The Bert Show – Vault: Jason's Cheating GF (November 4, 2025)

Episode Overview

In this throwback segment (“Vault”) from The Bert Show, the cast fields a heart-wrenching call from a listener—"Jason" (using a voice disguiser)—who is seeking advice after discovering his girlfriend has been unfaithful. Despite repeated betrayals and ongoing trust issues, Jason struggles with whether to stay in the relationship or walk away. Hosts Bert, Kristin, Adam, and others facilitate a candid, empathetic discussion involving personal experiences, tough questions, and calls from listeners who have faced similar situations.

Key Discussion Points & Insights

1. Jason’s Story: The Infidelity and Emotional Fallout

• Background: Jason has been with his girlfriend for about 2.5 to 3 years, describes her as the love of his life, but recently serious trust issues have surfaced.
• Discovery: His girlfriend claimed to go on a business trip, but Jason found evidence she went to the Virgin Islands with a coworker (brochures, post-it love notes). Upon investigation, Jason confirmed through her boss she was not on the supposed business trip.
• Confrontation & Aftermath: (03:01)
  • Jason: “Finally confront her. And she didn’t really give me any really good reason about what she did other than she was sorry and she felt stupid about it. Of course. Big part of me wants to take her back and big part and big partner says, you know, dude, what are you thinking? Move on with your life.”

2. Weighing the Decision to Stay or Leave

• Repeated Betrayals: The relationship has seen other incidents suggesting a pattern of dishonesty and taking advantage of Jason’s kindness.
• Trust Issues: (05:41)
  • Jason: “That’s the thing. I really don’t know. I really don’t know. I guess my question, I know the obvious question everyone’s gonna say is that is get out. Yeah, get out, dude, come on. You’re never gonna trust her again.”
• Love vs. Misery: Hosts press Jason on whether staying with the "love of his life" is worth a potential lifetime of doubt and unhappiness.
  • Host 3: (07:41) “Have you equated the balance of having being with the love of your life versus a life of misery?”

3. Listener Calls: Stories of Staying and Surviving

• Callers Share Real Struggles and Successes
  • Kimberly’s Story (12:04):
    • Survived multiple instances of cheating and drug addiction over 13 years, chose her children first, but ultimately got back together after her husband got clean:
      • “He’s...done a complete turnaround. He’s not on drugs. He’s not talking to any of those people anymore. I mean, he’s all about his children and his family ... It did take a long time to get over that though.” (12:37)
  • Patrick’s Story (13:48):
    • Broke up with his fiancée due to suspicions of cheating, gave her another chance and rebuilt the relationship to the point of engagement:
      • “Of course, the biggest issue is the trust factor...It just started working its way up, and now we’re engaged to be married. So it can work, but it’s just gonna take time. And if she’s willing to gain the trust back, that’s gotta be at least half the equation.” (14:58)
  • Jackie’s Story (16:08):
    • Began with infidelity on both sides, endured rocky starts, now together but still deal with trust challenges:
      • “Even to this day, I mean, he forgave me for everything, but yet he still...checks my phone, does all that.” (17:11)

4. Candid Advice and Takeaways from the Hosts

• The Emotional Toll: The hosts acknowledge both the emotional cost and the resilience needed to try again—highlighting exhaustion, suspicion, and the need for energy to rebuild trust.
  • Host 3: (15:22) “She has to be able to say, sure, hey, let me look at you...She has to be okay with that.”
• Recognizing Relationship Imbalance:
  • Host 2: (19:07) “You sound like you've got a lot of love to give, man. A lot of love. And you should get a puppy or a goldfish...But it doesn't sound like she does...She doesn’t deserve your love.”
• On Creating an Environment of Acceptance:
  • Adam: (19:27) “If she's not regretful and you make it okay for her not to be regretful and you stay and you put up with whatever, then you've created an environment where she can take advantage of you again and it’s going to be okay...”
• Classic Wisdom Shared:
  • Caller 1: (20:12) “Fool me once, shame on you, fool me twice, shame on me.”
  • Host 3: “And that year old saying, there’s a sucker born every minute.”
  • Hosts joke with other proverbs (“Don’t take a wooden nickel,” “A stitch in time saves nine”).

5. Closing Thoughts

• Jason seems to accept the advice and the reality that the relationship is imbalanced and damaging to his self-worth.
  • Jason: (18:41) “Yeah, I'm trying to feel that, too.”
• The cast encourages self-respect while acknowledging the heartache involved:
  • Host 2: “What is she going to have to do to prove to you that she really wants to be part of this?” (20:03)

Notable Quotes & Memorable Moments

• On Confronting Cheating
  • Jason: “That's the thing. I really don't know...the obvious question...is get out. Yeah, get out, dude, come on. You're never gonna trust her again.” (05:41)
• On Lasting After Betrayal
  • Kimberly: “It did take a long time to get over that, though. He's gonna...It's not gonna be an overnight thing, and he's gonna go through ups and downs for a long time.” (13:02)
• On What it Takes to Rebuild Trust
  • Patrick: “It's just gonna take time. And if she's willing to gain the trust back, that's gotta be at least half the equation.” (14:58)
• On Relationship Exhaustion
  • Caller 1: “It just sounds like a life of struggle and turmoil, questions and love of earth life just untrust and. Oh, it just sounds exhausting.” (18:07)
• On Self-Respect
  • Host 2: “It just feels to me like you're just kind of a pushover.” (18:22)

Timestamps for Important Segments

• [01:46] – Introduction to Jason, set-up of his dilemma
• [03:01] – Jason narrates the discovery of his girlfriend’s infidelity
• [04:51] – Assessing the emotional vs. physical nature of the affair
• [05:41] – Jason wonders if he can ever trust her again
• [06:27] – Host elaborates on pattern of her taking advantage
• [07:41] – Questioning Jason’s calculation of love versus long-term misery
• [09:07] – Listeners begin to call with stories of surviving infidelity
• [12:04] – Kimberly shares a survival and recovery story
• [13:48] – Patrick discusses regaining trust and reconciling
• [16:08] – Jackie calls with her complicated relationship history
• [18:07] – Cast reflects on the emotional exhaustion of such relationships
• [19:07] – Hosts gently urge Jason to recognize his own worth
• [19:27] – Adam on creating negative relationship patterns
• [20:03] – Final reflections, classic sayings, and closing advice

Summary Tone and Style

The Bert Show approaches Jason’s situation with a blend of humor, empathy, and tough love—balancing direct advice with space for real listener experiences. The cast keeps the tone conversational and authentic, with plenty of relatable banter while never losing sight of the emotional gravity of the subject.

For listeners grappling with complex relationship trust issues, this episode showcases both the formidable challenges and the rare, but possible, rebuilding journeys—reminding everyone of the value of self-respect, honest communication, and the hard work required for reconciliation.