Chicks in the Office — "Celebrity Gossip w/ Justin Sylvester + Owning Manhattan's Chloe Tucker Caine Interview"

Release Date: December 5, 2025
Hosts: Ria & Fran (Barstool Sports)
Guests: Justin Sylvester (celebrity host), Chloe Tucker Caine (Owning Manhattan), plus cameo by Hunter & Holland for trivia

Episode Overview

This high-energy episode of Chicks in the Office is a pop culture buffet featuring:

• A deep-dish chat with celebrity host Justin Sylvester on Hollywood gossip, reality TV crossovers, and celebrity encounters (especially Scarlett Johansson).
• An in-studio interview with Chloe Tucker Caine from Netflix's Owning Manhattan, unearthing the dance between real estate, reality TV, and Broadway dreams.
• The always-iconic trivia face-off, "Beatrie and Fran," bringing in listeners for pop culture stumping. The tone is lively, gossipy, candid, and laced with the signature quick wit and camaraderie Ria and Fran are known for.

Key Segments & Insights

I. Justin Sylvester Joins for Weekly Gossip Radar

Starts ~02:09

1. Justin's NYC Whirlwind & Star-Heavy Week

• Justin has been spending time with Kyle Richards and Scarlett Johansson.
• He raves about Scarlett’s confidence and presence, especially during her recent hosting stints.
  • "I've never met a woman more confident in my life." (Justin, 02:52)
  • "She called me the king of f**ing Hollywood."* (Justin, 04:36)
• Discussion about celebrities transitioning into hosting roles, taking seats from seasoned hosts like Justin himself.

2. Scorpio Energy: Confidence & Success

• They reflect on how some women, like Scarlett or Oprah, seem to have “figured out” who they are early on, and how financial success can embolden that persona.
  • "There's something about a woman who just knows who she is." (Justin, 06:17)
  • "She's also very rich. That helps." (Fran & Justin, 06:52)

3. Hair & Makeup Artists: The Real Gatekeepers

• Anecdotes about how the real backstage dirt often comes from hair and makeup teams.
  • "The hair and makeup artists know everything." (Fran, 08:56)
  • Justin shares a story about a celebrity tracking leaks by spreading multiple versions of a sensitive story—real Hollywood detective work.

4. Football, Reality Hot Seat, and the Taylor Swift Effect

• Justin discusses his role on Sunday Night Football’s Reality Hot Seat—crossing sports, reality TV, and pop culture.
  • "It's for the guy who loves football and for the girl who pretends like she does." (Justin, 26:05)
• Speculation on Taylor Swift’s attendance at Chiefs games and Blake Lively possibly joining her:
  • "If Taylor shows up with Blake Lively…that would give me three hours of content." (Justin, 18:07)
• Reflections on the Chiefs' struggles and parallels to past celeb-athlete dramas (Jessica Simpson/Tony Romo).
  • "His check engine light's on." (Justin, 18:53)

5. Pop Culture Deep Dive: Movie Rights Messes & ‘Oscar Curses’

• Discussion of ongoing Blake Lively/Justin Baldoni drama and the Colleen Hoover book adaptations.
• Sympathy for everyone involved in the messy production:
  • "No one wins at this point…everyone loses." (Justin, 20:33)
• Skepticism about sequels and movie rights issues:
  • "Zero reason to make the second one." (Ria, 21:57)
• Anne Hathaway's career-strategy praised for alternating visibility to avoid audience fatigue.
  • "I like Anne Hathaway because…I'll put my sht out for a year, and then I'll hide for a year…"* (Justin, 22:37)

6. Euphoria S3 and the Risk of High Expectations

• Anticipation for Euphoria S3, the creator’s bold claims, and cast age jumps.
  • "Season three better be better. You had six years to think about it…All these motherf**ers are 30."* (Justin, 25:28)
• Spoilers: Cassie and Nate reportedly getting married.

7. Fashion Real Talk: Birkins, Priorities & Quiet Luxury

• Extensive, hilarious breakdown of how to spot a fake Birkin and the psychology of matching luxury accessories to lifestyle.
  • "If you're walking out of your car into a locker room and your Birkin looks a little stiff and a little fake, I'ma call your ass out." (Justin, 27:08)
• Justin’s client stories: two separate Birkin-smelling rooms, E.J. Johnson’s “Birkin test” in clubs.
• Spirited rundown of the etiquette of fashion flexing vs. being “bad with your money.”
  • "If you have a Range Rover Sport and two roommates at 40…your priorities aren’t straight." (Justin, 31:57)
• "Quiet luxury" vs. "loud money" debate; hair and shoes as the real tells of style.

8. Nails, Maintenance, & Friendship ‘Bullying’

• Wildly relatable spiral about nail routines, peer pressure, and the “Russian manicure wave.”
  • "If you have more than 2mm between your cuticles and your last manicure, bitch, we're fighting." (Justin, 34:04)

9. Spotify Wrapped: The Ultimate Validation or Algorithmic Mess?

• They dissect their Spotify Wrapped results, the basicness of posting, and the anxiety over “off” results.
  • "That's a basic white girl and gay thing. The basic white gays do it. The basic white girls do it." (Justin, 38:34)
• Fran’s wrapped glitched—her top song surprised even her. Justin’s is “Morgan Wallen problematic,” and Ria’s is “bubblegum pop.”
• Separating art vs. the artist—mini debate citing Morgan Wallen, R. Kelly.

10. Variety’s “Actors on Actors” Pairings—Predictions & Hot Takes

• The group analyzes the oddest and most intriguing pairs: Ariana Grande/Adam Sandler, Gwyneth Paltrow/Jacob Elordi, Anne Hathaway/J.Lo.
• General consensus: Julia Roberts should have been paired with someone younger, Kate Hudson and Jeremy Allen White will flirt, and Jennifer Lawrence will pull “unhinged” fun out of Leo.

11. Hollywood Beef: Quentin Tarantino vs. Paul Dano

• Tarantino called Paul Dano "the weakest actor in SAG" and “limpest dick in the world” over There Will Be Blood.
  • "He pissed him off, and he's been waiting for years…" (Justin, 52:48)
• Hosts note this may ironically help Dano get more (contrarian) roles.

II. Chloe Tucker Caine Interview — Owning Manhattan

Starts ~58:07

1. Chloe’s Path: From Broadway Dreams to Real Estate Queen

• Chloe details her unique journey: musical theater background, landing the lead in Mamma Mia at her very first audition, moving from bartending to Airbnb entrepreneur to real estate star.
  • "No one told me I wasn’t good enough but me, when I really think about it." (Chloe, 61:18)

2. Blending Theatrical Flair with Real Estate Hustle

• Discusses merging performance skills with real estate—literally putting on a show to sell properties (including staging actual musicals in townhouses to lure buyers).
  • "It's all a performance. Places, people, it's time to start the show." (Chloe, 64:45)

3. The Reality TV Experience

• Chloe talks about the “weirdness” of living a year ahead of what’s airing, her initial anxieties over edits, and the thrill/fear of seeing “real life” translated for Netflix.
• She emphasizes that Owning Manhattan is less manufactured drama and more, "Success-ion with real deals."
  • "We're going to take your real lives and set it up looking like succession…You're really seeing us fight each other—not necessarily on a personal level." (Chloe, 67:58)

4. Navigating Friendship, Trust, and Betrayal on TV

• Recounts her on-and-off friendship with Jade and how reality TV blurs lines between real emotion and storyline creation.
  • "I literally thought Jade, my best friend, was making up a storyline that her husband was cheating on her…It turned out that wasn't the case—he really was cheating." (Chloe, 74:00)

5. Owning Her Broadway Ambitions (and Defying Self-Doubt)

• Chloe is candid about wresting with self-esteem and expectations, especially after theater “setbacks,” and her plans to fuse both passions.
  • "I want to do Broadway. I want to do Dancing with the Stars, and I want to be able to perform at night and do real estate by day." (Chloe, 78:00)
• She talks about not wanting her daughter to inherit her anxieties and manifesting big opportunities.

6. Real Estate Hot Tips

• “There’s always a catch in New York City…you need somewhere with good light, a good building, a doorman you love.” (Chloe, 80:43)
• Talks candidly about rental scams on TikTok, advises renters to have docs and deposits ready (“If it looks too good to be true, it is!”).

7. Behind the Scenes: Musical Salesmanship

• Chloe elaborates on producing an actual musical staged in a townhouse to help it sell—her multi-hyphenate career in action.

III. "Beatrie and Fran" Trivia Segment

Starts ~90:22

• Listener guests (Hunter and Holland) join for a trivia face-off—15 questions on pop culture (from Love is Blind and The Princess Bride to Lizzie McGuire lyrics).
• Notable moments:
  • Ria’s self-deprecating humor: “I have never felt worse at trivia than I do today.” (105:38)
  • Fran’s deadpan on fashion: “Where are the priorities? Let me tell you something.” (30:49)
• Final Score: Hunter and Holland win. "You beat the crap out of us and you get shirts that say you beat us," Fran jokes (113:52).

Notable Quotes & Memorable Moments

"I've never met a woman more confident in my life. Never in my life." — Justin Sylvester on Scarlett Johansson (02:52)

"If you have a Range Rover Sport and two roommates at 40…your priorities aren’t straight." — Justin Sylvester (31:09)

"It's for the guy who loves football and for the girl who pretends like she does." — Justin Sylvester on Reality Hot Seat (26:05)

"If Taylor [Swift] shows up with Blake Lively…that would give me three hours of content." — Justin Sylvester (18:07)

"No one told me I wasn’t good enough but me, when I really think about it." — Chloe Tucker Caine (61:18)

"It's all a performance. Places, people, it's time to start the show." — Chloe Tucker Caine (64:45)

"That's a basic white girl and gay thing. The basic white gays do it. The basic white girls do it." — Justin Sylvester on Spotify Wrapped (38:34)

"There’s always a catch in New York City." — Chloe Tucker Caine (88:14)

Timestamps for Key Segments

| Timestamp | Segment | Details | |-----------|-----------------------------------|-------------------------------------------------------------------| | 02:09 | Justin Sylvester Interview Start | Weekly catch-up, Scarlett Johansson, “King of Hollywood” | | 06:52 | Rich & Confident Women | Oprah and ScarJo—power, confidence, and authenticity | | 08:34 | Backstage Celebrity Stories | Hair & makeup teams, Hollywood leaks | | 12:20 | Football/Pop Culture Broadcast | Reality Hot Seat, Chiefs, Taylor Swift segment | | 20:33 | Book Adaptation Drama | Blake Lively/Justin Baldoni/Colleen Hoover movie adaptation mess | | 22:37 | Anne Hathaway/J.Lo Career Paths | | | 25:28 | Euphoria Season 3 Hype | Six-year wait, cast age topic | | 27:08 | Fashion Priorities/Birkins | How to spot fakes, stories of luxury mismatches | | 34:04 | Nails and Peer Pressure | The Russian manicure wave, self-care & friend “bullying” | | 38:34 | Spotify Wrapped | Validation, algorithm angst, “basic” debate | | 45:00 | Trivia Segment Start | Beatrie and Fran with Hunter & Holland | | 58:07 | Chloe Tucker Caine Interview | Real estate, Broadway, reality TV, and hustling in Manhattan | | 80:43 | Real Estate Hot Takes | NY property advice, scamming data, and bargaining | | 90:22 | Trivia Returns | Games, laughs, pop culture knowledge tested | | 113:52 | Trivia Results Wrap | Hunter and Holland declared winners |

Tone & Style

• Light-hearted, witty, often self-deprecating
• Candid opinions about pop culture, but with affection
• Blend of sharp humor and sincerity (especially regarding career insecurities, therapy, and confidence)

Takeaways for Listeners

• Justin Sylvester’s stories offer a peek behind Hollywood’s "velvet rope" and how celebrity culture and hosting gigs are evolving.
• Chloe Tucker Caine’s candidness demystifies reality TV production, the grit behind real estate, and chasing big dreams even after “wins” and “losses.”
• The show is ultimately about women supporting women—calling out the mess while also rooting for growth, whether in music, film, business, or personal life.

For Pop Culture Fans Who Haven’t Heard the Episode:

You’ll walk away with tons of Hollywood insider tea (Scarlett Johansson is as cool as advertised), real estate shenanigans (NYC never changes), and feel both seen and roasted for your Spotify Wrapped—and you just might check your nails.