Podcast Summary: Brooke and Jeffrey – Second Date Update

Episode: Awkward Tuesday: Dark Side of the Costume Contest
Date: October 28, 2025
Host: iHeartPodcasts

Main Theme / Purpose

In this special Halloween-themed Awkward Tuesday episode, the Brooke and Jeffrey team helps listener Darius navigate a tricky situation involving friendship, costumes, and money. After lending his creative Darth Vader T-Rex costume to his friend Sharice for a Halloween contest—which she (or rather, her cousin) won—Darius feels he deserves a share of the $500 prize. The episode explores the awkwardness of mixing money with friendship, especially when unexpected twists come into play.

Key Discussion Points & Insights

1. Darius’s Halloween Dilemma

• Darius, a self-proclaimed Halloween enthusiast, explains (05:49) how he created a unique costume: an inflatable T-Rex decked out as Darth Vader.
• Unable to attend a downtown Halloween party due to illness, he lends his costume to his friend Sharice so she won’t go without one.
• The costume wins Sharice (or so it seems) the $500 prize in the event’s contest (08:29).

2. Should the Winnings Be Split?

• Darius expresses discomfort with the situation: Sharice never offers to share the winnings despite using his costume (09:10).
• The hosts chime in with sympathy and opinions ("Friends and money is so tricky. It really is." – Brooke, 10:29).
• Darius is unsure how to address the issue without seeming petty, hoping for a fair split (10:21).

3. Advice from the Hosts

• Brooke suggests Darius use the “wild assumption” technique: act as if splitting is already decided, focusing on how they’ll each spend “their half” (13:04).
  • "How are you going to spend your half? This is what I plan to do with my half of the winnings." – Brooke (13:04)
• Jose proposes tugging on Sharice's sympathy by mentioning financial hardship, possibly combined with a sickly cough (13:36).
  • “Maybe cough, like, make it sound more pathetic.” – Brooke (13:43)

4. The Awkward Phone Call

• Darius blends the techniques, congratulating Sharice and immediately implying he plans to use "his half" to pay rent (14:49).
• Sharice laughs it off ("That's hilarious. That's funny. Yeah." – Sharice, 15:05) and later resists the topic (15:28).
• Darius gently presses, explaining he feels their friendship means the win was a team effort (16:08).

5. The Plot Twist: The Cousin Reveal

• Sharice reveals that she also caught Darius’s sickness and ended up lending the costume to her cousin, who actually won the contest (17:14).
  • “I had to let my cousin go in the costume, and she's actually the person that won, so we split the money.” – Sharice (17:21)
• Darius is stunned to learn his costume was ‘sublet’ to someone else, and the winnings already divided (17:40).

6. Debate & Resolution Attempts

• The hosts press Sharice about whether Darius’ effort creating the costume should count for something (18:31).
  • "Darius is the one who put all the effort into putting the costume together, coming up with the idea, buying all the supplies." – Jeffrey (18:31)
• Sharice remains firm, noting there was no prior agreement and the money is already spent (19:05; 18:24).
• Brooke argues that the fairest outcome is that both Sharice and the cousin owe Darius a cut (20:12).
  • "Honestly, though, I think you owe Darius 125. And I think your cousin also owes Darius 125." – Brooke (20:12)
• Sharice offers Darius a partially used $50 Home Depot gift card as consolation (20:39), which Darius accepts (21:01), noting it’s better than nothing.

7. The Hosts’ Reflection

• The team reflects on how friendship and finances rarely mix well, especially when expectations aren't explicitly set (23:06).
  • “When that's the problem, it's difficult for us to tackle.” – Jeffrey (23:06)
• They agree the outcome, though imperfect, might have been for the best, given the cousin's intimidating reputation (23:17).

Notable Quotes & Memorable Moments

• Darius (on his costume):
  "Darth Vader T-Rex outfit mixed together…with a lightsaber and a Darth Vader hat." (07:13)
• Jose:
  "At least split in half or a nice dinner." (08:49)
• Darius (on splitting):
  “I do totally agree with it. And when she won, we both were very happy…but she didn't offer me anything.” (08:52)
• Brooke:
  “Friends and money is so tricky. It really is.” (10:29)
• Brooke (on tactics):
  "I want you to just make the call with the wild assumption that you already have it…This is what I plan to do with my half of the winnings." (13:04)
• Sharice (revealing the twist):
  “I actually got sick because of you, so I had to let my cousin go in the costume, and she's actually the person that won, so we split the money.” (17:21)
• Brooke (proposal for fairness):
  "I think you owe Darius 125. And I think your cousin also owes Darius 125." (20:12)
• Sharice (final offer):
  "I have a $50 Home Depot gift card. That's the best I can do." (20:39)

Timestamps for Important Segments

• Darius introduces his Halloween predicament: 05:49 – 08:29
• Darius discusses Sharice not offering to split winnings: 08:44 – 10:10
• Host advice session: 12:47 – 14:18
• Awkward phone call with Sharice: 14:31 – 21:04
  • Darius confronts Sharice: 14:49 – 15:56
  • Sharice reveals cousin won the contest: 17:14 – 17:40
  • Debate about fairness and splitting: 18:12 – 20:39
  • $50 Home Depot gift card offer: 20:39 – 21:01
• Hosts reflect and wrap up the call: 23:00 – 23:49

Overall Tone

The episode keeps its classic playful, comedic tone, with the hosts riffing on Halloween, the awkwardness of financial discussions among friends, and the surprise twists in Darius’s story. Both hosts and callers engage in clever banter and supportive humor, with a throughline of empathy for Darius’s awkward position—even if the resolution is a bit underwhelming.

Summary

This Halloween Awkward Tuesday showcases just how complicated costume contests and cash can make friendships. Darius’s joke-turned-awkward request for half the prize money unfolds into a web of germs, cousins, and unexpected cash grabs. The hosts offer both creative and manipulative strategies, resulting in a memorable, laugh-out-loud confrontation that concludes with a compromise—albeit one involving a used Home Depot gift card rather than a cash payout. It’s a quintessential dose of Brooke and Jeffrey: real human dilemmas, ridiculous solutions, and a reminder of just how unpredictable holiday mishaps with friends can be.