With The Perrys – "Storytime with Jackie"

Date: November 14, 2022
Hosts: Jackie Hill Perry & Preston Perry

Overview

In this lively and candid episode of With The Perrys, Jackie Hill Perry shares several memorable stories from her past, with Preston Perry as the interviewer and cheerleader. The episode centers on personal transformation, vulnerability, and God’s grace as Jackie recounts moments of mischief, fear, and divine intervention from her pre-Christian life, all delivered with the Perrys’ signature humor and unfiltered honesty.

Key Discussion Points & Insights

1. Introduction: Setting the Storytime Vibe

Timestamps: 00:09 – 01:13

• The Perrys set a playful tone, poking fun at each other's slang and “storyteller” abilities.
• Preston expresses excitement for “storytime” episodes, insisting Jackie has the best stories.
• Jackie clarifies that while she doesn’t have many stories, “the few I have...are worth telling.” [01:02 – Jackie]

2. The Misdemeanor & Canada Debacle

Timestamps: 01:28 – 09:16

Story: Jackie almost wasn’t allowed into Canada due to a 10-year-old misdemeanor.

• Jackie admits to past theft driven by a shrewd, “efficient” approach: stealing outfits saved money for weed and going out. [02:06 – Jackie]

  “I used to steal all the time...if I steal the outfit, then I got money for the weed...Don’t it make sense?” [02:54 – Jackie]

• She emphasizes: “I’m not advocating for theft. Okay, let’s be clear. That grieves the Lord’s heart.” [03:25 & 03:30 – Jackie]
• Jackie skillfully describes avoiding theft detection, her “skills as a Christian communicator” having been used for crime before conversion.
• Details a botched theft at Macy’s with a friend; both are arrested and subjected to the humiliating “walk of shame” through the mall.
• After conversion, while on a ministry tour, Jackie discovers her record disqualifies her from entering Canada. She has to plead her case at the border and is only admitted due to intervention by her friends.

  “I promise I’m a new person. I’m changed. Like, we were doing my Instagram. I’m literally here for Jesus.” [08:47 – Jackie]

3. High School Fights, Fear, and “Not About That Life”

Timestamps: 09:32 – 16:18

Story: Jackie reflects on not being a fighter, despite growing up among people who were.

• Preston jokes about Jackie appearing tough but not actually being able to fight.

  “Jackie face falls like she can fight, but...she really can’t.” [09:34 – Preston]

• Jackie describes the anxiety of being perceived as weak or “soft” in a Black school environment:

  “You don’t want to be in school at a Black school—one, can’t fight, or soft. Those two things are just such bad categories to live in.” [10:10 – Jackie]

• She recounts being caught in the middle of a brewing group fight at a friend’s house, where the friend's mother prepares a sock filled with rocks as a weapon—escalating the tension.

  “She’s like...‘When people come on this door, I’m dropping them. If you ain’t ready to fight, you can get the F out.’” [13:27 – Jackie]

• Admits to plotting an escape: has her godbrother fake a call as her mom so she can leave without looking frightened. [15:11 – Jackie]
• Compares the constant need to defend herself as a teen to the relief of later being in Christ-centered communities, where “it was a relief to not have to always be on guard.” [16:18 – Jackie]

4. Spiritual Encounters: The Demon in the Bedroom

Timestamps: 17:20 – 21:22

Story: Jackie’s mother witnesses a demonic presence in Jackie’s room during her teen years.

• Described vividly:

  “‘She saw a figure...five feet tall...all black...leathery or reptilian...His hands were [through] the door, him peeking at her, then going back inside my room.’” [18:12 – Jackie]

• Jackie recounts being unnerved, sleeping with lights on, and continuing that habit into adulthood.
• Reflects on spiritual consequences:

  “Demons...have domain and they have liberty where darkness and sin exists. And so I wasn’t a Christian...I was opening myself up to all types of demonic stuff.” [19:53 – Jackie]

• Preston closes this with appreciation of God's providence:

  “Stories like that...it’s kind of creepy, but it’s also...encouraging to know that God had a plan for your life.” [21:04 – Preston]

5. Breaking Illusions: Vulnerability and Gender Identity

Timestamps: 21:50 – 25:39

Story: Jackie describes a moment in her “stud” lesbian identity where her sense of masculinity was shattered.

• While in a motel with her girlfriend, a threatening large man causes Jackie to realize her own vulnerability:

  “I am in this world where I’m living this illusion of being male or masculine...in this moment, I knew I was a woman. I knew I was vulnerable and I was weak and...I could not protect her and I could not protect myself.” [23:15 – Jackie]

• Reflects on God using the situation to confront her identity:

  “The Lord was using it to speak to my gender and my biology and how God had made me to exist and be—and how I was functioning completely opposite of that, which was not reality.” [24:48 – Jackie]

• Confesses that even in fear, she managed to create a diversion so she and her girlfriend could safely leave, without breaking the “hard” facade.

Notable Quotes & Humorous Moments

• On Old Ways Fueling New Skills:

  “All of my skills as a Christian communicator and as a preacher, I had then—I was observant...I paid attention to people...” [03:53 – Jackie]

• On the "Walk of Shame" after shoplifting:

  “You just walk through the mall with handcuffs on. They gotta make an example out of you.” [08:02 – Jackie]

• On the DIY Weapon:

  “She got a sock, and she putting an eight ball and rocks in the sock...she finna swing on whoever come to this doorstep.” [13:27 – Jackie]

• On Seeking Escape from a Fight:

  “I text my godbrother, and I said, call me and act like you my mama.” [15:11 – Jackie]

• On Wrestling with Spiritual Reality:

  “I watch [porn] all the time. I love demonic music and I listen to it all the time. I was in a world of darkness, but I also had a call.” [20:18 – Jackie]

• On Identity and Vulnerability:

  “In this moment, I knew I was a woman...I could not protect her and I could not protect myself. The Lord was using it to speak to my gender and my biology...” [23:15 & 24:48 – Jackie]

Timestamps for Important Segments

• Intro/Banter: 00:09–01:13
• Theft & Canada: 01:28–09:16
• Fights & Flight: 09:32–16:18
• Demonic Encounter: 17:20–21:22
• Motel Showdown & Gender Reflection: 21:50–25:39

Conclusion

Jackie’s stories—of theft, intimidation, spiritual darkness, and pretending to be tough—are relayed with a mix of hilarity, humility, and grace. Preston’s interjections keep the episode brisk and fun. Each story drives home a message about God’s redemptive power, the unmasking of false personas, and the freedom Jackie felt over time, moving from “thug life” bravado to honest vulnerability and belonging in Christ.

The episode’s tone is real, raw, and often laugh-out-loud funny, but always circles back to gratitude for God’s transformative love and the improbability of Jackie’s storylines ending any other way.

Note: This summary skips advertisements, intros/outros, and technical credits to focus on the core content.