Murder, Mystery & Makeup · Audioboom Studios

From Obsession To Murder: The Girlfriend Who Couldn't Let Go - Shayna Hubers

·1 hr 10 min·3 clips

Shayna jokes about giving Ryan the nose job he always wanted after shooting him

Bailey opens by warning that this Monday story is going to stress you out, then quickly frames Shayna Hubers as the Kentucky Jodi Arias. She describes her as young, smart, ambitious, and gorgeous, but says the one thing she could not control was her obsession. Shayna was not just in love with her boyfriend Ryan, she was consumed by him. When he tried to leave, Bailey says she was not going to let him walk away, and what followed became a dark mix of jealousy, manipulation, and violence. The episode leans hard into the central question of motive. Bailey keeps asking whether Shayna acted in self-defense or carried out a cold execution. She also points to the case’s messy trail of evidence, including interrogation tapes, bizarre behavior, and never-ending trials, all of which make the story feel more chaotic the deeper it goes. A big part of the episode focuses on digital evidence. Bailey says police reviewed more than 50,000 text messages, 20,000 Facebook messages, and photos exchanged between Shayna and Ryan. That material helped investigators conclude the relationship was highly toxic and very on-again, off-again. The ordinary details are what make the dynamic feel even stranger. Shayna texted Ryan almost every day about dinner, asking what he wanted, whether she was cooking, ordering, or picking something up. Even when she went out with friends, she would send him a menu photo and offer to bring food home. Bailey also says Shayna would bring him practical things, like his wallet if he forgot it at work. Those actions can look caring, but in the context of the case they also read as constant attention. Bailey adds that Shayna had access to Ryan’s Facebook and was reading his messages. She says that likely led her to see messages about him dating someone else and to search that woman online. One especially suspicious detail is an internet search for how to unlock a house door with a bobby pin just an hour before calling 911. Bailey is careful to note that it is speculation, but she treats it as a very bad look. The episode also includes group-chat chatter about Ryan’s new girlfriend, with Bailey using it to show how petty social-media drama can feed something much darker. By the end, Bailey pulls the story back from pure spectacle and reminds listeners that stalking and harassment are serious. She says people should not be afraid to reach out and ask for help. It lands the episode on something practical and direct instead of leaving it only as true-crime chaos.

As heard by us

A toxic relationship case that moves through obsession, messages, and a self-defense-or-murder question.

The episode tracks Shayna Hubers from a young, smart, ambitious woman into a relationship defined by obsession, jealousy, manipulation, and violence.

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Why you'd press play

You want a breakup case that starts clingy and goes bad in a hurry.

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