The Bert Show – Full Show PT 3: Thursday, January 22 [Vault]

Air Date: January 22, 2026
Host: Bert
Cast: Jeff, Jen, Melissa, Michelle, Robin, Tommy, Abby, Kristen, Cassie
Special Guest: Jake Gyllenhaal

MAIN THEME

This episode of The Bert Show delivers its signature combination of humor, authenticity, and candid real-life stories. The crew opens up about parenting challenges—specifically, the shocking and hilarious moments when young kids drop their first curse words. The conversation evolves into a lively call-in segment about “recycled” engagement and wedding rings (and the drama they cause). The episode wraps up with an entertaining and slightly chaotic interview with actor Jake Gyllenhaal, who discusses his movie choices, Brokeback Mountain, tabloid rumors, and big-headed hat shopping.

Key Discussion Points & Insights

1. Kids and Their First Curse Words

Timestamps: 00:00–13:15

• Bert’s Parenting Confession: Bert kicks off sharing the unforgettable moment his 3-year-old, Hayden, loudly dropped the F-bomb ("effin cup") in a silent movie theater during Chicken Little. The family tries to play it off at first, but it’s clear Hayden picked up the word—complete with correct context—from his parents.

  "He gets upset. And he said, he drops the F bomb—‘effin cup’—in the middle of the theater."
  —Bert (02:41)

• Handling Kid Cursing: The crew debates whether to ignore the behavior or correct it, sharing personal philosophies and moments when their children swore in public.

  "You don’t wanna laugh. You don’t wanna come down too hard. You don't wanna bring attention to it."
  —Bert describes parenting strategy (04:13)

• Blaming the Other Parent: Bert admits it’s common to privately blame the other spouse for a child’s bad language, only to realize both are guilty.

  "Privately, when something happens with your kid like that, in the back of your mind, you immediately blame the other parent."
  —Bert (05:31)

• Callers’ Own Cursing Kid Moments:

  • Michelle shares her son swearing at Sunday brunch ("sh*t" over dropped casserole) in front of relatives and church folks (07:02).
  • Jake’s daughter, when offered Barney, calls him a “bitch” ("Nah, Barney's a bitch") at age two—leaving the family both horrified and dying of laughter (09:12).
  • Robin’s story: Her three-year-old slams her fist at the table, yelling “GD it, Cosby, shut up!” at their barking dog (10:21).
  • Several parents decide they’d be terrible role models given their own frequent cussing, especially when driving.

2. The Case of the Ex’s Ring

Timestamps: 13:16–32:33

• Listener Dilemma Recall: The show recaps a listener story—Michelle’s ex-husband requests her old wedding ring to propose to his new girlfriend due to financial hardship.

  "Don't you wish there was just some way that you could have cameras on people's lives all the time so we could TiVo that…because she must have been just like: you're out of your mind, right?"
  —Bert (13:31)

• Debate:

  • Some cast members are strongly against giving the ring back; others see it as a way to clear up debts or obligations.
  • Jen notes Michelle owed her ex money (overpaid child support) and considered exchanging the ring for that debt.

• Michelle’s Update (resolution): Michelle negotiates to give her ex only the diamond from the ring, keeping the band/setting for sentimental/family reasons; the deal clears her debt.

  "You can have the diamonds inside the ring, but I want the rest of it back, okay?"
  —Michelle (17:04) "So your feeling is… if they [daughters] wanted to use this ring in the future, they certainly could."
  —Bert (19:37)

• Practical Advice: The crew suggests having the diamond removed by a jeweler with written documentation to avoid disputes.

• Call-In Stories about “Recycled” Rings:

  • Robin: Unwittingly proposed to with her fiancé’s ex’s ring; the ex recognizes her own ring while Robin is drawing her blood (she’s a nurse), leading to an awkward confrontation (23:43).
    • "That's my ring! I wanted to die." —Robin (25:14)
  • Sydney: Willingly wears her husband’s ex-wife’s ring, insisting it doesn't bother her at all—her focus is practicality, since she’s supporting his college (26:39).
  • Nicole: Discovers in a club that her ex-fiancé gave her his old girlfriend’s ring, only after said ex-girlfriend physically snatches her hand on the dance floor (29:31).
  • The hosts debate whether using an ex's ring is ever really acceptable ("I’d rather wear a piece of tin foil than have that reminder"—Bert, 27:13).

3. Celebrity Interview – Jake Gyllenhaal

Timestamps: 32:18–42:04

• Movie Choices: Jake discusses his preference for indie films early in his career, which allowed him to “stretch” as an actor, but says he enjoys big blockbusters too.

  “They were the ones where I could kind of stretch myself and push myself. ... I've always wanted to do blockbuster movies and stuff, but the other ones are more for the acting.”
  —Jake Gyllenhaal (34:15)

• Turning Down Roles: Jake reveals he was close to starring in Moulin Rouge (lost to Ewan McGregor) and that he and Heath Ledger became friends despite both wanting the role (35:27).

• Brokeback Mountain: Jake addresses the “gay cowboy” label, emphasizing there's more depth to the film, and notes no one discouraged him from the role.

  “The thing about that film is … it has a stigma on it already as being sort of the gay cowboy movie. … It's much more than that. And I know there are people who will support it more than anything they've ever supported.”
  —Jake Gyllenhaal (36:04)

• Relationship with Kirsten Dunst: The hosts press Jake for gossip about his rumored romance with Kirsten Dunst. He’s diplomatic, only saying:

  “She’s such an amazing, amazing girl and is always in my life, no matter what.”
  —Jake Gyllenhaal (36:52)

• Humor & Banter: Jake jokes along about large heads, fitted hats, and gets genuinely playful with the crew.

  “I liken the movie (Jarhead) to like really great sex without an orgasm.”
  —Jake Gyllenhaal (39:34)

  “Where do you find big hats?” (41:28) "I just go to the store…give me the biggest thing you got.”
  —Jake Gyllenhaal (41:33)

Memorable Moments & Notable Quotes

• Hayden’s First F-bomb:

  “Effin cup.”
  —Hayden (Bert’s son, via Bert) (02:41)

• Blame Game:

  “Privately…you immediately blame the other parent.” —Bert (05:31)

• Surprise Ring Reveal:

  “That’s my ring! I wanted to die. It was embarrassing.”
  —Robin (25:14)

• Jake Gyllenhaal’s Wry Honesty:

  “I liken the movie to like really great sex without an orgasm.”
  —Jake Gyllenhaal (39:34)

  "She's such an amazing, amazing girl and is always in my life, no matter what."
  —Jake Gyllenhaal (36:52)

Segment Timestamps

• 00:00 – Hayden’s first curse word in public; roundtable on cursing kids
• 07:00 – Callers share tales of kids swearing in public places
• 13:16 – Recap & update on Michelle’s ex-husband wedding ring dilemma
• 17:04 – Live call with Michelle: ring compromise, legal paperwork, future inheritance
• 23:43 – Callers: Stories of recycled engagement/wedding rings, messy breakups
• 26:39 – Sydney: Why she’s fine with her husband’s ex’s ring
• 29:31 – Nicole: Club confrontation over an ex’s ring
• 32:18 – Jake Gyllenhaal interview (Jarhead, Brokeback Mountain, Kirsten Dunst rumors, and hat sizes)
• 41:42 – Banter about big heads, hat shopping, and sign-off with Jake

Tone and Language

The episode maintains the show’s signature light, irreverent, and honest tone throughout. Bert, Jeff, Jen, and Melissa riff off each other with a blend of playful teasing and genuine curiosity, while callers and guests add authenticity, laughter, and a touch of drama.

Who Should Listen?

Fans who love candid parenting talk, relationship dramas with a comedic twist, and celebrity interviews that go off-script will find this episode quintessential Bert Show—heartfelt, hilarious, and a little bit chaotic.