Chicks in the Office

Celebrity Gossip w/ Justin Sylvester + Owning Manhattan's Chloe Tucker Caine Interview

December 5, 2025

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  • Justin Sylvester described Scarlett Johansson as the most confident woman he has ever met, noting her seamless transition into hosting the *Today Show*. 
  • The hosts and Justin Sylvester agreed that hair and makeup artists are trusted confidantes who often know the most intimate celebrity details. 
  • The conversation touched on the perceived 'Oscar curse' where winning an Academy Award can negatively influence an actress's subsequent career choices, citing examples like Gwyneth Paltrow and Jennifer Lawrence. 
  • The hosts and guest Chloe Tucker Caine discussed pairings from Variety's Actor on Actors lineup, including Michael B. Jordan and Jesse Plemmons, and Oscar Isaac and Teyana Taylor. 
  • Chloe Tucker Caine detailed her transition from a career in theater, including booking the lead in *Mamma Mia* right out of school, to becoming a successful real estate agent inspired by Ryan Serhant's social media presence. 
  • Hunter and Hollyn won the 'Beat Ria & Fran game 199' segment of the "Chicks in the Office" episode "Celebrity Gossip w/ Justin Sylvester + Owning Manhattan's Chloe Tucker Caine Interview" with a final score of 4-3. 
  • The trivia game featured questions spanning pop culture, including music lyrics (Olivia Rodrigo, Fall Out Boy, Lizzie McGuire), film knowledge (Juno, Ratatouille, Pretty Woman), and television trivia (Friends, Raven's Home). 
  • The segment concluded with advertisements for Planet Fitness and Mazda, followed by the podcast's outro song highlighting the hosts' success and relevance in the media landscape. 

Segments

Justin Sylvester on Scarlett Johansson
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(00:02:15)
  • Key Takeaway: Scarlett Johansson exhibits extreme confidence and treats hosting duties like a seasoned talk show host.
  • Summary: Justin Sylvester found Scarlett Johansson to be the most confident woman he has ever met during her guest hosting stint on the Today Show. She fully embodies the role, acting like a dedicated talk show host rather than a celebrity guest. This experience highlights the positive environment created by Jenna Bush and her team, which attracts A-listers like Johansson, Leslie Bibb, and Brooke Shields.
Celebrity Trust and Leaks
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(00:08:38)
  • Key Takeaway: Hair and makeup artists are privy to the most sensitive celebrity information, often serving as an unofficial sanctuary for secrets.
  • Summary: The people responsible for hair and makeup are considered the most knowledgeable sources on set because celebrities often overshare during long appointments. One anecdote detailed a celebrity who identified a leak by intentionally telling different versions of a major story to various team members. This highlights the high-stakes environment where even supposed ‘sanctuaries’ like the makeup chair can become sources of leaks.
RHOSLC Plane Incident Speculation
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(00:11:03)
  • Key Takeaway: The lack of public audio or video from the ‘RHOSLC’ plane incident suggests someone involved, possibly the flight attendants, is protecting the narrative.
  • Summary: The hosts expressed intense curiosity about the unreleased footage or audio from the infamous Real Housewives of Salt Lake City plane incident. They urged Bravo and Andy Cohen to find the passenger who posted a photo and the two flight attendants involved. The hosts believe the flight attendants’ silence implies they were being intentionally ‘messy’ but ultimately chose not to escalate by calling the police or speaking out.
Ambient Side Effects Anecdote
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(00:16:34)
  • Key Takeaway: Taking the sleep aid Ambien can lead to unpredictable and memorable behavior, including actions the user has no memory of performing.
  • Summary: Justin Sylvester shared a personal story about taking Ambien and waking up to a partner claiming he was ‘on fire’ the night before. He admitted to having done wild things while on the medication, emphasizing that users should be cautious about intimacy while under its influence. This anecdote related to Meredith Marks’ potential memory lapse during the plane incident, showing how blackouts can affect public perception.
NFL Broadcast Crossover Content
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(00:17:30)
  • Key Takeaway: The Sunday Night Football Reality Hot Seat broadcast on Peacock blends football analysis with reality TV and pop culture commentary.
  • Summary: Justin Sylvester is participating in a special broadcast for Sunday Night Football that caters to both football fans and pop culture enthusiasts. The show is designed for the partner who pretends to like football while the hosts gossip about reality moments. The upcoming broadcast features Heather Gay fresh off a reunion and will cover the Texans versus Chiefs game, with Taylor Swift’s presence being a major talking point.
NFL Player Fashion and Birkin Bags
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(00:27:09)
  • Key Takeaway: NFL players are increasingly focusing on high-fashion pregame outfits, leading to scrutiny over the authenticity of luxury accessories like Birkin bags.
  • Summary: The NFL players’ pregame fashion has significantly improved, with some carrying Birkin bags, though some are suspected to be fake. Justin Sylvester noted that a stiff Birkin that doesn’t ‘jingle the right way’ when tapped is a tell-tale sign of a counterfeit. The hosts agreed that prioritizing flashy designer clothing over foundational items like cars indicates poor financial priorities.
Spotify Wrapped Reactions
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(00:38:31)
  • Key Takeaway: Spotify Wrapped results are seen as validation of one’s identity, though algorithmic errors can lead to questionable top songs.
  • Summary: Justin Sylvester enjoys seeing others’ Spotify Wrapped results because it validates his commentary on artists throughout the year, noting his listening age was calculated as 17 with bubblegum pop as the top genre. Fran expressed distrust in her own results, as her top song was Kendrick Lamar’s ‘Squabble Up,’ a track she frequently skips. The hosts noted that most users receive extreme age results (like 17 or 70) rather than ages close to their actual age.
Variety Actor on Actor Pairings
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(00:45:33)
  • Key Takeaway: The Variety Actor on Actors pairings included notable matches like Ariana Grande/Adam Sandler and surprising pairings like Gwyneth Paltrow/Jacob Elordi.
  • Summary: The announced pairings featured strong matches such as Ariana Grande and Adam Sandler, and the pairing of the new Superman, David Corenswet, with Jonathan Bailey. The pairing of Gwyneth Paltrow and Jacob Elordi was deemed awkward, suggesting they might only whisper during their interview. Dwayne Johnson and Brendan Fraser were paired together, which the hosts anticipated would be a sweet conversation.
Variety Actor Pairings Reaction
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(00:46:48)
  • Key Takeaway: The hosts reacted positively to the Variety Actor on Actors pairings, specifically noting the pairing of Oscar Isaac and Teyana Taylor for the film One Battle After Another.
  • Summary: The pairing of Michael B. Jordan and Jesse Plemmons was mentioned, and the film One Battle After Another, starring Oscar Isaac and Teyana Taylor, was highly praised. The pairing of Julia Roberts and Sean Penn sparked a brief discussion about desired generational pairings. Dwayne Johnson and Brendan Fraser were noted as a sweet pairing.
Revisiting Jennifer Lawrence/Leo Movie
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(01:04:47)
  • Key Takeaway: The Jennifer Lawrence and Leonardo DiCaprio movie pairing was discussed, with a warning that the film is emotionally heavy and requires viewers to be prepared for sadness.
  • Summary: The hosts recalled seeing Jennifer Lawrence and Leonardo DiCaprio being giggly in interviews, leading one host to see their movie without knowing the plot. The film was described as sad, prompting a recommendation to bring Lexapro to the theater. The hosts noted that the actors later warned audiences about the movie’s actual tone.
Analyzing Kim K’s Acting
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(01:05:01)
  • Key Takeaway: Kim Kardashian’s performance in her Ryan Murphy show was attributed to the writing style, suggesting the show adapted to her acting skills starting in episode three.
  • Summary: The speaker suggested that Ryan Murphy wrote the show initially for his typical over-the-top style, which did not suit Kim Kardashian’s monotone delivery. The writing reportedly improved for her starting in episode three, focusing more on co-stars like Sarah Paulson and Niecy Nash. This adjustment allowed Kim K to perform at a pace better suited to her current acting skill level.
Tarantino Slams Paul Dano
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(01:05:12)
  • Key Takeaway: Quentin Tarantino publicly called Paul Dano the ‘weakest actor in SAG’ and the ‘big giant flaw’ in There Will Be Blood, potentially due to a past personal slight.
  • Summary: Quentin Tarantino ranked There Will Be Blood at number five on his list of 21st-century films, citing Paul Dano as the major flaw preventing it from ranking higher. The speaker speculated that Tarantino’s harsh criticism, including calling Dano the ’limpest dick in the world,’ stemmed from Dano once being unavailable to Tarantino. Despite the insult, the speaker suggested this publicity might ironically lead to more roles for Dano.
Guest Introduction and Show Anxiety
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(01:08:11)
  • Key Takeaway: Chloe Tucker Caine expressed anxiety about watching the new season of Owning Manhattan with the public because filming spanned nearly two years, covering significant personal changes.
  • Summary: Chloe Tucker Caine was introduced alongside her dog, Sadie, ahead of discussing the new season of Owning Manhattan. She admitted to being terrified to watch the new season because filming began when her baby was six months old and concluded when the child was almost two. The long filming gap means the show captures a year and a half of personal and business changes, making the final edit unpredictable.
Chloe’s Career Pivot to Real Estate
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(01:09:32)
  • Key Takeaway: Chloe Tucker Caine pivoted from a successful theater career, including touring with Mamma Mia, to real estate after struggling as a bartender and realizing the potential in the housing market.
  • Summary: Chloe initially pursued theater, attending the Boston Conservatory and booking the lead in Mamma Mia professionally right away, but struggled upon moving to New York City. After being fired from bartending jobs, she got her real estate license at her then-boyfriend’s suggestion and found immediate success, completing 100 rentals in her first year. She was inspired to copy Ryan Serhant’s video style and was recruited by his team after only six videos.
Theater Skills in Real Estate
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(01:04:50)
  • Key Takeaway: Chloe believes her theater background is beneficial in real estate because selling a home is essentially a performance requiring the agent to maintain a professional presentation regardless of personal mood.
  • Summary: The performance aspect of acting directly translates to presenting apartments to clients, requiring the agent to ‘put on a show.’ This means maintaining energy and professionalism even on a bad day. This mindset helps her put on the ‘costume’ and go to work, treating each showing as a performance.
The Townhouse Musical Production
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(01:05:26)
  • Key Takeaway: Convincing Niall to participate in the townhouse musical listing promotion was difficult, as he initially thought the idea was crazy and then experienced an internal crisis fearing his own performance.
  • Summary: Chloe organized a full musical production for a townhouse listing, complete with an orchestra and dancers, which initially caused Niall to stop answering her calls. As he saw her seriousness, he became excited but then terrified about performing well on camera. The successful social media promotion of the musical later led Chloe to create a musical web series.
Owning Manhattan’s Scripted Approach
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(01:08:35)
  • Key Takeaway: Owning Manhattan is intentionally produced to resemble a scripted show like Succession by capturing real-life deals and conflicts rather than fabricating drama.
  • Summary: Ryan Serhant and the producers aimed to create a reality show that felt more like a scripted drama, focusing on capturing actual deals and professional conflicts. The high stakes of New York real estate, involving large commissions, naturally create intense competition and drama. This approach allows viewers to see the genuine competitive nature of the business.
Chloe’s Non-Robot Routine
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(01:09:50)
  • Key Takeaway: Unlike Ryan Serhant’s highly regimented routine, Chloe operates chaotically as an ADHD queen, structuring her day around her 20-month-old daughter and varying professional demands.
  • Summary: Chloe contrasts her routine with Ryan Serhant’s robotic schedule, noting that as a new mother, her mornings are unpredictable based on her child’s sleep. Her day is managed by a nanny after the initial hours, and her schedule varies based on whether she has showings, recording sessions, or musical commitments. She admits she cannot adhere to strict regimentation and thrives on the daily variation.
Friendship Dynamics and Distrust
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(01:11:19)
  • Key Takeaway: The competitive nature of real estate makes maintaining friendships difficult, but surviving the process builds deep mutual respect among colleagues who succeed.
  • Summary: The inherent competitiveness in real estate makes it hard to separate business conflicts from personal friendships, often leading to taking professional slights personally. However, succeeding alongside friends fosters immense mutual respect for their capabilities. Chloe noted that theater training made her sensitive to comparison, but real estate taught her that not every agent is right for every client.
Conflict with Jade Over Cheating Story
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(01:13:07)
  • Key Takeaway: Chloe and her best friend Jade experienced a major rift after the cast initially distrusted Jade’s claim that her husband cheated, only to later realize the infidelity was real and severe.
  • Summary: The distrust among the cast regarding Jade’s husband cheating storyline caused significant tension, as the group initially believed she fabricated it for television. Chloe felt guilty after learning the cheating was real and involved seven instances, contradicting the ’twice’ she thought was reported. The hosts believe they have finally worked hard to move past the crossed wires and hurt from that period.
Authenticity and Confrontation on Reality TV
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(01:16:05)
  • Key Takeaway: Chloe realized her season one behavior, characterized by unnecessary confrontation, was inauthentic, stemming from a theater background where she felt pressure to ‘put on a show’ for the cameras.
  • Summary: Chloe felt pressure as a short woman in real estate to be confrontational on camera to prove herself, leading to scenes where she confronted people without context. She recognized this behavior as inauthentic upon rewatching, comparing it to how performers like Whitney are more comfortable playing up to the camera. She has since promised herself to stop looking at comments and stay in her own lane.
Manifesting Future Goals
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(01:18:03)
  • Key Takeaway: Chloe is actively working to overcome self-doubt to pursue her long-held goals of performing on Broadway and competing on Dancing with the Stars while continuing her real estate career.
  • Summary: After therapy, Chloe decided to stop being afraid to state her ambitions, recognizing she has been ready for Broadway since childhood. She is actively warming up and taking dance classes, ready to pursue performing at night and real estate by day. She is determined not to let self-doubt prevent her daughter from seeing her pursue her talents.
NYC Apartment Hunting Advice
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(01:20:33)
  • Key Takeaway: Key advice for NYC renters includes prioritizing good light, loving the building staff (like doormen), and having all necessary documents prepared as a PDF to secure a spot quickly.
  • Summary: Chloe, being from LA, finds NYC apartment costs hard to contextualize but stresses the importance of good light to combat seasonal depression. Loving the building staff and community is crucial, as she stayed in one rental building for ten years due to her attachment to the doormen. For renters, having all documents ready in a PDF allows them to secure a spot immediately when a landlord is choosing between applicants.
Warning Against NYC Rental Scams
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(01:25:15)
  • Key Takeaway: TikTok accounts advertising gorgeous NYC apartments for unrealistically low prices are often bait-and-switch scams, sometimes escalating to outright financial fraud where deposits are requested.
  • Summary: The hosts identified TikTok listings showing stunning Tribeca lofts for low prices (e.g., $5,000/month) as a ‘classic bait and switch.’ These scams lure newcomers who don’t know NYC real estate norms, sometimes involving brokers showing alternative units after claiming the original is unavailable. The situation is worse when scammers ask for applications and deposits upfront, turning the tactic into a full scam.
Townhouse Sale Details
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(01:27:41)
  • Key Takeaway: The townhouse featured in the musical promotion initially fell through after an accepted offer due to New York City’s rigorous due diligence process, but it eventually sold via a subsequent offer.
  • Summary: The townhouse listing seen during the musical segment initially had an offer accepted, but it did not go through due to the extensive due diligence and inspections required for NYC properties. Fortunately, a second offer came in, and that deal successfully closed. Chloe noted that in New York City, there is always a catch, even with high-value properties.
Beat Ria & Fran Game 199 Start
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(01:30:26)
  • Key Takeaway: The ‘Beat Ria & Fran’ game began its 199th installment with guests Hunter and Holland, using the Rotten Tomatoes score of You’ve Got Mail to determine who would guess first.
  • Summary: The game started with the introduction of contestants Hunter and Holland, who were wearing matching ‘Chicks in the Office’ hoodies. The first round required guessing the Rotten Tomatoes critic score for the movie You’ve Got Mail. Hunter’s guess of 85 was closest to the actual score of 72, giving her team the first turn.
Beat Ria & Fran Game Start
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(01:37:14)
  • Key Takeaway: The ‘Beat Ria & Fran game 199’ commenced with a lyric recall question regarding Olivia Rodrigo’s ‘Sour’ tour opener.
  • Summary: The game began with a question about which pop star opened the first half of Olivia Rodrigo’s 2022 ‘Sour’ tour. Hunter and Hollyn initially answered incorrectly, with the correct answer being Gracie Abrams. The score stood at 0-0 after the first question.
Friends Trivia Question
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(01:39:15)
  • Key Takeaway: Ross and Rachel’s first night together in the ‘Friends’ series occurred at the Dinosaur Museum.
  • Summary: Rhea and Fran correctly answered a question about the location where Ross and Rachel spent their first night together in the TV show ‘Friends,’ identifying it as the museum. This answer brought the score to 2-1 in favor of Hunter and Hollyn.
Harry Potter Department Mystery
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(01:39:57)
  • Key Takeaway: Employees of the Department of Mysteries in the ‘Harry Potter’ book series are called Unspeakables.
  • Summary: Hunter and Hollyn missed a question asking for the title of employees in the Department of Mysteries from the ‘Harry Potter’ series, incorrectly guessing ‘Aurors.’ The correct term, ‘Unspeakables,’ is noted as being a book reference rather than a movie detail.
Melanie Smooter Movie Identity
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(01:41:25)
  • Key Takeaway: Melanie Smooter is the original name of Reese Witherspoon’s character in the movie ‘Sweet Home Alabama.’
  • Summary: Rhea and Fran correctly identified both the actress (Reese Witherspoon) and the movie (‘Sweet Home Alabama’) associated with the character name Melanie Smooter. This answer tied the game score at 2-2.
Fall Out Boy Lyric Identification
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(01:42:03)
  • Key Takeaway: The lyrics “She says she’s no good with words, but I’m worse. Barely stuttered out a joke of a romantic stuck to my tongue” belong to the Fall Out Boy song ‘Dance, Dance.’
  • Summary: Hunter and Hollyn failed to identify the song from the provided lyrics, guessing incorrectly before the answer was revealed as ‘Dance, Dance’ by Fall Out Boy. The score remained tied at 2-2 following this question.
Planet Fitness Sponsorship Read
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(01:43:54)
  • Key Takeaway: Planet Fitness offers high-value memberships, over 2,700 locations, and features brand new plate-loaded machines like hack squats.
  • Summary: Planet Fitness promotes its fitness journey support through high-value memberships available at numerous 24-hour club locations. They offer high-quality equipment comparable to more expensive gyms, including new plate-loaded machines, and provide unlimited free fitness training.
Movie Clip Identification
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(01:45:12)
  • Key Takeaway: The movie clip featuring dialogue about spending money and needing help was from ‘Pretty Woman.’
  • Summary: Rhea and Fran correctly identified the movie clip, which featured dialogue about needing help sucking up to customers, as being from ‘Pretty Woman.’ This answer tied the game score again at 2-2, despite the hosts feeling the audio sounded older.
Juno Adopting Couple Actors
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(01:47:25)
  • Key Takeaway: Jennifer Garner and Jason Bateman played the couple planning to adopt Juno’s baby in the film ‘Juno.’
  • Summary: Hunter and Hollyn correctly named Jennifer Garner and Jason Bateman as the actors playing the prospective adoptive parents in the movie ‘Juno.’ This answer advanced their lead to 3-2.
Summer I Turned Pretty Books
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(01:48:41)
  • Key Takeaway: The three ‘The Summer I Turned Pretty’ books are titled ‘The Summer I Turned Pretty,’ ‘It’s Not Summer Without You,’ and ‘We’ll Always Have Summer.’
  • Summary: Rhea and Fran successfully named the three books in ‘The Summer I Turned Pretty’ series in order, securing the correct answer despite initial memory lapses. This brought the score to 4-2 in favor of Hunter and Hollyn.
Raven’s Fashion Label Name
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(01:49:58)
  • Key Takeaway: Raven’s fashion label in the later seasons of ‘That’s So Raven’ was called ‘Ravenous Fashions.’
  • Summary: Hunter and Hollyn missed the question regarding the name of Raven’s fashion label, incorrectly guessing ‘Raven’ and ‘Revelation.’ The correct answer, ‘Ravenous Fashions,’ was revealed after the attempt.
Ratatouille Nickname Question
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(01:51:29)
  • Key Takeaway: In the movie ‘Ratatouille,’ Linguine calls Remy the ‘Sous Chef.’
  • Summary: Rhea and Fran correctly identified that Linguine calls Remy the ‘Sous Chef’ in the movie ‘Ratatouille.’ This answer made the score 4-3, setting up the final question.
Lizzie McGuire Theme Lyric
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(01:52:24)
  • Key Takeaway: The missing lyric from the ‘Lizzie McGuire’ opening song is ‘but we get one step closer each and every day.’
  • Summary: Hunter and Hollyn failed to complete the lyric from the ‘Lizzie McGuire’ theme song, missing the line that follows ‘Sometimes we make it, and sometimes we fake it.’ This incorrect answer secured the win for Rhea and Fran.
Game Conclusion and Outro
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(01:53:51)
  • Key Takeaway: Hunter and Hollyn won the game, earning ‘Chicks in the Office’ merchandise for their victory over Rhea and Fran.
  • Summary: The segment concluded with congratulations for Hunter and Hollyn’s win, followed by the podcast’s outro jingle praising the hosts’ success and relevance. The final segment included additional sponsor reads for Mazda and Sierra.