The Bert Show - Full Show PT 2: Friday, January 23 [Vault] (Aired January 23, 2026)

Episode Overview

In this quintessential episode of The Bert Show, the hosts dive into a series of real, relatable listener-driven conversations. The main themes revolve around navigating social pressures and family dynamics—whether that's finding the "perfect" wedding date to save face at a high-school reunion, managing an over-invested "mama's boy" situation, or supporting a young listener bravely navigating coming out and pushing for acceptance at school and at home. With humor, candor, and plenty of empathy, the show remains true to its fun, authentic tone—mixing lighthearted matchmaking with profound discussions about identity and family.

Key Segments and Insights

1. The Perfect Wedding Date: Crowd-sourcing a Plus One

(00:00–09:25)

Summary

• The team invites self-described "expert matchmakers" from their audience to help a listener, “Emma” (a pseudonym), find the perfect date for a high-stakes wedding. It’s not just any wedding—it’s a high-school reunion where Emma is the only single attendee and three now-married ex-boyfriends will be present.
• Both the hosts and Emma stress the need for a companion who is not just attractive, but can also “work the room,” be a great conversationalist, dance, and generally impress.

Notable Discussion Points

• Emma’s requirements: someone impressive, personable, responsible, but not necessarily rich or “movie star hot.”

  “I think just looking for someone that's impressive. So attractive, great personality. At weddings, the girls all get together. So it's the type of guy that can have conversation with anybody. Somebody that the whole group will look at and say, that's a great person.”
  — Emma (03:06)

• The date should be ready to flesh out a believable history to play the part convincingly (“flashcards” encouraged!), and—crucially—should not embarrass her after too many drinks.

• Compensation: Emma offers to be a designated driver for her date and his friends one night, in exchange for his help at this challenging social event.

  “A night for a night.”
  — Host (06:09)

• Listeners phone in, and logistics like age and appearance of the date are raised. Hosts reassure “Emma” her identity is safe, noting her real name is not being used.

Memorable Moment

• “It's a high school friend—so it'll essentially be a reunion as she said it. In addition, my high school was small and catty, so even people that do not attend the wedding will hear the gossip if I show up alone, no less than three now-married ex-boyfriends will be attending. Oh, so she is in need of someone to play the role of her boyfriend who is completely perfect. No pressure, though.”
  — Host (02:01)

Timestamps

• [00:00] Call for matchmaker assistance
• [01:08] Introduce “Emma” and her dilemma
• [03:06] Emma describes her ideal date
• [06:09] “A night for a night” – compensation arrangement

2. When the Boyfriend’s Mom is Overbearing

(09:26–22:59)

Summary

• “Veronica” (another pseudonym, with a voice disguiser) calls in about her boyfriend’s extremely close relationship with his mother. She describes frequent daily calls, multiple dinners per week, and intrusive behavior from his mother—including comments about being “replaced” and suggesting sleepovers at their apartment.
• The hosts and listeners weigh in, mixing advice, empathy, and dark comedy.

Key Insights

• Veronica says she was initially drawn to the boyfriend because he was close to his mother, but now sees red flags:

  “She uses him as a security blanket. [...] I'm the first girlfriend that she's ever met of his. And keep in mind, he's in his mid-30s. So for him to keep every woman away until me, I think that speaks volumes.”
  — Veronica (15:46)

• Listeners share their own war stories—some have “mama’s boys” as husbands, some urge patience (“they don't go away”), while another warns: “Run! If he's not putting his foot down now... you're never going to win.”
• Hosts advocate for open communication—suggesting Veronica try to win the mother over with empathy and maybe a one-on-one outing, while others say to be wary of power struggles.

Notable Quotes

• “I do think overbearing parents are...doing a disservice to their child. But there is responsibility when you are the girlfriend of a mama's boy…the mother's not going anywhere.”
  — Host (17:40)

• “You're just going to have to put up with it. They don't go away. They really, really don't. [...] You can't take a boy away from his mom. You cannot do that because then you'll lose him and you don't want to do that, Right?”
  — Susan, listener (17:37)

Timestamps

• [10:01] Veronica introduces her situation
• [15:46] Revealing the boyfriend’s mother’s influence
• [17:11] Listener advice: “They don’t go away.”

3. Coming Out Young, Staying Strong: Julian's Story

(23:09–39:19)

Summary

• 17-year-old Julian openly discusses coming out as gay to his parents at 15—foregoing the voice disguiser and even declining a fake name, which the hosts commend him for.
• Julian describes his journey: seeking therapy to work up to coming out, his parents firing the initial counselor, then sending him to a Christian therapist, and the ongoing struggle to get real acceptance.

Key Insights

• Julian’s resilience and self-awareness stand out. He acknowledges the cycle of his mother “accepting” then backtracking (“I just don’t understand it”), and his father’s silence (“he just doesn’t ever talk about it...just beats himself up…”).

• He seeks advice about bringing a male date to his conservative public school prom—raising questions about personal safety, school policy, and whether this action is for him, or to “make a point” to his parents.

• The conversation shifts to the broader challenges faced by LGBTQ youth, and how progress for one generation can help the next.

  “At 17, I was in relationships. I'd already been with women, but yeah, I was by no means as strong as you are. And that's, you know, a lot to take on.”
  — Melissa, co-host (30:45)

Notable Quotes & Moments

• “I’m so proud of you. I’m 36 and I came out when I was 30...the fact that you have done this at your age is amazing.”
  — Sherry, listener (35:47)

• “You are who you are. Don’t let your parents negatively affect you. [...] Just stay where you are, man, you’re doing great.”
  — Sherry, listener (36:21)

• “If you want to bring a guy home, great. But do it authentically…not to challenge your dad or challenge your mom.”
  — Melissa (38:15)

Timestamps

• [23:09] Julian is introduced
• [23:46] Julian recounts coming out to his parents
• [26:06] Parents’ reactions and ongoing struggle with acceptance
• [30:38] Julian’s concerns about bringing a boy to prom
• [35:47] Sherry calls to commend and encourage Julian
• [38:15] Melissa’s advice on authenticity and parents’ journeys

Notable Quotes, Attributions, & Timestamps

• On what makes a perfect wedding date:

  "I think just looking for someone that's impressive. So attractive, great personality...Somebody that the whole group will look at and say, that's a great person."
  — Emma, [03:06]

• On being the girlfriend of a mama’s boy:

  "But there is responsibility when you are the girlfriend of a mama's boy… the mother's not going anywhere. He's already shown you his relationship with his mother."
  — Host, [17:40]

• On coming out young:

  “I am so proud of you. I’m 36 and I came out when I was 30… the fact that you have done this at your age is amazing.”
  — Sherry (caller), [35:47]

Tone & Language

True to The Bert Show style, the tone oscillates between playful and deeply sincere. The candid, humorous banter among hosts brings levity, even to serious conversations (“You should have dated a meth head manslut…” [21:53]), but the show never shies away from emotional topics or validating lived experiences.

For Listeners Who Missed the Episode

This episode is an excellent showcase of why The Bert Show is so beloved: it weaves together lighthearted matchmaking, relatable day-to-day challenges, and meaningful, real-world advice. Whether you’re in need of a wedding plus one, navigating complicated family ties, or embracing your authentic self against the odds, you’ll find humor, empathy, and encouragement.

Segment Timeline (Quick Reference)

• 00:00 — Search for "perfect wedding date"
• 09:26 — “Mama’s boy” dilemma and relationship advice
• 23:09 — Julian’s coming out journey and prom planning
• 35:47 — Calls of support for Julian and concluding advice

Links & Resources Mentioned:

• Youth Pride (Atlanta LGBTQ+ youth support organization)
• The Bert Show website for follow-up on matchmaking segment

“We serve the laughs while bringing you into our world so you can take a break and escape yours.” — The Bert Show