Unsupervised with Syd & TP – "Joy Started It"

Released: November 27, 2025 | Host: Dear Media

Episode Overview

This vibrant and freewheeling episode spotlights the unique friendship and unfiltered humor of hosts Syd Colson and Theresa Plaisance (TP). Best friends, former teammates, and seasoned storytellers, they dive into topics ranging from thrift shop altercations and Broadway adventures to heartfelt discussions on holiday giving, Friendsgiving traditions, and family dynamics. True to their reputation, the duo frequently veer off topic—peppering their conversation with playful games, personal confessions, unplanned tangents, and rich laughs—while circling back to themes of community, gratitude, and belonging.

Major Discussion Points & Insights

1. The Not-So-Joyful Joy: Thrift Shop Saga

• TP’s Thrift Shop Drama:
  • TP recounts an altercation with a thrift store employee named Joy over the purchase of a shirt with no price tag. Store policy required her to come back the next morning when the "pricers" were in.
  • TP narrates her competitive drive to get the shirt, arriving early, only to fear someone else would snatch it up first. In the end, Joy provides the shirt (for $7.99, a steal), but not before some morning suspense and low-key suspicions that Joy wanted the shirt herself.
  • Notable Quote:
    • TP: "It's always the ones named Joy that, like, aren't joyful." (00:20)
    • TP (on her competitiveness): "I've never woken up to be at any store, much less a thrift store... my competitiveness is really coming out right now." (11:31)
• Names and Expectations:
  • The duo riff on the pressure of "namesake" personalities (e.g., people named Joy should act joyful).
  • Syd suggests maybe people rebel against namesake expectations:
    • Syd: "Maybe that's not inside of them... Maybe Joy decided, I'm about to start acting how I want to act, how I truly am. I'm not Joyful." (11:05)

2. Broadway Adventure in NYC

• Lion King, Aladdin & Rockettes:
  • Syd describes a family trip to New York planned around a "Home Alone" experience for her niece, Logan.
  • She marvels at the production and athleticism of Broadway shows, particularly "The Lion King," comparing it to sports in terms of preparation and performance.
  • Discusses the temptation (and anxiety) of trying to sneak photos during the show ("My heart is starting to race... I can’t get kicked out of my first Broadway show." 16:08–17:33).
• Theater as Athletic Performance:
  • Comparisons between athletes’ routines and stage performers’ demands.
  • Interjects a playful suggestion to unionize for Broadway performer benefits.
• Strength of Live Shows:
  • Syd’s regret at not having experienced more theater sooner; plans to catch up on her theater knowledge.

3. New York Nostalgia & Food Memories

• Hilarious Eating Out Stories:
  • The hosts reminisce about NYC, including outings to a comedy club where they were "held hostage by Dave Chappelle" and late-night ramen at Ichiran ("it's worth the line"—25:50).
  • Syd’s famously picky eating habits and TP’s pride in her culinary adventurousness.
• Friendsgiving Traditions & Red Flags:
  • Both share signature Friendsgiving dishes (TP: smothered green beans; Syd: sweet potato casserole with a pecan topping—37:03).
  • The perils and etiquette of Friendsgiving: food hygiene worries, who gets to eat first, and inheriting the "kids’ table" well into adulthood.

4. Holiday Values & Giving Back

• Angel Tree Projects:
  • TP introduces "Angel Trees," where people anonymously sponsor a family or child’s holiday wishlist at local stores.
  • Advocates for thoughtful, non-material ways to give, especially during tough times.
  • Encourages making kindness and community the center of the holiday season:
    • "If your gift is kindness... just make sure you’re giving this holiday season in any way you can. It’s what makes the world a better place and... builds community." (32:10)
• Social Media & Giving:
  • A nuanced discussion about publicizing charitable acts versus genuine giving.
  • Syd emphasizes the importance of intention and recipient dignity.

5. Games and Segment Highlights

• Family Roleplay – Stirring the Pot:
  • Skits on classic family holiday archetypes: the drunk uncle, the grandma who belittles your job, and more.
  • Memorable Moment:
    • "Your aunt left me."
      TP: "So you’re on the prowl. Single, my man!" (41:12)
    • "Are you still working on that little job?"
      Syd (deadpan): "It’s called the WNBA, Grandma. Stop calling it a little job." (43:43)
• This or That – Thanksgiving Edition:
  • Riff on holiday food preferences, seating politics (kids’ table vs. adult table), leftovers, hosting styles, and the optimal time to eat Thanksgiving dinner.
  • TP confesses her preference for eating at 3 PM: "It carries into the evening of conversation, a few adult beverages, and definite family games and trivia." (50:01)
• Cooking vs. Cleaning:
  • Syd: "I make my sweet potato casserole, then I help with other stuff, but I’m always the person, I’ll start washing dishes... whoever hosted needs to be off their feet." (50:40)
• How to Politely End a Party:
  • Playful mock-dialogues on hustling guests out ("Y’all heading anywhere after this?" 53:28).

6. Current Events: Week in Headlines

• Women in Art:
  • Frida Kahlo’s The Dream (The Bed) sells for $54.7M, setting a new record for a woman artist at auction.
  • Hosts joke about painting their own masterpieces for charity but insist, "If it doesn’t reach $54.7M, I’m not selling it." (47:44)
• NWSL Soccer on the Bay:
  • Congrats to Gotham FC for winning the NWSL Championship in a game played on a pitch beneath the Golden Gate Bridge.
• Celebrity News:
  • Cardi B makes a gold pendant from her baby's umbilical cord (“seemingly affordable for anyone—roughly $500” 49:10).

7. Listener Letters ("Down in the DM"): Surviving Failure

• Anonymous Jennifer’s Dilemma:
  • Freshman engineering student fears failing a class, struggles with perfectionism and how to tell her parents.
  • Warm, affirming advice:
    • TP: "School is about learning about yourself... Give yourself some grace." (57:12)
    • Syd: "F stands for 'figure it out.' You're just figuring it out, babes." (61:24)
  • Emphasis on framing failures as learning experiences and pacing one's own journey.

8. Notes of Gratitude

• Hosts’ Reflections:
  • Both express deep thankfulness for family, friends-turned-family, and—perhaps most tenderly—pets:
    • "I’m most grateful for three little years ago, Yams stumbled into my life on Thanksgiving, which is why her name is Yams." (62:26)
  • Closing challenge to listeners:
    • “Cherish the people that are your blood, family, or friends who became family and just let the people that are in your life, let them know you love them, you care, you appreciate them.” (62:59)

Notable Quotes & Moments

• On Names:
  • TP: "If your namesake is Joy, bring that. If your name is Blessing, be a blessing." (10:59)
• On Broadway’s Physicality:
  • Syd: "What kind of core engagement you gotta have? ...How are they this synchronized?" (14:35–22:21)
• On failing a class:
  • TP: "Frame it properly... I had a learning experience. I failed a class, and I learned I feel uncomfortable failing. I never want to do that again." (58:54)
• This or That—food edition:
  • Syd: "Sweet potato pie." (52:10)

Key Timestamps for Major Segments

• Thrift Shop/Joy Story: 00:06 – 10:59
• Broadway Adventure & NYC Trip: 12:12 – 22:56
• Friendsgiving Dishes & Red Flags: 36:47 – 38:13
• Angel Tree & Holiday Giving: 30:52 – 34:23
• Family Roleplay Skits ("Stirring the Pot"): 40:14 – 44:40
• Week in Headlines: 44:40 – 49:12
• Thanksgiving "This or That": 49:36 – 55:51
• Listener DM – "Anonymous Jennifer": 56:19 – 62:16
• Closing Gratitude: 62:26 – 63:27

Summary Takeaway

This episode is classic Syd and TP—hilarious, chaotic, heartfelt, and always delivering nuggets of wisdom between playful jabs. They cover everything from petty thrift shop rivalries and deeply nostalgic NYC trips to the challenges of adulting and the profound rewards of giving. The laughter is infectious; the life advice is practical and sincere. And above all, they celebrate the holiday season as a chance to lean into community, kindness, and connection—encouraging listeners to "throw kindness around like confetti." (63:27)

For anyone needing a dose of joy (or a reminder of what that really means), "Unsupervised" continues to deliver.