With The Perrys: "The Grief and Relief of Obedience in Dating"

Release Date: November 10, 2025
Hosts: Preston Perry & Jackie Hill Perry
Guests: Melody & CD

Episode Overview

This episode of With the Perrys dives into the nuanced dynamics of dating as a Christian, especially for those navigating singleness or dating past their 20s. The conversation, rich in personal stories and biblical counsel, unpacks the grief and relief that come from obeying God in the dating process—highlighting both the costs and the joys of pursuing God's best in relationships. The discussion casts vision for dating as a process of preparation, healing, and discernment, emphasizing prayer, accountability, community, and spiritual maturity.

Key Discussion Points & Insights

1. Dating Beyond College: Unique Wisdom and Challenges

• Many dating resources focus on college-aged Christians, leaving singles in their 30s, 40s, and beyond—or those who are divorced or widowed—without tailored guidance.
• Melody underscores the reality of feeling like "it's too late" but urges ongoing prayer and preparation, regardless of age.

  “Some people have stopped praying for a spouse because it hurts them...but it's okay to pray for what you want, for the desire of your heart.” — Melody [01:20]

2. Active Preparation and Community Accountability

• Preparation for marriage isn't just about prayer—it includes learning through books, conferences, and seeking wise counsel.
• Melody recounts guiding a close friend through a careful, boundaried dating process as a single mom in her 30s, emphasizing discernment and community input at every step.

  “You could change a man's clothes, but you cannot change his character.” — Melody [03:39]

• The importance of intentional boundaries: setting communication expectations, safeguarding children, and maintaining purity.

  “Do not share your location with anybody but your spouse. They don't have the right. That's a covenant thing.” — Melody [06:39]

3. Pace in Relationships: The Value of Boundaries

• The difference between friendship/courtship (which may be longer) and engagement (which the group strongly recommends keeping short to minimize temptation and confusion).

  “Long dating, very short engagements. If you've been friends for five, ten years, dating, and now another four or five years—what is happening?” — CD [09:04]

• Community agrees that short engagements (six months or less) are ideal for maturity, focus, and spiritual safety.

  “The warfare increases in the engagement period… Nah, we need to…” — Baxter [10:19] “It should be six months or less.” — Melody [10:41]

4. Leadership, Submission, and Spiritual Discernment in Dating

• The necessity for men to lead with intentionality, prayer, and spiritual pursuit—starting in dating and carrying into marriage.

  “If you practice being a leader now, things will be easier for you when you're married. Set the tone.” — Jackie Hill [14:29]

• Healthy leadership involves both submission to God and mutual submission within the relationship.

  “Leadership doesn’t look like, ‘I tell you what to do.’” — CD [18:19]

• Both men and women must seek confirmation and guidance through prayer, fasting, and godly counsel before major relational steps.

5. Healing from Father Wounds or Past Patterns

• Melody and others discuss how “father wounds”—or cultural patterns picked up in place of direct fathering—can distort attraction and discernment.
• She stresses the irreplaceable value of godly mentors and spiritual mothers/fathers in navigating blind spots.

  “If you don’t have a mentor… get around older godly women.” — Melody [26:22]

• Letting go of surface-level criteria (like appearance or salary) for godly, character-rich connection.

  “Take the picture of what you think your husband's gonna look like out of your mind, lest you miss what God has for you.” — Melody's father [29:05]

6. The Hard Work and Fruit of Obedience: Grief, Relief, & Peace

• Melody details a painful breakup that brought both grief and profound relief after obeying God's promptings—even when everyone else could see the red flags first.

  “You can be in peace but in pain and still be obeying me.” — Melody [39:42]

• Disobedience can lead to spiritual and emotional oppression; obedience, while painful, brings lasting peace.

  “The previous pain… I think it was akin to a demonic oppression because of disobedience.” — CD [40:10]

• The panel emphasizes the power of humility, fasting, and prayer to break cycles of idolatry and self-wisdom.

  “If everyone in your circle is giving you the red flag, even if you don’t believe it… just fast, pray.” — CD [42:32]

7. Fasting and Clarity in Decision-making

• Fasting (not just from social media, but from food) is championed as a route to real clarity—not simply to demonstrate self-control, but to humble oneself and hear God’s voice.

  “Fasting breaks the will; helps you see.” — CD [46:18]

• Both Preston and Melody share testimonies of God redirecting their hearts and affections through fasting in pivotal dating moments.

8. Dating as a Reflection of the Gospel

• CD connects marriage and dating to the gospel narrative—how our unions on earth are a living image of Christ and the Church.

  “Every marriage is a gospel presentation… Who we date and who we marry is the most important decision you’re going to make after giving your life to Christ.” — CD [56:51]

• Emphasizes generational impact and the necessity of a God-centered vision for relationships.

Notable Quotes & Memorable Moments

• On Boundaries:
  “She said, ‘I'm saving sex until marriage… I would like to save kissing for marriage.’… He said, ‘I respect that. I'm willing to wait.’” — Melody [07:13-07:39]

• On Accountability:
  “She would not disappear. She would be like, ‘Hey, he just came over.’… That was her accountability.” — Melody [08:09]

• On Knowing When to End a Relationship:
  “I need an obedience pill… I broke up with him. Good guy. The next day, I was healed of this sickness.” — Melody [38:32]

• On Letting Go of Control:
  “It's a call… We knew we were called to each other… Even when married, we started to see our differences… and we'd go, ‘No, we're called to be together.’” — Melody [47:03]

• On Prayer and Fasting Clearing Confusion:
  “Fasting, humbles us, but it actually shows us who we are… I honestly think if I would have married that girl… I don’t think that I would like, like her.” — Preston [44:55]

Timestamps for Important Segments

• 00:00-02:15 — Dating after 30: The overlooked demographic and the importance of preparation and prayer
• 03:30-06:50 — The boundaries and pace of dating; prayerful decision-making
• 09:00-10:45 — Advice against long engagements
• 13:44-16:11 — Leadership, submission, and intentionality in the dating process
• 21:12-30:50 — Father wounds, expectations, and discerning godly character (letting go of superficial standards)
• 36:09-40:03 — Breaking up out of obedience, even when it brings grief
• 44:26-47:26 — Fasting as a tool for relational clarity and hearing God's plan
• 56:51-58:10 — Casting a gospel vision for singleness and marriage

Final Takeaways & Gospel Vision for Singles

• Dating, whether as a young adult or later in life, should be marked by prayerful pursuit, boundaries, community accountability, and a willingness to yield desires to God’s will.
• It’s vital to heal from past wounds, confront unhealthy patterns, and let godly counsel speak into your process—God’s timing and standards always lead to deeper peace and purpose.
• Marriage (and dating on the way to it) paints a living picture of Christ and the Church; it matters deeply whom you choose to pursue and partner with.

  “Who we date and who we marry is the most important decision you’re going to make after giving your life to Christ.” — CD [56:51]

Connect with Melody & CD:
For relationship coaching and their story in full, check their website, as recommended on the show.

(This summary highlights wisdom for all stages of Christian dating, with a balance of doctrine, humor, and vulnerability, in the trademark With the Perrys style.)