16x07: Valentine Nightmares

16x07: Valentine Nightmares

Update: 2026-02-163
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Digest

This podcast features a collection of unsettling true stories detailing various forms of stalking, harassment, and dangerous encounters. The narratives include a persistent and obsessive classmate named Randall, a possessive ex-girlfriend who resorts to psychological terror, a frightening dating app match who later commits a violent crime, and individuals who are harassed online and in person. The stories emphasize the escalating nature of such behaviors, the fear they instill, and the interventions, both personal and official, that sometimes bring them to a halt. The podcast also touches on the importance of safety, awareness, and the lasting psychological effects of these experiences.

Outlines

00:00:00
Early Encounters with Obsessive Behavior

The podcast opens with a disclaimer and listener story requests. The first narrative details a young person's experiences with an increasingly obsessive and threatening classmate named Randall between 2007 and 2009, whose behavior escalated from silent observation to online threats after intervention.

00:00:04
Escalating Obsession and Violent Threats

Randall's obsession intensifies with persistent contact, unwanted gifts, and the creation of a fake online persona. After the narrator's mother intervenes, Randall retaliates with violent online threats, leading to police involvement during the narrator's senior year.

00:13:14
Psychological Torment and a Possessive Relationship

This section recounts a relationship with a possessive girlfriend, Marianne, who engages in psychological torment after a breakup, even involving the narrator's dog in disturbing ways.

00:22:14
Dating App Dangers and Real-World Fears

A woman shares a frightening experience with a dating app match who became aggressive and later committed a violent crime, sparking fear and "what if" scenarios. Another story details a man named Robbie who falsely claimed to have met someone at an event and persisted with unsettling messages.

00:32:12
Persistent Harassment and Predatory Encounters

This chapter covers instances of persistent harassment, including a man who followed and harassed a woman while she was walking her dogs, and online dating harassment that escalated to in-person confrontation.

00:41:10
Relentless Online Pursuit and Intervention

A young woman details a week-long ordeal with an acquaintance named Daniel who relentlessly texted and called, using gathered information to pinpoint her location, leading to fear and her mother's intervention.

00:55:05
Resolution and Reflection on Obsessive Behavior

Following intervention from the narrator's mother and a friend, Daniel's harassment ceased. An acquaintance explains Daniel's past obsessive behavior, and the narrator reflects on the experience, hoping for Daniel's growth.

Keywords

Stalking Behavior


A pattern of repeated, unwanted attention and contact that causes fear or distress, including following, unwanted communication, and surveillance.

Online Harassment


The use of electronic communication to bully, threaten, or harass individuals through social media, email, or messaging apps, including cyberstalking.

Dating App Dangers


Risks associated with online dating platforms, such as encountering dangerous individuals, experiencing harassment, or stalking.

Psychological Terror


The use of manipulation and intimidation to instill fear and distress, often by exploiting vulnerabilities.

Obsessive Fixation


An unhealthy preoccupation with a person or object, leading to intrusive thoughts and behaviors that can escalate to stalking.

Escalating Behavior


Actions that gradually increase in intensity or severity over time, indicating a worsening threat level in harassment or stalking.

Socially Inept


Lacking the skills to navigate social situations effectively, potentially leading to awkward interactions and misunderstandings.

Q&A

  • What was Randall banned from doing at school, and why?

    Randall was banned from using school computers after a serious infraction involving violations of confidentiality and obsessive effort, possibly hacking emails or changing grades.

  • How did Marianne escalate her harassment after the breakup?

    Marianne escalated her harassment by involving the narrator's dog, Arnold. She left a new toy on the porch, then later replaced it with an older, damaged one, and ultimately took Arnold, leaving a paw print and the word "mine" on the door.

  • What was the outcome of the police involvement in the story about Randall?

    The police spoke with Randall and his parents, warning him to cease contact with the narrator. While this initially seemed effective, Randall's behavior later escalated to violent threats online.

  • How did the woman in the "Bumble match turned killer" story confirm the identity of the perpetrator?

    She confirmed the identity by comparing a screen recording of the man's harassing messages to a news article about the shooting, matching his name and face.

  • What actions did the narrator's mother take to stop Daniel's harassment?

    The narrator's mother intervened by speaking directly with Daniel and his mother, warning Daniel to stop contacting her daughter and threatening further action if he continued.

  • How did the man in the "I'm looking for a girlfriend" story try to intimidate the narrator?

    He followed her persistently, got uncomfortably close, and made suggestive comments. He was deterred when she made a point of interacting with a family, making him aware he was being observed.

  • What was the final straw that led the narrator to break up with Marianne?

    The final straw was when Marianne, in a jealous rage, dragged the narrator to the waterline and screamed accusations of cheating during an innocent conversation with a new girl at a bonfire.

  • How did Daniel's persistence in the "boyfriend I didn't know I had" story manifest?

    Daniel relentlessly texted and called, even showing up in the narrator's area multiple times. He used information from their conversations to pinpoint her location and continued to harass her even after she refused to meet him.

Show Notes


Stories in this episode:

He Walked Over A Mile int he Freezing Rain for Me | Anonymous (0:38 )
My Psycho Ex Girlfriend | Anonymous (13:14 )
Bumble Match Turned Killer| danifishy (22:15 )
Secret Admirer | ATru05 (28:19 )
"I'm Looking for a Girlfriend" | Illy Stylez (32:21 )
I Left All Dating Apps and Never Went Back | olive (36:14 )
The Boyfriend I Didn't Know I Had | xgemmax (41:15 )

Extended Patreon Content:

The Officer | Elm13
Different Names, Different Ages | Darian
50 Shades of Sketchy | Kat
Rural Regrets | Mike

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16x07: Valentine Nightmares

16x07: Valentine Nightmares

Cryptic County