Unsupervised with Syd & TP — "Grinch, Gas, & Childhood Lies"
Podcast: Unsupervised with Syd & TP
Host: Dear Media
Episode Date: December 18, 2025
Episode Overview
This episode is a freewheeling blend of humor, nostalgia, and lively debate as best friends Syd Colson and Theresa Plaisance — former pro basketball teammates — veer from rehab routines and queer dating apps to childhood holiday memories and road trip etiquette. True to the podcast's reputation, topics bounce rapidly: from deep dives into reality TV, the psychology of the Grinch, wild travel stories, gas station snacking strategies, and the hot button debate — who really deserves the window seat? Throughout, Syd and TP’s vibrant rapport and relatable stories create an “in-real-life group chat” vibe, leaving listeners both laughing and nodding along.
Key Discussion Points & Insights
1. Discipline, Periods, and Workout Mentality
- (00:00–01:12) Syd opens with candid humor about being on her period while commending herself for sticking to rehab workouts despite discomfort.
- Quote (Syd, 00:31):
"So life is about discipline... Y'all need to have some discipline. If you were supposed to do something today and you didn't do it, shame on you. But do it tomorrow."
2. Fan Love and ‘Babysitters’ Recognition
- (02:11–03:12) The duo reflects on listener support pre- and post-sponsorship, sharing funny stories about being recognized by fans and the joys of community engagement.
- Quote (Syd, 03:09):
"But yeah, it's nice seeing y'all in the wild. Babysitters, we love y'all. Appreciate it."
3. Queer Dating App Chat
- (03:45–05:36) Spotlight on ‘Her’ dating app, the importance of queer safety when traveling, and the hypothetical building of a dating profile for TP, focusing on voice audio as a unique trait.
- Quote (Syd, 04:00):
"Being queer, going into a country, how do people view homosexuality there?... You want to find people who are similar to you."
4. Upcoming Live Show and College Hoops Memories
- (05:47–07:45) Announcement of live taping at Women’s Champions Classic in NYC. The hosts reminisce about their own college basketball experiences and the strict rules (e.g., confiscated cell phones, “basketball jail”).
- Quote (Syd, 07:32):
"You had to, like, turn in your phone the night before the game. I'm just like, is this necessary?"
5. Ink Master Obsession & Tattoo Talk
- (08:19–16:02) TP gushes over reality TV show “Ink Master” and the artistry of tattoos, sparking a debate: neither host has tattoos, but both have strong opinions on styles, preferences, and whether they’d ever get inked.
- Quote (TP, 10:26):
"They're creating things that look like a sticker that you could just peel right off of somebody's body. It's insane."
- Both fantasize about what tattoos they would (or would not) get, leading to discussions about fleeting ideas and ADD.
6. Santa Claus & The Lies of Childhood
- (16:02–21:08) A candid exchange about whether or not they believed in Santa as kids, with TP sharing the devastation of “the talk” from her grandma and Syd staunchly claiming never to have believed, advocating for parents getting credit for gifts.
- Quote (TP, 17:44):
"I'm like, wait, what? What are you talking about, Grandma?... I've been lied to for 11 years."
- Quote (Syd, 19:25):
"I think it's about time we stop acting like Santa is real. It's time to tell kids, okay? They can handle hard things."
7. Holiday Trolley Problem (Game Segment)
- (22:04–24:32) Syd presents a darkly funny “trolley problem” using the Polar Express as a scenario — would you sacrifice a family member or a hundred strangers (who turn out to be January 6th insurrectionists)? TP humorously refuses to play.
- Quote (TP, 24:28):
"I'm cranking that lever the other way. I would jump on that lever."
8. Overseas Hoops Stories: Sparkling Water & Language Fails
- (25:08–29:40) Hilarious tales from their time as basketball pros abroad, including unexpected sparkling water on the sidelines and a mishap-laden translation moment with their anxious Italian team translator, Massimo.
- Quote (TP, 25:55):
"Sparkling water in a basketball game?... I was choking on it."
- Quote (TP, 28:50):
"There were two truths here. He did say it, but in Italian... We didn't end up fighting him, but it was a very uncomfortable moment for everyone involved."
9. Movie Nostalgia: Kicking & Screaming & The Grinch Analysis
- (29:40–39:19) From underappreciated Will Ferrell movies to a deep dive into Jim Carrey’s “The Grinch,” the hosts dissect bullying, outsider narratives, and identify with misunderstood green characters — drawing parallels to “Wicked.”
- Quote (Syd, 34:34):
"The Grinch was never the problem... They created the monster."
- Quote (TP, 36:50):
"Shouldn't have been a big Grinch there. Shouldn't have been a big Grinch there."
10. Middle Seat Debate: Love, Logic, and Chivalry
- (39:35–43:28) Extended riff on viral social media debates about who should sit in the middle seat during travel. Considerations include physical size, chivalry, and relationship dynamics — plus swapping seats for couples or children.
- Quote (Syd, 40:18):
"If a man makes you sit in the middle seat, he doesn't like you..."
- Quote (TP, 41:11):
"Rules should depend... If your boyfriend's 6'8", he should definitely not be in the middle."
11. Exit Rows & Travel Etiquette
- (43:28–48:39) The hosts vent about undeserving passengers in emergency exit rows, the need for “willing and able” seat occupants, and the importance of paying attention to flight safety instructions.
- Quote (TP, 45:14):
"My beef is when there's someone sitting in the emergency exit that doesn't look willing or able."
12. Holiday Road Trips: Shotgun Rules & Passenger Duties
- (49:03–56:08) Best practices for shotgun passengers: bring snacks, manage music and navigation, keep the driver company, and always offer gas money. The pair roast friends who never chip in.
- Quote (Syd, 55:54):
"Offer some gas money, too... For you to never offer is absolutely insane and wild."
13. Weird Food Combos (DM Segment)
- (57:22–61:27) Listeners ask for favorite “weird” food combos. TP defends pineapple pizza (extra pineapple!), while Syd’s go-to is toasted cinnamon raisin bread with cheese and maple-glazed turkey, microwaved just right.
- Quote (TP, 57:56):
"I love pineapple on pizza. Like, I'll get double pineapple on pizza."
- Quote (Syd, 61:37):
"It's so good. I'm about to go buy this stuff now."
Notable Quotes & Memorable Moments
- Syd on discipline: "Life is about discipline. It's not about whether I felt like getting up." (00:31)
- TP on childhood Santa trauma: "I've been lied to for 11 years." (17:44)
- Syd on telling the truth re: Santa: "Enjoy them. That's another thing, because... you're just gonna give us this chubby white dude that's like, coming down the chimney, Right?" (20:01)
- TP on sparkling water in sports: "Sparkling water in a basketball game, like...I was choking on it." (25:55)
- Syd on The Grinch: "The Grinch was never the problem... Y'all did that." (34:34)
- TP on middle seat etiquette: "If your boyfriend's 6'8", he should definitely not be in the middle." (41:11)
- Syd on gas money: "For you to never offer is absolutely insane and wild. You have to know, I'm judging you..." (56:08)
- TP, closing sentiment: "Don’t forget to throw kindness around like confetti." (62:27)
Segment Timestamps
- Opening & Discipline Chat: 00:00–01:12
- Thanking Babysitters/Fan Love: 02:11–03:12
- HER Dating App/Queer Safety: 03:45–05:36
- Live Show in NYC/College Basketball: 05:47–07:45
- Ink Masters/Tattoo Obsessions: 08:19–16:02
- Santa Claus & Lies: 16:02–21:08
- Holiday "Trolley Problem" Game: 22:04–24:32
- Overseas Hoops Tales: 25:08–29:40
- Kicking and Screaming/Grinch Deep Dive: 29:40–39:19
- Middle Seat/Plane Travel Etiquette: 39:35–43:28
- Exit Row Rants: 43:28–48:39
- Road Trip Rules & Gas Money: 49:03–56:08
- Weird Food Combos (DM): 57:22–61:27
Tone & Vibes
- Playful, irreverent, and honest, Syd and TP exchange rapid-fire jokes and realness while seamlessly blending humor and serious advice. The episode is full of “let’s-just-say-it” moments, with the energy of a boisterous 2 a.m. text thread between close friends.
Summary for New Listeners
If you’ve never listened before, this episode is a standout example of why “Unsupervised” works: The hosts’ chemistry makes even the most random topics (e.g., sparkling carbonated water during a pro basketball game, or the psychological roots of the Grinch’s misanthropy) entertaining and relatable. Whether dissecting pop culture or real-life dilemmas, Syd and TP’s banter is both unhinged and insightful — always landing on the side of “what would your group chat say?” Listeners walk away with laughs, useful (if quirky) travel rules, and the reassurance that sometimes the best conversations are the ones that don’t stay on topic.
Final Thoughts
- Syd: “Great episode, TP. Proud of you.”
- TP: “Proud of you, Sid. You’re still hella funny.” (61:46)