The Bert Show (Pionaire Podcasting)

Episode: Vault: Her Friend Is Jealous Of Her Relationship
Date: December 31, 2025

Episode Overview

This episode dives into the thorny issue of jealousy and sabotage among friends—particularly when a woman’s friend appears to undermine her romantic relationships due to her own unhappiness or lack of experience with successful partnerships. The Bert Show crew (Bert, Melissa, Dee Dee, Tracey, Phil, Jeff) and callers share personal anecdotes, challenge gender stereotypes, and offer sometimes controversial perspectives on friendship, competition, and loyalty.

Key Discussion Points and Insights

1. Opening Story: Sabotaging Friendships in Relationships

[01:06]

• Tracey shares a story about her friend who can't get legitimate advice from her "real best friend" anymore because that friend consistently overreacts and tries to make her leave a seemingly good boyfriend.
• The panel reflects on whether this is rooted in disappointment, jealousy, or just bad luck in love.

"She thinks it's because her best friend is a little bitter and upset that she's really hasn't ever had a boyfriend, therefore wants her to be alone too." – Tracey [01:59]

2. Is It Unconscious—Or Malicious?

[02:28 – 03:13]

• Dee Dee wonders whether women consciously sabotage friends’ relationships, or if it’s more subtle, stemming from their own negative experiences and inability to relate.
• Melissa and others discuss “soul searching” and whether happiness is truly possible for one friend when another is struggling.

"If her experience with men is all negative, then she's gonna see this friend's boyfriend's, you know, signs as being worse than they really are because her experience is that way." – Dee Dee [03:19]

3. Admitting to Envy

[03:41 – 04:11]

• Phil recounts a friend who finds it “hard to be happy for every single one of our girlfriends from college getting engaged, getting married, doing all that stuff.”
• The panel acknowledges it’s normal to have mixed feelings when friends hit major milestones first.

4. Calls from Listeners: Real-Life Sabotage

[04:15]

• Rebecca calls in to say her own single friends have actively tried to undermine her relationships so she’ll remain “single to party with them.”
• She claims: “Women are very conniving...especially if it’s a best friend—they do want to make you single with them.” [04:44]
• The phrase “misery loves company” is invoked repeatedly.

5. Is This Just a 'Woman Problem'? – Gendered Perspectives

[05:02 – 06:40]

• Debate erupts: Is this behavior unique to women?
  • Melissa, Dee Dee, and Jeff weigh in, with Jeff claiming women operate “in competition” more than men.
  • Some (Jeff) assert men tease friends but stop short of actively sabotaging, while Dee Dee insists men can be just as unsupportive.

"Everything with women is a competition...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." – Jeff [05:34]

6. Men’s Perspective: Ribbing, Not Ruining

[06:26 – 06:47]

• The men clarify: guys may encourage singlehood in jest, but rarely plot to end a friend's relationship.
• Tracey notes: “[The difference] is that what you guys do to each other is to make you feel better about your own situation … whereas this girl specifically wants her best friend to break up with the guy.” [07:06]

7. A Dramatic Caller Story: Sabotage “For Her Own Good”

[07:46 – 13:29]

• Dee Dee (caller/storyteller) relates an extraordinary tale:
  • She “saves” her best friend from a “loser” boyfriend by sleeping with him to expose his character, but never admits the truth to her friend—only letting the boyfriend claim it happened.
  • The friend chooses her over the boyfriend; he’s out of the picture.
  • Dee Dee defends her actions as what was necessary for her vulnerable friend.

"I screwed the guy…she doesn’t know...It was the best thing I could have ever done. I have no regret over it." – Dee Dee (caller) [08:22 & 09:59]

• The Bert Show crew is incredulous and skeptical of her motives, questioning:
  • Why go that far to prove a point?
  • Was it truly selfless, or just as selfish as the "problem" she was "solving"?

8. Listener Reactions: Judgment and Advice

[14:06 – 15:22]

• Chris calls “BS” on Dee Dee’s justification: “If you couldn’t stand the guy, how could you stomach sleeping with him?” [14:16]
• Keisha labels it the “most despicable thing I have ever heard.” She urges Dee Dee to come clean:

"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 live this thing right." – Keisha [14:37]

• Dee Dee (caller) remains unrepentant: “I don’t feel bad about it. That's why I don't have any remorse about holding it in. It was the right thing to do at the time.” [15:22]

9. Panel Reflections & Closing Thoughts

[15:41 – 16:43]

• The Bert Show crew split between disbelief and resignation:
  • Did Dee Dee just rationalize selfish behavior, or is friendship sometimes “messy”?
  • Is there ever a “right” reason to betray a friend (even for their own good)?
  • Phil: “Stories like that make me feel so normal.” [16:39]

Notable Quotes

• “If her experience with men is all negative, then she's gonna see this friend's boyfriend's, you know, signs as being worse than they really are because her experience is that way.”
  — Dee Dee [03:19]

• “Women are very, very conniving, and they do try to get what they want. And especially if it's a best friend, they do want to make you single with them, and they want somebody to party with them, and they don't care if it is a good man or not.”
  — Rebecca (Caller) [04:44]

• “Everything with women is a competition ... if that means breaking up a relationship, she will do it.”
  — Jeff [05:34]

• “I screwed the guy…she doesn’t know...It was the best thing that I could have ever done. I have no regret over it.”
  — Dee Dee (Caller) [08:22 & 09:59]

• “The fact that she would sleep with her best friend's man says way more about her than it ever says about the guy.”
  — Keisha (Caller) [14:37]

• “Stories like that make me feel so normal.”
  — Phil [16:39]

Important Timestamps

• [01:06] – Kickoff of the main topic: jealousy and sabotage among friends.
• [03:13] – Deep-dive into whether sabotage is conscious or unconscious.
• [04:15] – Caller Rebecca shares a firsthand account of friendship sabotage.
• [05:34] – Gendered debate: Are women really more competitive and conniving?
• [07:50] – Dramatic caller: “I slept with my best friend’s boyfriend to save her.”
• [14:37] – Caller Keisha delivers a harsh moral reckoning.
• [16:39] – Panel reflects on the soap-opera intensity of real-life friendship betrayals.

Tone and Style

The Bert Show’s signature mix of candid, witty, and sometimes sharply irreverent dialogue drives the episode. Hosts challenge each other, poke fun, and encourage real talk—even when things get awkward. Listeners’ unfiltered stories add shock, confusion, and laughter, making for a lively, relatable exploration of the complexities of female friendship and jealousy.