The Bert Show – Full Show PT 2: Wednesday, January 14 [Vault]
Date: January 14, 2026
Host: Bert, Kristin, Abby, Cassie, Tommy, & the Bert Show Cast

Episode Overview

This Bert Show "vault" episode offers a blend of listener-driven relationship drama, humorous real talk, and in-depth exploration of everyday personal dilemmas. Memorable moments include outrageous stories about inappropriate sexual requests, an emotionally charged “Deadbeat Mom Patrol” segment, and a check-in with Dana, a woman navigating her first-ever relationship—one with a significant age gap. Throughout, the show's signature blend of laughs, empathy, crowd participation, and unfiltered authenticity shines through.

Key Segments & Discussion Points

1. Leftover Teasers & Listener Vote ([02:00]–[04:09])

• Cast introduces several potential leftover stories, including:
  • Things stolen during hookups.
  • A friend whose style went "frumpy" and the effect on her marriage.
  • Finding out the truth about match.com users.
  • The most inappropriate request for sex ever (the clear audience favorite).
• Phones open for listeners to vote. The audience shows overwhelming interest in sex-related stories.
  • Quote: "There’s not many things that are more interesting than sex, so." – Caller ([03:17])

2. “Worst Timing for Sex?” Call-In Segment ([04:10]–[13:27])

• Bert’s Story ([04:09]–[08:13]):
  • Bert recounts a friend's experience: After a tense day when her husband unexpectedly quits his job (with a newborn and mortgage to worry about), he tries to initiate sex that night—demonstrating the classic male “bad timing” trope.
  • Quote: "There could be no worse case of a request for sex than that." – Bert ([07:51])
• Ridiculously Poorly Timed Sex Requests: Listener Stories
  • Caller Ray: Ex-girlfriend wanted sex during her next seizure ([08:25])
    • "That goes under inappropriate categories." – Bert ([09:00])
  • Caller: Husband wanted sex on the day of her father’s funeral—with brother in adjoining hotel room ([09:48])
  • Veronica: Husband hit on her after her facelift and breast implant surgery—while she was “mummified, wrapped up and stuff” ([11:03])
  • Caller: Cheating husband returns, tries to initiate sex just weeks after abandoning her and their child ([11:43])
  • Mandy: Ex insisted on sex while she was in labor because “it’s going to be another six weeks!” ([13:01])
  • Summary Quote: "We have no boundaries, man. We're always ready, man. We can always turn it around." – Bert ([13:27])

3. Deadbeat Mom Patrol: Turning the Tables ([15:41]–[32:13])

• Introduction & Format ([15:41]–[16:38])
  • Normally, “Deadbeat Dad Patrol” calls out absent fathers not paying child support.
  • This episode: Focus shifts to a “deadbeat mom” who is wealthy, refuses to pay, and seems to dodge responsibility purposefully.
• Brian’s Story ([17:14]–[21:18]):
  • Brian, a restaurant manager, has full custody of his two daughters; ex-wife (an accounting manager earning double) has stopped paying support, jeopardizing planned vacation and basic expenses.
  • Ex-wife owes him $4,400; he fears losing custody if he pursues legal action.
  • Quote: "I'm a restaurant manager, so I don't make anywhere near as much as she does... She hasn't paid a dime of child support." – Brian ([18:00], [19:13])
• Phil’s House Call Attempt ([21:17]–[24:49]):
  • Field producer Phil attempts surprise visit to ex-wife’s house; she isn’t there (in Miami with a new boyfriend, according to a coworker).
• Coworker’s Inside Scoop ([25:22]–[26:37]):
  • Call from a coworker reveals ex-wife BRAGS about not paying child support to “starve” Brian into surrendering the kids.
  • Quote: "She brags about it every single day...because she wants her ex-husband to go broke so that he'll just hand the kids over to her." – Coworker ([25:36])
• Beth (Ex-Wife) Confronted On Air ([26:38]–[31:14]):
  • Beth is defensive, dismissive, and unapologetic.
  • Explains her strategy: withhold money to force custody transfer. Cites past depression as reason for initial distancing, claiming now to be “fit” after medication and therapy.
  • Memorable Quotes:
    • "First of all, it’s none of any of your business. This shouldn't be done on the air...You should have no knowledge of this." – Beth ([27:40])
    • “Maybe the idea is that since they can’t afford it, maybe I should just take them back, which is what I’m trying to do.” – Beth ([28:05])
    • “Why don't you up your prescription, then? Because you're still not thinking clearly.” – Bert ([30:02])
  • Bert pushes for her moral responsibility; Beth remains cold, leading to a tense on-air confrontation.
• Brian’s Reaction ([31:57]–[32:13]):
  • Brian expresses regret and disbelief at his ex-wife’s attitude: “I actually feel like an idiot every time I listen to her talk.” ([32:13])
• General Takeaway:
  • The Bert Show exposes an unusual deadbeat parent situation, stirs empathy, anger, and debate among listeners.

4. "Dana & the 58-Year-Old": Relationship Dilemmas ([33:43]–[49:43])

• Recap & Listener Predictions ([33:43]–[39:01]):
  • Dana, 27, had never dated—parents set her up with Carl, 58. Relationship accelerated rapidly: talks of marriage and kids.
  • On vacation, Dana meets a charming guy her own age by the pool, leading to confusion and self-doubt.
  • Listeners (and hosts) predict possible outcomes: new relationship, engagement, or clinging to the familiar for safety.
  • Humorous moment: Wild predictions, including “vegetable enema” ([38:41])
• Dana’s Update & Reflections ([39:01]–[49:10]):
  • Dana admits she didn't pursue the younger guy, afraid to risk losing Carl.
  • Admits to growing feelings of boredom, lack of excitement, desire for space, and conflict about July 4th plans: hang out with friends or go to New York with Carl.
  • Listeners and hosts urge her to gain experience, not to lock herself into a marriage with her first-ever boyfriend, especially with red flags (like boredom) so soon.
  • Notable Exchanges:
    • "I mean, I just feel like I need to have a little bit of space and have a little bit of fun with my girlfriends..." – Dana ([43:24])
    • "Anybody who went out on their first date, one date, and then decided that’s the person they want to spend the rest of their life with is wrong. Like, don’t do that." – Bert ([48:05])
  • Recap concludes with Dana undecided on her July 4th plans, intending to check in again after the holiday.
  • Host Observation: Dana sounds notably more mature and less giddy than in past check-ins ([49:29])

Notable Quotes & Moments

• "There could be no worse case of a request for sex than that." – Bert, on mind-blowing bad timing ([07:51])
• Caller Ray's unforgettable story: "Her request was the next time she had a seizure was we had sex while she was having a seizure..." ([08:30])
• Beth’s cold rationale: “Maybe the idea is that since they can’t afford it, maybe I should just take them back, which is what I’m trying to do.” ([28:05])
• Empathy from callers: "Normally when you're in a relationship and you've only been together for a little while, it should stay new for a while...Maybe you don't know what you really want yet." – Kelly ([44:01])
• Show’s Moral Stance: "Anybody who went out on their first date, one date, and then decided that's the person they want to spend the rest of their life with is wrong. Like, don't do that." – Bert ([48:05])

Timestamps for Key Segments

• [02:00] Leftover teases and audience voting
• [04:09] Bert’s “worst timing for sex” story
• [08:25] Listeners’ stories of sexual requests with terrible timing
• [15:41] Deadbeat Dad/Mom Patrol intro and Brian’s case
• [21:17] Phil’s house call to ex-wife
• [25:22] Coworker outs “deadbeat mom”
• [26:38] Live confrontation with Beth
• [33:43] Recap of Dana’s story and relationship predictions
• [39:01] Dana’s on-air update: torn between Carl and independence
• [43:24] Listeners and hosts give relationship advice to Dana
• [49:29] Observations on Dana’s emotional growth

Tone & Style

• The show features the hosts’ signature blend of playful ribbing, blunt honesty, and spontaneous audience interaction.
• There is real empathy for listeners’ struggles combined with irreverent humor and bold, sometimes provocative, commentary.

This episode is a quintessential Bert Show experience: outrageous and relatable stories, authentic listener participation, deep dives into serious relationship issues, and a vivid sense of community—even when the topics get heated or uncomfortable.