Podcast Title: Brooke and Jeffrey: Second Date Update
Episode: Awkward Tuesday: I Want To Date My Friend's Ex
Host/Author: iHeartPodcasts
Release Date: June 10, 2025

Introduction

In the June 10, 2025 episode of Brooke and Jeffrey: Second Date Update, titled "Awkward Tuesday: I Want To Date My Friend's Ex", hosts Brooke and Jeffrey tackle one of the most delicate dilemmas in the realm of modern friendships and dating. This episode delves into the complexities of navigating romantic interests that intersect with existing friendships, providing both entertaining and insightful perspectives for listeners who might find themselves in similar situations.

Listener Interaction: Celebrating Milestones

Before diving into the central topic, Brooke and Jeffrey engage with their listeners, highlighting a heartfelt message from Jen590:

• Jen590: "I've been listening to you guys since my freshman year and now I'm a high school graduate. Can't wait for another four years of laughs with y' all in college. He, I hope you take us to so many college parties. Please. I would like to go back to some frat parties." ([04:20])

This interaction sets a warm, community-focused tone, emphasizing the podcast's role in listeners' lives.

Main Segment: Monica's Dilemma

Monica's Situation

The core of the episode revolves around a listener named Monica, who reaches out with a challenging predicament:

• Monica: "I want to date my friend's ex-boyfriend." ([07:12])

Monica grapples with the unspoken rules of friendship, seeking advice on how to approach her friend Erin for permission before pursuing a relationship with Erin's ex, Ben.

Hosts Discuss Friendship Rules

Brooke and Jeffrey explore the traditional and often unwritten rules that govern friendships, particularly regarding romantic relationships:

• Jeffrey: "But honestly, would you?" ([04:56])

• Brooke: "You don't ever date your friend's ex. It's just. What? You just. You just don't." ([07:50])

These discussions highlight the tension between personal desires and maintaining harmonious friendships.

Advice from Brooke and Jeffrey

The hosts offer Monica various strategies to navigate her situation:

1. Brooke's Strategy: Compliment and Sympathize

   • Brooke: "You need to maybe speak on how easy it is for her to get a man and how charismatic and beautiful she is and how maybe it's not quite as easy for you." ([13:15])

2. Jeffrey's Suggestion: Self-Deprecation and Distraction

   • Jeffrey: "Paint her with the pathetic brush." ([14:07])

3. Additional Insights: Keeping an Open Mind

   • Brooke: "Maybe your friend isn't that close with you. Like, maybe it's like a friend, like a co-worker." ([08:37])

These approaches aim to help Monica present her intentions thoughtfully while respecting her friend's feelings.

Making the On-Air Call

Determined to handle the situation correctly, Brooke and Jeffrey support Monica as she makes an on-air call to Erin:

• Monica: "I want to ask my friend a very controversial question that could easily throw a wrench into their relationship." ([05:19])

During the call, Monica attempts to convey her feelings and seek Erin's blessing to date Ben. The interaction unfolds as follows:

• Monica: "I noticed you were talking to that, like, really tall guy." ([16:12])
• Erin: "Oh my God. No, no, no. We just like, we made out a little bit. But nothing happened." ([16:26])
• Monica: "So the guy that I'm kind of talking to is your ex." ([17:53])
• Erin: "I think you just need to pick me or him." ([20:35])

Conflict and Resolution

The conversation becomes tense as Erin expresses her discomfort with Monica dating her ex:

• Erin: "I think you need to pick. I think you just need to pick me or him." ([20:35])
• Monica: "I really don't think that I could." ([14:43])
• Brooke: "I mean, no, I wouldn't either. I wouldn't give it either. It sounded like you were gonna cheated. He's a gross dude." ([19:47])

Ultimately, Erin declines to give her blessing, prompting Brooke and Jeffrey to reflect on the complexities of such situations.

Conclusion and Reflections

Brooke and Jeffrey wrap up the episode by acknowledging the awkwardness and emotional weight of Monica's situation:

• Jeffrey: "It's awkward Tuesday phone call. Cool people let their friends date their exes, and we're about to find out if Monica's friend is cool." ([12:11])

They emphasize the importance of communication and respecting boundaries within friendships, even when emotions run high.

Additionally, they tease a potential follow-up, mentioning that their producer reached out for updates, keeping listeners engaged and invested in Monica's story.

Notable Quotes with Timestamps

• Brooke on Asking for Permission:
  "I mean, not a great move, but you're doing it in the right way." ([10:29])

• Jeffrey on Friendship Sacrifices:
  "What are the unspoken rules of friendship? No, everybody else, not those ones." ([05:54])

• Monica on Breaking Rules:
  "I want to date my friend's ex-boyfriend." ([07:12])

• Erin on the Relationship:
  "He's a gross dude. Like you don't care about him. Yeah, let somebody else take the leftover." ([19:47])

Final Thoughts

This episode of Brooke and Jeffrey: Second Date Update masterfully blends humor with genuine emotional discussions, offering listeners both laughter and relatable content. Through Monica's story, the hosts explore the delicate balance between pursuing personal happiness and maintaining meaningful friendships, providing valuable insights for anyone navigating similar romantic and social challenges.

Stay Connected:
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