Brooke and Jeffrey: Second Date Update

Awkward Tuesday: Never Hire Friends

Release Date: September 16, 2025
Host: Brooke & Jeffrey || Guests: Kristen, Matt

Episode Overview

The central theme of this episode is the classic dilemma of mixing friendship and business. The listener, Kristen, finds herself deep in regret after pulling strings to hire her best friend Matt as her assistant. Three years later, the situation has devolved—Matt is underperforming and their friendship is suffering. Kristen seeks help from the Brooke & Jeffrey team to navigate a delicate, and very awkward, conversation: how to push her best friend to move on from his cushy, underwhelming role—without ruining the friendship.

The story unfolds in classic "Awkward Tuesday" fashion, culminating in a big twist that nobody saw coming.

Key Discussion Points & Insights

1. Setting the Stage: Regrets About Hiring a Friend (04:54–06:45)

• Jeffrey observes the perils of blending personal and professional life.
  "Are there any warnings about don’t hire your friends to work with you at your company?" (06:26)
• Brooke delivers the classic wisdom:
  "'Friends and business don't mix.' That is literally the saying." (06:31)
• Kristen emails in because she ignored this rule—she not only got her best friend a job but made him her assistant.

2. Kristen’s Backstory: How It All Went Wrong (07:02–10:47)

• Kristen explains she's been at her company seven years and brought in Matt after her assistant quit, stipulating they hide their friendship.
• The plan: Matt would use the assistant job as a stepping stone, then transfer.
• The reality: "That was three years ago, and he’s still my assistant." (09:29)
• The toll: Matt has grown complacent, regularly skipping meetings and neglecting tasks.
  "He’s gotten in a pattern of skipping meetings or taking long lunches or forgetting to do little tasks." (09:43)
• Kristen admits: "Yo, it is horrible." (09:32)

3. The Hosts Weigh In: How to Break the News? (10:47–14:44)

• Panel debates whether Kristen should speak to Matt as a boss or as a friend.
• Brooke suggests focusing on Matt’s financial interest:
  "'You deserve more money. Everybody wants more money...We are going to find you a better job and we are going to get you paid.'" (13:43)
• Jeffrey and Jose recommend using humor and emphasizing that a change will benefit their friendship, referencing the old adage: "Absence makes the heart grow fonder."

4. The Awkward Tuesday Phone Call (15:16–20:15)

• Kristen nervously calls Matt while he’s on the job, and the following gems are exchanged:
  • Matt: "I am your assistant, you know. If you remember. You do have to tell me things." (15:35)
  • Kristen tries to broach the subject tactfully, and Matt initially worries it’s about missing a meeting. She builds up to her point:
    • "You need to go out there. You need to be making more money." (16:54)
• Surprise TWIST:
  Matt confesses: he’s been interviewing for the Director of Business Development—a role that would make him Kristen’s superior and pays more than her current job!
  • Matt: "I'm actually in the final interviews for the Director of Business Development...I just didn't know really how to go about, you know..." (17:01)
  • Kristen is floored: "Who is my assistant is going to be...you’re going to be my superior. That’s what’s happening right now." (18:52)
• The hosts jump in to clarify the situation (and Matt’s confusion that he’s on radio!) and everyone processes the dramatic news together.

5. The Meta-Awkward Resolution (20:15–21:54)

• Both acknowledge the working relationship had grown stale, and Matt claims:
  "I just feel like it was starting to get a bit stale. Like even our relationship, our friendship dynamic, I really just needed a place to grow and I just feel like I wasn’t really growing anymore with you as my boss." (20:15)
• Kristen, stunned, decides she needs to take the rest of the day off to process it all. Matt offers to buy drinks in celebration:
  "We have drinks to get and celebrate and you know." (21:15)
• Brooke quips: "Well, drink’s on Matt this time since he can afford it." (21:24)

Notable Quotes & Memorable Moments

• Brooke (on classic friendship/business wisdom):
  "Friends and business don't mix. That is literally the saying." (06:31)
• Kristen (on her ongoing hell):
  "Yo, it is horrible." (09:32)
• Matt (realizing change is coming):
  "Girl, I don't like the tone of your voice right now." (16:21)
• Matt (revealing the twist):
  "I'm actually in the final interviews for the Director of Business Development." (17:01)
• Kristen (stunned):
  "Did we break her Swayze? … I'm shaking over here." (21:03)
• Brooke (wrapping up):
  "Well, drink's on Matt this time since he can afford it." (21:24)

Key Segment Timestamps

• [04:54–06:45] – Introduction of the friend hiring dilemma; developing the theme.
• [07:02–10:47] – Kristen details the history and breakdown of her working friendship.
• [10:47–14:44] – Host panel offers advice on how to “break up” work-wise but save the friendship.
• [15:16–20:15] – The Awkward Tuesday Phone Call: confrontation, confession, and the twist.
• [20:15–21:54] – Aftermath, processing, and attempts at closure.

Takeaways

• Even the best intentions in mixing friends and business can backfire—often in ways nobody expects.
• Direct communication, approached with kindness and an eye for both parties’ best interests, is essential but not always easy.
• Sometimes, problems resolve themselves—in this case with a surprising promotion.
• The Brooke & Jeffrey team highlights how awkward conversations, when aired out with a little humor and authenticity, can end up strengthening relationships rather than breaking them.

Episode Tone

Light, comedic, and full of the playful banter that typifies Brooke & Jeffrey’s style—even as they tackle the real anxieties and complications of life, work, and friendship.

This summary covers all major discussion points, pivotal exchanges, and the memorable, twist ending. Listen for candid, relatable confessions—and that signature Brooke & Jeffrey blend of heart and humor.