Brooke and Jeffrey: Second Date Update – “UPDATE: Age Is Just A Bummer”

Date: December 4, 2025
Podcast Host: iHeartPodcasts

Episode Overview

In this “Second Date Update UPDATE,” the hosts reconnect with Phil and Mandy to revisit a memorable second date story steeped in awkward age differences, generational quirks, and a now-famous restaurant faux pas. The episode takes listeners through the original call (where Phil was ghosted by Mandy after a cringeworthy dinner), then provides a postscript: Are they dating now? What actually happened? Did anyone find romance? The show expertly mixes humor, light roast comedy, and genuine relationship insights as it follows the saga from uncomfortable first date to an unexpected family twist.

Key Discussion Points & Insights

1. The Setup: Phil and Mandy’s Awkward Dinner Date

• Hosts introduce Phil: A recently divorced, slightly older guy jumping back into modern dating via apps.
• Phil’s nerves: “It’s been a long time since I had a first date, so I was a little nervous.” (07:23 – Phil)
• Age difference in the spotlight: Phil recalls his first concert (Aerosmith, 1989), contrasting with Mandy’s (Ariana Grande) (08:15)
• Generational gags: “Was it the app Coffee meets Metamucil?” (06:55 – Jeff)
• The cringe moment: At dinner’s end, the waiter says:

  “We hope you and your daughter have enjoyed this meal.” (08:47 – Phil)

• Both Phil and Mandy are embarrassed; it becomes the elephant in the room post-date.

2. Ghosting and Generational Disconnect

• Phil is ghosted by Mandy and doesn’t want to come off as desperate. “I just haven’t heard back. And I don’t want to be one of those people that over text, you know?” (09:49 – Phil)
• Hosts debate whether Phil is too out of touch to notice a reply—“Are we worried she is hitting him up, but it’s on TikTok, and he just doesn’t know how to work it?” (11:52 – Brooke)
• Mandy’s verdict: Phil’s age wasn’t a surprise, but he presented himself as much younger online and old-fashioned behavior (milk with dinner, the fanny pack, talking credit scores) turned her off. (14:23–16:14)

3. The Confrontation: Honest Feedback On Air

• Mandy joins the call, revealing:

  "I mean, I’m into dating older guys, but... Phil’s picture, it was a lot younger than what he made it out.” (14:23 – Mandy) “He basically ordered a glass of milk.” (15:05 – Mandy) “And he pulls out a full fanny pack and a large pack...[it] was a super pack in the fanny pack.” (15:11 – Mandy)

• Phil, hearing the feedback live, protests:

  "One glass of milk before seafood helps with the gut." (17:33 – Phil)

• Mandy jokes he was more financial advisor than romantic interest:

  “He did start talking about my credit score and my IRA. That’s not romantic.” (15:58 – Mandy)

4. Offer for a Second Date—And a New Plan

• Hosts encourage Mandy to give Phil another chance:

  "You admit yourself that you like older men." (18:30 – Jeff)

• Mandy declines a romantic date but offers to help Phil as a wingwoman:

  “As a wing woman, not any romance. No.” (18:51 – Mandy)

5. Update Segment: Where Are They Now?

• Phil and Mandy return for a status check:

  “Are you two together now?” (21:06 – Jeffrey)
  “No, God no.” (21:10 – Phil)

• Mandy successfully played matchmaker, introducing Phil to her Aunt Sadie:

  “I definitely introduced him to my aunt Sadie.” (21:36 – Mandy)

  • They confirm Phil and Sadie are now together:

    “Phil, are you in a relationship with her aunt?” (22:05 – Jeffrey)
    “Oh yeah... and smoking hot.” (22:08 – Phil)

• Mandy approves of the pairing:

  “They came over for Thanksgiving this year and it was really fun.” (22:37 – Mandy)

Noteworthy Quotes & Memorable Moments

• On awkward age gaps:

  "Mine was a Smith in ’89, when rock was real." (08:15 – Phil)
  "And hers was... Ariana Grande." (08:20 – Phil)

• When the waiter screws up:

  “We hope you and your daughter have enjoyed this meal.” (08:47 – Phil)

• On second date rejection:

  “As a wing woman, not any romance. No.” (18:51 – Mandy)

• Phil’s comeback:

  “One glass of milk before seafood helps with the gut.” (17:33 – Phil)

• On the update call:

  “Are you in a relationship with her aunt?” (22:05 – Jeffrey)
  “Oh yeah... and smoking hot.” (22:08 – Phil)

• Hosts’ wrap-up banter:

  “Not the happy ending I saw coming, but it’s much better than what I was envisioning.” (22:54 – Jeff)

Timestamps for Key Segments

| Time | Segment/Highlight | |-----------|------------------------------------------------| | 05:42 | Show intro to Phil & his age anxieties | | 08:47 | Restaurant “daughter” comment | | 09:49 | Phil describes ghosting and reaching out | | 11:52 | Hosts discuss social media and generational gaps| | 14:23 | Mandy’s honest feedback about Phil | | 15:11 | The infamous fanny pack moment | | 16:14 | Mandy: “He did start talking about my credit score…” | | 18:51 | Mandy offers to be Phil’s wingwoman | | 21:00 | The update: Phil and Mandy reunite on air | | 21:36 | Mandy introduces Phil to Aunt Sadie | | 22:08 | Phil and Aunt Sadie are officially together | | 22:37 | Mandy reports about Thanksgiving | | 22:54 | Hosts’ wrap-up reactions |

Overall Tone & Takeaway

With playful roasting, classic Second Date Update awkwardness, and a dash of family matchmaking, the episode is lighthearted, self-deprecating, and genuinely warm. The hosts keep up their trademark banter, never missing an opportunity for a generational joke or affectionate ribbing.

Bottom Line:

Phil and Mandy weren’t meant to be, but with Mandy’s help, Phil found romance—with Mandy’s aunt Sadie. Sometimes, the second date isn’t the story you think you’re getting. Ages may be “just a bummer,” but in this update, everyone lands exactly where they belong.