The Bert Show – Full Show PT 3: Friday, November 7 [Vault]

Date: November 7, 2025
Cast: Bert, Kristin, Abby, Cassie, Tommy, Jen Hobby, Jamie Massey, Jeff, Jessica, Melissa
[Episode Runtime: ~52:00]

Episode Overview

This episode of The Bert Show explores the genuine, funny, and sometimes vulnerable experiences of the cast as parents, daters, and regular people living life. The show kicks off with a hilarious and heartfelt discussion about the fine line between encouraging kids and pushing them too hard—particularly when it comes to sports and parental expectations. It then veers into the misadventures of adult dating—highlighting age gaps and the reality checks they bring—before diving into nightmare babysitting stories from listeners and hosts that are equal parts jaw-dropping and hilarious.

Key Discussion Points

1. Bert’s Quest to Spark a Sports Interest in His Son

Timestamps: 01:16 – 14:00

Topic Summary:

• Bert confesses to borderline obsession with getting his almost-4-year-old son, Hayden, interested in sports—but insists it’s just “exposure,” not pushiness.
• Jen cautions Bert against repeating her father's mistake of pushing his own athletic dreams onto his kids, referencing “The Great Santini” as a warning about overbearing parenting.
• The team laughs about Bert’s increasingly desperate (and creative) tactics, like playing ball with a neighborhood kid in hopes his son will join in.
• The conversation gets playful as they challenge Bert about whether he’d support Hayden’s interests if they turned out to be non-traditional, like cheerleading or ballet.

Notable Quotes:

• Jen Hobby [03:31]: “I brought up Great Santini... the overbearing father who just forces the children to hate to grow up too fast.”
• Bert [05:16]: “In a sea filled with hundreds of children sweating, tackling each other, testosterone flying all over the place... my son takes a look at all the football players and then makes a beeline over the cheerleaders and wants to learn how to cheer.”
• Jeff [07:15]: “You’re creating a great spectator.”
• Bert [08:06]: “I don't care where he poops so long as he has a bat in his hand while he's doing it.”

Themes:

• The struggle of letting kids find their true interests versus living vicariously through them.
• Defining the difference between “exposing” kids to opportunities and “pushing” them into roles.

2. Jamie Massey’s Dating Life: Age Gaps, Virgins, and More

Timestamps: 14:10 – 27:56

Topic Summary:

• Jamie admits she’s been dating younger—specifically, a 20-year-old guy as her self-proclaimed “hot summer fling.”
• The table debates the “ick factor” of age gaps, applying the “half your age plus seven” rule to see if it’s “acceptable.”
• The situation gets awkward (and funny) when Jamie reveals the 20-year-old is a virgin and intends to save himself for marriage, putting a damper on expectations for a wild summer romance.
• Listeners call in with their own age gap love stories, including one where a woman “waited six months” before her younger boyfriend proposed and ex-virginity was guilt-free.

Notable Quotes:

• Jamie Massey [15:28]: “He is so hot. I can’t help it.”
• Jessica [17:01]: “You’re borderline icky—like a piece of chicken that’s just raw still, like in the very middle. You’ll probably not get that sick, but you’ll still throw up a little in your mouth.”
• Jamie Massey [19:08]: “He—I—you say it, but I don't want to say it because I would look like a…”
• Jeff [22:09]: “He’s lasted like 20 years. Well, nowadays he's lasted eight.”
• Melissa (Caller) [24:07]: “I’m actually married to a 23-year-old and he was a virgin when we started dating... Six months [until we had sex].”

Themes:

• Societal double standards around age differences in relationships.
• The challenges of staying true to one’s values (and libido) when dating someone at a different life stage.
• Virginity, sexual pacing, and pressure in modern dating.

3. Seven Body Parts Men Don’t Think Women Notice (But They Do)

Timestamps: 28:11 – 36:38

Topic Summary:

• Jessica introduces a list of seven body parts that men overlook but women absolutely notice—offering grooming advice for guys heading out for weekend fun.
• The crew gives first-hand tips on eyebrows, fingernails, dry skin, feet, ear and nose hair, yellow teeth, and back hair, with plenty of self-deprecating humor and practical examples.
• Jeff shares his own eyebrow grooming experiences, and Jen underlines why “attention to detail” is a surprisingly sexy trait.

Notable Quotes:

• Jessica [28:53]: “Okay, so these are parts that women notice on guys. But you guys don’t think you have to do anything to take care of these body parts. But you do.”
• Jen Hobby [31:29]: “Men or women—if you don’t take care of your hands...people will notice your hands faster than they notice other things.”
• Jessica [34:30]: “When I get finished with the manicure-pedi, I can’t stop looking at my hands and my feet.”
• Jessica [36:29]: “Eyebrows, nails, dry skin, jacked up feet, ear and nose hair, yellow teeth and back hair. Seven things you guys gotta take care of. Cause we notice, we pay attention.”

Themes:

• Modern grooming expectations for men.
• Women’s perspective on “little things” that affect attraction.

4. Babysitting Gone Wrong: Listener Calls & Host Stories

Timestamps: 36:45 – 51:07

Topic Summary:

• The show opens the phones for “Nightmare Babysitting Stories,” and audience members do not disappoint.
• Hosts and listeners share jaw-dropping stories: locked out of the house, roof rescues, loaded guns for self-defense, children smearing feces on walls, being wrongly accused of theft, wild kids attacking with golf clubs and knives, and even a kid stuck in a tree by her underwear.
• The conversation is peppered with empathy, laughter, and a healthy dose of “never again” when it comes to babysitting.

Notable Quotes:

• Erin (Caller) [39:31]: “We got locked out of the house...cats got locked in my car and used the back of my car as a litter box all night long.”
• Melissa (Caller) [41:16]: “...the mom showed me where the handgun was. It was loaded and let me know if her ex-husband showed up to shoot first and ask questions later.”
• Jessica [44:01]: “If your child is wiping poop on the walls, you stay home during that phase.”
• Jessica (Caller) [50:55]: “...she’s hanging from her underwear off of a tree branch...her parents come home and she didn’t want her underwear on. So her tush is in the air and her parents are like, what’s going on?”

Themes:

• The unpredictable, sometimes hazardous world of babysitting.
• How formative (and traumatic) first jobs can be.
• Sometimes, the parents are more problematic than kids.

Memorable Moments

• Bert’s Desperation to Connect Through Sports: Humor shines through as Bert gamely admits to borrowing kids from the neighborhood just to “expose” his son to athletics, and the group ribs him mercilessly for his tactics ([07:11]).
• Age-Gap Double Standards Debunked: The entire panel uses math (the “icky factor equation”) and straight-shooting banter to dissect what’s okay—and what’s just awkward—when it comes to dating across generations ([17:01]).
• The List of Seven: The honest truth about “men’s hidden grooming pitfalls” is both practical and side-splitting as the guys admit to eyebrow trims and the panel discusses the allure of clean nails ([28:53]–[36:38]).
• Babysitting War Stories: A parade of wild, once-in-a-lifetime babysitting fails—culminating in one girl dangling from a tree by her underwear—leaves the cast (and listeners) equal parts horrified and endlessly amused ([50:55]).

Important Timestamps (MM:SS)

• 01:16: Bert’s sports-parenting dilemma begins.
• 03:31: Warning against becoming “Great Santini.”
• 05:16: Cheerleading subplot and Bert’s failed sports demo.
• 07:11–08:10: Bert’s stealth coaching and “sports exposure” philosophy.
• 14:10: Jamie’s dating a much younger guy.
• 17:01: Age-gap “icky factor” math.
• 19:08: The twist—he’s a 20-year-old virgin.
• 24:07: Married caller shares her own younger-dude, ex-virginity story.
• 28:11: List of “seven body parts” begins.
• 36:45: Babysitting disaster calls start.
• 39:31: The car-cats-lockout-litter-box story.
• 41:16: Babysitter given a loaded gun for self-defense.
• 44:01: Babysitter encounters a “poop Picasso.”
• 50:55: Child rescued from a tree by her underwear.

Final Thoughts

This episode of The Bert Show delivers everything promised in the tagline: irreverent laughs, a bit of self-deprecation, heartfelt commentary on parenting and relationships, and an interactive slice of real life from listeners. The cast’s willingness to poke fun at their own missteps—as parents, friends, or daters—makes the show authentic and magnetic.

Quote of the Episode:

• Jessica [44:01]: "If your child is wiping poop on the walls, then you stay home during that phase."

Whether you’re looking for parenting advice, a reality check on age-gap love, or just want to laugh at the perils of babysitting, this episode is packed with relatable moments, hot takes, and the signature wit of The Bert Show team.