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The Nightly

Category Is: Sleep w/ Bob The Drag Queen

Wils Pelton and Josh Gondelman welcome Bob the Drag Queen for a surprisingly heartfelt late-night chat about Broadway, stand-up comedy, internet outrage, and whether the universe actually cares about any of us.

What You’ll Hear

Broadway Dreams, Broadway Schedules: Bob reflects on performing in Moulin Rouge, surviving eight shows a week, and why exhausting experiences can still feel deeply worth it.

The Internet Is Yelling Again: A conversation about accidental AI art drama, public scrutiny, and the strange emotional math of being perceived online by millions of strangers.

Karma, Nihilism, and Bedtime Thoughts: The trio wanders into a warm existential detour about meaning, bad luck, grief, and the tiny frameworks people build to get through the day.

CHAPTERS
00:00 Intro & Bob the Drag Queen arrives
01:45 Broadway life and Moulin Rouge
05:45 Building a stand-up tour
09:00 Reality TV and staying authentic
12:30 AI poster backlash and internet outrage
16:00 Karma, grief, and existential bedtime thoughts
19:20 Good nights and six-fingered posters

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  • Getting Lost in a Dream About Paris

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    Josh Gondelman talks with caller Ana about the recurring dream that drops her, lost and hungry, into a Paris she's never actually visited.What You'll HearA Toddler, a Seltzer, and a Book Missing All Its R's: Josh recaps a visit from an old friend's three-year-old, who pounds a full seltzer in one go and then, with impeccable manners, announces she'd like to go home now, please.Lost, Hungry, and Somehow Always in Paris: Ana has never set foot in France, but for the third time this month she's found herself wandering an unfamiliar Parisian neighborhood in her dreams, always trying and failing to reach a restaurant.The Dreams Where She's Not Even Herself: Ana and Josh dig into her other recurring dreams, the ones where she's watching from the outside or living in someone else's body, and how her dreams have grown strangely more vivid and controllable in recent years.CHAPTERS00:00 A toddler, a seltzer, and a book missing all its R's03:53 Welcome caller Ana04:08 A recurring dream of getting lost in Paris13:36 The dreams where she's not even herself21:04 One more question, and the best ramen she's never eaten24:19 Goodnight to Ana's dream friends (and real ones too)
  • Sunday Edition: Writing Your Way to Sleep

    21:34|
    Josh Gondelman talks with psychologist Dr. James Pennebaker about the science of expressive writing, why finger-writing works as well as pen and paper, and how putting an upsetting thought into words can help you fall right back to sleep.What You'll HearThe Journal Entry That Cut Doctor Visits in Half: Dr. Pennebaker traces his research back to a 1984 study where college students who wrote about traumatic experiences got sick, and visited the doctor, half as often as those who wrote about nothing in particular — and slept better, too.Blowing Off Steam vs. Actually Figuring It Out: The people who benefit most from a midnight journaling session aren't the ones who feel like they've vented, they're the ones who walk away saying "now I understand why." Pennebaker explains why turning a spiraling thought into an actual sentence forces your brain to build a story, and why that story is what finally lets you stop chewing on it.Be Your Own Scientist (No Rules Required): Don't worry about handwriting, spelling, or sounding smart. Pennebaker's advice is to just start writing and see what works for you, whether that's a diary entry, a poem, or even writing in the air with your finger.CHAPTERS00:00 Intro & welcome to Dr. James Pennebaker01:43 How he got into the psychology of journaling02:34 The 1984 study: writing about trauma cuts doctor visits in half07:28 How to get started without feeling self-conscious12:44 Sofija's fairy-tale approach, and why fiction can heal too19:41 A closing prescription: write for 15 minutes and go back to sleep
  • The Taurus Who Won't Leave Santa Fe

    10:20|
    Josh Gondelman talks with Listener Jake about whether to trade fifteen years of Sante Fe memories for a house in Asheville, ticks and all.What You'll HearSetting Down Roots at 7,000 Feet: Jake explains why quitting air conditioning, chasing the desert night chill, and pantsless summers made Santa Fe feel like home for fifteen years.The Family House in Asheville: The grandparents-built property, the six-month test run two years ago, and the pull of cousins just a day's drive away.Decided by the Stars: Josh and Jake talk horoscopes, settle who's the homebody and who's the free spirit, and then land on an 80/20 lean that still leaves plenty to figure out.CHAPTERS00:00 A new neighborhood and an old "magic" sign03:20 Welcome, Caller Jake!07:30 The big decision: stay or move to Asheville11:00 The weight of saying it out loud16:59 Taurus vs. Aquarius: whose sign wins?19:45 You have two good options
  • Throwing People Under Buses Since the ’80s

    21:50|
    Matt Bragg talks with caller Elise from Brooklyn about the sudden takeover of the phrase "throw someone under the bus," decades-old naval idioms, and the eternal question of what a scapegoat actually is.What You'll HearA Cupboard Door, a Bag of Matchsticks, and Regret: Matt kicks off the show mid-meltdown, recounting the exact glue-and-matchstick trick that saved his kitchen cabinet and, eventually, his mood.The Phrase That Broke Elise's Brain: Caller Elise explains how "throw someone under the bus" seemed to appear out of nowhere the moment she heard it on Top Chef, and why she still can't shake the feeling everyone else got the memo first.A Very Deep Dive on Sailor Slang: Matt and Elise trace "chock-a-block," "taken aback," and "turn a blind eye" back to 18th-century ships, then get stuck on the surprisingly tricky question of whether a scapegoat is a type of goat.CHAPTERS00:00 Intro & the cupboard door disaster02:05 Caller Elise joins from Brooklyn03:20 Where "throw under the bus" actually comes from09:12 Ballroom slang and the word "irregardless"13:26 A deep dive on naval idioms16:36 Goodnights and a shoutout to the original bus-thrower
  • A Kitchen That Only Exists in Memory

    21:28|
    Matt Bragg talks with caller Victoria about her parents' newly remodeled kitchen, the rotary phone that outlived a whole house, and the strange nostalgia of rooms that now only exist in memory.What You'll HearThe Etiquette of Bad Directions: Matt recaps a very British standoff in Brighton, getting pointed the wrong way to the car park by a proud local venue owner and choosing to just walk it out rather than correct him.The Kitchen That Only Exists in Her Head Now: Caller Victoria talks with Matt about her parents' freshly remodeled kitchen, the childhood home she can still walk through in memory, and the odd melancholy of a room that technically doesn't exist anymore.Rotary Phones, VR Headsets, and a Streamer from the Blue Man Group: From her nana's still-working landline to a hypothetical AI-rebuilt kitchen to a single kept paper streamer, Matt and Victoria weigh how much of the past is worth holding onto, and when nostalgia edges into something a little more Black Mirror.CHAPTERS00:00 Intro & the Brighton directions dilemma02:16 Victoria calls in from Massachusetts02:40 Rooms that now only exist in memory08:56 What if AI could rebuild your childhood kitchen?14:57 The kept streamer from Blue Man Group16:23 Goodnights
  • Honk If You Hate Bumper Stickers

    23:10|
    Matt Bragg talks with caller Sarah, from Rockville, Maryland, about honor roll bumper stickers, headlight eyelashes, and the neighbor who compares herself to a worm mid-road-rage.What You'll HearA Rough Week in Car Buying: Fresh off a trip to Benidorm, Matt recaps a car-shopping saga full of vanishing adaptive cruise control and a salesman who suggests, unprompted, that he try a Skoda.Sarah Takes the Stand Against Stickers: Caller Sarah joins from Rockville, Maryland to make her case: baby-on-board stickers might be useful, but honor roll brags and student driver signs can go.Eyelashes, Antlers, and a Sticker for Haters: The two land on the truly indefensible bumper decorations — headlight eyelashes, Christmas reindeer antlers, and a neighbor who calls herself a worm and still expects road rage sympathy.CHAPTERS00:00 Benidorm recap & a new car buying nightmare05:09 Sarah joins from Rockville, Maryland06:19 Baby on board and the great sticker debate09:21 Honor roll brags & student driver stickers13:00 Headlight eyelashes & reindeer antlers16:56 The neighbor who calls herself a worm
  • In Defense of Big Jersey

    25:42|
    Josh Gondelman talks with caller Charlie about which "New" places have quietly out-shined their namesakes, from Jersey to Mexico to a very polite British devil.What You'll HearThree Coffee Tables Too Many: Josh recaps trading a cluttered old apartment for a fresh one, and the quiet triumph of finally buying a proper trunk for the towels.New Jersey vs. Jersey, UK: Charlie lays out his theory that a "New" place should only keep its modifier if the original still out-shines it, starting with New Jersey's total takeover of the name.Meet Alastair, the Polite Jersey Devil: From New Hampshire's stolen mountain to a very charming imaginary cryptid across the pond, Josh and Charlie crown their favorite Big, Little, and Lil place names.CHAPTERS00:00 Saying goodbye to three coffee tables04:47 Welcome, Caller Charlie!07:38 The New vs. Old place-name theory begins09:00 New Hampshire vs. Hampshire, adjudicated11:28 New Orleans, New Mexico, and earning the "new"17:49 Big Jersey, Little Jersey, and the Jersey Devils' cousin
  • A Lithuanian Fairy Tale for Grief

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    Josh Gondelman talks with caller Sofija about turning her nightly journaling into a Lithuanian fairy tale, and using fiction to process grief and hope.What You'll HearA Pug Among Angels: Josh recaps settling into his new apartment building and the strange relief of realizing his scrappy pug Maggie isn't the most chaotic dog on the block.The Fairy Baby in the Journal: Caller Sofija describes how a nightly journaling habit — started while she and her husband navigate infertility — grew into a recurring story about a laumė, a chaotic Lithuanian fairy spirit.Folklore as a Safe Distance: Josh and Sofija dig into Lithuanian, Celtic, and Native American folklore, and how a little fictional distance makes it easier to sit with grief, longing, and hope.CHAPTERS00:00 The joy of imperfect neighbors 04:55 Welcome caller Sofija!06:59 A nightly journaling practice08:04 Enter the laumė: a chaotic Lithuanian fairy baby14:36 Celtic fae, Native lore, and finding comfort in folklore17:49 A five-minute ritual that became a nightly habit
  • Sunday Edition: Practicing Affirmations

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    Josh Gondelman invites his wife, author Maris Kreizman, into the Pillow Fort to test-drive real compliments and affirmations on each other.What You'll HearUntangling the Difference: After a caller named Lucy stumped over the line between a compliment and an affirmation, Josh brings the debate home to Maris, and they work out where the surface-level nice thing ends and the deeper truth begins.Practicing Out Loud: Josh and Maris try the exercise on each other live, trading affirmations about diligence and connection for compliments about newsletters, earrings, and the art of small talk done right.The Compliments That Stick: From a stranger admiring Josh's secondhand sneakers on the train to Maris's advice for under-appreciated creative friends, they trade the kind of praise that actually lands.CHAPTERS00:00 Revisiting Lucy's call about affirmations01:35 Welcoming Maris Kreizman to the Pillow Fort!04:21 Practicing an affirmation and a compliment08:00 What makes praise feel sincere?11:53 Getting meta about real connection18:29 Closing affirmations to the world