Podcast Summary: The Bert Show

Episode Title: Vault: Would You Ever Date A Cheater?
Date: January 8, 2026
Host: Pionaire Podcasting (Bert, Kristin, Abby, Cassie, Tommy & The Bert Show Cast)

Overview

This episode of The Bert Show dives deep into the provocative question: "Would you ever date a cheater?" Using a storyline from "Desperate Housewives" as a springboard, the hosts and callers explore trust within relationships that started with infidelity. The discussion centers on whether trust can ever be fully restored once broken and what it's like to be "the other woman"—and then become the primary partner. Throughout, real callers share their raw, personal experiences, generating candid, sometimes heartbreaking, and often thought-provoking moments.

Key Discussion Points & Insights

1. TV Inspiration: Desperate Housewives as Catalyst (01:48 – 03:59)

• The episode opens with a recap of a "Desperate Housewives" plot, where Lynette discovers her husband Tom began their own relationship by cheating on his ex, Annabelle. Lynette finds out Tom rehired Annabelle without telling her for three months, leading to trust issues.

• The hosts play and dissect a heated clip between Lynette and Tom, fueling the core episode question about trust after infidelity in relationships.

  Key Quote:

  “Are you so insecure that you have to pull that crap?... Anyone is capable of anything. The first time we ever met, you were cheating with you. Cheating with you. It's a pattern of behavior.” – Lynette, TV Clip (03:22)

2. The Trust Issue: Can You Ever Fully Trust Again? (03:59 – 06:18)

• The team discusses whether, after infidelity, it's possible to ever trust a partner 100% again, especially if you started as "the other woman."

• Host Bert notes that prior callers overwhelmingly say trust was never quite fully restored, even if relationships continued.

  Key Quote:

  “If he's just late, you know, by 30 seconds, I start thinking, okay, who's he screwing around with? So the trust was never quite restored.” – Bert (03:59)

• Question posed: If you started out as the 'other woman,' do you ever fully trust the person—or do you suspect a pattern?

3. Callers Share Their Experiences (06:45 – 19:32)

a) Maryanne: The Lingering Distrust (06:47 – 07:17)

• Maryanne shares her experience: three years into a relationship that started when he was with someone else, she admits ongoing trust problems, always fearing he’ll cheat again.

  Key Quote:

  “We always have, like, problems in our relationship just because of that, because I know that he did that, and he probably will do it again.” – Maryanne (07:12)

b) Anna: The Paranoia Never Quite Goes Away (07:27 – 08:22)

• Anna describes similar doubts: “If he left somebody else for you, he could always leave you for somebody else.”
• The hosts probe whether Anna also struggles with guilt or trust as "the other woman." Anna is candid: “It’s hard... I’m not that special that he might not up and leave me one day.”

c) Callers and Hosts on Attraction vs. Action (09:05 – 10:26)

• Anna brings up whether cheating is "hereditary," referencing outside radio chatter.
• The hosts debate free will:
  • Some argue you can’t help who you’re attracted to, but you can decide your actions.
  • “You control who you’re attracted to and who you’re not... that’s what it’s about.” – Host (10:02)

d) Sally: Ongoing Insecurity and Regret (10:26 – 15:18)

• Sally tells a detailed, emotional story: she got into a relationship without knowing the guy had a girlfriend (“I had no clue he had a girlfriend...”), later learned the truth, but stayed.
• Two and a half years later: she’s plagued by mistrust, especially with long-distance logistics.
• Sally strongly warns other women:
  Key Quote:

  “I advise every girl out there that is in a situation to get out of it as soon as possible because you never get over it and it puts you through hell... it’s always going to be in the back of your mind.” – Sally (12:20)

e) The Hosts Offer Tough-Love Advice (13:01 – 16:21)

• The hosts tell Sally: If you have no trust, why stay? "Just leave," they repeatedly urge.

• Sally struggles, explaining her isolation and lack of friends. The hosts note that obsessive relationships can cause further social isolation.

• Emotional low point: Sally reveals exhaustion and a wish to forget her boyfriend entirely.

  Key Quote:

  “I want something to happen. I want to, like, be put in a coma or something just so I can forget this guy ever existed in my life.” – Sally (16:21)

  • The hosts respond with empathy and encouragement, highlighting the universality of heartbreak and the necessity of learning from hard experiences.

f) Jackie: “I Trusted Him—But I Was Stupid” (18:03 – 19:38)

• Jackie recounts her story: her partner left his wife for her; they had eight years of marriage, divorced, and he remarried his first wife two days after.

• Jackie reflects: she unreservedly trusted him and regretted it, signaling that patterns can—and do—repeat.

  Key Quote:

  “Because I was stupid. I mean, I was just absolutely stupid. And then we ended... and on the 62nd day, he remarried the woman that he was with, and he met me.” – Jackie (18:14)

Notable Quotes & Memorable Moments

• “Everyone is capable of anything.” – Lynette, from "Desperate Housewives" clip (03:24)
• “If he's just late, you know, by 30 seconds, I start thinking, okay, who's he screwing around with?” – Host (Bert) (03:59)
• “If he left somebody else for you, he could always leave you for somebody else.” – Anna (07:48)
• “I advise every girl out there that is in a situation to get out of it as soon as possible because you never get over it and it puts you through hell.” – Sally (12:20)
• “He doesn’t have any respect for you because you’re not respecting yourself.” – Host, to Sally (15:49)
• “I trusted him, but I shouldn’t have.” – Jackie (19:32)

Timestamps for Key Segments

• 01:48 – 03:59: Desperate Housewives recap and opening roundtable on trust and infidelity
• 06:47 – 07:17: Maryanne’s story (persistent distrust)
• 07:27 – 08:22: Anna’s story (trust issues and mutual suspicion)
• 10:26 – 15:18: Sally’s story (regret, mistrust, and host advice)
• 18:03 – 19:38: Jackie’s story (cycle repeats, post-divorce regret)

Tone & Takeaways

The episode maintains The Bert Show’s signature blend of authenticity, humor, and empathy. The tone is conversational yet deeply compassionate, especially when callers share emotional struggles. The hosts challenge, encourage, and offer practical advice—but always in a way that’s relatable and non-judgmental. Listeners are left with the sobering but empowering message: if a relationship begins with betrayal, regaining full trust is rare, and self-respect should never be sacrificed for companionship.

For listeners who haven’t tuned in:

• You’ll gain insight into the emotional aftermath of dating “a cheater,” hear honest advice from both hosts and callers, and witness the turmoil and hope interwoven in real-life stories of love, regret, and moving on.
• The episode stands as both a cautionary tale and a supportive conversation for anyone questioning the foundations of their relationship—or weighing the risk of trusting after betrayal.