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Are You REALLY Ready To Date?

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With Riley and Jack Kehoe

Today we’re diving into season 15 where Jack and Riley share their journeys with closed and open singleness, offering insights on personal growth, fulfillment, and intentional dating!

Introduction

Hiii HOD fam! We are so excited to kick off season 15 of Heart of Dating with a resonant topic: Closed vs Open Singleness. This is one for us all, whether you're embracing singleness or actively exploring dating. We had an insightful discussion with our amazing guests, Jack and Riley, who shared their personal journeys and wisdom, helping us delve deep into finding contentment and purpose in every season. Let’s dive in and learn more about navigating these unique times with grace!

Jack's Experience with Closed Singleness

Jack's journey with closed singleness is a testament to spiritual growth. He shared how taking a Nazarite vow for six months and committing to a year of closed singleness transformed his perspective on life and faith. Initially struggling with casual dating slips, Jack found deeper fulfillment in committing fully to a period of spiritual growth.

Through this, he cultivated a richer relationship with God, pursued dreams like starting a business, and led a church group. Jack beautifully illustrated how viewing singleness through Apostle Paul's lens provided him with a sense of purpose, allowing him to see it as a divine gift rather than a mere waiting period.

Riley’s Insights on Embracing Singleness

Riley’s story mirrors a journey of reframing singleness from a period to bypass into one richly filled with self-discovery and divine fulfillment. Prompted by a reflection on God's sufficiency, she embraced a year of closed singleness with initial hesitation. Through struggles and internal growth, Riley felt a transformation, living in alignment with her purpose much like Ruth from the Bible.

Her perspective shifted towards seeing singleness as an attractive period for personal development, making herself better for future relationships. Riley's insights remind us that the journey with God through singleness can be profoundly fulfilling and preparatory for future stages of life.

Contentment in Singleness: A Shared Vision

An engaging part of the episode was the discussion on the importance of contentment. Jack highlighted how striving for contentment during singleness can benefit one’s overall well-being, while Riley pointed out that one doesn't need to achieve absolute contentment to be ready for marriage. This dynamic view encourages finding peace and joy in one's current season without the pressure of perfect readiness.

Kait added a valuable perspective here, emphasizing that our desires shouldn't eclipse our focus on God. She and JJ shared their own experiences with desires and patiently waiting on the Lord, illustrating the balance of hope and contentment.

Riley’s Relationship Background & Dating Wisdom

Riley's personal story of initially friend-zoning Jack and later realizing his value is heartwarming and instructive. They navigated their early marriage as missionaries and experienced the joys and surprises of God's timing, like discovering their pregnancy in Uganda.

Riley also introduced crucial dating wisdom, advocating courageous honesty in exploring relationships. She warned against “friendationships” where intentions are vague and urged for clarity and genuine interest, which fosters healthier connections.

Addressing the idea of “a pot on every burner,” Kait emphasized dating with intentionality and avoiding leading others on, aligning with the mindset of leaving people better than you found them.

Seeing Singleness as a Gift and Season of Growth

The heart of this episode resides in viewing singleness not as a 'holding period' but as a divinely appointed season for growth and deeper intimacy with God. Whether in active dating or closed singleness, the focus is on pursuing personal dreams, spiritual maturity, and genuine connections.

Jack and Riley’s experiences serve as beautiful reminders that our seasons of singleness, whether closed or open, are opportunities for incredible personal and spiritual growth. Each period can be filled with purpose and fulfillment, making us better individuals and future partners.

Conclusion

As we close this insightful discussion on closed vs open singleness, remember, Heart of Dating fam, to embrace your current season with grace and purpose. Whether you’re nurturing your relationship with God or exploring new connections, find joy and contentment right where you are.

Don't forget to check out Riley’s new book, "Three Seconds of Courage," and get excited about our upcoming conference where we dive deeper into these valuable topics. Keep tuning in for more wisdom and encouragement from Heart of Dating!

Stay blessed and let’s keep dating with heart and purpose!

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Riley and Jack Kehoe

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Jack and Riley Kehoe are a husband-and-wife team united by a passion for serving others, sharing stories of faith and courage, and embracing life’s adventures. In 2024, they traveled the globe, dedicating their time to mission work in orphanages, safe homes, and churches. Now settled in Franklin, Tennessee, they are eagerly preparing for their greatest journey yet—becoming parents. Together, they run a podcast called Called For More, inspiring young adults to kill apathy and live radically.

Riley is an accomplished author, speaker, and podcast host whose work inspires others to overcome fear and live boldly, with her forthcoming book, Three Seconds of Courage, set to be published on January 28. Jack is an entrepreneur and revivalist who overcame addiction as a teenager through a life-changing encounter with Christ. Since then, he has dedicated his life to cultivating presence-centered communities through discipleship homes, house churches, and prayer gatherings. He currently leads Purpose Properties, a real estate development company, and mentors young men to become effective leaders.

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