20 Questions

100 Questions to Ask Before You Get Engaged PDF

Comprehensive questions to ask before getting engaged, covering all aspects of life together to ensure you're truly ready for marriage.

1

What are your core values and how do they align with mine?

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Why this works

Establishes the foundation of your relationship by ensuring you share fundamental beliefs and principles that will guide your life together.

2

How do you envision our future together in 5, 10, and 20 years?

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Why this works

Reveals long-term compatibility and helps ensure you both have similar visions for your life together.

3

What are your financial goals and how do you handle money?

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Why this works

Addresses one of the most common sources of marital conflict by ensuring you're aligned on financial values and practices.

4

How do you handle conflict and disagreements?

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Why this works

Reveals your conflict resolution styles and helps ensure you can work through problems effectively as a couple.

5

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

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Why this works

Addresses one of the most important life decisions and ensures you're aligned on family planning and parenting philosophies.

6

How do you handle stress and what do you need from me during difficult times?

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Why this works

Reveals coping strategies and helps ensure you can support each other during challenging periods.

7

What are your career goals and how do they fit with our relationship?

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Why this works

Ensures your professional aspirations are compatible and that you can support each other's career development.

8

How do you like to spend your free time and what are your hobbies?

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Why this works

Reveals lifestyle preferences and helps ensure you can enjoy time together while respecting each other's individual interests.

9

What are your thoughts on religion and spirituality?

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Why this works

Addresses spiritual beliefs and practices, which can be fundamental to how you live your lives together.

10

How do you handle family relationships and what role do they play in your life?

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Why this works

Reveals family dynamics and helps ensure you can navigate relationships with each other's families.

11

What are your thoughts on household responsibilities and division of labor?

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Why this works

Addresses practical aspects of living together and ensures you have similar expectations about domestic responsibilities.

12

How do you like to celebrate special occasions and what traditions are important to you?

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Why this works

Reveals cultural and personal traditions while helping you understand how to create meaningful celebrations together.

13

What are your thoughts on travel and adventure?

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Why this works

Reveals lifestyle preferences and helps ensure you can enjoy shared experiences and adventures together.

14

How do you handle change and what do you need from me during transitions?

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Why this works

Reveals adaptability and helps ensure you can support each other through life's inevitable changes.

15

What are your thoughts on personal space and alone time?

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Why this works

Addresses individual needs and helps ensure you can maintain healthy boundaries while staying connected.

16

How do you like to communicate and what do you need from me in terms of emotional support?

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Why this works

Reveals communication styles and helps ensure you can meet each other's emotional needs effectively.

17

What are your thoughts on social relationships and friendships?

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Why this works

Reveals social preferences and helps ensure you can navigate friendships and social situations together.

18

How do you handle mistakes and what do you need from me when you're wrong?

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Why this works

Reveals humility and helps ensure you can work through problems and learn from mistakes together.

19

What are your thoughts on health and wellness?

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Why this works

Addresses lifestyle choices and helps ensure you can support each other's health and well-being.

20

How do you envision our roles in the relationship and what do you expect from me?

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Why this works

Reveals expectations and helps ensure you have compatible views on relationship dynamics and responsibilities.

Best Practices for Pre-Engagement Conversations

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

Best Practices

Create a Safe and Open Environment

Ensure both partners feel comfortable sharing honestly without fear of judgment or criticism.

Listen Actively and Show Empathy

Pay attention to your partner's responses and show understanding for their perspectives, even when you disagree.

Be Honest and Authentic

Share your true thoughts and feelings. Honesty is essential for building a strong foundation for marriage.

Question Sequences

The Foundation Building

1
What are your core values and how do they align with mine?
2
How do you envision our future together in 5, 10, and 20 years?
3
What are your financial goals and how do you handle money?
4
How do you handle conflict and disagreements?

The Lifestyle Assessment

1
What are your thoughts on having children, and if so, how many?
2
What are your career goals and how do they fit with our relationship?
3
How do you like to spend your free time and what are your hobbies?
4
What are your thoughts on travel and adventure?

Common Pitfalls

Don't Avoid Difficult Topics

Address challenging subjects like finances, children, and family dynamics. Avoiding these topics can lead to problems later.

Avoid Making Assumptions

Don't assume you know your partner's thoughts or feelings. Ask questions and listen to their actual responses.

Don't Rush the Process

Take time to have these conversations thoroughly. Rushing through important topics can lead to misunderstandings.

Conversation Templates

The Values Assessment

1
Step 1: Start with: "What are your core values and how do they align with mine?"
2
Step 2: Explore with: "How do you envision our future together?"
3
Step 3: Assess with: "What are your financial goals and how do you handle money?"

The Lifestyle Compatibility

1
Step 1: Begin with: "What are your thoughts on having children?"
2
Step 2: Probe with: "What are your career goals and how do they fit with our relationship?"
3
Step 3: Clarify with: "How do you like to spend your free time and what are your hobbies?"

Further Reading

"The 5 Love Languages" by Gary Chapman
"Getting the Love You Want" by Harville Hendrix
"The Seven Principles for Making Marriage Work" by John Gottman

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