Good Guys Podcast: Khakis, Granola & Other Poor Choices

Date: September 4, 2025
Hosts: Josh Peck & Ben Soffer

Overview

This episode is a classic blend of humor, cultural commentary, and personal anecdotes from Josh and Ben. The main theme centers on lifestyle choices, from fashion and parenting to real estate dreams and the quirks of modern life, all delivered in the duo’s signature self-deprecating, observational style. The episode weaves through discussions on wearing women’s clothes, the challenges and privileges of living in major cities, political scuttlebutt, fall coffee menus, and listener dilemmas ranging from new parent struggles to granola company branding.

Key Discussion Points & Insights

Fashion Choices & Gender Bending (00:37–05:54)

• Ben reveals he’s wearing his wife Claudia’s sweatshirt and discusses his tendency to steal her socks, even though they don't fit. Socks seem to vanish, leaving him perpetually borrowing from her collection.
  • “Somehow she always has socks and she wears those, like, mid ankle socks... I’m wearing her socks right now.” – Ben (02:07)
• Both hosts joke about wearing women's clothing and the comfort in "oversized" women's styles, referencing cultural icons like Ina Garten.
  • “Ina is the goal, right? Because she’s basically wearing tarps.” – Josh (04:59)
• Josh recounts making social media videos in a women’s thong, humorously reflecting on the sense of feeling “beautiful,” and Ben admits thriving in large, drapey women's clothes, particularly for costume or comedic effect.

Celebrity Anecdotes & Tipping Habits (05:54–08:33)

• Josh shares stories about hairdressers who work with famous “bobs” such as Ina Garten and Anna Wintour.
  • “She tips her with a crisp $50 bill every time.” – Josh (07:12)
• Ben suggests tipping in gold bullion and muses on Florida legalizing gold as currency: “We should start tipping in bullion.” (08:28)

Real Estate & Parenting: City vs. Suburb Life (11:20–19:24)

• Ben discusses anxiety about moving back to NYC with a newborn after a peaceful stay in the suburban Hamptons.
  • “I am nervous about the city walks because… the city is significantly less safe than it’s been, and walking around with a three month old is significantly less enjoyable...” – Ben (11:52)
• Josh pitches an “ideal schedule” of rotating between NYC, the Hamptons, and Florida, maximizing weather and comfort. They both reflect on the “privilege” of these choices but frame them as attainable, not just luxury.
• Both host a lively dream-real-estate chat—citing LA’s proximity to both beach and countryside, the value of having a house nearby for quick escapes, and the differences in affordability between major metro areas and just-outside suburbs.

Politics, Public Figures & Social Media Strategies (19:24–32:27)

• Brief discourse on “derangement syndromes” regarding Trump, Hillary, and Kamala, critiquing extreme fandom or opposition.
  • “People need to stop blindly hating and loving people. It’s not cool. No matter who it is, you need to be informed...” – Ben (32:03)
• Discussion about Spencer Pratt’s transformation into a political activist against local California officials, citing possible government negligence around recent disasters.
  • “He’s made it his life mission to take these people down.” – Ben (21:24)
• Josh describes encountering Spencer Pratt at Monster Jam, and both reflect on the difference between viral fame and true financial security.
• Commentary on government response to natural disasters and the political polarization of such responses, especially in California:
  • “It should be a moment to galvanize and not to be like, let’s dunk on the other side and their tragedy that they’re enduring.” – Josh (28:59)
• Ben draws parallels to why the media hyper-focuses on certain kinds of disasters or conflicts, notably California wildfires and Israel.
  • “Why do we only talk about California when it comes to a natural disaster? And why do we only talk about Israel when it comes to a war? So Jews.” – Ben (29:58)
• Fun moment: Josh reads Gavin Newsom’s Trump-style tweets out loud, both marveling at and lampooning the strategy (30:17–31:29).

Fall Coffee Menus & Birthday Snafus (35:57–41:19)

• The hosts discuss new and returning fall drinks at Dunkin', Starbucks, and Tim Hortons, debating the merits and health perils of sugary lattes and pumpkin-flavored treats.
  • “Cereal and milk latte – I would definitely try that.” – Josh (36:30)
• Producer Olivia’s birthday is revealed (26), leading to playful ribbing about remembering (or forgetting) birthdays and whether $200 is an appropriate gift.
  • “Do you want stone? Hold on... 200, that’s nice, right?” – Josh (38:33)
• Commentary on regional differences in coffee shop offerings, the sadness of some “franchise-dunkin’s,” Blank Street Coffee’s rise in NYC, and Starbucks loyalty.

News Oddities & Ridiculous Headlines (45:23–48:30)

• Ben jokes about a viral tabloid story: “Man with world’s largest penis slips, breaks arm in shower.”
  • Both riff on the practical challenges such…endowments might present.
  • “He also reported his own wang to the Guinness Book of World Records. Like, how do they know?...He’s like, hey, look at me and my khakis.” – Ben (47:13)
• The story leads to extended, juvenile banter about khakis as “big wang highlighter,” and whether penile reduction should be considered analogous to breast reductions.

Listener Questions & Advice (Speakpipe Q&A) (48:33–59:08)

1. Living with Your Mother-in-Law as New Parents (49:29–51:42)

• Caller is conflicted about temporarily staying with mother-in-law after being forced to move while expecting a baby.
  • Both hosts agree: take the help, set boundaries, treat it as temporary.
  • “You'll be so thankful,” – Josh (51:21)

2. Divorced Parents & Grandkid’s Parties (51:54–57:58)

• Listener laments having to orchestrate split family gatherings because divorced dad refuses to attend joint events.
  • Ben: It’s about the grandchild, not the parents—feels they should set aside differences.
  • Josh: Empathizes, but ultimately says the listener can’t expect people to behave differently—they need to make peace with it.
  • “You live in the world that is, not the world we wish we lived in.” – Josh (58:05)

3. Granola Branding Dilemma (59:15–61:05)

• Entrepreneur asks for advice on renaming her granola brand: “Slow Street” vs “Park Day.”
  • Ben: “Short and distinct is all that matters; Slow Street is fine.”
  • Josh jokes: “Sounds like an episode of Sesame Street for kids with special needs!”

Notable Quotes & Memorable Moments

• “What ladies clothes do I enjoy wearing? I exclusively wear my wife's socks.” – Ben (01:59)
• “I thrive in oversized women’s clothing. How easy is that?” – Ben (04:43)
• “She tips her with a crisp $50 bill every time.” – Josh, on Anna Wintour (07:12)
• “We should start tipping in bullion.” – Ben, on what’s next for gratuities (08:28)
• “If you had like a boatload of money...the real hack of life is...an hour away, you had the polar opposite [of your main home].” – Josh (16:14)
• “People need to stop blindly hating and loving people. Yeah, it’s not cool.” – Ben (32:03)
• “You could bring it to the beach, but that’s not…that’s nice.” – Ben, on a Dunkin’ menu gimmick (40:07)
• “Do you want stone?” – Josh, on birthday gifts (38:30)
• “He also reported his own wang to the Guinness Book of World Records…” – Ben, still processing the bizarre headline (47:13)
• “Elmo Road, the small bus, today. Little busy.” – Ben (61:05)
• “What are you, nuts?” – Recurring tagline/segment.

Timestamps for Key Segments

• 00:37–05:54 | Women's clothing, fashion comfort, and Ina Garten talk.
• 05:54–08:33 | Celebrity hairdressers and tipping stories.
• 11:20–19:24 | Parenting in city vs. suburb, dreaming up the ideal home schedule.
• 19:24–32:27 | Political flame wars, Spencer Pratt’s activism, disaster relief debate.
• 35:57–41:19 | Fall coffee menus, producer Olivia’s birthday.
• 45:23–48:30 | Viral headline: world’s largest penis mishap.
• 48:33–59:08 | Speakpipe listener questions.
• 61:34–63:40 | “What Are You Nuts?”: Airplane air conditioning rant.

Original Tone & Language Summary

The hosts’ exchanges are fast-paced, self-aware, irreverent, and loaded with sarcasm. They riff on serious topics (like disaster relief and the emotional fallout of divorce) with empathy but never lose sight of the playful “what are you, nuts?” perspective that defines their brand. Quotables, pop culture references, and personal stories make for a highly relatable and comedic experience.

For longtime fans, this episode delivers the classic blend of banter, neuroses, and real-world advice, while newcomers will find plenty of laughs and a few genuine takeaways about life’s daily dilemmas.