Ride with Benito Skinner and Mary Beth Barone

Episode Title: Always Checking a Bag + Sharing Clothes
Date: November 19, 2025
Podcast Network: Dear Media

Overview

In this freewheeling episode, hosts Benito Skinner (aka Benny Drama) and Mary Beth Barone bring their signature chaotic, witty banter to two lifestyle debates: the merits of always checking a bag when traveling and the beauty (and petty politics) of sharing clothes, especially among friends and family. Along the way, they riff on glam routines, personal style evolution, cultural moments, and the emotional dynamics that come with lending, borrowing, and packing clothes. With digressions into pop culture, friendship, and travel, this episode offers plenty of laughs but also manages to celebrate self-expression and communal living.

Key Discussion Points & Insights

1. Embracing Unglamorous “Off-Days” (00:40–02:10)

• Benito and Mary Beth open by addressing how they “look like absolute dog shit” (00:40) after a day with no glam or makeup, underscoring their commitment to authenticity even as their lives become less relatable to their audience.
• Notable Quote:

  “It’s important to show that we are still real as we become less and less relatable in our day to day lives to our listeners.” – Mary Beth (02:46)

• They poke fun at the pressure to always look good, sometimes even managing their bathroom schedules based on podcast timetables (01:06).

2. Pop Culture Tangents, Nostalgia, and Film Talk (04:12–07:09)

• The hosts riff on micro-moments, like lash extension horror stories and comparing beauty services to scenes in films like “The Island,” “Don’t Worry Darling,” and “Stranger Things.”
• Discussion on the “yassification of Sadie Sink” as a meme-worthy phrase for child stars’ adulthood transitions (05:37–06:22).

  “Doesn’t it have such a nice, like, rhythm, the yassification of Sadie Sink? …I think it might be the most genius thing I’ve ever heard in my life.” – Benito (05:44–06:03)

• Tangents include admiration for Florence Pugh, the pressures of growing up under the public eye, and odd sleeping patterns post-travel (11:16–12:14).

3. GQ Man of the Year Awards & Travel Mishaps (08:45–09:40)

• Excitement at hosting the GQ Men of the Year Awards in London, with both jesting that they never have all the details about their own schedules.
• LAX travel mishap story: Mary Beth nearly gets into the wrong Uber due to similar cars/plates (09:40–10:06).
• They emphasize the philosophy of general “surrender” when traveling and working as public figures (09:26–09:40).

4. Sharing Clothes: Sisterhood, Etiquette, and Emotional Economics (23:34–33:02)

• Mary Beth shares her enduring love for borrowing and lending clothes – from family to friends to red carpet looks:

  “I love sharing clothes. I think not only does it create sisterhood...I have two older sisters and was constantly sneaking into their rooms and taking stuff.” (23:34)

• The politics of borrowing: always ask first, don’t borrow high-use or signature pieces before the owner wears it (26:03–26:23).
• Designer jeans lending among high school friends – the status symbol and complex logistical coordination of swapping (24:41–25:20).
• Powerful anecdotes of lending showstopper pieces to friends for their big moments, and overcoming the middle school-style jealousy of seeing someone else get compliments on your clothes (26:37–27:22).
• On the spiritual element: “I think we need to change the conversation around penises...Was the dick nice to you? Was it friendly? Did it create a safe space?” – Mary Beth (21:37–21:43)
• The existential (and often tongue-in-cheek) value of letting clothes circulate and live multiple lives via borrowing, RealReal resale, or as a sign of love as the “youngest child” (27:28–28:07).

5. The Dilemmas and Pleasures of Always Checking a Bag (37:50–44:41)

• Benito makes a case for "always checking a bag," arguing that living out of a carry-on is unrealistic for those who want options:

  “There is nothing I hate more than taking a skincare routine and putting it into some bullshit little bottle that it doesn’t belong in.” – Benito (39:10)

• Packing larger means you can shop on the trip; friends always want your extra space.
• The agony of baggage claim vs. the ecstasy of wardrobe choice; Mary Beth admits to being a “carry-on warrior” originally, but now concedes it’s not possible with a busy social and media schedule (43:06–43:25).
• Gate checking and its various joys and horrors (41:52–42:13).
• Shared wisdom: get rid of shame and stigma about checking bags, let people have their travel preferences (44:37–44:38).

6. Ride or Die Segment (45:36–end)

• The hosts debate: Mary Beth ultimately “dies for” always checking a bag (she dislikes it in principle but concedes it’s sometimes necessary), while Benito “rides for” sharing clothes but yearns to one day enjoy the benefit more as the lender than borrower (47:36–48:15).
• Both recall the family roots of their lending/borrowing ethos: stealing from moms and dads as an act of love (47:51–48:08).

Noteworthy Quotes & Memorable Moments

| Timestamp | Speaker | Quote/Highlight | |-----------|---------|------------------| | 00:40 | Benito | “We have boldly chosen to look like absolute dog shit today.” | | 02:46 | Mary Beth | “It’s important to show that we are still real as we become less and less relatable in our day to day lives to our listeners.” | | 05:44 | Benito | “I think it might be the most genius thing I’ve ever heard in my life. I’m not kidding.” (re: “yassification of Sadie Sink”) | | 21:37 | Mary Beth | “Was the dick nice to you? Was it friendly? Did it create a safe space?” | | 23:34 | Mary Beth | “I love sharing clothes. I think not only does it create sisterhood… I have two older sisters and I was constantly sneaking into their rooms and taking stuff.” | | 39:10 | Benito | “There is nothing I hate more than taking a skincare routine and putting it into some bullshit little bottle that it doesn’t belong in.” | | 44:37 | Mary Beth | “Get rid of the stigma, you know? So much hate. There’s so much...you’re checking a bag.” | | 47:36 | Benito | “We’re dating. You said it.” (running joke about the closeness of their relationship) | | 48:08 | Benito | “Yeah, nothing could matter less. It’s intimate to see. That’s 100% into me you see.” |

Important Segments & Timestamps

• Opening and Realness About Glam (00:40–02:46)
• Film and Pop Culture Tangents (04:12–07:09)
• Travel Mishaps and The Philosophy of Surrender (09:40–10:06, 09:26–09:40)
• Deep-Dive: Sharing Clothes (23:34–33:02)
• Checking a Bag: Pros, Cons, and Emotions (37:50–44:41)
• Ride or Die: The Final Stance (45:36–48:15)

Tone & Style

Benito and Mary Beth keep the energy irreverent, playful, and occasionally absurd—mocking their own lifestyles as they gain fame, reminiscing about their “bimbo” days, then pivoting to heartfelt observations on friendship, fashion, and self-acceptance. The dialogue is raw but warm, fast-moving but packed with inside jokes and relatable moments about travel, style, and growing up.

Episode Takeaways

• Sharing clothes is more than practicality—it’s about memory, emotional ties, and communal joy (with a side of etiquette).
• Always checking a bag can be liberation for those who crave options and indulge in fashion, especially as careers, events, and expectations escalate.
• Rejecting shame, embracing travel and wardrobe quirks, and supporting each other is the way forward, both on the road and in friendships.
• Pop culture, personal taste, and the desire to be seen—in clothes or experiences—are all part of being a “ride or die.”

Summary by Ride with Benito Skinner & Mary Beth Barone Recap
Dear Media, November 2025