Bellied Up Podcast Ep. 177: "The Most Dysfunctional Family We've Ever Seen"

Hosts: Myles "You Betcha Guy" & Charlie Berens
Date: November 26, 2025

Overview

This episode kicks off with lighthearted banter about Thanksgiving, seasonal changes in the Midwest, and childhood insecurities, before diving into one of the wildest listener calls in recent memory—a saga of relationship dysfunction, family chaos, and more cheating scandals than a season of Jerry Springer. The callers and hosts riff with their signature blend of dry wit and Midwest charm, tackling not just the listener’s problems but also pet peeves, “heaven or hell” hypotheticals, and the deep mysteries of fashion crimes like flip flops with jeans.

Key Discussion Points & Insights

Midwest Fall & Childhood Insecurities

[00:00–06:14]

• Myles and Charlie banter about Midwest fall: all colors gone, everything’s “deer colored.”
• The origins of "fall" and "spring" are discussed, with some creative (and ribald) theorizing.
• They reflect on their childhood insecurities:
  • Myles wanted to play QB but was “chunkier and slower”:
    “You gotta have wheels to play quarterback... I was always the first loser, got 2nd in Taekwondo every time.” — Myles [03:33]
  • Charlie shares his recurring feeling of just missing greatness, as summed up by a teacher:
    “You’re always on the edge of greatness, aren’t you?” — Ms. Steinberg, via Charlie [04:39]

Inside Jokes & Family Stories

[06:14–16:20]

• They discuss a recent social media “rap beef” that fizzled before it started, with good-natured ribbing.
• Charlie tells stories of his Grandma Sue—88 years old, a gambling Hallmark movie fan, Catholic, and a lover of road trips to the casino.
  • Anecdotes about buying “apparition dirt” at a shrine and repeatedly getting pulled over for expired registration.
  • “Forget about paying your car registration. We got pulled over on the way back from the casino because my grandma didn’t pay her car registration. I’ve gotten pulled over with my grandma, like, three times.” — Charlie [11:00]
• Transition to Myles's Aunt Mary and the challenges of older dating, mentioning the “Golden Bachelor,” downsizing houses, and suburban tailgating.

Thanksgiving Food & Last Meal Fantasies

[16:21–20:34]

• They debate the worst Thanksgiving dishes (green bean casserole gets shade).
• Absurdist conversation about choosing Thanksgiving dinner as a “last meal,” whether in prison or at a nursing home.
• Myles is “analytics guy”:
  • “I’m probably gonna die of either a stroke, cancer, or heart attack… If you’re really playing the numbers.” — Myles [22:04]
• Charlie considers wandering into the woods “dressed as a deer” as a poetic end:
  • “I think I’m gonna go off like a wounded deer and just find a tree and lay down for a little bit.” — Charlie [19:16]
• Heaven, hell, and purgatory tailgating are discussed.
  • “We’re gonna be tailgating heaven.” — Charlie [25:22]

Main Caller Segment: “The Most Dysfunctional Family”

[28:28–76:04]

(Brady from Florida/Michigan)

Heaven, Hell, or Tailgate (Purgatory)?

• Brady self-selects “tailgating at heaven”—the purgatory middle ground [28:51].

The Bacon, the Lies, and the Rings

• Confesses to stealing bacon from his grandpa as a kid [29:29], then “bad boyfriend” behavior:
  • Lied about buying an engagement ring, used his sister's wife’s ring, staged a fake proposal, got caught after 15 minutes [31:15-32:23].
  • Relationship spans 8-9 years, broken up and reconciled multiple times, with long distance, cheating, and a second legitimate ring bought (and returned).
  • "So you just keep getting under the hood?" — Charlie [37:04]
  • "This relationship’s been totaled twice, though, to be quite honest with you.” — Charlie [36:55]

Family Dynamics: Four Divorces, Choir Affairs, and Crap Hits the Fan

• Brady’s parents: married and divorced four times—to each other!
  • Cheating, drama, and a wild revelation that "on a high school choir trip, my dad ended up sleeping with my choir director" [39:38].
  • Choir director later also sleeps with Brady—making him and his dad “Eskimo brothers.”
  • "Unfortunately, you hit up your choir… When did you sleep with your ex choir director?” — Charlie [43:19]
  • This is all casually confirmed, with the host incredulous at the “love octagon.”

Retaliation Cheating, Disney Drama, and Financial Mayhem

• Cycle of infidelity with his girlfriend:
  • Both cheat in retaliation; she buys a house with another guy (Chase) while Brady is still financially supporting her.
  • "You realize you're not in a relationship. She is just your sugar baby, and you are her sugar daddy.” — Myles [64:44]
  • Over $200,000 given to his girlfriend over 9 years—just this February, he sent $6,000 [65:35].

Advice from the Hosts

• Myles and Charlie employ every analogy in the book, from totaled cars to Jenga towers, to persuade Brady to cut the financial cord.
  • "Don’t break up with her. Just stop giving her money starting today and call us back when the relationship’s over." — Charlie [64:08]
  • They encourage him to regain his confidence:
    “You were able to buy one engagement ring, you also had sexual intercourse with your choir director, and she was hot… You got game.” — Charlie [72:48]
• Brady agrees (tentatively) to stop the payments and promises to call back with an update.

Mini-Caller: Flip Flops & Blue Jeans Fashion Debate

[78:45–84:32]

• Jordan from Texas wants Midwestern perspective on men wearing flip flops with blue jeans, calling it “the dumbest shit in the world.”
• Consensus: It was a 2000s thing, maybe only forgivable at beachy venues.
  • "For me, it was if I'm on a tropical vacation or somewhere warm, but you're going out to dinner..." — Myles [80:19]
• They debate which fashion crimes are worse and reflect (with some Boomer energy) on the cyclical nature of trends (baggy jeans, Crocs, etc.).

Notable Quotes & Memorable Moments

• On Family Dysfunction:
  “When we asked for hometown drama, I could have never imagined a love triangle. You’re like, in a love octagon right now...” — Myles [43:06]

• On Retaliation Cheating:
  “Monkey see, monkey do, right?” — Brady [53:14]

• On Bucket Lists:
  “Charlie was asking me about my bucket list earlier, that's one thing I haven’t knocked off that list—choir director.” — Myles [45:09]

• On Self-Awareness:
  "You realize you’re not in a relationship. She is just your sugar baby, and you are her sugar daddy.” — Myles [64:44]

• On Fashion Crimes:
  “Flip flop might be the worst shoe to put a bottle opener... just no leverage.” — Charlie [79:47]

Timestamps to Key Segments

• Midwest Fall / Banter: [00:00–06:14]
• Grandma Sue & Family Road Trips: [07:45–13:49]
• Thanksgiving & Last Meals: [16:21–20:34]
• Heaven, Hell & Tailgating: [23:43–26:31]
• Main Caller, Dysfunctional Family: [28:28–76:04]
• Fashion Debate (Flip Flops & Jeans): [78:45–84:32]

Tone & Style

The episode carries its signature Midwest blend of gentle roasting, dry irony, and ironic self-help. Both hosts toggle easily between supportive advice and relentless ribbing, with Brady’s saga providing a jaw-dropping peek at modern relationship chaos that’s both tragic and, through the duo’s lens, unavoidably comedic.

Summary Verdict

This episode is a must-listen for fans of chaotic life stories, bone-dry Midwestern humor, and emotional trainwrecks. Whether it’s tales of gambling grandmas, generational family cheating, or flip flop faux pas, Charlie and Myles deliver a therapy session for all of us—one where laughter is half the cure and honest-to-God advice sneaks in behind the jokes.