The Bert Show – Full Show PT 3: Monday, March 23 [Vault]

Date: March 23, 2026
Episode Overview:
This episode of The Bert Show is a lively, candid, and often humorous exploration of real-life relationship dilemmas as experienced by listeners and the show hosts themselves. The cast tackles complicated family drama, friendship betrayals, age-gap romances, and the enduring question of "the one that got away." The tone is authentic, supportive, and occasionally irreverent, as the team offers advice, debate, empathy, and trademark wit throughout the varied calls and stories.

Main Topics and Segments

1. Family Meddling: A Daughter's Failed Attempt to Reunite Divorced Parents

[00:45 – 13:26]

Background

• Last week, listener Laura revealed her mom’s wild plan to surprise Laura’s dad (divorced 5 years) with a “reunion” dinner, using Laura as the unknowing middleperson.

Key Events

• Execution: Laura follows through with the plan, having dinner with her dad, then abruptly leaving so her mother could swap in as a surprise date.
• Immediate Aftermath: Laura can’t bear to witness the outcome and leaves, ignoring her dad’s call right after.
• Emotional Fallout: Dad is hurt and frustrated, expressing disappointment via voicemail. Mom, meanwhile, is convinced something magical happened.
• Hosts’ Reactions: The cast calls out both the unfairness of putting Laura in this situation and her avoidance in dealing with the consequences.

Notable Quotes

• Host: “The fact that this thing could have been such a train wreck that you couldn't even bear to watch should have been an indication to you that you shouldn't have done it.” – [03:42]
• Co-host: "It's unfair to your dad not to talk to him or explain anything." – [08:12]
• Host: "You gotta call your dad today. I mean, you're late on that now. He reached out to you as soon as he realized what was going on." – [09:23]

Key Point

• Laura is urged to have honest conversations with both parents: apologize to her dad and gently ground her mom's expectations.

2. Betrayal by a Best Friend: Is It Worse Than a Cheating Ex?

[15:04 – 24:58]

Caller: Jessica

• Jessica discovered her best friend Sarah was secretly texting and meeting up with her ex-boyfriend—the same guy Sarah convinced her to break up with.

Key Discussion

• The “Code”: Is it ever okay for friends to see an ex, especially in secret?
• The Snooping Debate: Is looking at a friend’s unlocked phone as bad as secret friendship with an ex?
• Advice:
  • Some, especially male co-hosts, think the breach is irreparably bad.
  • Others (Erica) counsel a direct conversation but stop short of insisting on ending the friendship.
  • Dramatic suggestion: crash their next coffee shop meetup instead of confessing the snooping.

Memorable Moments

• Host (sarcastically): “It jumped off the counter into your hand and started scrolling by itself. I don't even know how it happens, but it does.” – [16:21]
• Co-host: “You only pick up a phone when you already have an idea that something's not right.” – [18:37]
• Erica: "It's worse to have problems with a best friend than I think it is any guy. You know, it's more hurtful in that way." – [17:44]

3. Age Gap Relationships: Callers Share Their Stories

[27:06 – 35:42]

Conversation Starter

• Celebrity discussion: Paul Walker (35) engaged to a 19-year-old he'd been dating since she was 16.
• Callers weigh in anonymously with stories of dating across wide age gaps—both as older men and as much younger women.

Highlights

• Caller Johnny: 41, dating a 22-year-old, met her when she was 18; open relationship setup.
  • Host: “What could a 38-year-old possibly have in common with an 18-year-old?” – [28:38]
  • Female Co-host: "I feel it is robbing her of her...true experience as a college student." – [30:31]
• Caller Dwayne: Met wife when he was 18 and she was 14; married at 19 and 15 due to pregnancy, have lasted nine years.
  • Host: “When you're a freshman in college and you're dating a freshman in high school...that looks pretty pathetic.” – [34:19]
• Other callers: Share both positive and failed outcomes (“now I’m dating someone 12 years older than me!”).

Tone

• Nuanced, at times skeptical, but open to hearing real-life outcomes.

4. "The One That Got Away": Reaching Back for Lost Love

[44:17 – 51:23]

Caller: Michelle

• After a divorce, Michelle finds herself yearning for her high school boyfriend—the one her parents forced her to abandon because he "wasn't good enough."

Key Discussion Points

• Nostalgia vs. Reality: The hosts caution Michelle about romanticizing past relationships that ended when both parties were very young.
  • Host: “The people you were 10 years ago are gonna be so different when we track this guy down.” – [47:17]
  • Erica: “He might not be completely gone...but his life circumstances could be completely different.” – [48:06]
• Resolution: The show’s producer has tracked down the old boyfriend and will attempt a reconnection, using “10 questions” to vet his willingness and current situation first.

5. Memorable, Lighter Moments & Show Culture

• Discussions throughout are laced with playful banter, role-play, and self-aware humor.
  • On avoiding uncomfortable situations: “I wish we could do that in person where we just turn around and run away.” – [32:21]
  • Hosts joke about “walks of shame,” pillow fights, and gender-differences in handling betrayal.
• Listeners are frequently involved, both as callers and through advice or real stories.

Notable Segment Timestamps

• [00:45] – Listener’s parental trap drama introduction
• [03:42] – “Should have been an indication” observation about messy plans
• [09:23] – Hosts press Laura to call her dad
• [15:04] – Jessica’s best friend betrayal dilemma begins
• [17:44] – The pain of best friend betrayals
• [21:27] – “Dump this friend” vs “Talk it out”
• [24:01] – “Show up at coffee shop” revenge plan
• [27:06] – Discussion of older men dating much younger women
• [28:38] – “What could a 38-year-old possibly have in common with an 18-year-old?”
• [34:19] – "Freshman in college dating a freshman in high school..." critique
• [44:17] – Michelle’s “one that got away” segment begins

Tone & Takeaways

• The Bert Show blends seriousness with jokes and relatability.
• They provide tough love: “Stay out of your parents’ love lives,” “Dump the friend,” “Don’t fantasize about the past,” but also listen compassionately.
• Relationship rules ("the code") are debated, not dictated; hosts often bring in personal anecdotes or pop culture.
• Show culture is lively and interactive, jumping quickly between heartfelt and hilarious.

For First-Time Listeners

If you haven’t caught this episode, expect a vibrant ride through complicated, sometimes awkward real-life relationship scenarios, punctuated with laughter, honesty, and the occasional hard truth. The Bert Show crew excels at being both friendly confidents and no-nonsense straight shooters, always rooting for listeners—no matter how tangled their lives might get.