20 Questions

Questions to Ask a Guy Before Sleeping with Him

Important questions to ask a guy before sleeping with him that help you understand his intentions, ensure mutual consent, and make an informed decision about intimacy and your relationship.

1

What are your intentions with me, and what do you want from this relationship?

Click to see why this works

Why this works

Critical for understanding his intentions and ensuring you're both on the same page about what this means for your relationship and future.

2

What are your thoughts on commitment and exclusivity?

Click to see why this works

Why this works

Important for understanding his relationship values and ensuring you're aligned on what commitment means to both of you.

3

What are your thoughts on communication and emotional intimacy?

Click to see why this works

Why this works

Essential for understanding his approach to emotional connection and ensuring you can communicate openly and honestly about your feelings.

4

What are your thoughts on consent and boundaries?

Click to see why this works

Why this works

Critical for understanding his respect for consent and ensuring you both feel safe and comfortable with the physical aspects of your relationship.

5

What are your thoughts on trust and honesty?

Click to see why this works

Why this works

Important for understanding his values around trust and ensuring you can build a foundation of honesty and transparency in your relationship.

6

What are your thoughts on respect and equality in relationships?

Click to see why this works

Why this works

Reveals his values around respect and helps you understand how he views equality and mutual respect in intimate relationships.

7

What are your thoughts on emotional support and being there for each other?

Click to see why this works

Why this works

Critical for understanding his approach to emotional support and ensuring you can rely on each other during both good and challenging times.

8

What are your thoughts on personal growth and supporting each other's goals?

Click to see why this works

Why this works

Important for understanding his approach to personal development and ensuring you can support each other's growth and aspirations.

9

What are your thoughts on conflict resolution and handling disagreements?

Click to see why this works

Why this works

Reveals his approach to conflict and helps you understand how you can work through disagreements and challenges together.

10

What are your thoughts on future planning and long-term goals?

Click to see why this works

Why this works

Critical for understanding his long-term perspective and ensuring you're aligned on your future goals and aspirations.

11

What are your thoughts on family and relationships with loved ones?

Click to see why this works

Why this works

Important for understanding his family values and ensuring you can navigate relationships with each other's families and loved ones.

12

What are your thoughts on independence and maintaining your own identity?

Click to see why this works

Why this works

Reveals his approach to independence and helps you understand how you can maintain your own identity while being in a relationship.

13

What are your thoughts on shared values and what matters most to you?

Click to see why this works

Why this works

Critical for understanding his core values and ensuring you're aligned on what's most important to both of you in life and relationships.

14

What are your thoughts on intimacy and what it means to you?

Click to see why this works

Why this works

Important for understanding his perspective on intimacy and ensuring you both have similar views on what physical and emotional intimacy means.

15

What are your thoughts on communication about needs and desires?

Click to see why this works

Why this works

Reveals his approach to communication and helps you understand how you can discuss your needs and desires openly and honestly.

16

What are your thoughts on respect for each other's boundaries and comfort levels?

Click to see why this works

Why this works

Critical for understanding his respect for boundaries and ensuring you both feel comfortable and safe in your relationship.

17

What are your thoughts on supporting each other's dreams and aspirations?

Click to see why this works

Why this works

Important for understanding his approach to support and ensuring you can encourage each other to pursue your dreams and goals.

18

What are your thoughts on building a life together and what that means to you?

Click to see why this works

Why this works

Reveals his perspective on building a future together and helps you understand what a long-term relationship means to him.

19

What are your thoughts on being vulnerable and open with each other?

Click to see why this works

Why this works

Critical for understanding his approach to vulnerability and ensuring you can be open and honest about your feelings and experiences.

20

What are your thoughts on what makes a relationship successful and fulfilling?

Click to see why this works

Why this works

Important for understanding his relationship philosophy and ensuring you both have similar views on what makes a relationship work and thrive.

How to Have Important Conversations Before Intimacy: Essential Questions and Considerations

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

Best Practices

Create a Safe Space

Choose a comfortable, private setting where you can have an open and honest conversation without distractions or interruptions.

Be Direct and Honest

Ask direct questions and be honest about your own thoughts and feelings. Clear communication is essential for understanding each other's perspectives.

Listen Actively

Pay attention to his responses and ask follow-up questions. Understanding his perspective will help you make an informed decision about your relationship.

Respect Boundaries

Respect his boundaries and comfort level. If he's not ready to discuss certain topics, give him space and time to process.

Question Sequences

The Intentions and Values Sequence

1
Start with: 'What are your intentions with me, and what do you want from this relationship?'
2
Follow with: 'What are your thoughts on commitment and exclusivity?'
3
Deepen with: 'What are your thoughts on shared values and what matters most to you?'

The Communication and Intimacy Sequence

1
Begin with: 'What are your thoughts on communication and emotional intimacy?'
2
Explore with: 'What are your thoughts on consent and boundaries?'
3
Connect with: 'What are your thoughts on intimacy and what it means to you?'

Common Pitfalls

Don't Rush the Conversation

Avoid rushing through important topics. Take time to discuss each question thoroughly and ensure you both understand each other's perspectives.

Avoid Making Assumptions

Don't assume you know his thoughts or feelings. Ask direct questions and listen to his actual responses to avoid misunderstandings.

Don't Ignore Red Flags

Avoid ignoring warning signs or concerns. If something doesn't feel right, address it directly and trust your instincts.

Avoid Pressuring for Answers

Don't pressure him to answer questions he's not comfortable with. Respect his boundaries and give him time to process and respond.

Question Templates

The Comprehensive Approach

1
Step 1: Start with intentions and relationship goals
2
Step 2: Explore values and commitment
3
Step 3: Examine communication and emotional intimacy
4
Step 4: Discuss boundaries and consent
5
Step 5: End with future planning and long-term goals

The Values-Focused Method

1
Step 1: Begin with core values and what matters most
2
Step 2: Explore relationship philosophy and approach
3
Step 3: Discuss communication and emotional connection
4
Step 4: Examine boundaries and respect
5
Step 5: Connect on future goals and aspirations

Further Reading

"Healthy Relationships and Communication" by Relationship Counseling Institute
"Consent and Boundaries in Relationships" by Intimacy Education Resources
Relationship Communication and Intimacy
Healthy Relationship and Consent Resources

Find Your Perfect Questions

Search our collection of thoughtful questions for any conversation or situation