Hosted by Derrick Levasseur and Stephanie Harlowe
Written by a model from the transcript; not yet reviewed.
This episode examines the final hours and immediate aftermath of Ashley Flynn's murder, detailing the frantic text exchanges between her husband Caleb and his mistress Aaliyah, the incriminating digital and physical evidence discovered by investigators, and the critical flaws in Caleb's alibi. The hosts break down Caleb's bizarre digital surveillance of Aaliyah through Snoop Report and catfishing attempts, the suspicious timeline of his Apple Watch steps and AirPods activity during the night of the murder, and his unconvincing 911 call where he claimed an intruder shot his wife while two sleeping daughters remained untouched down the hall. Despite Caleb's attempts to stage the scene by damaging an exterior garage door and placing a refrigerator against it, investigators quickly realized there was no forced entry, no footprints in the dew, and no neighborhood camera footage of any intruder.
Hosts introduce Part 3 of the Ashley Flynn case and recap key events from Part 2.
Stephanie and Derek discuss a theory that Caleb may have wanted Aaliyah to kill Ashley.
Aaliyah explains how Caleb accessed her Instagram and the laptop password, revealing surveillance tactics.
Evidence shows Caleb created a fake Instagram account to lure Aaliyah into a trap.
Aaliyah’s plan to manipulate Caleb by cutting off contact and provoking jealousy is detailed.
Caleb’s plan to use a burner phone to update Aaliyah while he prepares to kill Ashley is revealed.
Hosts pause for a brief break and promote Talkiiatry, then resume the narrative.
The hosts examine Caleb Flynn’s phone logs from 11:00 PM to 2:30 AM, noting app deletions, step counts, and the moment he finally unlocked his phone to call 911.
The conversation explores Caleb’s movements, his use of AirPods, and the suggestion that he staged the crime scene to appear as a victim.
The hosts discuss theories about when the shooting occurred relative to Caleb’s phone activity, weighing evidence for a pre‑ or post‑911 call murder.
The coroner’s testimony details two close‑range 9 mm gunshot wounds, a bullet in Ashley’s elbow, and the discovery of a handgun in Caleb’s truck.
The recorded 911 call is played, revealing Caleb’s frantic description of a double gunshot wound and the dispatcher’s attempts to guide him through basic safety steps.
Officers arrive, describe the lack of forced entry, the intact front door, and the peculiar open side garage door with a refrigerator blocking it.
The hosts recount Caleb’s calls to his mother and Ashley’s mother, the emotional toll on the family, and the broader public response to the case.
Investigators explain the forensic findings on the garage door, concluding the damage was likely inflicted while the door was already open, not by forced entry.
Hosts discuss how investigators used silicone casts to compare tool marks and assess forced entry evidence.
Caleb's Catfishing Attemptstory
Caleb created a fake Instagram account named Derek Hammett using stolen photos to test Aaliyah's fidelity, but she recognized it was him immediately.
Subscribing to Snoop Reportdata
Caleb paid for a monthly service to track Aaliyah's Instagram likes and follows after she changed her password to lock him out of her account.
Caleb's Apple Watch logged over a hundred steps and heart rate readings during the exact window he claimed to be sleeping in the children's room.
The Suspicious 911 Callinsight
Caleb immediately told the 911 dispatcher that his wife had been shot twice in the head, matching details the medical examiner could only verify after shaving her head.
Staging the Garage Doorstrategy
Investigators discovered that a heavy refrigerator blocked the open garage door, and Caleb's palm print was found on the side where he reached around to fake a break-in.
Lack of Intruder Evidenceinsight
K-9 units, drone thermal imaging, and a massive canvas of neighborhood security cameras revealed zero footprints, heat signatures, or footage of any outside intruder.
“People are really loving your dramatic readings of the text messages. People are getting a kick out of that.”
“I thought Caleb was hacking into my Instagram.”
“I don't know. I don't know. I am very uncomfortable.”
“He was still paying money to find out what Aaliyah was doing on social media and who she was talking to or following.”
“The fact that he was able to say automatically within quote unquote moments of him finding her, she's been shot twice.”
“I think he, he kills her and then now he can stage the scene and not have to worry about her walking in on it.”
“The door, yes, yes, yes, yes.”
“The door was open about 45 degrees.”
“If we find burglary tools on someone, you basically would, what I would do is put like cardboard around it.”
“That's a great point, Stephanie.”
In the early morning hours of February 16th, 2026, Ashley Flynn was shot and killed inside the home she shared with her husband, Caleb, and their two daughters. Caleb told police that someone had broken into the house, murdered his wife, and disappeared. Up until that night, Caleb’s life had been deeply intertwined with Ashley’s. They had been married for fifteen years. They were raising two daughters together. They attended church together. Caleb worked for Ashley’s father, was close with her family, and had spent years building a life that was connected to hers in almost every possible way. But investigators would soon discover that there was another version of Caleb Flynn’s life. One that Ashley did not fully see. A secret relationship. Thousands upon thousands of messages. Lies, hidden accounts, deleted conversations, and a second life running parallel to the first. And as police began pulling those two lives apart, they also began uncovering something else: the story of what Ashley had been seeing, questioning, and trying to make sense of in the months before she died.
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Speaker names marked are inferred from speaking time and the show’s known hosts — they are not voice-verified.
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