Bellied Up Podcast – Episode #182

"Dating Someone 28 Years Older" – January 8, 2026

Episode Overview

In this lively and candid episode recorded at the Blarney Stone in Fargo, ND, hosts Charlie Berens (Emmy-winning comedian) and Myles "You Betcha Guy" belly up to the bar to kick off the new year and dive into a truly unusual caller story: a 22-year-old firefighter, Ryan, who’s dating a woman 28 years his senior. Sprinkled with Midwest banter, comedy, and the guys’ signature offbeat advice, the episode blends relatable resolutions, lighthearted roasting, and sincere support as the trio discusses family, societal norms, and romantic age gaps.

Key Discussion Points & Insights

1. New Year's Small-Town Vibes & Banter

• The show opens with classic Midwest humor and playful debate about vests, the merits of hoodie/vest combos, and Charlie “stealing” a vest in chilly bar conditions.
  • [01:35] Myles to Charlie: “I just haven’t seen you in many vests. Are you a vest guy or not?”
• They riff on using one’s kid as an excuse, winter fashion (“protect your vitals!”), and the utility of bar vests versus winter coats.

2. DIY Projects & Bench Philosophy

• Both hosts commiserate over unfinished home improvement projects, such as Charlie’s half-done garage bench.
  • [07:23] Charlie: “Garage has gotten way out of hand…projects everywhere, half done…I got a bench that I’m redoing that’s just chilling there.”
• The “bench-as-life-metaphor” comes up, with jokes about riding the pine and not needing to ever do a bench project again.

3. Rubik’s Cube and (Not) New Year’s Resolutions

• Myles shares his quirky goal to lock himself in a room and solve a Rubik’s Cube (with absolutely no prior research), currently stuck in “pre-mental preparation.”
  • [13:10] Myles: “Just put me in a room with a Rubik’s Cube. I just want to…me and the cube. I don’t come out until I solve it.”
• Charlie talks about his never-ending list of projects and a content but restless approach to self-improvement.

4. Learning the Loon Call

• In a classic Midwest moment, the hosts try to teach Charlie how to mimic a loon call using his hands, leading to comedic play-by-play and physical comedy.
  • [18:13] Charlie: “You know, I want to learn, Miles. I want to learn how to do a loon call just like you.”
  • [20:37] Myles on Charlie’s failed attempt: “You’re too tense. Your knuckles are literally white.”
• This segment’s playful energy reflects the light, improvisational tone of the podcast.

Main Caller: Ryan and His 28-Year Age-Gap Relationship

Setting the Scene

• [22:00] Ryan calls in—after being screened by his phone's virtual AI assistant!—to discuss his new relationship:
  • [26:34] Ryan: “My girlfriend is fantastic…we haven’t been dating very long…but she happens to be 28 years older than me.”

Hosts’ Reaction

• Charlie and Myles react with equal parts surprise and genuine curiosity.
  • [26:59] Charlie: “Wow.”
  • [27:00] Myles: “Dude, it’s fine!”

Getting to Know Ryan & Anna

• Age specifics: Ryan is 22, Anna is 50.
• They are both volunteer firefighters in the Stevens Point, WI area.
• Relationship Origin:
  • Met during fire station meetings and began connecting during firefighter training.
  • Their first “real” date was an impromptu, classmates-turned-couples motorcycle ride after everyone else bailed.
    • [34:35] Ryan: “Everybody canceled except for me and her…Ended up going on this motorcycle trip up north…all the trees changing colors…stop at a bar, have some drinks, get some food…”
  • Night culminated with three bottles of wine at Ryan’s place; he claims he was a gentleman, despite Anna’s inebriated advances.

Laugh-Out-Loud Moments

• Hosts tease out details, riffing on firefighter innuendos:
  • [31:01] Myles: “So she knows how to work a hose, is what you’re saying.”
• Playful roasting about “starting over” and “being professional” after rocky AI-assisted call setup.

Family Dynamics & Upcoming Introductions

• Anna’s kids: 28 (son), 23 (daughter), and 14 (son).
• Ryan is preparing to meet Anna’s daughter for the first time at Thanksgiving, despite being almost the same age.
  • [42:15] Myles: “So, yeah, what’s that gonna be like? …You think they’re cool with you or weirded out?”
• Ryan’s strategy for meeting the family: bringing his (allegedly award-winning) homemade pumpkin pie and defaulting to small talk about weather and current events.
  • [44:07] Ryan: “I make a really good pumpkin pie…I’m bringing pumpkin pie.”

Potential Awkwardness & Self-Deprecation

• Ryan shares his low expectations and deadpan humor about his “plan” to die alone, owning his lack of urgency and setting the bar low for life outcomes.
  • [52:31] Ryan: “My plan has kind of been for the past four or five years that I just die alone.”
• Hosts encourage him, referencing movie "Dodgeball" and jokes about not setting goals so you’re never disappointed.

Addressing the Elephant in the Room

• The potential issue of having children together is dismissed; Ryan is content without kids.
• He shares his mother would find the whole thing hilarious, while his father would probably be confused, then disappointed.

AI Assistant Gag & Future Tech

• The conversation circles back to the AI call screener and then becomes delightfully morbid/absurd:
  • [55:06] Ryan: “When she dies, because she’s 28 years older than me…I should make her into a robot. I’m sure the technology will be there.”

Midwest Wisdom and Final Advice

• Hosts send Ryan off with encouragement, Midwest practicality, and jokes about “orchestrating” Thanksgiving like Anna orchestrates their romantic evenings.
  • [57:29] Myles: “Love is love. It don’t matter the age.”
  • [57:36] Charlie: “Well, good, good. Hopefully she orchestrates for your Thanksgiving evening too, to bring it all back home.”

Other Notable Segments

Tattoo Advice – Chicken Wings on Your Back!

• Caller Nick asks for advice on tattooing chicken wings on his back, instead of angel wings.
  • [59:49] Nick: “I want to get chicken wings on my back. Like how you get angel wings…and I just kind of want to know your opinion.”
• Hosts riff:
  • [60:49] Charlie: “A chicken wing is way too easy to look like a wiener, though.”
  • [61:13] Myles sets his price high (“a million bucks”) while Charlie would do it for $10k.

Classic Bellied Up Farewells

• Charlie vows to work on his loon call; Myles, the Rubik’s Cube.
• Charlie, on Ryan:
  • [63:15] “I’ll work on my loon call, you work on your Rubik’s Cube, and Ryan will work on Anna.”

Notable Quotes & Memorable Moments (with Timestamps)

• [02:05] Myles: “If someone sees one of us in a vest, it’s probably going to be me.”
• [09:06] Charlie: “Ride pine. See, I was never bad at sports. That’s what people on the bench talked about while I was out there starting.”
• [13:10] Myles: “Just put me in a room with a Rubik’s Cube…me and the cube. I don’t come out until I solve it.”
• [40:43] Ryan: “Sorry to any exes listening out on the show, but she blows them out of the water…It’s not even a competition.”
• [46:56] Charlie: “So, her daughter’s not your type because she doesn’t have her sh*t together.”
• [52:31] Ryan: “My plan…has kind of been for the past four or five years that I just die alone.”
• [55:20] Ryan: “When she dies…because she’s 28 years older than me, I should make her into, like, a robot.”
• [57:29] Myles: “Love is love. It don’t matter the age.”

Important Segment Timestamps

• Vest Run-Down & New Year Talk: 00:45 – 06:30
• Rubik's Cube & Project Jokes: 12:08 – 14:00
• Loon Call Comedy: 18:09 – 21:33
• Main Caller Ryan Joins: 26:34
• Ryan’s Age-Gap Love Story: 26:34 – 57:49
• Tattoo Caller (Chicken Wings): 59:29
• Sign-offs & Show Close: 63:00

Conclusion

Through Midwestern wit and compassion, Charlie and Myles expertly blend off-the-cuff comedy with surprisingly thoughtful advice. Whether you’re pondering a new tattoo or carrying pumpkin pie as an olive branch to your 50-year-old girlfriend’s family, Episode #182 will leave you entertained, smiling, and perhaps a little more comfortable bellying up to your own life’s awkward conversations.