The Bert Show – Full Show PT 1: Wednesday, December 31 [Vault]

Date: December 31, 2025
Host: Carol (with Dee Dee, multiple callers, and other cast members)
Podcast by: Pionaire Podcasting

Episode Overview

This episode dives into the complexities and sometimes the darker side of friendships and love lives, focusing on relationship sabotage, jealousy among friends—especially among women—and the awkward world of post-breakup dating as a single parent. The Bert Show crew and their listeners candidly share opinions and real-life stories, leading to a lively conversation full of laughs, drama, and thought-provoking moments.

Key Discussion Points & Insights

1. Are Women Their Own Worst Enemies in Relationships?

• Main Topic: The show opens with the question of whether women, particularly those who are single, intentionally or subconsciously sabotage their friends' relationships out of jealousy or loneliness.
• Listener Callers: Multiple stories and opinions flood in about friends who critique others' relationships harshly, sometimes rooting for their friend's unhappiness to lessen their own feelings of being left out or alone.

Notable Quotes:

• “A woman's worst enemy are other women.” – Carol (Host) [01:19]
• “She just wants her best friend, I guess now.” – Female Caller [03:03]
• “Misery loves company. I don't think it's necessarily just a woman thing. I think it's an anybody thing.” – Unidentified Male Caller 1 [05:05]

Interesting Exchange:

• The hosts debate whether guys do the same “sabotaging” as women. Differences between men’s and women’s approaches emerge, with men described as ribbing or joking, while women sometimes take active steps to undermine.

• “Here's a girl who's happy and things are going great. It's another woman's job to try to make herself an equal with that girl. And if that means breaking up a relationship, she will do it.” – Unidentified Male Caller 2 [05:47]

2. Extreme ‘Sabotage’ Stories: Is This Really About Friendship?

Wild Caller Story:

A female caller shares an intense confession about sleeping with her best friend’s boyfriend purely to expose him as a cheater—without ever revealing this to her friend.

Notable Quotes & Moments:

• “You had sex with your friend's boyfriend just to prove to her how bad a guy he was?” – Carol (Host) [08:44]
  • “Yeah... She's my best friend. Today you were saving her.” – Female Caller [08:50]
• “As you were screwing your best friend's boyfriend, you were thinking about how much you care about her. Right.” – Dee Dee [10:07]
• “Let me tell you, this was at a different time, too. This was a zillion years ago... I'm sorry. I don't regret it at all.” – Female Caller [11:30]

Callers React:

• Listeners express shock and condemnation, highlighting better alternatives and emphasizing how some lines shouldn't be crossed, no matter the intention.

• “I think the fact that she would sleep with her best friend's man says way more about her than it ever says about the guy. ... She needs to go to her friend and confess what she has done and try to make this thing right.” – Caller Keisha [14:50]

• Dee Dee directly challenges the caller’s motives and honesty, suggesting selfish intent:
  “I think she wanted her best friend's boyfriend and she had him.” – Dee Dee [15:54]

3. The Single Mom Dating Dilemma

Listener Story:

A single mom shares her struggles re-entering the dating world:

• Meets a guy at a bar, he calls, makes a date, then stands her up.
• Gives him a second chance when meeting again; after inviting him over for movies (with son away), he leaves abruptly when it's clear she won’t have sex, disappearing without a word.

Notable Quotes:

• “He never came back.” – Female Caller [21:21]
• “It will never get better in a relationship than the first couple of weeks... If a guy doesn't call you back, doesn't have the respect for you to even just spend five seconds on the phone and say... I can't make it tonight... end the relationship.” – Carol (Host) [23:19]
• “You’re vulnerable. I mean, he blew you off and he didn't call you back, yet here you are still hanging out with him in a bar.” – Carol (Host) [25:13]

Advice & Analysis:

• Hosts and callers urge: Be pickier, especially when kids are involved. If someone treats you poorly early, it won't get better.
• Single mothers’ perspective: Caller Betty highlights safety and self-respect for single parents:
  “You need to be a bit more picky because I'm a single mother myself, and I can't have any guy who I'm not comfortable with around my child up until we get to the point where we have established some sort of commitment.” [27:28]

4. Broader Lessons

• Recognizing Red Flags:
  Both segments stress the importance of seeing people for who they are early in a relationship, rather than making excuses or taking mistreatment personally.

• Patterns of Self-Justification:
  Both with friends and in dating, the conversation exposes how people often rationalize or minimize actions that are ultimately self-serving or damaging to others.

Notable Segment Timestamps

| Timestamp | Segment/Topic Highlights | |-------------|--------------------------------------------------------------------------------------------| | 01:19-03:24 | Opening debate: Do women sabotage each other's relationships out of jealousy or bitterness? | | 03:54-06:22 | Hosts and callers discuss the difference between male and female approaches to sabotage | | 08:03-11:41 | Shocking caller story: “I slept with my best friend's boyfriend to show she could do better”| | 14:50-16:38 | Callers react to the story, heated commentary on loyalty and honesty in friendship | | 18:37-21:14 | Single mom describes being stood up, then ghosted after refusing sex | | 23:19-26:06 | Hosts and callers give frank advice about self-respect, repeat behavior warning signs | | 27:24-29:12 | Caller Betty gives perspective on single moms dating and child safety | | 30:01-31:08 | Show wraps with reflection: Actions speak louder than words in early relationships |

Memorable Quotes

"A woman's worst enemy are other women."
– Carol (Host) [01:19]

"Misery loves company... I don't think it's necessarily just a woman thing."
– Unidentified Male Caller 1 [05:05]

"You had sex with your friend's boyfriend just to prove to her how bad a guy he was?"
– Carol (Host) [08:44]

"That is the most... despicable thing I have ever heard tell of. And she needs to go to her friend and confess what she has done."
– Keisha (Caller) [14:50]

"It will never get better... than the first couple of weeks, first couple of months of you dating."
– Carol (Host) [23:19]

"You don't know who he is. You don't know what he's about. God forbid he was some sort of lunatic..."
– Caller Betty [27:28]

Tone & Style

The episode is candid, sometimes harsh but always engaging. The hosts keep a real and humorous tone, even when addressing sensitive or shocking situations. Listener stories add drama and authenticity, prompting open discussion and blunt advice.

Takeaways

• Jealousy and Insecurity: These can result in “sabotage” between friends, though intentions are often debated.
• Friendship Boundaries: There are lines not to be crossed, regardless of motivation; "helping" a friend doesn't justify betrayal.
• Early Red Flags: Disrespectful behavior early in dating is a reliable predictor—it doesn't improve with time.
• Self-Respect: Particularly for single parents, setting boundaries is crucial both for personal well-being and children's safety.
• Honest Advice: Sometimes the truth stings, but open dialogue can help listeners make better choices.

Listeners looking for honest, unfiltered takes on today’s relational issues—served up with wit and occasional disbelief—will find this episode a must-listen.