The Bobby Bones Show – Monday, September 22, 2025

Episode: MON PT 1: Amy Admits To Doing Something Illegal + Can You Ask Your Girlfriend To Pay For the Engagement Ring? + 90’s Masterpiece Theater + Who Bobby Loved At iHeartRadio Music Festival

Episode Overview

In this lively Monday edition of "The Bobby Bones Show," the crew dives into a mix of confessions, life dilemmas, pop culture fun, and festival recaps. Amy comes clean about an illegal decision regarding her driver’s license, sparking both jokes and real talk about adult responsibilities. The team debates a relatable relationship question: is it ok to ask your girlfriend to pay for her engagement ring? There’s also a spirited round of "90’s Masterpiece Theater" and stories from the iHeartRadio Music Festival, with special backstage interviews. Throughout, the episode balances humor, vulnerability, and playful debates, reflecting the show’s signature mix.

Key Discussion Points

1. Amy Admits to Driving Illegally

[03:18–08:21, 22:54–29:08]

• Amy reveals she let her driver's license expire and, as a result, has been driving illegally.
  • “I have to go everywhere with my passport... I’m driving, yes, to come to work today. Illegal.” – Amy [06:09, 06:29]
• She discusses missing the renewal deadline and now needing to retake the written (and possibly driving) exam to get her license and the new Real ID.
• There's debate about whether Amy “forgot” on purpose for a bit for the show or just procrastinated.
  • “Do we believe she forgot on purpose?” – Bobby [04:27]
  • “No, because I don't. I mean, maybe.” – Eddie [04:28]
• Amy admits to purposefully letting the license expire because of long Real ID lines and dreading the process:
  • “No, I did. I let it run out on purpose because also, I wasn’t looking forward to going to renew my license.” – Amy [07:39]
• Bobby quizzes Amy on sample written test questions with the group chiming in. Amy does surprisingly well.
  • “You should pass the test. These are the jobs. Just eliminate the idiot ones.” – Bobby [28:55]
• The group jokes about how long Amy can push her luck.
  • “How long can I last with an expired license?” – Amy [07:23]
  • “No, that’s not a fun game.” – Bobby [07:25]

2. Relationship Dilemma: Should You Ask Your Girlfriend to Chip In For The Engagement Ring?

[08:43–13:17]

• A listener asks if it’s reasonable to request help from his girlfriend to buy the expensive engagement ring she wants.
  • “So I’ve been thinking about whether it’s reasonable to ask her to help pay for it since it’s the ring she really wants...” – Bobby (reading listener letter) [08:43]
• Bobby’s take: If the element of surprise is already out and there’s open communication, it’s ok to bring it up honestly and offer options (wait and save, take a loan together, or she chips in).
  • “I don’t think that is an unacceptable option here.” – Bobby [09:34]
• Amy is uncomfortable with the idea but comes around to see nuance:
  • "I can't see a scenario... I would just advise them to wait and save.” – Amy [10:20, 10:39]
  • “If it’s that important to her, then yeah, she might be willing to throw down...” – Amy [12:09]
• Eddie asks if a downgrade is possible; Amy says she’d downgrade or wait rather than insist her partner stretch beyond his means.
• Consensus: Communication is key; if you’re already discussing rings, keep talking honestly about money.

Notable Quote:

• “No one wants to be asked. You want to pitch in for your ring.” – Amy [12:44]
• “You make a good point there. Because she's gonna have to pay for it anyway if they take out a loan.” – Eddie [12:27]

3. iHeartRadio Music Festival Recap & Vegas Stories

[13:17–17:50]

• Bobby recounts his hectic experience at the festival and in Vegas:

  • Got a nosebleed while waiting at the airport due to dry air.
  • Shout-out to John Fogerty (Creedence Clearwater Revival) for performing like a 30-year-old at 80.
  • Describes explaining The Offspring to his younger wife.
  • Amy’s 21-year-old niece loved the festival, even acts she didn’t know.

• Gambling adventures:

  • Bobby tries to prove he’s not lucky.
  • Turns $400 into $1,600 at the craps table, then loses $400 in slots, ends up way ahead after another craps win.
    • “Now, here's where the luck separates itself from just being lucky. I didn’t go back the whole rest of the weekend.” – Bobby [17:02]
  • Eddie finds $100, bets it, doubles it, then loses it.

Notable Moments:

• “The festival was great... It was incredible. And get ready to relive the once in a lifetime moments starting October 2nd, only on Hulu.” – Bobby [15:26]
• “That was me making the conscious decision to take the money that I had won and not gamble it back. Because that’s how people lose money.” – Bobby [17:02]

4. 90’s Masterpiece Theater: Movie Scene Game

[30:14–35:57]

• Bobby and Raymundo act out famous movie scenes; Amy, Eddie, and Lunchbox guess the movies.
  • Scenes included:
    1. “Show me the money!” from Jerry Maguire [31:09]
    2. The Sandlot “Just let it go...” baseball scene [31:57]
    3. Mufasa’s ghost from The Lion King (Lunchbox gets it; Amy and Eddie guess wrong) [32:10–33:21]
    4. Toy Story: Buzz and Woody’s flying debate [34:47]
    5. Dumb & Dumber: The worm store and cry scene [35:43]
  • Lively reactions, quotes, and playful groans from incorrect guesses.
  • Lunchbox wins the round, with lots of laughter and good-natured ribbing.

5. Lunchbox’s Price Is Right Fiasco and Update

[36:26–41:04]

• Lunchbox shares he mistakenly reserved Price is Right tickets for the wrong month, leading to someone on standby attending instead.
  • “That’s what I do is I’m out here making dreams come true...” – Lunchbox [36:26]
• Determined, he secures tickets for three days in October to maximize his “come on down” chances.
• There’s joking about whether he’s actually allowed to take multiple days off (“Scuba” voices used).
  • “I feel like you’re about to have a stroke.” – Bobby to Lunchbox [37:22]

6. Good News & Other Segments

[29:08–30:14, 48:33–50:10, 51:09–51:52]

• Tell Me Something Good:
  • Story of ICU nurse Grady who saves a runner’s life with 10 minutes of CPR [29:12]
  • Story of Sean Davis from Texas who finds and returns an envelope full of cash to daycare owner [48:38–49:29]
• Morning Corny:
  • “Why did the man with amnesia go for a run? To jog his memory.” – Amy [50:52]
• Bonehead Story of the Day:
  • CEO in Alexandria, VA moves herself into a home meant for housing program recipients [51:09]

7. Special Backstage Interviews: iHeartRadio Music Festival

[52:16–58:07]

Jelly Roll Interview

• Discusses meeting the Pope (“He comes in mighty popish!” – Jelly Roll [52:54]), nerves (“I had diarrhea... that’s a scale” – Jelly Roll [53:25]), and his pre-show ritual (“We sing ‘Oh Happy Day’ from Sister Act before each show.” [53:59])
• On music’s power:
  • “I’ve had songs transform me right in my spot, you know, that’ll change the way I’ve looked at life forever. Hearing them once.” – Jelly Roll [54:49]

Bailey Zimmerman Interview

• Talks about telling real love stories in music and feeling vulnerable in songwriting.
• His favorite love song: “‘Perfect’ by Ed Sheeran.” – Bailey [56:28]
• Shares his tour excitement, his signature stage jump, and “pinch me” moments, like getting a call from Morgan Wallen to tour [57:25]
• How his collab with Diplo started: “Diplo showed up at my house... and now we're here performing that song.” [57:41]

8. Bonus: Behind the Scenes of Dancing with the Stars

Emma Slater Mini-Interview
[45:19–48:23]

• Emma Slater addresses social media backlash about her partner Andy Richter, saying she loves working with “funny guys with special qualities.”
• Reveals she vocally guides partners during the dance for support and structure.

Notable Quote:

• “Andy, to me, is the best partner... I love being partnered with the funny guys.” – Emma Slater [46:05]

Notable Quotes & Memorable Moments

• Amy (on driving without a license): “I have to go everywhere with my passport... I’m driving, yes, to come to work today. Illegal.” [06:09, 06:29]
• Bobby (on ring finances): “I will give you the option on what to do. I don’t think that is an unacceptable option here.” [09:34]
• Amy (on paying for her ring): “I do not ever want to be asked. You want to pitch in for your ring.” [12:44]
• Bobby (on Vegas): “That was me... not gamble it back. Because that’s how people lose money.” [17:02]
• Jelly Roll (on meeting the Pope): “He comes in mighty popish!” [52:54]
• Bailey Zimmerman (on songwriting): “It’s from the heart. Like, real emotion... That’s what music’s all for.” [55:44–56:16]
• Emma Slater (DWTS): “Andy, to me, is the best partner. I love being partnered with the funny guys...” [46:05]

Timestamps for Major Segments

• Amy's expired license confession and test questions: [03:18–08:21, 22:54–29:08]
• Engagement ring debate: [08:43–13:17]
• iHeartRadio Music Festival recap: [13:17–17:50]
• Gambling/luck stories: [16:05–17:50]
• 90’s Masterpiece Theater: [30:14–35:57]
• Price Is Right update: [36:26–41:04]
• Dancing with the Stars (Emma Slater): [45:19–48:23]
• Jelly Roll interview: [52:16–55:13]
• Bailey Zimmerman interview: [55:18–58:07]

Overall Tone and Vibe

The episode is quintessential Bobby Bones – rapid-fire, bantery, honest, and packed with pop culture, self-deprecating humor, real-life confessions, and moments of connection. The crew’s chemistry shines through in every segment, with listeners getting both laughs and genuine advice.

Summary Takeaway

On this Monday show, the crew shares laughs and lessons about responsibility, relationships, and the unpredictability of life. Amy’s “illegal” confession, relationship debates, festival highs, and cult movie nostalgia deliver entertainment and relatable moments, while backstage music fest stories add star power and inspiration.

Listen to “The Bobby Bones Show” daily for more real-life, ridiculous, and always heartfelt content!