Bellied Up Podcast – Episode #185

"Timmy Tango is Hunting For Cougars"
Hosts: Charlie Berens & Myles “You Betcha Guy”
Air date: January 29, 2026

Episode Overview

In classic Bellied Up fashion, Emmy-winning comedian Charlie Berens and Miles the You Betcha Guy belly up at a small-town bar and field calls from across the Midwest. This episode delivers a double-helping of Midwest charm, warmth, and offbeat humor, centering around two distinct but equally engaging main conversations:

1. Midwest transitions and culture (with caller Greg)
2. An outrageous “cougar chronicles” update (courtesy of recurring caller Timmy Tango)

Packed with banter about Midwest sports fandom, small-town quirks, mom-hunting at Pilates, and the ever-evolving etiquette of barroom life, this episode blends advice, storytelling, and lighthearted riffing—plus some unexpected life lessons along the way.

Main Discussion Segments & Timestamps

1. Opening Banter, Midwest Life & Bar Setting

[00:00–07:00]

• Charlie and Miles riff about awkward junior high dances, the mysteries of skeet shooting, the unpredictability of birds vs. clay pigeons.
• Bar review: They’re recording at Cleveland Pub in New Berlin, WI—admiring its space, abundant drink taps, and “You Betcha Old Fashioned” special.
• Photo op plans: Discussion of Charlie’s patented “open mouth point” pose and insecurities about his smile.
  • "I do like the open mouth thing... it takes attention away from other facial features." – Charlie [04:32]
• Addressing a previous caller's roast about Charlie's dirty glasses and his “flying blind” without them.
  • "No, I just lost my glasses because I have special needs, and my need is my glasses right now." – Charlie [06:02]

2. “You Might Be a Fake Packers Fan If…”

[07:47–14:18]

• Miles challenges Charlie on how to spot fake Packers fans.
• Charlie’s Guide To Real vs Fake Packers Fandom:
  • Only fake fans ask if food at a Packers tailgate has gluten ([08:12])
  • Not wearing hunting gear to a winter game is a red flag ([10:03])
  • Not complaining about beer prices at Lambeau ([10:55])
    • "Going to Lambeau and complaining about the beer prices is like going to church and blessing yourself with holy water. You have to do it." – Charlie [11:04]
  • Real fans always try to smuggle booze in
  • Sitting outside in jeans at a December game = rookie mistake
  • Advanced fan tips: BYO seat cushions, “insulation insulation” with DIY duct-taped foam

3. Caller: Greg’s Midwest Migration and Adaptation

[15:37–46:47]

Greg’s Backstory

[16:07]

• Born and raised in Tucson, Arizona (deserts, cacti, no lawns).
• Married to a Midwesterner; recently moved to a small Minnesota town.

Midwest Life Pros & Cons

• Winters: Hard at first, now appreciated for their beauty and the ease of “hiding” unfinished yard work ([18:14–19:02])
  • "It's the ultimate just kick-the-can-down-the-road." – Miles [18:18]
• Seasonal contrasts: Dazzling for former Arizonans ([19:02])
  • "Every three months, it's completely different... in Arizona there's hot and damn hot." – Greg [19:09]
• New experiences: Caught his first fish (a bass) at 52 ([19:21])
• Kayaking-fishing journey: Stories of improvising fishing with bare jig, upgrading to trolling motor, later a tricked-out boat with WiFi and CarPlay ([21:27–23:37])
  • "I have tricked it out, man... it's got WiFi, CarPlay, everything." – Greg [22:37]

The “Midwest Slippery Slope”

[23:05–24:27]

• Miles & Charlie outline the progression: move to the Midwest → get a kayak → add motors & fans → upgrade to a boat → inevitably want a Winnebago-pontoon hybrid.

Pontoon Bathroom Engineering & Midwest Innovations

[24:25–27:18]

• Humorous stories about friends retrofitting pontoons for bathroom/fishing hybrid use.
• "You can't just go around doing that. That's terrible." – Charlie's friend's reaction [25:43]

Discovering New Midwest Hobbies

[27:42–32:18]

• Greg loves mowing: contrasts it to "rearranging rocks" in Arizona.
• Gardening is easier: seed in ground, crops practically grow themselves.
  • "Here, you just poke a seed in the ground and it grows." – Greg [28:17]

Wanted: Authentic Mexican Food

[31:00–37:00]

• Greg’s “Mayor for a Day” fantasy: Bring real Mexican food to his small town.
• Critiques Midwest Mexican cuisine as poor Tex-Mex imitations (e.g. BBQ sauce-chimichangas, bland salsa).
• Discussion of actual spice vs. “Midwest spice” (horseradish as a gateway), and acclimating the local population to heat year by year.
• Miles shares his "spiciest sandwich ever" story ([34:33])
  • "My face was beet red and I was actually just sweating sitting there." – Miles [34:59]

Small Town Rituals & Midwest Retail

[38:45–41:46]

• Food trucks trump fancy Mexican restaurants ("authenticity" often means a spray-painted food truck).
  • "If you roll up to a food truck that's got a nice vinyl wrap, you know, you're about to get some fake Mexican food." – Miles [38:54]
• Love for Menards and Fleet Farm: Midwest retail as entertainment
• Podcast recommendations (Radiolab, Hardcore History, “You Betcha Radio”): Bellied Up dubbed “official podcast of driving to your nearest Fleet Farm.”

Final Midwest Problem-Solving

[42:35–45:47]

• Tree maintenance woes: frost guards, trunk splitting, replacing dead yard trees.
• Greg touts the joys of Midwest state parks and exploring new activities.
• Local winter skateway (ice skating trail) delights.

4. Caller: “Timmy Tango”—The Cougar-Hunting, Wine-Night Strategist

[49:11–85:49]

Timmy’s Recap and Last Episode Drama

[50:16–51:41]

• Last time: Mid-20s Timmy ends up kissing a married mom at a concert (accidentally, post-reveal, does NOT slide into her DMs).

The Quest for Cougars: Gym Edition

• Self-styled as a “Ferrari at the racetrack,” Timmy dials in on group fitness classes (Pilates, yoga) as his new hunting ground ([52:44])
  • "I've been getting to know some of these moms, some are even grandmas. I'm not into that, but..." – Timmy [53:26]
• Investigative tip: Wedding rings come off during workouts, so post-class coffee is key for recon ([53:49])

Gym Mom Dynamics—Friend-Zone or More?

• Miles, Charlie, and Timmy riff on being possibly seen as the “gay best friend,” getting friend-zoned, plus roleplaying “Pilates moms" plotting to set Timmy up with their friend Carl ([57:02–58:08])
  • "Maybe we should bring Carl to the class and they can hit it off." – Charlie-as-mom [57:48]

“Benefits of Older Women” Discussion

[55:49–56:45]

• Timmy’s preference: Mature conversation, less drama, and real meals post-bar (vs. forgetful young women who leave ovens on).
• "If I bring these girls home, they're gonna burn my house. If I bring a mom home, she's gonna cook me the best damn meal I've ever had." – Timmy [85:13]

Breakdown of the “Pilates Class Prospects”

[67:40–71:43]

• Timmy rates three main “natural” (i.e., non–plastic surgery) potential interests:
  1. Jenna (approx. 45, works at a law firm, genuine, personable, “number one prospect”)
  2. Lily (38, “drop dead gorgeous”, “best asset is her boobs”, possibly not natural)
  3. Third (divorced mom, nine-year-old kid, seems more accessible as a dating prospect)

Timmy’s Wine Night Gambit

• The Plan: Get invited (or initiate) a wine night with the Pilates crew as the next move.
  • "Hopefully we can build off that [rapport]...and then we move to wine night." – Timmy [66:15]
• Charlie & Miles offer to sponsor the wine if Timmy succeeds ([76:02])
• Advice: Ask wine questions, act curious, avoid awkward innuendos but use flirty wine lingo if the moment is right ([78:02])
  • "This wine must work out quite a bit. The legs on this thing..." – Miles (demonstrating wine flirtation) [78:35]
• Bonus tips: Wear a mock turtleneck to wine night for full “cougar-hunter” effect ([81:08])

Life Lessons & Self-Awareness

• The dangers of being “used” as an ego-boost for lonely moms ([59:56])
• Timmy is urged to avoid fallback plans with women his own age and go all-in on the moms ([60:19])
• The nature of flirting, reading signals, and not getting friend-zoned.
  • "I'm terrible. I can't ever catch a sign...she's just working for the tip." – Timmy [74:39]

Final Encouragement and Next Steps

• If Timmy successfully initiates wine night, a Bellied Up–funded update (with drink sponsorship and more advice) is on deck.
• Hosts express genuine admiration for Timmy’s commitment and promise ongoing support.
  • "You’ve been bitten by the bug, and you’re biting back." – Charlie [83:48]

5. Closing Banter: Midwest Niceness & Listener Logistics

[85:49–90:16]

• Timmy calls out the classic “Midwest nice” asking-for-free-tickets move.
• Charlie pledges a 2026 “less people-pleaser” resolution…except (maybe) for Miles.
• More character-building Midwest wisdom—tip your bartender and always bring a seat to Lambeau.

Notable Quotes & Memorable Moments (with Timestamps)

• “Going to Lambeau and complaining about the beer prices is like going to church and blessing yourself with holy water. You have to do it.”
  — Charlie [11:04]

• “Here, you just poke a seed in the ground and it grows.”
  — Greg, on Midwest gardening vs. Arizona [28:17]

• “If you roll up to a food truck that's got a nice vinyl wrap on the side... you know you're about to get some fake Mexican food.”
  — Miles [38:54]

• “If I bring a mom home, she's gonna cook me the best damn meal I've ever had after the bars.”
  — Timmy [85:18]

• "I feel like I'm not even interested in the girls my age anymore. Once you get the maturity level of a woman… you just— all the other girls, that ain't it."
  — Timmy [83:32]

• "Pilates class is just like high school all over again. You've got your groups."
  — Timmy [67:55]

• "Timmy Tango is a doer. The fact that he's doing two Pilates classes a week—this guy is committed!"
  — Charlie [81:47]

Episode Tone, Style, and Takeaways

• Homely & Unapologetically Midwestern:
  The hosts’ banter is both affectionate and relentlessly self-deprecating, revelling in the rituals, quirks, and gentle absurdity of Midwest life.

• Mix of Absurd Humor and Life Coaching:
  Advice is given (both earnest and tongue-in-cheek) on sports fandom, dating older women, reading social cues at Pilates, and how not to burn your house down.

• Warmth and Listener Camaraderie:
  The episode’s callers are celebrated for their curiosity and bravado, and the hosts offer support—both emotional and (possibly) financial for Timmy’s future wine exploits.

How to Enjoy This Episode if You Missed It

Whether you’re a Midwest transplant, aspiring cougar-hunter, or just in it for the barstool ridiculousness, this episode offers equal parts homespun wisdom, outrageous dating strategy, and genuine laughs.
Recommended for: Anyone who wants real advice on living (and loving) in the Midwest—delivered with a chaser of Old Fashioned, and a wink.