Brooke and Jeffrey: Second Date Update – "30 for 30"

Date: November 5, 2025
Podcast: Brooke and Jeffrey: Second Date Update
Hosts: Brooke, Jeffrey
Guests: Angela (the dater), Damon (the date)

Overview

In this episode, Brooke and Jeffrey delve into the modern dating challenge of their listener, Angela, who created her own “30 for 30” dating experiment: going on 30 dates with 30 different men during her 30th year. After stopping at date 19, having met Damon—her favorite so far—Angela is ghosted and enlists the show’s help to find out what went wrong and if there’s hope for another date.
The episode offers an engaging, comedic, and surprisingly candid look at dating in today’s social media age, highlighting the intersection of digital content and real-world connections.

Key Discussion Points & Insights

Angela’s "30 for 30" Challenge

• Angela’s Premise: Freshly 30 and single, Angela vows to try new tactics; "I came up with 30 for 30 dating," she explains. "That means I have vowed to go out on 30 dates before the end of the year." (04:37)

  • Motivation: To break out of her rut, and possibly find “the one” by casting her net wide.
  • Progress: She’s on date 19, ahead of schedule but reluctant to continue after meeting Damon.
  • Transparency: Initially disclosed her challenge to dates, but "they acted all weird, so three and on I haven’t said anything about what I’m doing." (06:40)

• Memorable Moments from Her Dates:

  • "Four was a nightmare. He took me...and I beat him...he was just sulking." (05:58)
  • "Twelve brought his mom...she ended up staying the whole date." (06:10)
  • Hosts joke, "At least you got a mom out of it." (06:27)

Angela and Damon’s Date (#19)

• Setting: Dinner at a Mexican restaurant
• Vibe: "He's a genuine guy...We had a really nice kiss, it was super cute, and I thought he would be calling." (07:16)
• Cost: Damon paid about $200 for the meal.
• Post-date Silence: Over a week and a half passes; Angela texted and called once. No response from Damon. (08:54)

The Investigation

• Possible Reasons for Ghosting:
  • Did Damon discover the “30 for 30” challenge online?
  • Angela says she posts about it on Instagram but never gives dates her socials: "Not my name on my Insta." (08:29)
• Hosts’ Strategy: They call Damon to get his side but decide not to reveal the challenge unless he already knows.

The Second Date Call

Damon’s Perspective — Starts at 11:33

• Initial Reaction: Damon is confused and caught off guard by the radio call.
• Reason for Ghosting: “I've been blowing her off a lot...I kind of don’t want to hang out with her no more.” (12:25)
  • Why? “I feel more taken advantage of...I feel violated. My pocket.” (12:47)
  • Clarification: Damon recounts Angela’s behavior during dinner: "She does videos...she was doing food reviews. That’s why she ordered $200. It wasn’t that we were caught up having a great time." (13:26)
    • Angela "ordered one of everything," and filmed the meal, asking Damon to hold the camera.
    • Damon felt ignored, “She told me to kind of be quiet so I don’t interrupt.” (13:53)

Notable Quote:

Damon: “You had your phone out the whole time. We really didn’t connect on anything. And you didn’t even eat all the food. It was just like, you would order the most expensive dish to take one bite and move on to the next dish.” (14:50)

Angela Reveals Her Side — Angela Joins at 14:27

• Her Defense: Asserts it wasn’t a food review, but "just doing my own little silly 30 for 30. That’s it." (15:43)

  • "I like you...I don’t want to go on the 20th. And that’s the video was about."
  • Explains that Damon wasn’t filmed for privacy.

• Host Inquiry: “Did the other 18 dudes all have to pay for your meals too and film you eating?” (16:49)

  • Angela: “There’s no have to, right? ...It’s not making anybody, strongly suggested that they do, I guess.” (16:56/16:59)

• Damon Stance: He’s frustrated with “being part of somebody’s elaborate game...I mean, I have my games though.” (17:09)

  • Angela pushes back, "It's not games, it's goals. It’s goals and objectives." (17:19)

Negotiation for a Second Date — At 18:11

• Damon’s Terms: “No phone. How about this: we go out again, you spend $200 on me.” (18:14)
• Angela’s Response: “No, I don’t like his energy now.” (18:32)
  • She refuses to pay, claims Damon’s attitude changed.
• Hosts’ Outrage: Playfully scold Angela for bailing after getting a perfectly fair reciprocal challenge from Damon.

Notable Exchange:

Damon: “Don’t let the game play you, play the game.” (19:13)
Brooke: “Well, you kind of got played, bro.” (19:16)
Jeffrey: “Says the guy that’s out 200 bucks.” (19:18)

Hosts’ Wrap-Up & Analysis

At 21:12

• Brooke & Jeffrey reflect:
  • Joke about "60 for 60" as Angela ages.
  • Jeffrey: “She said no. I know. What is that? Now I’m like, there’s a reason she’s been on 19 and nobody…” (21:17)
  • Brooke: “Her intentions were a little shady at the end there.” (21:23)
  • Jeffrey: “He was matching her energy...you want a person that’ll push back a little bit. The give and take.” (21:26)
  • Brooke sums up: “Angela has to move on to guy number 20 in her 30 for 30 quest. And I just hope whoever that guy is has a good job and steady hands—dinner’s not going to be cheap and he’s going to have to hold the camera the entire night.” (21:37)

Memorable & Notable Quotes with Timestamps

• Angela (describing her challenge):

  "I came up with 30 for 30 dating. That means I have vowed to go out on 30 dates before the end of the year." — Angela (04:37)

• Angela recounting bad dates:

  "Twelve brought his mom. She was only supposed to stay for like 30 seconds, and she ended up seeing the whole date." (06:10)

• Damon, on being used:

  "I feel violated. My pocket." (12:54)
  "You had your phone out the whole time...you will order the most expensive dish to take one bite and move on to the next dish." (14:50)

• Angela defends herself:

  "It wasn’t for a food review...I turned 30...just made a personal goal to go out on 30 dates for my 30th year of life. And I wanted to do a video for Instagram. And you’re number 19." (15:43)

• Negotiation standoff:

  Damon: "We go out again, you spending 200 on me." (18:14)
  Angela: "No, I don’t like his energy now." (18:32)

• Damon’s parting philosophy:

  "Don’t let the game play you, play the game." (19:13)

Important Timestamps

| Time | Segment | |-----------|-----------------------------------------------------------------| | 03:20 | Show and Angela’s challenge introduced | | 05:58 | Angela shares date horror/comedy stories | | 07:16 | Angela describes the date with Damon | | 08:54 | Angela reveals she's been ghosted, asks for help | | 11:33 | Call to Damon, he gives first reaction | | 12:25 | Damon explains why he ghosted Angela | | 13:26 | Damon details "food review" and feeling used | | 14:27 | Angela joins, clarifies her intentions | | 18:14 | Damon’s counter: “You spend $200 on me.” | | 18:32 | Angela refuses, cuts off the possibility | | 21:17 | Hosts recap, analyze and joke about modern dating |

Tone and Style

The conversation is playful, direct, and candid. Brooke and Jeffrey provide supportive but humorous commentary, poking fun at dating challenges while acknowledging both guests’ feelings. Angela is energetic, defensive but honest; Damon is blunt and a bit wounded but good-natured.

Summary

This episode dives headfirst into the realities of contemporary dating, social experiments, and the expectations (and pitfalls) of mixing content creation with real relationships. Angela’s “30 for 30” approach is ambitious, but her surprise at Damon’s pushback after feeling used highlights the complications of dating in an age where every experience might be performance. Ultimately, neither is willing to budge, and both part ways—Angela onto date #20, and Damon $200 lighter but a little wiser. The hosts deftly balance comedy and empathy, making this a must-listen for anyone navigating, or simply bemused by, the modern dating scene.