Podcast Summary: Holmberg's Morning Sickness – "WWBD" Segment

Episode Date: March 2, 2026
Time Range: 01:03–28:03 (Main Content)
Hosts: John Holmberg, Brady Bogen, Bret Vesely, Dick Toledo

Overview

This episode's central focus is the ever-popular "What Would Brady Do?" (WWBD) segment, where Holmberg and the crew field listener letters about sensitive, embarrassing, and bizarre personal dilemmas, letting Brady provide (sometimes tongue-in-cheek, sometimes legitimately heartfelt) advice. The crew tackles three unforgettable questions: a wife's anatomy reminiscent of a "beat up first base mitt," a girlfriend feuding with her boyfriend’s dog, and a pegging-for-backdoor sex quid pro quo gone awry. Discussion is frank, irreverent, and comedic, blending real empathy with constant riffing.

Key Discussion Points & Insights

1. Listener Dilemma: "My Wife's Vagina Resembles a Beat Up First Base Mitt"

• Timestamp: 04:23–12:26

The Question

A male listener laments that his wife’s anatomy has radically changed for the worse since they first got together, comparing it to a "first base mitt with the laces pulled out." The couple has no kids, and he’s unsure how to broach the topic or if such changes are normal.

The Crew’s Response

• Brady (04:17): Lightens the mood with, "There's good news, you can always relace the gloves."
• Holmberg (05:24): Riffs about it being irreversible: "Once it starts to tumbling out, it tumbles out...once the mudslide happens...you're susceptible to it forever."
• Brady adds (05:55): "You want to do that [tightening] before the mudslide."
• The group humorously debates: Is it because of natural aging, potentially large toys (“extra innings”), or unknown causes?

Notable Quotes

• Holmberg (06:33): "It’s basically marionette strings holding that thing up, and eventually one might pop, and down she goes."
• Caller/Co-hosts (09:10): Joke about hinting by taking her to Arby’s, "She sees the Arbecue up there."
• Holmberg (11:09): Offers a tactful, if self-deprecating, idea: "Watch the video together and say, 'Look at my gut. I used to be a man.' Then ask, 'What do you see different about you?' ...That's a nice fake compliment."

Advice Recap

• No easy fix: Surgery is expensive and not a lasting solution.
• The group agrees: Bringing it up to his wife is almost impossible without wounding her pride.
• Suggestion: Frame the conversation by discussing mutual aging, using humor and empathy.
• Holmberg (11:54): Ultimately, "You just have to grin and bear it...get beat up by that car wash every once in a while."

2. Listener Dilemma: "His Dog Doesn't Like His New Gal"

• Timestamp: 12:26–18:55

The Question

A man’s beloved four-year-old Presa Canario dog and his new girlfriend despise each other, to the point that she’s issuing ultimatums: “It’s me or the dog.”

The Crew’s Response

• Brady (13:17): "I would see if I could find a dog trainer...I think that's a correctable thing."
• Holmberg counters (13:34): "Dogs know. If it's friendly to other people and doesn't like just one person, that means...it's a bad person."
• The crew (16:29–19:33): Swaps real-life stories about dogs' instincts.
  • Holmberg: Tells about his dog who inexplicably hated his sister’s friend—with later rumors of a coke problem ("Dogs know").
  • Consensus: If a partner issues ultimatums against something you love, it’s a red flag.
  • Brady (18:45): "Ultimatum, period."
  • Holmberg (19:34): "Anyone who cares about you would not make you suffer emotionally to be with them."

Notable Quotes

• Caller/Co-host (16:48): "Dogs are great judges of people. Ditch the bitch."
• Holmberg (19:57): "We don't negotiate with hostages."

Advice Recap

• If the dog is generally aggressive, consider professional training.
• If this is an isolated dislike, dogs’ instincts may be at play.
• Do not stay with anyone who makes you choose between them and your passions/pets.
• Ultimatums are unhealthy; real love doesn’t require them.

3. Listener Dilemma: "She Welched on the Pegging Deal"

• Timestamp: 19:34–27:49

The Question

A man allowed his wife to peg him in exchange for “backdoor” access to her, but she now won’t reciprocate, claiming she didn’t expect him to enjoy it.

The Crew’s Response

• Brady (20:48): "She cannot...hold her end of the deal [i.e., she must reciprocate]."
• Holmberg (21:01): "He wants it more. He likey."
• The group debates punishments
  • Kidding about forced reciprocation or a humorous tattoo ("liar's hole" on her butt – 22:48).
• Brady (25:04): Suggests, "Find a dude" if he really likes pegging and isn’t getting it at home.
• Holmberg (25:20): Asserts there are plenty of women willing to play along—"Be happy he discovered he liked the pegging part."

Notable Quotes

• Holmberg (23:45): "You can get pegged by a woman and it's still very heterosexual. It's got some flavors of gay—vanilla with some gay sprinkles."
• Brady (25:23): "Be happy he discovered he liked the pegging part."
• Holmberg (27:01): "Dress her up like Hitler and have her peg you. You like it, and you can use it later for psychological warfare."
• Holmberg (27:49): "Guys who've been pegged from the future, keep it to yourselves. It's uncomfortable and gay."

Advice Recap

• If a partner reneges on a sexual bargain, have an honest conversation but don’t expect easy fixes.
• Don’t coerce; find creative, consensual ways to address disappointment (or move on if there’s no compatibility).
• Comedy as coping: The crew lampoons the situation relentlessly but underscores the need for fairness and communication.

Memorable Moments & Quotes

• Arby’s Vagina Comparison: The panel riffs extensively on comparing anatomy to fast food, showing their signature irreverent sense of humor.
  • Holmberg (09:19): "Take her to Arby's and turn your sandwich sideways and eat it like that...it just looks so familiar."
• Brady’s Verbal Shrugs: Multiple times, Brady admits, "I don't know," signaling that sometimes, even 'Dr. Brady' is stumped (10:35).
• Dogs Know! Holmberg’s anecdote about a dog sniffing out a guest’s secret drug problem becomes a show highlight (16:29).
• The Pegging Wordplay: The word “pegging” leads to running gags, gay jokes, and banter about semantics—all characteristic of Holmberg’s tone.

Timestamps for Key Segments

• WWBD Segment Begins: 03:02 (Set-up and intro)
• First Base Mitt Question: 04:23–12:26
• Presa Canario/Dog vs. Girlfriend: 12:26–18:55
• Pegging Quid Pro Quo: 19:34–27:49

Language & Tone

The conversation is explicit, fast-paced, and irreverent, with a persistent undercurrent of brotherly ribbing and crude humor. Despite the rowdy banter, there’s an underlying message of empathy and realism—especially about relationships, body image, and partnership boundaries.

Final Takeaways

Holmberg and crew bring their trademark blend of “real talk,” outrageous jokes, and surprising empathy to extreme interpersonal woes. Their advice may be unorthodox, but it’s always candid: let humor help you face tough conversations, but don’t stay where you’re not respected or happy—be it in the bedroom or with a pet-hating partner.

Recommended for: Listeners who like their advice brutally honest, unfiltered, and laced with comedy—even (especially) when it comes to the most awkward personal problems.