Hey Riddle Riddle Ep. 394: "Jokes We Don't Get"

Podcast: Hey Riddle Riddle (Headgum)
Date: February 4, 2026
Hosts: Adal Rifai, Erin Keif, John Patrick Coan ("JPC")

Overview

This episode continues the Hey Riddle Riddle tradition of goofing on classic (and baffling) riddles, groaner puns, and dubious jokes—with the added twist that a good portion of them just do not make sense to the hosts. Expect the usual blend of loose improv, meta-commentary on the nature of wordplay humor, personal anecdotes, and ace riffing when riddles turn out to be weird, poorly written, or from another century.
Throughout, the crew leans into their confusion and mutual disbelief—delivering a very "if you don't like riddles, don't worry, this podcast is barely about them" kind of energy.

Main Discussion Points

1. Movie and Lunchbox Banter (00:05-05:18)

• JPC raves about the new mockumentary "Nirvana, the Band, the Show, the Movie," claiming it’s "fucking excellent" and features wild twists. (00:13)
• The trio riff on theatrical comedy movies, name-checking reviews with increasingly absurd taglines.
• Nostalgic improv ensues around school lunches and "rich kid" tropes, including Lunchables and trading checks for money.
  • Notable quote:
    • JPC (as a kid): “My dad packed me a check for $11.50.” (03:53)
    • Adal: “That’s like three lunches.” (04:04)

2. The “Host Eating on Mic” Running Gag (05:03-07:18)

• Erin tries to covertly eat gluten-free bread before recording. Banter turns to awkwardly timed snacks and height competitions.
  • JPC: “So I can always say ‘That’s Adal up there’ and it’s never wrong.” (06:00)
• Erin’s breakfast is a recurring punchline, likened to “the days of our lives.”

3. Small Talk, Wilt Chamberlain, and “Casey, Clip That” (07:22-09:25)

• The crew discusses making dad jokes and groaners to service industry workers, likening it to fans pestering Wilt Chamberlain.
  • Exchange about “that’s what she said” morphing culturally into “Casey, clip that.”
• Erin laments the podcast’s eternal push-pull between goofing off and actually getting to riddles.

4. Riddle and Joke Segment 1: “Jokes We Don’t Get” Begins (11:05-36:37)

Key Features:

• Erin introduces “The Everything Kid’s Giant Book of Jokes, Riddles, and Brain Teasers,” and notes that some jokes may be impossible to "get."
• Each riddle is met with wild guesses, detours, and often concludes with:
  • An improv scene about the riddle’s premise.
  • A meta-analysis of why the punchline does or doesn’t work.

Highlights:

• Glassblower Riddle

  • “Did you hear about the glassblower who inhaled?”
  • Erin: “He got a pain in his glass.” (12:44)
  • Leads to an improv scene with a glassblower-family car ride, milk burgers, and a rapidly escalating Arby’s order. (13:05-16:19)

• Cub Scout Horn Joke

  • “What did the Cub Scout say when he fixed the horn on his bike?”
  • Answer eventually: “Be prepared.” (17:52)
  • Scene follows—Roadrunner and Wile E. Coyote at dinner, dealing with dyn-o-mite wine and bolognese. (19:19-21:25)

• Southern California Smog

  • “What do you see when the smog clears in Southern California?”
  • Adal: “UCLA.”
  • JPC: “Wow. A college in a town.” (22:09–22:11)

• Silkworms Race

  • “Did you hear about the two silkworms who had a race?”
  • After much guessing: “They ended in a tie.” (23:44)
  • Leads to deep cut meta discussion on Diamond and Silk, plus politics and Trump eulogies.

• Lighthouse Keepers' Marriage

  • “I feel sorry for the two lighthouse keepers who are in love—their marriage is on the rocks.” (28:38)
  • Improv: Two lighthouse keepers in a failing marriage, peppered with threats and anniversary reveals. (28:48-30:15)
  • Banter about actually visiting lighthouses and Michigan’s surprise status for most lighthouses.

• Lobster Buys a Car

  • “Did you hear about the lobster who bought a new car?”
  • Punchline: “Crustacean wagon.” (32:54)
  • Scene: Crabby crab dad takes family on a road trip, tackles driving side to side, cannibalism, and sandwich choices. (33:03-34:53)

• Eye Check Joke

  • Doctor: “Have your eyes ever been checked?”
  • Answer: “No, they’ve always been blue.” (37:25)
  • The hosts are deeply unimpressed by the logic.

• Burping Amy

  • Teacher: “My goodness, Amy, you’ve been burping all morning.”
  • Answer: “Belgian waffles.” (53:24)
  • Improv: Amy turns out to be a Jim Carrey clone. (54:02–57:17)

5. The Absurd, Ancient Riddles Segment (61:34–68:04)

• Listener Milo submits riddles from "old ass books" of puns and riddles from 1870.
  • “What musical instrument invites you to fish?”
    • A: “Castanets” (“cast a net”) (63:20)
  • “What’s the difference between a fisherman and a lazy schoolboy?”
    • A: “One baits his hook, the other hates his book.” (64:07)
  • “How do we know that the dove is a very cautious little deer?”
    • A: “Because he minds his own business.”
  • Erin’s Favourite Riddle, Ever:
    • “What’s the difference between a mouse and a young lady?”
    • A: “One wishes to harm the cheese, the other wishes to charm the he’s.” (68:04)
    • Prompts the episode's biggest collective disbelief and laughter.

6. Audience & Personal Anecdotes (vignettes, 71:02–end)

• Voicemail question about handling family group chats—should you respond to a morality rant or just comment on flower photos?

  • JPC: “I would go chaos option…I’m putting: ‘These flowers suck, dumbass.’” (71:58)
  • Erin: “Respond to the flowers honestly…emojis.”
  • Adal: “Throw your phone into the river.” (72:30)
  • Extended riff on trolling, GroupMe etiquette, and the philosophy of not engaging in bad faith debates.

• Thanksgiving prep and traditions:

  • Hosting, Friendsgiving dishes, and the horrors of deviled eggs.

Notable Quotes & Memorable Moments

• On jokes that make no sense:

  • Erin: “Some of these jokes…don’t make any sense. And some of them are crazy.” (51:01)

• Meta-commentary on podcast rhythm:

  • Erin: “I bullshit for 30 minutes to avoid riddles, everyone hates that. Then if I get right into riddles, people don’t like how curt that seems.” (09:44)

• On puns that push logic:

  • Adal: “One wishes to harm the cheese, the other wishes to charm the he’s.” (68:04)
  • C (JPC): “That is such a stretch. Harm the cheese…”

• On listener’s family drama:

  • JPC: "That's wild to demand that your family debate you on morality." (72:08)
  • Erin: "Throw your phone in a river." (72:30)

• On randomly assigned responsibility:

  • JPC: “If you don’t tell [sponsors] Hey Riddle Riddle sent you, we basically didn’t do anything.” (47:03)

Noteworthy Improv Scenes (with Timestamps)

• Glassblower’s hospital trip / Milk Burger drive-thru: [13:03–16:19]
• Roadrunner & Wile E. Coyote at dinner: [19:08–21:25]
• Silkworms at a wedding; awkward political convo: [24:01–25:50]
• Crab family on vacation, learning about cannibalism: [33:03–34:53]
• Amy, the burping Jim Carrey clone: [54:02–57:17]
• Worm (on a fishing hook) and a fish discuss existential death: [58:27–60:19]
• Mouse disguised as a young lady flirts with Victorian boys: [68:08–70:11]

Episode Vibe and Tone

• Highly playful and irreverent. The hosts lean into confusion and share their genuine frustrations/laughter at the logic (or lack thereof) in classic joke books.
• Improvisational. Segments frequently veer into character-driven scenes.
• Meta-humor and awareness that their show is as much about goofing around as it is about solving riddles.

Final Takeaways

• The episode is a masterclass in comedic riffing on truly baffling material—if you love puns, word games, and comedy that makes fun of itself, this installment delivers.
• Erin’s “favorite riddle ever” (“harm the cheese, charm the he’s”) is a particular highlight, met with the hosts’ mixture of exasperation and delight.
• As always, the riddles are just a jumping off point for jokes, scenes, and oddball tangents.

[Notable Quotes At-a-Glance]

• Erin (on ancient riddles): “This might be the only time I’ve ever laughed out loud [at a riddle].” (65:37)
• JPC: "That's wild to demand that your family debate you on morality." (72:08)
• Adal (summarizing the show): “If that philosophy of you, when you die, you have to live through all the suffering you cause…then we have to listen to probably every episode of Hey Riddle Riddle hundreds of thousands of times.” (61:00)

Key Segments (Timestamps)

• Opening movie/lunch jokes: 00:05–05:18
• "Casey, clip that" & small talk: 07:22–11:05
• Riddle/Joke Segment 1: 11:05–36:37
• Improv scenes & ancient riddles: 36:37–68:04
• Listener voicemail & advice: 71:02–76:00

This episode is recommended for fans who are in it for the chaotic fun as much (or more) than for tidy riddle solutions.