20 Questions

Questions to Ask Your Daughter's Boyfriend

Important questions to get to know your daughter's boyfriend, understand his character, and ensure he's a positive influence in her life.

1

What do you like most about my daughter?

Click to see why this works

Why this works

Helps you understand what he values about her and whether he sees her for who she truly is.

2

What are your goals and aspirations for the future?

Click to see why this works

Why this works

Reveals his ambition, values, and whether he has a clear direction in life that aligns with your daughter's goals.

3

How do you handle disagreements or conflicts?

Click to see why this works

Why this works

Shows his communication skills and approach to resolving problems, which is crucial for a healthy relationship.

4

What do you do for fun and how do you like to spend your free time?

Click to see why this works

Why this works

Helps you understand his interests, hobbies, and whether his lifestyle is compatible with your daughter's.

5

What's important to you in a relationship?

Click to see why this works

Why this works

Reveals his values and expectations, helping you understand if he's looking for something serious and meaningful.

6

How do you handle stress and difficult situations?

Click to see why this works

Why this works

Shows his emotional maturity and coping mechanisms, which are important for a stable relationship.

7

What do you think makes a relationship successful?

Click to see why this works

Why this works

Reveals his understanding of healthy relationships and whether he has realistic expectations.

8

How do you communicate with your family and friends?

Click to see why this works

Why this works

Shows his relationship skills and whether he maintains healthy connections with important people in his life.

9

What are your thoughts on marriage and long-term commitment?

Click to see why this works

Why this works

Helps you understand his views on commitment and whether he's looking for something serious.

10

How do you handle peer pressure and make decisions?

Click to see why this works

Why this works

Shows his character and whether he can make independent, thoughtful decisions that align with his values.

11

What do you do when you make a mistake?

Click to see why this works

Why this works

Reveals his accountability, humility, and whether he takes responsibility for his actions.

12

How do you support your partner when they're going through a difficult time?

Click to see why this works

Why this works

Shows his empathy and whether he's capable of being a supportive partner during challenging times.

13

What are your thoughts on education and personal growth?

Click to see why this works

Why this works

Reveals his values around learning and self-improvement, which can impact your daughter's development.

14

How do you handle money and financial responsibility?

Click to see why this works

Why this works

Shows his financial maturity and whether he has responsible money management habits.

15

What do you think about respect in a relationship?

Click to see why this works

Why this works

Reveals his understanding of mutual respect and whether he values treating his partner with dignity.

16

How do you handle disagreements with your parents?

Click to see why this works

Why this works

Shows his family dynamics and whether he can handle conflict in a mature way.

17

What are your thoughts on trust and honesty in a relationship?

Click to see why this works

Why this works

Reveals his values around trust and whether he understands the importance of honesty in relationships.

18

How do you handle social situations and peer pressure?

Click to see why this works

Why this works

Shows his social skills and whether he can make independent decisions in group settings.

19

What do you think about your future together?

Click to see why this works

Why this works

Helps you understand his level of commitment and whether he's thinking seriously about the relationship.

20

How do you handle criticism and feedback?

Click to see why this works

Why this works

Shows his emotional maturity and whether he can handle constructive feedback without becoming defensive.

Getting to Know Your Daughter's Boyfriend

Expert tips and techniques for getting the most out of these questions.

Creating a Comfortable Environment

Be Welcoming but Observant

Create a warm, welcoming atmosphere while paying attention to his behavior, responses, and how he treats your daughter.

Ask Open-Ended Questions

Use questions that encourage detailed responses rather than yes/no answers to get a better understanding of his character.

Listen to Both Words and Actions

Pay attention to how he treats your daughter, his body language, and whether his actions match his words.

Essential Areas to Explore

Character and Values

How he handles conflicts and disagreements
His approach to responsibility and accountability
His values around respect and honesty
How he treats others, especially your daughter

Future Orientation

His goals and aspirations
His thoughts on commitment and marriage
His approach to education and personal growth
His financial responsibility and planning

Relationship Skills

How he communicates and handles disagreements
His approach to supporting his partner
His understanding of healthy relationships
How he handles peer pressure and social situations

Common Pitfalls to Avoid

Don't Interrogate

Avoid rapid-fire questions that feel like an interrogation. Space out questions and let the conversation flow naturally.

Avoid Being Overly Critical

Don't look for reasons to dislike him. Be fair and objective while still being protective of your daughter.

Don't Ignore Red Flags

If you notice concerning behavior or responses, don't dismiss them. Trust your instincts as a parent.

Further Reading

"The 5 Love Languages" by Gary Chapman
"Boundaries in Dating" by Henry Cloud
"The Seven Principles for Making Marriage Work" by John Gottman

Find Your Perfect Questions

Search our collection of thoughtful questions for any conversation or situation