The Bert Show – Full Show PT 3 (Monday, Nov 10, 2025)

Engaging Morning Radio: Dating Dramas, Celebrity Chat, and Real-Life Laughs

Episode Overview

This episode is classic Bert Show fare—rolling through awkward dating mishaps, listener love lives, and celeb conversations with warmth, sass, and honest advice. The two standout arcs: the ongoing saga of Penelope’s office crush, which takes a messy, comedic turn, and an upbeat guest segment with R&B superstar Usher about his Broadway debut. Plus, a rapid-fire love lost-and-found story with caller Stacy. Throughout, the hosts (Bert, Kristin, Abby, Cassie, Tommy, and team) maintain their trademark playful and candid banter, pulling listeners into every high and low.

Key Discussion Points & Insights

1. Penelope’s Office Romance Rollercoaster

[01:15 – 18:58]

• Background Recap [01:16]:
  Penelope, confident in most areas but "clueless about dating," seeks the show’s guidance winning over co-worker Ian. Over several weeks, the cast advised her step-by-step (“how to get the guy”), including strategic run-ins and cold-shoulder games.

• The Phil Decoy & Date Gone Wrong [03:38 – 06:41]:
  To make Ian jealous, Penelope was supposed to be seen at lunch with another guy, Phil. Miscommunication leads to a no-show, resulting in much confusion and embarrassment for Penelope. Both Phil and Penelope share conflicting accounts—she insists Phil "stood her up," he details leaving multiple voicemails. Penelope waited, feeling "humiliated in front of Ian."

• Host Analysis on Penelope’s Struggles [09:15 – 12:02]:
  The crew points out Penelope’s lack of improvisation and tendency to get flustered:

  "Improvising in this situation would have been, you know, pretending to be on the phone or... faking a conversation… but the improvisation factor in this dating game has been missing from the start." – (Bert, 09:22)

• Listener Opinions & Tough Love [13:01 – 13:45]:
  Listeners and hosts question why Penelope remains fixated on Ian after his red-flag behavior and offer hard truths:

  “You want this guy so badly you can’t see things clearly... I don’t even know that I’m comfortable even still setting you up with this dude.” – (Bert, 13:24)

  "He could be a great guy that made a terrible dating mistake... Spending 90 minutes talking and arguing with your ex girlfriend while you're on a first date—normally, [you] just don’t recover from that." – (Host, 13:45)

• Penelope’s Perspective & Hang-Up [15:46 – 17:06]:
  Penelope insists Ian is "it for me" despite warnings, growing frustrated with the cast—eventually hanging up:

  “I’m gonna do it by myself... I’m gonna do it myself.” – (Penelope, 16:57, 17:01)

• Hosts Reflect & Advise Listeners [18:28]:
  The team wraps with broader lessons about over-eagerness and missed signals in early dating, noting Penelope’s mistakes as teachable moments.

2. Usher Interview: Broadway, Work Ethic, and Fame

[21:13 – 37:46]

• Broadway Challenge & Fearlessness [21:43]: Usher shares about his new role in Chicago:

  "I can't say that there's no fear. I'm just anxious to get started... Differently from acting—you can cut in acting, but on stage, you have to find the moment, live." – (Usher, 22:03)

• Respect for Broadway & Preparation [23:38]:
  Discusses his rookie status on Broadway but dedication to his craft:

  “Of course, I feel like I have something to prove… This will be the first musical I've ever played in, the first time I've ever been on Broadway.” – (Usher, 23:38)

• Actor Method Talk & Celebrity [22:49]:
  Hosts chat method acting (referencing Johnny Depp & Russell Crowe).

• Family Support & Atlanta Roots [27:17]:
  Usher talks about his mom's ongoing influence and his Atlanta favorites:

  "Yeah, my Porsche GT... I miss it more than anything." – (Usher, 36:19)

• Paparazzi & Public Life [29:40]:

  "The world is so busy trying to worry about everybody else's business that they don't pay attention to their own… There's a job for everybody... As long as paparazzi is not disrespectful...” – (Usher, 29:40)

• Ambitions and Next Steps [34:35]:

  “I want a Grammy, Tony, Oscar, Emmy.” – (Usher, 34:37) Hosts joke about his high bar and tease him about conquering all forms of entertainment.

• Candid Personal Reflection [33:54]:

  “I've learned to love myself enough to be patient... Eventually I'll make sure I get it right.” – (Usher, 33:54)

3. Love Lost & Found: Stacy and Byron

[37:53 – 49:40]

• Stacy’s Awkward Icebreaker [39:42]:
  Stacy makes a move on Byron at a bar with a “you look like my friend from home” line, but fails to close the deal. She regrets not following up after their photo together.

• Small World Connection [43:02]:
  Co-host Jen Hobby tracks down Byron via a friend’s sister, while the Burt Show community helps to confirm his identity and make the connection.

• Live Call & Playful Banter [45:11]:
  The team coaches Stacy to "keep it casual," joking about “touching his private parts” and “folding clothes at the Gap,” lightening the mood.

  “Stacy is hot?” – (Byron, 46:44)
  [Cue on-air fist pump from Stacy.]

• Potential Connection Made [47:16]:
  Byron agrees to let Stacy have his number, and the cast teases her about not scaring him off. They plan to follow up next week.

Notable Quotes & Memorable Moments

• Penelope’s Frustration:
  “Just because I feel like I'm supposed to have the guy by now.” – Penelope (10:42)

• Host Real Talk:
  “If you were gonna be a hot commodity, you would have just lost interest completely right there.” – Host (14:10)

• Usher on Acting:
  “You have to find the moment... because you’re acting live, man.” – Usher (22:12)

• On Paparazzi Culture:
  “As long as paparazzi is not disrespectful… when you sign up as an entertainer, anonymity goes out the window.” – Usher (29:40)

• Host Support:
  “We accomplished the goal. Yeah.” – Host (17:47)

• Stacy’s Victory Cheer:
  [Stacy pumps fist after Byron calls her hot.] (46:45)

Important Segment Timestamps

• Penelope Recap & Drama: 01:16 – 18:58
• Usher Interview: 21:13 – 37:46
• Stacy & Byron Love Story: 37:53 – 49:40

Overall Tone & Takeaways

The Bert Show strikes a familiar balance of empathy, humor, and gentle ribbing. They offer real talk about the perils of overinvesting in the wrong person, celebrate bold moves (however awkward), and keep things light with celebrity guests who are game for anything. The Penelope saga underlines the need for self-respect in dating; the Usher interview delivers star-power, humility, and ambition; and Stacy’s story wraps things up with hope and heart.

For listeners: You’ll laugh, you’ll cringe, and you might just pick up some dating do’s and don’ts—all served up with honesty and fun.