Brooke and Jeffrey: Second Date Update

Episode: Halloween Boos and Booze Bar Crawl
Release Date: October 31, 2025
Podcast Host: iHeartPodcasts

Episode Overview

This Halloween-themed episode of "Second Date Update" centers around Evan, who contacted Brooke and Jeffrey after being ghosted by Calista following what he thought was a promising bar crawl date. The show's hosts dig into not just what happened during their festive night out but also the reasons behind Calista's reluctance to see him again. Costumes, humor, dance floor disasters, and childhood pumpkin trauma all come to the surface in this lighthearted, banter-filled episode.

Key Discussion Points & Insights

1. Festive Atmosphere and Costumes

• The hosts open the show by celebrating Halloween and describing their costumes:
  • Brooke: Ursula
  • Jeffrey: Maleficent (aka "Maleficente")
  • Alexis: Cruella Deville
• "I am so proud of our costumes this year. Go look at the TikToks. Leave us a comment, let us know whose is your favorite." — Brooke [03:14]

2. Setting the Scene: The Halloween Bar Crawl

• Evan, the guest, explains he met Calista during a Halloween bar crawl, each embedded in their separate groups that eventually merged.
• Evan’s costume: Star Lord from Guardians of the Galaxy.
  • "I went as Star Lord from Guardians. I think I have a look that matches." — Evan [04:42]

3. Bar Crawl Connection

• Shared humor and a love of people-watching:
  • "We loved the people watching... the cheaper the better [with costumes], we really realized." — Evan [06:22]
• The groups started handing out fake 'awards' for best and worst costumes at each bar.
  • "We just started giving out awards...craziest food costume, ugliest blank costume, second worst costume of this bar." — Evan [07:15]
• The night concluded with a kiss at the bar, but Evan admits it wasn’t a full-on make-out.
  • "We definitely kissed at the bar." — Evan [07:33]

4. Dancing Dilemma: The Turning Point

• Calista wanted to go dancing at the last bar; Evan, burdened by a deep-seated reluctance, refused multiple times.
• "She really wanted to get out on the dance floor...I am not a dancer. It’s just not my thing." — Evan [07:49]
• Evan’s friends were more interested in drinking than socializing, while he was focused on Calista.

5. Texting after the Date — But No Real Progress

• Since that night, Evan and Calista exchanged messages, but she has been non-committal about another date.
• The hosts speculate:
  • "Maybe having a radio station call will prove you’re a fun guy?" — Brooke [08:56]
  • "If you’re out with a guy who won’t dance, is that a deal breaker?" — Jeffrey [09:04]
• "Think of all the weddings you have to go to in the future... dancing is such an important part of social life." — Brooke [09:17]

6. Calista’s Reason for Ghosting: “Pumpkin Man” Trauma

• Calista reveals a pivotal moment: Evan’s childhood trauma is a turn-off for her.
  • "He basically told me, he doesn’t like dancing because when he was 10, his mom put him in this play where he was a pumpkin and had to dance in front of everyone...If you’re that affected by something like that, you probably can’t handle anything in life." — Calista [14:10]
• Evan elaborates: For years, his mom made him wear a skin-tight orange suit and a pumpkin helmet to dance at the town Halloween festival, making him locally infamous as "Pumpkin Man."
  • "My mom would force me to wear a skin tight, like, orange suit and put a pumpkin on my head to go dance in front of the town." — Evan [15:57]

7. Judgment and Empathy

• The group debates whether this trauma is reasonable or if Calista is being harsh.
• "Maybe just give him a chance to dance with you eventually, because the good experience will outweigh the trauma that he had." — Brooke [17:25]
• Calista hesitantly agrees to one more chance, on the condition Evan tries dancing with her.

8. Resolution: Will They Try Again?

• Evan agrees to give dancing a shot, and Calista says she'll give him another date — as long as he gets out on the dance floor.
  • "I’ll get out there. I’ll show what little moves I have." — Evan [19:03]

Notable Quotes & Memorable Moments

• On Costume Judging:
  "You can go hop between bars and drink alone anytime." — Brooke [05:53]
• On Halloween Bar Crawl Romance:
  "Did you make out?" — Brooke [07:29]
  "I wouldn’t call it a make out, but yeah...we kissed." — Evan [07:33]
• On Dancing and Trauma:
  "If you’re out with a guy who won’t dance, is that a deal breaker?" — Jeffrey [09:04]
  "Dancing is such an important part of social life." — Brooke [09:17]
• On Past Scarring Experiences:
  "I became Pumpkin Man to everybody. I was known as Pumpkin Man every year." — Evan [16:13]
• On Relationship Expectations:
  "I just want to be with someone that is, like, fun and can dance, and I don’t want to be dealing with their past traumas." — Calista [17:38]

Timestamps for Key Segments

• Halloween Costume Banter: [03:07–03:43]
• Evan Describes Bar Crawl and Costume: [04:42–05:09]
• Connection and Joke Awards: [06:22–07:15]
• Kiss at the Bar: [07:33]
• Dancing Dispute: [07:49–08:16]
• Hosts’ Speculation and Social Life Debate: [08:56–09:25]
• Calista’s “Pumpkin Man” Turn-Off Revealed: [14:10–14:56]
• Evan’s Pumpkin Suit Childhood Story: [15:57–16:13]
• Resolution and Agreement for Second Date: [19:03–19:12]

Episode Tone and Style

The hosts keep a lively, playful banter, mixing playful teasing ("Lord of the Pumpkins!") with genuine empathy. They balance group support for both sides with typical morning show goofiness, especially when relating Evan’s story to cinematic references like "Footloose."

Conclusion

The episode wraps with both Evan and Calista cautiously agreeing to a future date — provided Evan is willing to face his dance floor fright. The story not only highlights the unpredictable nature of first encounters but also the humorous baggage people can carry from their childhoods, especially when it involves orange spandex and small-town notoriety.

Listen to full episodes and more second date updates on iHeartRadio, Apple Podcasts, or Spotify.