Relationships
- What do you think you’ve learned from your past relationships?
- Are there any mistakes you feel you’ve grown from in past relationships?
- How do you feel about discussing past relationships openly?
- Are there any red flags you’re more aware of now than before?
- How do you feel about staying friends with ex-partners?
- What’s something you’d want to approach differently in a new relationship?
- Are there any habits or patterns you’re actively working on?
- What’s one positive thing a past relationship taught you?
- How do you handle closure when a relationship ends?
- Do you believe in reconnecting with past partners?
- What’s something you’d avoid in a new relationship, based on your past?
- What’s one thing you’re grateful for from past relationships?
Questions to Identify Potential Red Flags
- How do you handle stress and pressure?
- What are your views on infidelity and commitment in a relationship?
- How do you typically handle anger or frustration?
- Have you ever been in therapy or counseling?
- What are your views on substance use (alcohol, drugs, etc.)?
- How do you feel about personal space and boundaries in a relationship?
- Have you ever been arrested or convicted of a crime?
- What are your views on honesty in a relationship?
- How do you feel about social media and online interactions with others?
- How do you handle disagreements with friends or family members?
- What are your views on gender roles and equality in a relationship?
- How do you handle criticism or feedback from others?
- How do you feel about seeking help or support when facing challenges?
- What are your views on privacy and sharing personal information in a relationship?
- How do you feel about making sacrifices for the sake of the relationship?
Final Thoughts
Remember, it’s not about asking everything all at once. Take it slow, enjoy each conversation, and let things unfold naturally. The goal isn’t to check off every question but to genuinely understand each other and feel closer along the way.
So, take your time, enjoy the process, and let these questions guide you toward a deeper connection.
