The Bert Show – "Vault: Over 30? It's Time to Leave These Things Behind"

Date: March 30, 2026
Episode Theme:
A humorous and relatable roundtable where The Bert Show cast and listeners riff on the unofficial "rules" for men over 30—habits, behaviors, and style choices that might need retiring as adulthood advances. Pulling inspiration from a "How I Met Your Mother" TV clip and an Esquire magazine article, they build a crowd-sourced, lighthearted checklist for proper adulting after the big 3-0.

Key Discussion Points & Insights

1. Inspiration for the Discussion

• TV Show Prompt:
  Burt kicks off by referencing a memorable "How I Met Your Mother" scene about the things people over 30 shouldn't do, setting a comedic, reflective tone for the episode.

  "This was circulating around the Internet... things after 30 you just can't do." – Burt (00:58)

• Esquire's Rules:
  Esquire magazine's list of "59 Things a Man Should Never Do Past 30" serves as a backbone for the conversation, with the group debating and riffing off individual items.

  "I'll read some of these from Esquire magazine, because a while ago they put together 59 things a man should never do past 30." – Burt (03:02)

2. Behavioral Red Flags: The Can'ts After 30

• Classic College/Young Adult Moves To Leave Behind:

  • Pulling all-nighters

  • Eating an entire pizza in one sitting

  • Hanging unframed posters or using thumbtacks for "artwork"

  • Crashing on or owning a futon

  • Doing laundry at a parent's house

  • Coining your own nickname

  • Using a Velcro wallet (recurring joke throughout the episode)

  • Owning or naming a bong, especially big or homemade ones

    "You shouldn't have a name for your bong either. After 30 in college." – Burt (03:43)

  • Playing beer pong (beer bonging likewise is out)

    "Beer pong after 30 has gotta go away. It's a sad day." – Burt (04:18)

• Holding Onto The Past:

  • Wearing old concert shirts or Greek letter shirts

    "I think they should give those up." – Heather (04:49)
    "You're proud that you were in SAE back in the day, but it doesn't mean anything when you're 30." – Burt (05:06)

  • Keeping old gym shorts

    "Guys for some reason will hang on to those gym shorts." – Jen (05:07)

3. Style Sins and Fashion Faux Pas

• The Panel Agrees:

  • No more Velcro sneakers or wallets

    "Anything Velcro, I think out the window, right?" – Burt (07:01)

  • Sideways baseball hats, skateboard lingo, or frequenting skate parks (unless with your kids)

    "Guys over 30 should not wear a baseball hat sideways or talk about skating skateboard tricks." – Heather (07:34)

  • Overly baggy jeans, excessively low "pull down" pants

    "If you're over 30, like, you can't overdo the baggie." – Unknown (09:36)

  • Biker shorts, unless exceptionally fit

    "Lose the biker shorts." – Heather (09:33)

  • Sunglasses on the back of the head or neck

    "Nobody should do that." – Jen (10:47)

4. Social Moves That Should Be Retired

• Outdated Party/Game Rituals:

  • Name your privates (especially adding "junior")

    "You should not name your unit... it says his name plus Junior. So, like, little Jeff. Jeff Jr." – Burt (07:53) "That's why I just stick with thunder. Stick." – Jen (08:10)

  • Shouting "Are you ready to rock?" outside of concerts

  • House meetings with roommates

  • Flashing or inventing gang signs for photos

    "How about making up your own gang with your own gang signs? Seriously?" – Jen (08:33)

  • Choosing "69" as your jersey number, or even wearing jerseys casually

    "That is an instant showstopper if you're with a woman. Come on. Yeah." – Burt (09:19)

  • Holding a lighter up at a concert ("It's all cell phones now")

  • Hacky sack at the park

5. Sports, Recovery, and "Trying Too Hard"

• Competitive Spirit Gone Awry:

  • Taking adult rec leagues too seriously (full uniforms, practices, trunk full of gear from "the glory days")

    "If you're not physically active, playing sports like you're in the high school championship is not a good idea." – Heather (05:33)

• Softball, kickball, or dodgeball obsessions:

  • The cast jokes about needing to abstain from sex for a dodgeball championship as taking things way too far.

    "No sex this week. I've got a dodgeball championship on Saturday, and I need to be focused." – Burt (05:47)

6. Healthy Debate, Exceptions & Guilty Pleasures

• Some Rules Are Meant to be Broken:

  • Oreos eaten in stages: OK, even after 30, as long as it's "in private."

    "I don't think it applies. If you can do it in private, then I think you're okay." – Jen (10:04)

  • Taking the day off for a concert: If you're over 30, maybe just take the day after, not the day of.

    "No, the thing is, over 30, you're gonna... it's harder to recover. So, okay, you take the day after than you do." – Unknown Female Speaker (11:12)

  • Party buses: Reserved for special circumstances, e.g., bachelor parties

Notable Quotes & Memorable Moments

• On Outgrowing the Beer Bong:
  "Beer pong after 30 has gotta go away. It's a sad day."
  – Burt (04:18)

• On Fashion Missteps:
  "Guys over 30 should not wear a baseball hat sideways or talk about skating skateboard tricks."
  – Heather (07:34)

• On Name-Brand Wallets:
  "Carrying an Ocean Pacific wallet at 40."
  – Jen (07:25)

• On Jersey Numbers:
  "If a guy has a jersey with the number 69 on it, you're not getting that."
  – Heather (09:29)

• On Nostalgic Sports Gear:
  "These are ones I've had since little League. I just can't let them go."
  – Burt (06:46)

• On Oreo Cookies:
  "Eat Oreo cookies in stages... Oh, you never have to let that go. If you do it, that's okay."
  – Unknown Female (10:00)

Engaging Listeners: Audience Interaction

The show actively fields calls from listeners, who contribute more questionable post-30 behavior and add personal stories or opinions, making the list more vivid and crowd-sourced.

• Examples:
  • Giving up college swag and gym shorts (Heather, 04:49)
  • Playing high school-level sports without the fitness to back it up (Heather, 05:33)
  • Ditching sideways caps and skateboard talk (Heather, 07:34)

Timestamps for Key Segments

• 00:58: Episode premise, inspired by "How I Met Your Mother"
• 03:02: Introduction of Esquire's "59 Things..." list
• 03:49–04:23: Debating the fate of beer pong, beer bongs, and bong-naming after 30
• 04:49: Listeners call in—college shirts, gym shorts, Greek letters
• 05:33–06:26: Taking rec sports way too seriously as an adult
• 06:53: Fashions that need to be retired—Velcro shoes, wallets
• 07:34: No more sideways hats or skateboard tricks
• 08:10: Naming one's privates—hard pass
• 08:22: Gang signs in photos and the absurdity of made-up gangs
• 09:10: The infamous number 69 jersey and the lost art of jersey-wearing
• 10:00: Oreos and private guilty pleasures

Closing Vibe

The episode is a lively and affectionate roast of the trappings of extended adolescence among men, especially as seen through the lens of 30-somethings. It's packed with jokes, a willingness to self-deprecate, and moments of genuine nostalgia—reminding listeners to take growing up with a dose of humor and not TOO much seriousness.