I can never forget when I visited my girlfriend for the very first time to see her house. I was anxious and simply wanted to present myself in the best possible light when, all of a sudden, her mom began questioning me.
At first, I thought it was just small talk, but soon I realized that getting to know me was her priority. There were playful questions and more serious ones.
However, in retrospect, I now realize that she just wanted to make sure I was the right person to be keeping her daughter. It was a combination of apprehension, interest, and care—everything that comes with being a parent.
In case you find yourself in a similar situation and your daughter has a boyfriend, you may be wondering how to handle the situation.
You don’t want to appear too threatening, but it’s normal to want to know more about the individual your daughter is associating with. By asking the right questions, you’ll be able to understand his motives, what kind of person he is, and whether he possesses the qualities you desire in her future partner.
I have come up with 100 questions to ask your daughter’s boyfriend that are both lighthearted and deep. These will give you an idea of his character, how he treats your daughter, and whether he can be trusted.
100 questions to ask your daughter’s boyfriend
Just for Fun Questions
These are great for breaking the ice and getting an overview of the type of guy your daughter is seeing.
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What is your hobby?
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Which is your favorite book/movie/TV show?
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What is your hometown?
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What is your most favorite trip?
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What do you like best about my daughter?
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What kind of music do you like best?
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What do you care about the most?
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Do you have any sports or hobbies?
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Are you a pet owner?
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What is one thing you cannot live without?
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Who would you like to meet, given a chance to meet any celebrity?
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How do you like to spend your weekends?
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What is your favorite meal?
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How do you imagine the perfect day?
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Are you more of a night owl or a morning person?
Related: Why Am I Obsessed With My Daughter’s Relationship?
Family & Background Questions
Learning more about his background and family can provide useful information about his character.
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What is your relationship with your family?
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What do your parents do?
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Are you an only child? If not, how many siblings do you have?
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What family traditions or holidays do you observe?
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How did your parents meet?
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What values were you brought up with?
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Do you have any family characteristics or eccentricities you’re particularly proud of?
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Do you feel you’re more like anyone in your family?
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What do your family members think of you being in a relationship?
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How does your family deal with disagreements?
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What is your favorite family moment?
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What is your position in your family?
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What is your sense of family?
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What phrase or piece of advice from your parents do you still follow?
Related; 7 Physical Traits of Daughters of Narcissistic Fathers
Individual Values & Character
These questions will help you understand what has shaped him into who he is, and they’re critical for deciding whether he’s a good match for your daughter.
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What do your friends say about you?
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What one thing would you most like to change about yourself?
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How do you handle stress or difficult situations?
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What is your greatest fear in life?
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What is your five-year life plan?
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How do you manage conflict or disagreements?
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What is the best advice you’ve received?
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What does success mean to you?
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What has been your greatest achievement?
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How do you handle failure?
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What do you feel good about yourself?
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What are the top three traits you seek in a friend?
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What is your biggest pet peeve?
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How do you keep yourself motivated during difficult times?
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What would you change about yourself?
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What is one thing nobody knows about you?
Related: 50 Engaging Questions To Ask A Book Lover
Relationship Questions
Ask questions that explore his values regarding relationships and his appreciation of commitment.
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What do you value most in a relationship?
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What do you think makes a relationship successful?
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How do you approach conflict in a relationship?
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What is your love language?
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What are your thoughts on commitment?
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How do you envision respect in a relationship?
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How do you keep your partner happy?
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How do you picture the perfect date?
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What is your ideal relationship?
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What makes you jealous in a relationship?
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Do you believe in soulmates?
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What do you think is the greatest problem in relationships?
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What does it mean to act in love with someone?
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What is the most romantic thing you’ve done?
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How would you address the flaws or weaknesses in your partner?
Related: 160 Fun Would You Rather Questions for Adults
Work, Education, and Career Questions
To understand his ambitions, it’s important to learn about his education and career goals.
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How do you make a living?
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What have you been learning at school, and why?
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Where do you see yourself professionally in a few years?
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What drives you in your career?
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Have you ever had a job where you learned an important life lesson?
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How do you balance work and life?
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Do you like your job?
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What is your dream job?
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Have you considered taking any additional courses or going back to school?
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Which skills are you currently working on?
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What is your greatest career aspiration?
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Do you have a mentor?
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How do you stay organized and manage tasks at work?
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What is the best thing you’ve learned in your career?
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Would you prefer to settle into one career, or explore different fields?
Lifestyle & Future Plans
Understanding how he prepares for the future is important, especially if he’s serious about a long-term relationship with your daughter.
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How do you spend your days?
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What is your approach to managing finances? Do you know how to budget?
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Are you worried about your future career or living situation?
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Do you see yourself getting married?
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What do you think you’ll be doing in five years?
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How do you feel about having children?
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Would you move for a job or a person?
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What do you do to stay healthy and active?
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How do you balance work, hobbies, and relationships?
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Are you a planner, or do you go with the flow?
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What do you value about personal growth?
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Do you think about long-term planning?
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How would you like to live your life?
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How do you handle unexpected changes or challenges in life?
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How do you define success in your personal life?
Money Values
Money can be a sensitive topic, but it’s important to understand his approach to finances, especially if he’s serious about your daughter.
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What is your approach to money in a relationship?
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Do you save money regularly?
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What are your thoughts on sharing finances in a relationship?
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What are your spending priorities?
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What has been your biggest financial decision?
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How do you feel about being in debt?
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What do you think about shared bank accounts in marriage?
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Would you prefer to spend or invest money on experiences?
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How do you plan for future investments?
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How do you define financial security?
Final Thoughts
Asking questions helps you understand who your daughter is dating. This is not about interrogating him but about demonstrating your genuine interest in her well-being and future. By asking these questions, you’ll also help him reflect on the type of relationship he wants to have with your daughter. After all, it’s her future, and she deserves someone who shares her values, goals, and dreams.
Keep the conversation light and respectful, so you don’t feel uncomfortable asking deeper questions. These discussions can build trust in your daughter’s boyfriend, ensuring she’s in a relationship with someone who will treat her with the love and respect she deserves.
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