25 Revealing Questions to Ask the Person You’re Dating
Dating with depth starts with asking better questions.
Whether you’re just getting to know someone or exploring long-term potential, these 25 questions help you connect through curiosity—not performance.
What You’ll Receive:
- eBook PDF: A thoughtfully curated list of 25 meaningful questions to help you deepen intimacy, spark vulnerability, and get real about what matters—early on. Designed for conscious daters who want clarity and connection.
- The 4 Pillars of Compatibility: A framework to help you assess whether you’re truly aligned—emotionally, spiritually, sexually, and practically. Includes reflection questions and rating tools to explore whether you’re building something that can last.
- Stories, Prompts & Real-Life Insight: Includes a candid glimpse into Gavin & Joy’s own dating journey, plus gentle encouragement and strategies for using the questions in real-time—without it feeling like an interview.
This gift is our way of supporting your communication.
We will never send SPAM
Courageous Conversations
Scripts for Dating
We’ve prepared these scripts to assist you in navigating your dating journey with more honesty and grace, and we invite you to modify and make these scripts your own.
Healthy conversations are a practice and an amplification of living in integrity with yourself, honoring your needs, and leaning into compassion. Speaking with a mixture of love and truth utilizes both wings of the heart. It’s been our experience that these skills can be learned by everyone, and that having courageous conversations gets more comfortable the more we do it.
