Brooke and Jeffrey: Second Date Update

Episode: Awkward Tuesday: Calling The Other Woman

Release Date: August 19, 2025
Podcast by: iHeartPodcasts

Main Theme & Purpose

This episode centers around an “Awkward Tuesday” phone call, where a listener named Sean enlists the show hosts—Brooke, Jeffrey, and their team—to help him deliver a tough truth to another woman. After being left by his girlfriend Nicole for another man, Sean discovers that Nicole’s new partner, Mitch, is also in a relationship. Sean wants to warn Mitch’s girlfriend, Michelle, potentially blowing up two relationships in the process.

The purpose: To explore what happens when someone, hurt by infidelity, takes it upon themselves to warn another possible victim—live, awkwardly, and with a lot of moral ambiguity, on the radio.

Key Discussion Points & Insights

1. Sean’s Relationship Fallout

(Starts ~04:13)

• Sean and Nicole (previous “Second Date Update” couple) dated for three months. Nicole moved in after just one month.
• Sean comes home to find Nicole gone, his front door left open, and a handwritten note:

  “I feel awful that I couldn’t tell you this in person, but I met someone else. You’re a great guy. I’m so sorry.” — Nicole’s note [06:38]

• He's left in shock and with unanswered questions.

2. Sean’s Investigation

(06:58–09:51)

• Nicole stops responding to all texts, calls, and DMs.
• Sean goes to her workplace, sees her get out of a pickup truck, kissing a new man—Mitch.
• Out of hurt (and a little obsession), Sean follows Mitch to his home, notes his address, and discovers through social media sleuthing that Mitch has a serious girlfriend, Michelle.

  “This guy named Mitch… I found his Instagram, and he has a girlfriend. Not Nicole. A different girl.” — Sean [09:28]

3. Should He Make the Call?

(10:12–12:32)

• The team debates whether it's right for Sean to tell Michelle about the alleged cheating.
• Brooke and others bring up the risk of misunderstandings and jumping to conclusions.
• The radio hosts and producers ultimately encourage Sean to make the call, mainly for “ratings reasons,” openly admitting to the entertainment value:

  “I want to do this just for a pure ratings reason… I think it’s just interesting to hear.” — Jeffrey [10:27]

4. The “Awkward Tuesday” Phone Call

(13:14–17:23)

• The hosts coach Sean on how to approach Michelle, suggesting he impersonate one of Mitch’s coworkers for credibility.
• Sean places the call, awkwardly tries to hint that Mitch is “going home for romance” on his lunch breaks and returning to work with a grin, but Michelle is confused and skeptical.
• Eventually, Sean bluntly implies:

  “I think he’s donating to my ex-girlfriend.” — Sean [17:14]

• Michelle is flabbergasted, the execution is messy, and the hosts can’t help but laugh at the trainwreck.

5. Full Reveal & Michelle’s Reaction

(17:36–21:13)

• The hosts interrupt and reveal to Michelle that she’s on a radio show, and summarize the story directly.
• Sean takes the line and tells Michelle directly what he saw. Michelle is, at first, incredulous:

  “I’m finding this very hard to believe... having some random person call me through the radio and make these wild accusations which cannot be true.” — Michelle [18:41]

• Brooke gently advises:

  “Maybe this will lead to some conversations that you should have with your boyfriend Mitch about where you guys are at in your relationship.” — Brooke [18:49]

• Michelle tentatively agrees to meet Sean and check out the supposed evidence for herself:

  “I need to figure this out for myself, whether it’s true or not... Give me the address. Yeah, we’re going stalking.” — Michelle [20:06]

6. Aftermath & Lack of Closure

(23:36–24:48)

• The hosts did not hear back from either party, joking about possible outcomes: maybe nothing was wrong, maybe they all broke up, maybe everyone just wants to forget about it.
• The episode closes with banter: “You’re either a cheater, why would you want to revisit that?” — (Brooke/Jeffrey) [23:59]
• Listener comments urge for an update and joke about the “cheated-on” parties getting together out of pettiness.

Notable Quotes & Memorable Moments

• Brooke: “Even cheaters hate cheating. It’s weird, right?” [03:12]
• Jeffrey (about Sean’s sleuthing):
  “He went to his house and I wrote his address down.”
  — Sean, with the hosts joking uncomfortably about how “creepy” it is [08:53]
• Advice from the hosts:
  “If you want to sound believable, you can’t be yourself. What if you come across as a scorned ex?” — Jeffrey to Sean, suggesting impersonation [12:32]
• Sean’s awkward call:
  “Maybe you mean he had a great lunch and it’s affecting his work... Whatever you’re doing to entice Mitch to come home with you for, you know, romance, good loving, whatever, he’s not doing his job.” [15:33–15:48]
• Michelle’s incredulity:
  “I have my own job. I literally could not do that. That’s certainly interesting because you think he might be meeting someone else.” [15:54]
• Comic relief after the messy call:
  “That conversation couldn’t have gone worse.” — Jeffrey [17:25]
• Host’s dry humor:
  “That’s an invitation you won’t find on a Hallmark card.” — Jeffrey, after Sean suggests Michelle and he should stake out Mitch’s lunch spot together [19:13]
• Listener comment referenced on-air:
  “Someone did say that they think the two callers should get together. The two people both being cheated on. That would be… But that’s more petty to get back at people. You know what I mean?” [24:23]

Timestamps for Key Segments

• 03:24: Sean finds his apartment empty and Nicole gone
• 06:38: Sean reads Nicole’s breakup note
• 07:55: Sean discovers Mitch and starts sleuthing
• 09:28: Sean finds out Mitch has a girlfriend
• 10:12: Discussion about whether to call Michelle
• 13:07: Hosts strategize with Sean on how to make the call
• 14:35: Awkward call to Michelle begins
• 15:33–15:48: Sean’s failed innuendos about Mitch’s lunch breaks
• 17:36: Hosts break in and clarify the call for Michelle
• 18:41: Michelle’s denial and pushback
• 20:06: Michelle reluctantly agrees to investigate
• 23:36: No closure; hosts discuss possible outcomes and share listener feedback

Episode Tone

• Playful, irreverent, and empathetic—basketballing between humor, awkwardness, and moments of real compassion.
• The hosts lean into the “awkward” with comic relief, while still thoughtfully encouraging honesty between partners.
• Candid about the show’s entertainment value, yet still hoping for a genuine resolution for those involved.

Summary

In “Awkward Tuesday: Calling The Other Woman,” Brooke, Jeffrey, and friends orchestrate an uncomfortable but gripping confrontation. Betrayed by his girlfriend Nicole, Sean uncovers a web of infidelity involving Nicole’s new boyfriend and his own girlfriend. Wrestling with whether to expose the other couple, he makes an awkward call to Mitch’s girlfriend Michelle, coached and supported (and roasted) by the show’s hosts. After a series of cringe-worthy communication failures, the truth comes out, and Michelle decides to see for herself.

Listeners are left with suspense—no tangible update on what happened next, but plenty to debate about trust, revenge, and how far you should go to “warn” someone else about a cheating partner. The episode wraps up with jokes, reflections, and a reminder that—sometimes—the messiest stories don’t end with closure.

For more “Awkward Tuesday” moments, check out the full show on iHeartRadio.