The Red Weather – Episode 2: "Tomshanigans"

Podcast: The Red Weather
Host: Ryder Strong, iHeartPodcasts
Release Date: January 30, 2026

Episode Overview

In this gripping second episode, Ryder Strong continues his investigation into the 1995 disappearance of Anna Trainor, his best friend’s sister, from their Northern California hometown. The episode dives deeper into Ryder’s memories and personal guilt, reconstructing the events of the infamous Halloween night. With childhood friends, police, and local reporters, Ryder tries to piece together the hazy, conflicting recollections around Anna’s last known hours, the infamous “yurt tape,” and a barn-burning incident—all while wrestling with nostalgia and the morality of teen shenanigans gone terribly awry.

Key Discussion Points & Insights

1. Reflections on Adolescence & Misguided Actions

• Ryder opens with a story from his father's youth—an elaborate prank involving a supposed affair with “Sally Chase” (09:00 – 14:00). This anecdote serves as a lens for examining the impulsive, morally ambiguous choices teens make.
• Direct comparison is drawn between his dad’s youthful misadventure (which turned out to be harmless) and the life-altering night that ended with a fire and Anna’s disappearance.

“When you’re a teenager, you don’t think these things through. You’re caught up in the moment, in your age, in your friend group. You’re completely in a bubble.”
– Ryder Strong (14:50)

2. Re-examining the Night Anna Disappeared

• Ryder and Chris, childhood friends, retrace their steps in the woods behind Ryder’s parents’ house, encountering the remnants of their old fort, “the rat hole.” (23:00 – 28:00)
  • They discuss their teenage plan—intended to protect Anna’s reputation from a damaging tape—unfolded with misguided bravado, fireworks, and costumes.
• They reflect on Anna’s struggle to fit into the mainstream after growing up on a commune, “Tender Hearts,” and how her attempt to assimilate into public high school led to isolation and rumors. (32:00 – 36:00)

“This was a girl who’d never set foot in a classroom... she’d never done a book report, let alone dealt with the kind of social pressure of a typical American high school.”
– Ryder Strong (33:30)

3. The Yurt Tape & Small-Town Scandal

• The notorious “yurt tape”—a video from a party involving Anna and two boys—is discussed with local reporter Monica Tremblain and friends. It became a pivotal source of rumor and shame. (41:00 – 46:00)
  • The plan: to lure Mick (Anna’s ex) into the woods, distract him, and steal the tape.
• Friends playfully argue over their memories of the night, recalling costumes, props, and their 15-year-old logic.

“Our idea was to get Mick out to the woods and distract him long enough to grab the yurt tape from his car. But in order to do that… we decided to not only lure him out but also scare the crap out of him.”
– Ryder Strong (46:20)

4. Fire, Guilt, and Coming Forward

• The plan devolved into chaos, leading Willow—Anna’s sister—to burn down a barn full of drying marijuana, believing it a necessary act. (54:00 – 58:00)
• Ryder struggles with the idea of coming clean to the authorities, especially after learning that his and Chris’s memories (and promises) differ. Chris gets cold feet about meeting with the former sheriff.
  • They unearth a green pager from Ryder’s parents’ garage, a potential clue, highlighting Ryder’s tendency to imbue old objects with meaning (61:00 – 64:00).

“It’s kind of crazy just finding a pager when we know Anna had one out here…”
– Ryder Strong (63:10)

5. Confronting the Authorities

• Ryder finally meets with Sheriff Maldonado (retired), admitting to past deception and seeking to provide clarity on the events of Halloween 1995. (69:00 – 74:00)
  • Maldonado offers insight into how police handled “Tomshanigans” (a blend of tomfoolery and shenanigans) and recommends Ryder contact current sheriff Grace Loughlin.

“If you want to move past—get beyond the Tomshanigans—then let’s go. But you gotta talk to Loughlin.”
– Sheriff Maldonado (74:50)

• On a call with Sheriff Loughlin (79:00 – 82:00), she underscores the legal risk in admitting to giving false statements, but assures Ryder the statute of limitations has expired.

“You made false statements... That's obstruction of justice. ...Lucky for you, frankly lucky for me, because I don't want the hassle, it's well past the statute of limitations.”
– Sheriff Grace Loughlin (80:40)

6. Breaking Down Nostalgia

• Ryder discusses the power and danger of nostalgia—how fond memories can obscure the truth and complicate self-reflection (84:00 – 86:00).
  • He reaffirms his commitment to objectivity and confronting uncomfortable truths, rather than self-serving sentimentality.

“Nostalgia is such a trap. It can make songs from your teens sound better... The more nostalgia draws you in, the more it just warps your perception of reality.”
– Ryder Strong (85:40)

7. Revisiting the Alibis and Next Steps

• Ryder learns from Maldonado and Monica that the alibi for the commune, Tender Hearts, is falling apart; not all members were where they claimed on the night Anna vanished (88:00 – end).
• He commits to digging deeper into the commune and Anna’s home life—the “Tender Hearts”—as the focus for the next stage of the investigation.

“If some or all of the Tender Hearts had lied, if their alibi had come crashing down, this was actually exactly what I wanted to hear.”
– Ryder Strong (90:50)

Notable Quotes & Memorable Moments

• Ryder, on adolescence and responsibility:

  “It was just like my dad, this adolescent misadventure that, if you look back with any perspective, you can't help but question your motivations, your intelligence, and even maybe your moral compass.” (15:50)

• Reporter Monica, on Anna’s scandal:

  “She had a reputation, being very sexually open, which I remember was unjustified... that concept of somebody being a slut only applies to a woman.” (44:10)

• Costume and caper confusion:

  “‘We called ourselves psycho mimes. And you were like, what, the Phantom of the Opera thing?’
  ‘Phantom of the Coffee Choppera. I had a Starbucks barista…’” (59:30)

• Maldonado on "Tomshanigans":

  “‘He was trying for tomfoolery and shenanigans, but never came out right… a lot of our job’s just pulling out the kid stuff.” (72:40)

Timestamps for Key Segments

• Adolescent Pranks & Parallels: 09:00 – 16:00
• Revisiting the Scene / The Rat Hole: 23:00 – 28:00
• Anna’s High School Turmoil: 32:00 – 36:00
• The Yurt Tape Plan: 41:00 – 46:00
• The Fire and Its Consequences: 54:00 – 58:00
• Finding the Pager: 61:00 – 64:00
• Meeting Sheriff Maldonado: 69:00 – 74:00
• Sheriff Loughlin's Legal Warning: 79:00 – 82:00
• Nostalgia and Self-Reflection: 84:00 – 86:00
• The Commune’s Alibi Crumbles / Next Steps: 88:00 – end

Conclusion

Episode 2 masterfully weaves together personal reckoning, unreliable memories, and the menacing mysteries of small town adolescence. Ryder’s search for the truth about Anna Trainor’s disappearance draws him deeper into uncomfortable confessions, strained friendships, and the tangled lies that grew from one terrible Halloween night. The next episode promises to pry open the secrets of the Tender Hearts commune—a shadowy cornerstone in Anna and Willow’s lives.