20 Questions

Questions to Ask Before Proposing

Essential questions to ask your partner before proposing that help ensure you're both ready for marriage and aligned on the most important aspects of your future together.

1

What does marriage mean to you and what are your expectations for our relationship?

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Why this works

Fundamental question that reveals their understanding of marriage and ensures you're both on the same page about what commitment means to each of you.

2

How do you envision our future together in terms of career, family, and lifestyle?

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Why this works

Critical for understanding their long-term vision and ensuring your life goals are compatible, especially regarding children, career priorities, and where you want to live.

3

What are your thoughts on having children, and if so, how many and when?

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Why this works

Essential question that can make or break a marriage. Understanding their views on children, timing, and parenting approaches is crucial for long-term compatibility.

4

How do you handle conflict and what's your approach to resolving disagreements?

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Why this works

Reveals their communication style and conflict resolution skills, which are fundamental to a successful marriage and help you understand how you'll work through problems together.

5

What are your financial goals and how do you approach money management?

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Why this works

Money is one of the leading causes of divorce. Understanding their financial philosophy, goals, and spending habits is essential for long-term compatibility.

6

How important is your relationship with your family, and how do you want to handle family dynamics?

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Why this works

Reveals their family values and helps you understand how they'll navigate relationships with in-laws, family traditions, and family obligations.

7

What are your thoughts on religion, spirituality, and how do you want to raise our children in this regard?

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Why this works

Important for understanding their spiritual beliefs and ensuring compatibility in how you'll approach faith, values, and raising children with shared principles.

8

How do you want to handle household responsibilities and division of labor?

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Why this works

Reveals their expectations about domestic life and helps ensure you're both comfortable with how you'll share responsibilities and maintain your home.

9

What are your thoughts on maintaining individual friendships and social lives while married?

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Why this works

Important for understanding their views on independence and social relationships, ensuring you both have healthy boundaries and expectations about personal space.

10

How do you want to handle major life decisions and what role should each of us play in decision-making?

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Why this works

Reveals their approach to partnership and helps ensure you're both comfortable with how you'll make important decisions together.

11

What are your thoughts on intimacy and physical affection in a long-term relationship?

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Why this works

Important for understanding their views on physical connection and ensuring you're both comfortable with expectations around intimacy and affection.

12

How do you want to handle holidays, traditions, and special occasions?

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Why this works

Reveals their approach to celebrations and traditions, helping you understand how you'll navigate family expectations and create your own traditions together.

13

What are your thoughts on career changes, relocating, or other major life transitions?

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Why this works

Important for understanding their flexibility and approach to change, especially regarding career moves, relocations, or other significant life decisions.

14

How do you want to handle disagreements about parenting, if we have children?

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Why this works

Reveals their approach to parenting and helps ensure you're both comfortable with how you'll handle different parenting styles and decisions.

15

What are your thoughts on maintaining your individual identity while being part of a couple?

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Why this works

Important for understanding their views on personal growth and independence, ensuring you both maintain your individual identities while building a life together.

16

How do you want to handle stress, difficult times, and supporting each other through challenges?

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Why this works

Reveals their approach to emotional support and helps ensure you're both comfortable with how you'll navigate difficult periods together.

17

What are your thoughts on therapy, counseling, or seeking help when we face relationship challenges?

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Why this works

Important for understanding their openness to professional help and ensuring you're both comfortable with seeking support when needed.

18

How do you want to handle differences in values, beliefs, or lifestyle preferences?

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Why this works

Reveals their approach to compromise and helps ensure you're both comfortable with how you'll navigate differences and maintain respect for each other's perspectives.

19

What are your thoughts on maintaining romance and keeping the relationship fresh over time?

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Why this works

Important for understanding their views on long-term romance and ensuring you're both committed to maintaining the spark and connection in your relationship.

20

What are your biggest fears about marriage, and how can we address them together?

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Why this works

Reveals their concerns and vulnerabilities, helping you understand what they're worried about and how you can support each other in addressing these fears.

How to Have Meaningful Pre-Proposal Conversations

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

Best Practices

Create a Safe, Open Environment

Choose a comfortable, private setting where you can both speak honestly without fear of judgment. Make it clear that these conversations are about understanding each other, not testing compatibility.

Listen Without Defensiveness

Approach these conversations with an open mind and heart. Listen to understand, not to respond. Your partner's answers may reveal differences that need to be addressed.

Be Honest About Your Own Views

Share your own thoughts and feelings openly. These conversations should be two-way, helping you both understand each other's perspectives and values.

Take Time to Process

Don't rush through these conversations. Take time to think about the answers and discuss any concerns or differences that arise.

Question Sequences

The Foundation Building Sequence

1
Start with: 'What does marriage mean to you and what are your expectations?'
2
Follow with: 'How do you envision our future together in terms of career, family, and lifestyle?'
3
Deepen with: 'What are your biggest fears about marriage, and how can we address them together?'

The Compatibility Check Sequence

1
Begin with: 'What are your thoughts on having children, and if so, how many and when?'
2
Explore with: 'What are your financial goals and how do you approach money management?'
3
Connect with: 'How do you want to handle major life decisions and what role should each of us play?'

Common Pitfalls

Don't Avoid Difficult Topics

Avoiding tough conversations now will only create problems later. Address difficult topics like money, children, and family dynamics before making a commitment.

Avoid Making Assumptions

Don't assume you know their answers or that they'll change their mind later. Ask direct questions and listen to their actual responses.

Don't Rush the Process

These conversations take time and may need to happen over multiple discussions. Don't try to cover everything in one conversation.

Avoid Getting Defensive

If you hear answers that concern you, don't get defensive or try to change their mind. Focus on understanding their perspective and discussing how to address differences.

Conversation Templates

The Comprehensive Compatibility Check

1
Step 1: Start with fundamental views on marriage and commitment
2
Step 2: Explore life goals and future vision
3
Step 3: Discuss family, children, and parenting
4
Step 4: Examine financial goals and money management
5
Step 5: End with relationship maintenance and growth

The Values and Beliefs Method

1
Step 1: Ask about their core values and beliefs
2
Step 2: Explore their approach to conflict and communication
3
Step 3: Discuss their views on family and relationships
4
Step 4: Examine their thoughts on personal growth and change
5
Step 5: Connect on shared values and address differences

Further Reading

"The Seven Principles for Making Marriage Work" by John Gottman
"The 5 Love Languages" by Gary Chapman
Pre-Marriage Counseling Resources
Relationship Compatibility Assessment Tools

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