Brooke and Jeffrey: Second Date Update

Episode: Say Yes To The Ex: You Remind Me

Date: September 11, 2025
Podcast: Brooke and Jeffrey
Host: iHeartPodcasts

Episode Overview

In this heart-thumping “Say Yes to The Ex” edition of Second Date Update, Brooke and Jeffrey help listener Evan reconnect with his ex, Abby. Evan’s relationship crashed and burned after a disastrously public breakup—a proposal via a Nickelback karaoke parody gone wrong. Six months later, Evan wants another chance with Abby and enlists the show for support. Through candid conversations, cringe-worthy confessions, and a major musical twist, the episode explores why relationships falter, the pain of being “always on,” and whether redemption is possible… or even wise.

Key Discussion Points & Insights

1. The Premise: "Say Yes To The Ex" – Setting the Stage

• Segment Introduction (04:17 – 05:36):
  • Brooke introduces the segment, explaining that they help listeners reconnect with their exes, impishly wondering if there's “residual flang left to be flung.”
  • Humor and playful skepticism set the tone, with the team poking fun at romantic nostalgia.
  • Notable Quote:
    • “It’s okay to wonder about your exes sometimes. Brooke certainly does.” —Brooke (04:30)

2. Meet Evan: The Heartbroken Comic

• Background on Evan and Abby (05:38 – 07:49):
  • Evan is nervous and openly sad, admitting, “I thought she was the love of my life.” (06:18)
  • The two dated for a year and a half, enjoying trivia nights, late-night Taco Bell runs, and matching Halloween costumes.
  • Co-hosts empathize, teasing Brooke about her own ex stories to lighten the mood.
• Cause of Breakup: The Infamous Proposal (07:49 – 09:18):
  • Evan reveals he proposed to Abby in a karaoke bar, parodying Nickelback’s “How You Remind Me” by changing the lyrics.
  • Abby was mortified and left mid-song, breaking up with him via a long text the next day.

3. Reflection and Regret: What Went Wrong?

• Evan’s Self-Assessment (09:36 – 10:00):
  • He admits Abby felt he was “always on” with jokes and pranks, describing the relationship as “a stand-up act” rather than a partnership.
  • “I think she was getting a stand-up act, not a boyfriend.” (09:34) —Evan
• Growth and Change (09:39 – 10:22):
  • Evan says he’s done the work in the six months since, learning to balance humor with sincerity.
  • “I can balance it now... I’m not over the top anymore.” (09:39) —Evan

4. The Setup: Getting Abby on the Line

• Contacting Abby (11:57 – 13:38):
  • Abby has no idea who’s calling, and the team preps Evan for possible disappointment.
  • “So if she has a bad reaction, don’t feel hopeless. I think we can come back from that.” (13:39) —Co-host

5. The Big Reveal and Raw Honesty

• Reuniting Evan and Abby (14:05 – 16:53):
  • Abby is surprised; she tells the group the proposal was a shock and space was necessary.
  • Evan expresses regret and vulnerability, telling her, “I’ve done the work. I don’t do armpit noises anymore. I still think I’m funny. But I can be serious, though. And I think you deserve a better version of me.” (17:31)
  • Abby appreciates the vulnerability and decides to also share something important.

6. The Plot Twist: Abby’s Nickelback Secret

• Abby’s Confession (18:11 – 19:39):
  • Abby admits she once dated a member of Nickelback, making Evan’s song choice an accidental trigger.
  • “I actually dated one of the guys from Nickelback a long time ago… I couldn’t have you propose with a song that obviously reminded me of my ex.” (18:33) —Abby
  • The group is floored by the coincidence and discusses how unexpected signs can end relationships.

7. Resolution: Cracking the Door Open

• Will She Say Yes To The Ex? (20:09 – 20:55):
  • Evan asks if Abby will meet for coffee to see the “new me.” Abby agrees, with one condition: “Oh, but you have to ask the coffee shop, please do not play Nickelback.” (20:20) —Abby
  • The team celebrates a tentative win and jokes about Canadian rockers never being on coffee shop playlists.

Notable Quotes & Memorable Moments

• On past relationships:

  • “It's always okay to wonder about your exes sometimes. Brooke certainly does.” (04:30) —Brooke

• On the failed proposal:

  • “I was proposing… I tried to sing Nickelback’s ‘How You Remind Me.’” (08:35) —Evan
  • “She walked out mortified.” (09:04) —Evan

• On self-awareness and change:

  • “There’s probably signs she was trying to tell me and I just wasn’t listening.” (10:46) —Evan
  • “I’ve done the work. I can balance it now.” (09:39) —Evan
  • “I can be serious, though. And I think you deserve a better version of me.” (17:31) —Evan

• On Abby’s big reveal:

  • “I actually dated one of the guys from Nickelback a long time ago… it was weird, but I couldn’t have you propose with a song that obviously reminded me of my ex.” (18:33) —Abby

• On giving Evan another chance:

  • “I think it’s a little weird for us to try again, but… I can do coffee. Oh, but you have to ask the coffee shop please do not play Nickelback.” (20:20) —Abby

• On the outcome:

  • “We got the door cracked open.” (20:57) —Co-host

Timestamps for Key Segments

• 04:17 – 05:33: Introduction to “Say Yes to The Ex” and Evan’s story
• 05:38 – 07:49: Evan explains his relationship and breakup with Abby
• 08:02 – 09:18: The details of the failed proposal
• 09:39 – 10:22: Evan talks about personal growth since the breakup
• 11:57 – 13:38: Setting up to call Abby
• 14:05 – 16:53: Abby joins, and the emotional reunion unfolds
• 18:11 – 19:39: Abby reveals her Nickelback dating history
• 20:09 – 20:55: Abby tentatively agrees to meet Evan for coffee, with the “no Nickelback” rule
• 23:08 – 23:40: Hosts reflect and joke about the strange fate of the episode

Tone and Style

• Lighthearted with a gentle edge; jokes abound but there’s genuine empathy for Evan’s predicament.
• Both self-deprecating (“We're not therapists”) and playfully snarky, especially regarding Nickelback.
• Honest vulnerability from Evan and a twisty, real-life complication from Abby keep the segment unpredictable and fresh.

Takeaway

This “Say Yes To The Ex” episode exemplifies the show's blend of humor, awkward confessions, and real emotional stakes. Evan’s earnestness, awkwardness, and humility win some hope—a coffee date (sans Nickelback)—but listeners are reminded that even with best intentions, relationships can hinge on the small, serendipitous details no one sees coming.