Hey Riddle Riddle – Episode #383: Don't Tell! (November 19, 2025)

Episode Overview

This episode of Hey Riddle Riddle is classic chaotic Clue Crew fun: hosts Adal Rifai, Erin Keif, and John Patrick Coan (JPC) bounce between riddle-solving, improv comedy, and affectionate ribbing—proving, once again, that the podcast is barely about riddles. The group tackles a new suite of “trios” riddles, improvises elaborate scenes on the fly (often at Erin’s expense), debates the merits and history of old-timey swearing, and gets lost in a deep well of nostalgia (and tangents) for 90s and 00s pop culture. The tone remains loose, playful, and irreverent, with their improvisational energy propelling the episode more than any head-scratching riddle.

Key Discussion Points & Insights

1. Post-Recording Chaos & Sleep Deprivation

• The episode opens with Adal, Erin, and JPC coming down from a wild previous recording. Erin jokes about not having slept, and everyone is in a slightly delirious mood, setting a frenetic comic tone.
  • Notable Quote (Erin, 08:05): “We are on week two of episodes where I have not slept. For you guys, it’s going to be weeks and weeks. Ten weeks. Ten weeks.”
• The dynamic is a bit slap-happy, fueling both sharper jokes and more off-the-wall improv.

2. Riddle Segment: “Trios”

• Adal introduces a recurring riddle format: three items, find the common thread.
• The riddles range from clever (Tropicana, accordion player, anaconda: “They all squeeze”) to pop culture-infused (The Great Barrier Reef, Alexander the Great, Frosted Flakes: “They’re all great”).
  • Notable Moment (10:13): JPC nails the first riddle instantly: “They all squeeze professionally.”
  • Notable Moment (14:33): Erin and Adal laugh at the word “fresh” as Boston slang for a rude child.
• The scenes spun off from solved riddles include:
  • A drunken new Tropicana employee (Erin) trying to spike mimosas at work (11:03).
  • Alexander the Great’s Thanksgiving with his underwhelming brother (15:06).
  • A rude Massachusetts kid trying to sneak onto a roller coaster (20:38).

3. Improv Scenes Galore

• The riddles are mostly springboards for long, winding improv scenes. Erin plays characters ranging from drunk Tropicana staff to Alexander the Great’s underachieving brother, to a Bostonian kid.
  • Examples include a fast-food “spy code" gone wrong (03:17), and an Old-Timey Newsroom (43:43).
  • Recurring Joke: Erin closing her eyes to “listen better” to riddles, which the guys spin into a running gag about her napping through the episode.

4. Pop Culture & Musical Tangents

• The hosts spiral into comedic debates about 90s/00s music (“Who sings that song?”), the Monkees, Smash Mouth vs. Lynn, and the oddities of celebrity nicknames.
  • Notable Moment (34:02): “What if A League of Their Own was all Disney characters?” prompts a mashup of Disney and baseball references.
• Extended digressions about old video games (NBA Jam, Bubble Bobble, Worms), revealing the trio’s nostalgia and willingness to follow any tangent.

5. Feminist & Social Commentary

• When discussing MLMs, Erin gets a bit pointed about how such schemes target women and stay-at-home moms:
  • Notable Quote (Erin, 69:46): “It’s so predatory to women and like young women and stay-at-home moms, and it’s just so cruel...”
• This pattern—serious point followed by an undercutting joke—is a trademark of the podcast’s humor.

6. Old-Timey Swearing & Trivia

• The trio explores historical curses like “bejabbers” and “arf, arf, and arf,” riffing on Victorian slang and joking about what words dogs would find offensive in the podcast.
  • Notable Moment (49:05, JPC): “Do you call someone a bejabbers or do you say what the bejabbers?”
• Classic old movie references, connecting Angela Lansbury, Agatha Christie, and Murder, She Wrote (51:03).

7. Inside Jokes & Self-Referential Humor

• Several running jokes rely on podcast lore, like coupons for “skip a riddle,” Tony Shalhoub as “Lebanese De Niro,” and recalling bits from previous years.
  • Notable Quote (JPC, 53:00): “It’s not what I say, it’s what I must say... It’s a compulsion.”

8. Listener Engagement & Plugs

• The episode closes with the group plugging Hello From the Magic Tavern, Gumshoes & Dragons, their Patreon, and reading a 5-star review that roasts the fact they’re “stuck on a riddle improv podcast.”
  • Notable Quote (71:57, JPC): “It is important to keep perspective... at least you’re not on a riddle improv podcast.”

Notable Quotes & Memorable Moments (with Timestamps)

• JPC (10:13): “They all squeeze professionally.” (Solves riddle: Tropicana, accordion player, anaconda)
• Erin (14:21): “Hopeful. Hopeful.” (Asked if it’s ‘sad’ that future grandmas/grandpas will have butt-chugged)
• Adal (20:00): “Fresh horses. That’s so funny.”
• Erin (25:04): “Does that mean that pantyhose are reptiles?”
• Adal (55:24): “They’re all liars.” (On the riddle: an ancient harp, perjury, boy who cried wolf)
• JPC (69:46): “It is so, like, terrifying and sad how much like of the economy is just MLMs.”
• Erin (69:48): “It’s so predatory to women ... so cruel that when you’re trying...”
• JPC (53:00): “It’s not what I say, it’s what I must say... [about Tony Shalhoub being called 'Lebanese De Niro']”

Timestamps of Important Segments

• Introduction/Post-Recording Banter: 00:01–02:47
• Fast-food "Spy Code" Improv: 03:17–06:02
• Best of Discussion & ‘Lynn’ Song Ban Era: 06:36–08:01
• Eyes-Closed Riddle Setup: 08:29–09:13
• First Riddle (Squeeze): 10:04–10:19
• Tropicana Improv Scene: 10:37–12:06
• Alexander the Great Family Improv: 14:41–17:31
• Boston Child/Roller Coaster Improv: 20:27–22:28
• Old-Timey Newspaper Improv: 43:43–47:38
• Discussion: Old Swears: 48:01–50:13
• Angela Lansbury/Manson Family Anecdote: 51:03–52:15
• Tony Shalhoub/Lebanese De Niro Running Bit: 52:47–53:35
• MLM Improv Scene: 65:50–69:46
• Episode Closing Plugs & Listener Review: 70:08–71:56

Episode Tone & Style

• Language/Tone: Irreverent, fast-paced, laced with inside jokes and playful digs. The hosts switch rapidly between earnestness (about gender politics, media nostalgia) and undercutting self-mockery.
• Improv Energy: Scenes get layered and absurd, with roles shifting quickly—and plenty of callbacks to earlier bits.
• Listener Engagement: Treats loyal listeners to callbacks, meta-commentary, and faux arguments about music, trivia, and podcast lore.

Summary for the Uninitiated

Hey Riddle Riddle #383 is a showcase of the show's unique blend of riddle-solving and improv. Most "riddles" serve as cues for comedic tangents and character scenes rather than solemn logic games. This episode features extended bits about old movies, women’s pantyhose in eggs, Alexander the Great’s family, and the perils of multi-level marketing, all while ribbing each other mercilessly and making pointed jokes about podcasting itself. Even if you come for the riddles, you’ll stay for the circus of character work and the lovingly anarchic chemistry of the hosts.

Recommended for: Listeners who enjoy comedy improv, unserious puzzle solving, and podcasts that come with their own internal mythology.