AI Summary
5 min readPreston and Jackie Perry, hosts of With The Perrys, sit down to revisit the two times they broke up before getting married—once when Jackie moved to Chicago, and again during a trip to Trinidad. The conversation is raw, self-deprecating, and avoids tidy moralizing. Instead of a simple "we worked it out" story, they dig into the specific failures on both sides: Jackie’s pattern of running from intimacy, and Preston’s tendency to lecture rather than listen. The central argument that emerges is that their relationship survived not because either of them was naturally good at it, but because they were forced to learn how to depend on something beyond their own instincts.
The first breakup: control and fear
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What you'll learn
- 1 (02:04) **Opening the story: “The time we broke up”** - Preston and Jackie introduce the episode’s topic: they broke up twice while dating, and both times felt traumatic.
- 2 (03:36) **Chapter 1: The first breakup** - Jackie moved from St. Louis to Chicago for a job, and the day she arrived, she texted Preston to break up.
- 3 (08:21) **Chapter 2: The second breakup – Trinidad** - The couple goes on a 7-day poetry trip to Trinidad and Tobago, and Jackie shuts down the first day.
- 4 (14:59) **What Preston would do differently now** - Preston reflects on how he would handle the situation after nine years of marriage.
- 5 (16:11) **Jackie’s growth: learning to name her feelings** - Jackie describes how therapy helped her put language to her emotions and anticipate triggering situations.
- 6 (20:20) **The breaking point in Trinidad** - During a basketball game, Jackie tells Preston, “I don’t even know why I’m with you.”
- 7 (24:50) **Preston’s fake prayer and the call from Brian** - Back in Chicago, Preston prays a “fake prayer” and then gets a call from his pastor/disciple, Brian.
+ Full timestamped outline available in the app
Guests on this episode
Show Notes
With The Perrys is taking some time this summer to revisit popular episodes from years past.
Jackie and Preston's relationship has had plenty of twists and turns. From long distance dating to a group trip to the Caribbean, things didn't get off to a smooth start. Jackie broke things off...twice. Preston admits he had a lot to learn about leading well, and together they look back on what they'd do differently.
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With The Perrys is a podcast where biblical truth meets honest conversation. Join Preston Perry and Jackie Hill Perry as they discuss theology, relationships, parenting, culture, and the everyday realities of following Jesus. With humor, transparency, and a deep commitment to Scripture, each episode aims to point listeners back to Christ, deepen their understanding of God's Word, and encourage faithful obedience in every area of life.
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