The JTrain Podcast: Pop Culture Thursday

Host: Jared Freid
Episode: Miley Cyrus Is Engaged, Simon Cowell Shades Ryan Seacrest, And Amy Schumer's Marriage
Date: December 4, 2025

Episode Overview

In this Pop Culture Thursday episode, comedian Jared Freid riffs on the latest celebrity headlines from Page Six, delivering his unique comedic take on stories like Miley Cyrus’ engagement, Amy Schumer’s marital troubles, and Simon Cowell’s comments about Ryan Seacrest. Expect witty observations, playful speculation, and a lens of self-deprecating humor as Jared navigates through Hollywood relationships, fashion choices, and comeback attempts.

Key Discussion Points

1. Miley Cyrus & Maxx Morando Engagement

[02:08–08:22]

• Headline: Miley Cyrus announced her engagement to fellow musician Maxx Morando after four years of dating.
• Jared admits he didn’t know Miley was dating anyone and jokes about his own unsuitability for her:
  “Miley is not into hairy Jewish man with a tissue box framed body that doesn't fit into an XL or a large T shirt.” [03:15]
• He riffs on how celebrities in the public eye either get engaged quickly or take extra time to work things out:
  “In the public eye, it’s either we connect, let’s get away from everything, we get engaged very quickly, or there’s things to work out. Four years of probes.” [04:06]
• Jared comments on engagement ring trends, comparing Miley’s chunky gold band to a superhero power source:
  “It almost looks like it’s her power source – for a superhero who wears a ring. Like, very Lanterns coded.” [07:20]
• Overall, he wishes them well and admits to being envious of Maxx’s effortless style:
  “Maxx Morando probably has hours of his day that I don’t have just in not thinking about his T-shirt and how it fits alone.” [05:59]

2. Sydney Sweeney’s Red-Hot Look

[10:25–13:48]

• Jared takes notice of Sydney Sweeney’s head-to-toe red ensemble while promoting “The Housemaid,” emphasizing her appeal to the “male gaze”:
  “She is a male wet dream. I’m telling you...She feeds a male gaze… I really think she knows what she’s doing with everything she’s doing.” [11:14]
• He analyzes how Sweeney uses her looks and career moves strategically, much like her business-minded approach to producing and publicity:
  “She is fully aware of power, money, capitalism. So why would it be any different for the look?” [12:10]
• Jared also speculates that Sweeney’s stylist must “work at Maxim magazine,” attributing her style choices to calculated marketing.

3. Amy Schumer’s ‘Conscious Uncoupling’

[13:56–20:27]

• Page Six reports Amy Schumer is “working out conscious uncoupling plan” with husband Chris Fisher.
• Jared interprets this carefully leaked phrase as a sign the couple has already split and is easing into a more public announcement: “To me, when I see Amy Schumer working out, quote, conscious uncoupling plan with husband sources, I would assume…they are slowly putting this out in an attempt to make this less of a news day burden for Amy.” [13:56]
• He relates this to personal experiences, cautioning that “conscious uncoupling” is essentially a pre-breakup: “Engaged to be engaged? That’s engaged to be broken up. To me, that is a pre-breakup.” [15:13]
• Jared also dissects how significant weight loss can signal relationship trouble:
  “You lose that much weight, the next question is, how’s the relationship?... Losing weight is a mind fuck. And I just think with like Ozempic and all this… there’s no real care taken for the brain.” [16:52–18:25]
• He reads parts of Amy’s social post:
  “Whatever ends up happening with me and Chris has nothing to do with weight loss or autism. Wow. Who brought up the autism?” [19:30]
• Madonna responds in the comments, encouraging Amy to do what feels right for herself.

4. Scarlett Johansson’s Awkward First Date with Colin Jost

[20:36–26:37]

• Celebrity headline teases Scarlett Johansson “ran out” on first date with husband Colin Jost.
• Jared speculates on clickbait motivations and imagines several comic scenarios (“she had to take a shit”), but ultimately guesses correctly:
  “Now what’s more likely is she had another event… So we really only had an hour and a half to get a drink... That would be a more normal one.” [21:06]
• The real story: Scarlett was flustered and ended the date after 90 minutes, spooking Jost but leaving him wanting more.
  “That’s probably the smartest thing any woman can do: ‘Hey, let’s go get another drink? No, I had a good time, but I gotta get going. Make yourself scarce.’” [23:53]
• Jared notes how these stories are beloved by women and often presented as “I’m so awkward!” tales:
  “Jenna Bush Hager probably, like, literally slipped off her seat. She made her so wet. Like, this is like one of those stories women love.” [26:12]

5. Julia Roberts’ Gotham Awards Look

[26:37–29:23]

• Jared examines a headline about Julia Roberts wearing a “1980s polka dot power suit” and riffs on the obscurity of the Gotham Awards:
  “What the fuck are the Gotham Awards?… Is it like, best Batman impressions?” [27:10]
• He comments that her suit looks “more Joker than polka-dot” until viewing it up close, then reminisces about red carpet fashion statements in general.
• Nods to Julia’s signature affinity for power suits dating back to the early 1990s.

6. Matt Lauer’s Rumored Media Comeback

[29:28–34:41]

• Jared expresses shock that Matt Lauer hasn’t tried to come back sooner, reflecting on the seriousness of his misconduct and the infamous “button under the desk.”
• He considers possible motives for Lauer’s long silence:
  “I think on the spectrum of choices, he really was trying to make himself a better person. I think chances are low for that… Or Matt Lauer thinks so highly of himself that he's like, I'M not coming back unless someone pays me what I was getting paid on the Today show.” [30:09–31:10]
• Observes that each year rumors are strategically floated, likely by Lauer’s own team, to test public sentiment:
  “This is all Matt Lauer's people because he's done this every year. Now. This is. This is clockwork.” [31:54]
• Addresses the lost trust and the impact of the scandal:
  “But dude, I can understand. You find out your friend is sending horrible texts to women that don't want those texts and you go, I don't know you.” [34:16]
• He notes Don Lemon’s comment that the public “misses” Lauer, but disagrees, clarifying:
  “I would say we are curious.” [34:41]

7. Simon Cowell Shades Ryan Seacrest

[34:45–39:41]

• Jared dives into Simon Cowell’s pointed remarks about former American Idol co-star Ryan Seacrest: “Simon Cowell shaded his former American Idol co star Ryan Seacrest by admitting he doesn't follow the lad the latter's career…. That's just like a crazy thing to say. You can't watch TV and not follow Ryan Seacrest career. Just not possible.” [35:46]
• He questions Cowell’s motives and tone:
  “That's a wildly jealous statement… Do you want nobody to have any money? Are you the only one who's allowed to be successful?” [37:38]
• Jared also shares a personal/family anecdote about the puzzling ubiquity of Ryan Seacrest:
  “My dad literally looked at the screen, goes, how does he have this job? … Wheel of Fortune is the job of a lifetime… Why him?” [38:23]
• Recaps the pair’s sometimes-contentious past on Idol, specifically recalling awkward, possibly scripted exchanges about Seacrest’s sexuality.

Notable Quotes & Memorable Moments

• On Miley’s Engagement Ring:
  “It almost looks like it’s her power source – for a superhero who wears a ring.” [07:20]
• On Sydney Sweeney’s Style:
  “It’s as if her stylist was working at Maxim magazine and she was like, get me the people from Maxim…” [12:04]
• On Amy Schumer’s Conscious Uncoupling:
  “Conscious uncoupling. What is that? Engaged to be engaged? That’s engaged to be broken up. To me, that is a pre-breakup.” [15:09]
• On First Dates:
  “That’s probably the smartest thing any woman can do. Hey, let’s go get another drink. I’m going with friends. No, I had a good time, but I gotta get going. Make yourself scarce.” [23:53]
• On Matt Lauer:
  “If you have what only an evil villain would have in your office, then you must be doing villainous things.” [30:09]
• On Simon Cowell & Ryan Seacrest:
  “That’s a wildly jealous statement. We rarely talk now. Not talking and not knowing what he’s done is two different things.” [36:20]
• On Julia Roberts’ Suit:
  “Honestly, weirdly enough, I would say this is the Gotham Awards is a Batman award show because she is in a very Joker-like pantsuit.” [27:30]

Structure & Tone

Jared Freid maintains a conversational, comedic style throughout, peppered with self-deprecation and candid cultural commentary. He openly speculates, provides hot takes, and infuses each topic with personal anecdotes and sharp observations, making the episode both accessible and entertaining for listeners regardless of their pop culture savvy.

Timed Segment Guide

• Miley Cyrus Engagement: [02:08–08:22]
• Sydney Sweeney’s Look: [10:25–13:48]
• Amy Schumer’s Marriage: [13:56–20:27]
• Scarlett Johansson’s First Date: [20:36–26:37]
• Julia Roberts at Gotham Awards: [26:37–29:23]
• Matt Lauer Media Comeback: [29:28–34:41]
• Simon Cowell / Ryan Seacrest: [34:45–39:41]

In Summary:
This Pop Culture Thursday features Jared Freid’s signature blend of humor and honesty as he riffs on the latest celebrity news, providing listeners with both laughs and unexpected insights into fame, relationships, and the absurdities of Hollywood culture.