Wait Wait... Don't Tell Me! – HTDE: OOO Baby

With Andy Samberg, Kate McKinnon, and U.S. Poet Laureate Ada Limón
Date: September 3, 2025
Host: Peter Sagal (NPR)
Guests: Andy Samberg, Kate McKinnon, Ada Limón

Main Theme / Episode Purpose

This special crossover episode is a revived installment of "How to Do Everything," featuring lighthearted problem-solving with host Peter Sagal, Mike Danforth, and Ian Chillag. This week, the show tackles questions about etiquette (wearing white after Labor Day), crafting memorable out-of-office email messages (with wisdom from Ada Limón), and the quirks of modern life, answered by beloved comedians Andy Samberg and Kate McKinnon. The recurring tone is witty, self-aware, and playfully absurd, aiming to both inform and entertain.

Key Discussion Points & Insights

1. Fashion Etiquette: Why Not Wear White After Labor Day?

Segment: [01:29–03:50]

• Origin: Ada Limón, Vogue senior lifestyle writer (and Poet Laureate), traces the “no white after Labor Day” rule to the Gilded Age elite who vacationed away from dirty cities in summer. White was a practical color for hot, clean environments but risky in filthier fall-era New York, where horse manure and garbage posed risks to pristine white garments.
  • Quote (Ada Limón):

    “New York City was just disgusting. ...your clothes would get really, really dirty quickly. So if you looked at the old issues of Vogue...they would say, you know, don't wear whites to town because it soils too easily.” [02:28]

• Modern Relevance: The rule is obsolete—modern cities have sanitation.
  • Quote (Ada Limón):

    “We have sanitation departments in our cities now. Feel free to walk around.” [03:25]

  • Advice: Wear white all you want—especially as the world gets hotter.

    “Please wear white. The world is getting hotter. It's probably more comfortable if you do.” [03:41]

2. Crafting the Ultimate Out-of-Office Email (OOO)

Segment: [04:00–13:33]

Listener Question

A listener ponders whether his OOO email should remain generic or inject humor/discourage replies.

• Peter’s Humor: Suggests redirecting urgent issues to Mike’s personal email for laughs. [05:00]
• Ada Limón’s Expert Insight:
  • Personalization Matters: Out-of-office messages needn’t be poetry, but should convey humanity—show there’s a real person on the other end.
    • Quote (Ada Limón):

      “Everyone loves a thoughtful message. Everyone wants to know that there’s a real human being that’s replying to you. ...They just need to know that you’re a real living human being on the other end.” [07:54]

  • Prompts for a Good OOO Message:
    • Consider your audience (“Who’s receiving this?”)

      “As poets, we often consider the reader. ...A good prompt...would be who is receiving the message?” [08:37]

    • Play with tone—be playful, clear, or even a bit mysterious (“I am a fish that can’t be caught.”) [10:18]
    • Endings (sign-off) are important—make them memorable/fun.

      “All poets really have to consider our endings.” [11:33]

• Notable Poetic OOO Ideas:
  Ada riffs a spontaneous poetic OOO:

  “I am a fish that can't be caught...” [11:02]
  “Don’t despair. Or rather do. I’ve gone away and so should you.” [11:53]

• Show Pledge: The hosts offer to be your emergency OOO contact (as a joke; not for real emergencies!).
  • Quote (Peter Sagal):

    “We could be your out of office emergency contact.” [12:15]

3. Listener Q&A with Andy Samberg and Kate McKinnon

Segment: [17:02–21:41]
In a press junket for their new movie “The Roses,” Andy and Kate answer unusual listener questions.

a) What should I do with my kid’s baby teeth?

• Kate McKinnon’s Practical/Mischievous Solution:

  “A husband should take it, say he threw it away, but keep it in a secret place.” [17:56]

• Ada’s Darkly Comedic Spin:

  “Make a very small hole in your sheetrock, drop [the tooth] through. When someone does a big reno, they'll find a tooth and call the police and it'll be a fun day for everyone.” [18:25]

• Kate (joking):

  “Dad, you were the jump rope killer.” [18:45]

b) How do you tell your partner they have bad breath (re: not into kissing)?

• Kate McKinnon:

  “I think ... you gotta tell that person.” [19:02]
  “I've certainly been told before—like, woof... I would be sad to know that I wasn't told and they had to suffer.” [19:11]

• Ada Limón:

  “Here’s how I'd like to be told: Gum?” [19:36]

c) What to do if your spouse can’t stand the sound of you eating potato chips?

• Kate McKinnon:

  “In a relationship you get a few things you get to ask for like this. ...If it's really a big priority you say, can you eat those somewhere else?” [21:02] “But be warned... bring it up, there's a strong chance you’ve got a few for them also, and it might come back at you.” [21:15]

• Ada Limón: Admits she doesn’t care for chips or bagged snacks at all. [20:39–20:53]
• Mike Danforth:

  “It's a real Pandora's box.” [21:36]

4. Closing Insights / What Did We Learn?

Segment: [21:47–23:16]

• Mike: Learns the roots of the white-after-Labor-Day rule are more about sanitation than fashion.

  “The whole white after Labor Day thing isn't so much about fashion as it is about how gross the city was....” [21:52]

• Peter Sagal:

  “You would look disgusting.” [22:06]

• Parenting & White Clothes: Anecdotes about the perils of wearing white with small children.
  • Peter:

    “I usually wear [white clothes]...after the children go to bed and remove them before the children wake up.” [22:29]

  • Pokes fun at mysterious stains and “coward” children who might sneakily stain your shirt from behind [22:55–23:16].

Notable Quotes & Memorable Moments

• Ada Limón (on OOO messages):

  “Poems don’t need to rhyme and yet it’s a joy to rhyme.” [12:03]

• Hosts Volunteering as OOO Contacts:

  “If you want, seriously take this thing... put it in your email and we'll see what happens.” — Peter Sagal [13:13]

• Kate McKinnon’s Relationship Wisdom:

  “If it's really a big priority, you say, can you eat those somewhere else? ...But be warned... it might come back at you.” [21:15]

• Andy Samberg & Kate McKinnon on Baby Teeth:

  “Make a small hole in your sheetrock, drop [the tooth] through. When someone does a big reno...they’ll find a tooth and call the police...” — Ada Limón [18:25]
  “Dad, you were the jump rope killer.” — Kate McKinnon [18:45]

Timestamps for Important Segments

• Origins of “No White After Labor Day”: 01:29–03:50
• Out-of-Office Message Advice: 04:00–13:33
• Andy Samberg & Kate McKinnon Listener Q&A: 17:02–21:41
• Wrap up / What Did We Learn: 21:47–23:16

Overall Tone & Takeaways

The episode is witty, informal, and inclusive—balancing genuine insight (fashion history, professional communication) with absurd and creative humor. Ada Limón’s poetic sensibility shines, making even an OOO message seem artful. Samberg and McKinnon bring playful banter and honesty to everyday dilemmas. Whether you’re crafting a witty away message or wondering what to do with a loose tooth, there’s something here for every listener.

Hosts: “Good luck everybody, and enjoy your time off.” [13:33]