Unsupervised with Syd & TP

Episode Title: Happy Halloween Boo!
Release Date: October 30, 2025
Hosts: Syd Colson & Theresa Plaisance (TP)
Podcast: Dear Media

Episode Overview

This Halloween special is classic "Unsupervised": unpredictable, irreverent, and full of best-friend chaos. Syd and TP surprise each other with costumes, dive into Halloween nostalgia, swap wild childhood stories, debate the best (and worst) Halloween candies, riff on music, bicker over true crime vs. scary movies, and close out with heartfelt (but hilarious) life and dating advice to a listener. Through it all, their chemistry and unscripted tangents keep things zany and fun—like a late-night group chat you never want to leave.

1. Halloween Costume Reveal (00:00–05:16)

• Big Reveal: Syd and TP attempt a simultaneous costume unveiling, after hyping up their surprise for each other (and “threats to quit the pod” if they can’t guess right).

  • TP goes as the Mona Lisa, complete with a makeshift picture frame.

    “I'm straight from the Louvre, baby. Mona Lisa is here with you.” – TP (02:08)

  • Syd is “Martin” from the sitcom episode where Martin thinks someone stole his CD player, complete with a blurred cam and mustache.

    “Call, sit your five dollar ass down before I make change. You know, do you know what it is?” – Syd (02:53)

• Instant Confusion: TP doesn’t recognize Syd’s reference; Syd threatens to quit due to this “cultural difference.”

• Hilarity Ensues: The costumes generate genuine laughs; TP references a previous TV episode dressing as a “Victorian white woman,” while both poke fun at each other’s ingenuity and dedication.

2. Childhood Halloween Memories & Family Traditions (07:46–15:17)

• TP’s Story:

  • Grew up with lots of cousins in a close-knit neighborhood.
  • They’d all meet at grandma’s house to trick-or-treat.
  • “We weren't big into scary trick or treating. It was more like just dress up in your favorite things.” – TP (09:14)
  • TP shares a photo of herself as a pirate. Syd quips, “You look like Kid Rock dressed up as a little kid being a pirate.” (09:48)
  • TP’s mom was strict about candy: only allowed to keep two pieces, so she hid the good stuff.

    “We started hiding the candy instead of keeping it in the bucket.” – TP (11:19)

• Syd’s Story:

  • Syd never really celebrated Halloween as a kid; her mom says it was out of “fear, simple.” (11:45)
  • Conversation with her mom (via formal text exchange) reveals she also associated Halloween with potential darkness and danger.

• Parental Halloween Paranoia:

  • Both recall parents warning about candy tampering (“razor blades stuffed in Tootsie Rolls”).
  • Syd jokes, “I have a deep mistrust for everything and everyone, but I play it off real cool.” (13:49)

• Neighborhood Dentist Story:

  • TP recalls getting “a dentist pack” instead of candy from a neighbor—much to their chagrin.

3. Halloween Activities: Pumpkin Carving, Bobbing for Apples, Haunted Houses (31:09–36:35)

• Both hosts reminisce about classic school Halloween games—pumpkin carving (“incredibly dangerous, parents watch your kids!”) and bobbing for apples (gross in hindsight).
• TP tells a haunted house story from college basketball pre-season (32:02), where the entire team went to a top-rated haunted house in Baton Rouge to avoid next day’s conditioning. One teammate was so scared she puked on someone and had to be medically removed.

  “If we have to run tomorrow, we're going to kill you.” – TP (34:54)

• Syd describes going to a haunted house as an adult, but only if the actors can’t touch you. She draws the line at waivers and physical contact.

4. Halloween Media Classics & Movies Debate (16:06–28:56)

• TP’s Faves:

  • TP and family were not into scary Halloween; more about fun and costumes.
  • Shares nostalgia for “Hocus Pocus” (17:13–17:56), “Halloween Town” (18:05–18:28; laments unnecessary sequels), and “Mom’s Got a Date with a Vampire” (18:41–19:37).

• Scary vs. Silly:

  • Both hosts share their feelings about horror:
    • TP dislikes visceral horror but likes true crime (“Don’t chop anybody’s arm off…definitely don’t do an exorcism… I could do without” – 25:01).
    • Syd enjoys true crime as well; finds the reality scarier than fiction:

      “No, it's actually Benjamin from next door that you had no idea was cutting up people and putting them in his freezer.” – TP (25:48)

• True Crime & Distrust:

  • Both riff on what Dateline reveals about “average people” being dangerous, and the underrepresentation of Black families in true crime narratives.
  • Syd tells a story of TP taking quarters with her into the bathroom, as a joke about trustworthiness among friends.

5. Candy Nostalgia: Best and Worst Treats (45:22–54:30)

(“This or That: Candy Edition”)

Rapid-Fire Candy Debates:

• Fun Dip vs Pixie Stix

  • TP: “Fun Dip all day.” Syd prefers Pixie Stix. (45:47–46:39)

• Dunkaroos vs Wonder Ball

  • TP: “Wonder Ball was so underwhelming…Dunkaroos, 1000%.” (45:52)

• Altoid Sours vs Retro Sours

  • TP prefers the variety of Altoid Sours, especially the mango/tangerine. (47:04)

• Granny Edition: Butterscotch vs Strawberry Bonbons

  • Both ultimately side with the strawberry bonbons (the ones in strawberry wrapping).

• Ring Pops vs Push Pops

  • Syd: “Push pops. I like seeing it get smaller…making it into a needle or sword and stab somebody…” (49:34)

• Gushers vs Fruit by the Foot vs Fruit Roll-Ups

  • Syd: Fruit Roll-Ups win for nostalgia and variety, especially the peel-apart, tattoo, and tie-dye variety. TP likes tie-dye as well, but Syd prefers single flavors. (50:25–51:42)

• Sour Skittles/Sour Patch Kids/Sour Punch Straws

  • Syd overrules the debate and champions Sour Punch Straws, ranking flavors and recalling snacking and using them as drink straws. (52:12–53:20)

• Candy Jewelry vs Candy Cigarettes vs Smarties

  • Syd: “Not a fan of any…going with Smarties.” TP recalls candy cigarettes for their "smoke" effect. (53:32–54:26)

6. Halloween-Adjacent Tangents

• NBA City Edition Courts: (36:44–41:14)

  • Minnesota Timberwolves pay tribute to Prince; the Lynx once celebrated at his place.
  • They joke about what a New Orleans or Houston city edition court would look like (“voodoo theme”, “NASA/strip club/purple syrup collab”).

• Music:

  • Michael Jackson “Thriller” Debate (41:22–44:46):
    • TP shocked that “Thriller” is only #22 on Halloween song charts.
    • Both agree nothing beats MJ for Halloween or pop music.

      “Stop trying to compare Michael Jackson to, like, people of today's time. Nobody is or will ever be like Michael Jackson in status.” – Syd (42:51)

7. Listener Advice: It Goes Down in the DM (57:24–66:09)

• Listener Message: “Jennifer” asks for dating advice as a self-described “elder millennial lesbian” frustrated with apps, local events, and societal pressures.

• Advice Highlights:

  • Syd: Prioritize self-love; learn to enjoy being alone so partners are “additions not necessities.”

    “If people aren’t adding something to your life…they shouldn’t be taking from you.” – Syd (60:00)

  • TP: Comfort with yourself is a muscle—practice it. Social media creates false expectations; don’t compare your timeline to others.
  • Both: Communicate, notice red flags, run your own race, don’t rush relationships just for the optics.

• Memorable Exchange:

  • “If you are wanting a relationship for the pictures, don't get in that relationship at all. Take not a good sign a picture. It's not worth it, bro.” – TP (65:32)

8. Notable Quotes & LOL Moments

• “Like a 2 a.m. group chat you accidentally walked into. You'll be glad you stayed.”
• TP: “We weren't down for the scary at all.” (09:14)
• Syd: “My mom instilled a sort of paranoia in me…all my warnings…my mom did this to me.” (13:32)
• TP (on haunted house): “One of my teammates pukes on the back of somebody. That person had to be medically removed from the haunted house.” (34:52)
• Syd (on true crime): “No, it's actually Benjamin from next door that you had no idea was cutting up people and putting them in his freezer.” (25:48)
• TP: “I like making [push pops] into a needle, like, you can make it…a sword and stab somebody.” (49:44)
• Syd: “This is so funny for me to be giving this advice as Martin…2 Mona Lisa, with my Rottweiler.” (59:40)

9. Episode Timestamps for Key Segments

• Costume reveal & riffing: 00:00–05:16
• Childhood Halloween Stories: 07:46–15:17
• Pumpkin Carving, Bobbing for Apples, Haunted Houses: 31:09–36:35
• Halloween Movies & True Crime: 16:06–28:56
• Candy Nostalgia (This or That): 45:22–54:30
• Music Tangent, “Thriller” soapbox: 41:22–44:46
• Listener DM (Dating Advice): 57:24–66:09

10. Closing & Final Thoughts

• Lots of love and humor for their “babysitters” (listeners).
• Joke about starting an annual Unsupervised Halloween Party.
• PSA: “Check that candy for razors and syringes.” (66:18)
• Playful sign-off: “Throw around kindness like confetti!” – TP (67:01)

Summary

This episode brings all the chaos, fun, and warmth of Syd & TP’s friendship to a Halloween backdrop. From costume antics to nostalgia, honest advice, biting commentary on pop culture, and surprisingly profound dating insights, it’s a rollicking hangout for anyone missing the wild, supportive energy of a best friend sleepover.

Happy Halloween from Unsupervised!

Listen if you enjoy:

• Unpredictable, hilarious banter
• Wild tangents that eventually circle back
• Real-life friendship and heartfelt life advice

Catch the next episode or DM your questions to @unsupervised.syd.tp!