Brooke and Jeffrey: Second Date Update

Episode: Awkward Tuesday: Buddy Roommate Sitch

Date: October 14, 2025
Podcast Host: iHeartPodcasts

Episode Overview

In this hilarious and cringe-worthy episode of "Awkward Tuesday," Brooke, Jeffrey, and the rest of the team take on a sticky roommate situation submitted by listener Chris. After graciously letting his buddy Ethan crash at his place following a breakup and job loss, Chris is left wondering how to address his friend’s freeloading ways—without torpedoing their friendship. The segment explores themes of boundaries, friendship, entitlement, and adulting, all with Brooke and Jeffrey's signature witty banter.

Key Discussion Points & Insights

Introducing Chris’s Dilemma

Timestamp: 04:27 – 10:41

• Chris took in his friend Ethan, who was down on his luck, into his spare room.
• Ethan has been living rent-free for four months, now has (only) a part-time job, but hasn't contributed to rent, groceries, or cleaning.
  • Chris: "He’s been eating all my groceries..." [07:53]
  • Brooke: "Has he offered to help chip in?" [07:35]
• Chris never set a concrete pay-back agreement, just said, "When the time comes, maybe help out."
• He feels guilty bringing it up but is becoming increasingly resentful and stressed by Ethan’s lack of help.

Hosts’ Reactions & Advice

Timestamp: 10:41 – 13:32

• Brooke suggests a "cooling off" period (inventing a visiting nephew) to get space before a hard talk—but Jeffrey basically vetoes dodging the issue.
  • Jeffrey: “So it sounds like again, Brooke, your advice is to not make the Awkward Tuesday Phone Call in this segment...” [12:20]
• Jose proposes blaming the landlord: say the landlord spotted Ethan and now needs him on the lease, which means rent discussions.
• Alexis jokes that her approach was simply “suffer in silence”—not recommended.

The Awkward Tuesday Phone Call: Confrontation in Real Time

Timestamp: 13:32 – 20:44

The Call Begins

• Chris calls Ethan at work, who instantly asks if Chris can Doordash him pizza to Chris's own apartment.
  • Ethan: “Could you, could you still like doordash from your phone? Would that be cool?” [14:07]
• Chris, clearly frustrated, explains that he feels taken advantage of and wants Ethan to contribute.

Ethan Flips the Script

• Ethan is baffled, defending himself by saying Chris makes more money and “said he’d take care of everything.”
• Then Ethan ups the ante: “How much money do you actually make? ... I came across some of your bank statements… Those numbers were ginormous.” [16:10]
  • Chris is appalled that Ethan went through his personal documents.
  • Brooke (jumping in): “Why are you going through his bank statements?” [17:48]
• Ethan takes entitlement to the max: “If you want to come at me asking for money, you should be making less than $200,000 a year.” [17:03]

The Hosts and Chris Respond

• The cast is floored that Ethan thinks Chris’s salary excuses any responsibility.
  • Brooke: “You’re not his like sugar baby, dude.” [18:22]
  • Jeffrey: “Sugar buddy—is that a thing?” [18:27]
• Chris points out Ethan's egregious habits: “You used my toothbrush and then told me to go to the store and get more.” [18:32]
• Ethan’s response: “Honestly, it feels weird that he’s not paying for more. We should have a better apartment. This apartment is crappy.” [18:57]
  • Brooke: “Probably why he has money.” [19:39]

The (Sort-of) Resolution

• Chris, using Jose's advice, claims the landlord requires Ethan on the lease—therefore Ethan must pay rent and contribute more. Ethan grudgingly agrees but demands the “bigger room.”
• Both reluctantly agree to discuss with the landlord and work something out.
  • Chris, trying to keep things friendly, says he didn't bring girls over out of respect, but will this weekend.

Notable Quotes & Memorable Moments

• On entitlement:
  • Ethan: “If you want to come at me asking for money, you should be making less than $200,000 a year.” [17:03]
• On boundaries and groceries:
  • Chris: “You used all my toothbrush and then you had the audacity to tell me to go to the store and get some more.” [18:32]
• On friendship:
  • Chris: “If the roles are reversed ... I wouldn’t ask you for a single dime.” [19:10]
• Brooke’s reality check:
  • Brooke: “You’re not his like sugar baby, dude.” [18:22]
  • Jeffrey: “Sugar buddy—is that a thing?” [18:27]

Hosts’ Takeaways & Wrap-up

Timestamp: 22:24 – 23:31

• The hosts joke that Chris might end up calling back a year from now with Ethan still living with him.
• They agree Ethan needs to take more responsibility and not just mooch off friends with bigger paychecks.
  • Brooke: “Find a girlfriend that’s making money so he can mooch off of her... poor Chris isn’t getting any bennies from this relationship.” [23:14]
  • Jeffrey: “Ethan just wants to keep living that sugar buddy life. And I’m all for it.” [23:26]
• They reiterate: If you want help with your own awkward call, the show’s always open for submissions.

Key Timestamps

| Segment | Timestamp | |----------------------------------------|-------------| | Chris’s Situation Introduction | 04:27–10:41 | | Hosts' Advice & Joking | 10:41–13:32 | | The Phone Call Itself | 13:32–20:44 | | Post-Call Analysis & Jokes | 22:24–23:31 |

Conclusion

This episode is a perfect comedy-of-errors about the dangers of mixing friendship and finances—and what happens when boundaries aren’t set from the start. Chris’s polite heart runs headlong into Ethan’s epic entitlement, all under the gleeful scrutiny of Brooke and Jeffrey’s panel. The outcome: no clear solution, a lot of laughs, and a new term (“sugar buddy”) coined live on radio.

If you're dealing with roommate freeloaders—or just want a good cringe-laugh—this episode is a must-listen.