Podcast Summary: The Bert Show – "Vault: Do Grandparents Still Give You Money Even After You're Grown?"

Release Date: November 25, 2025
Host: The Bert Show Cast (Bert, Kristin, Abby, Cassie, Tommy & others)

Episode Overview

This episode delves into a heartfelt and humorous discussion among The Bert Show cast and their listeners about a tradition common in many families: grandparents and older relatives continuing to give small cash gifts, like $5 or $10 bills, long after their grandchildren become adults. The conversation explores the sentimental value behind these gifts, varying family customs, memorable stories from callers, and wider reflections on generational differences.

Key Discussion Points & Insights

1. Opening Story: The $5 Christmas Card Tradition

• Bert shares how his wife Stacy’s aunt has given Stacy $5 in a Christmas card every year since she was born. Now 36, Stacy still receives it, sparking the question: Is this a common tradition in “healthy” families, or just a quirky family thing?
• The cast agrees it’s a sweet, widespread tradition, not unique to just one family.

"Every single Christmas. And the Christmas card came yesterday. And this is a grown woman—she’s 36 years old now, and this aunt has given the $5 in the Christmas card every single year." — Bert (03:15)

2. Cast Members’ Personal Stories

• Kristin reminisces about a grandmother who mailed her $10 annually, whether for a birthday or Christmas, and notes how the value of money and meaning changes as you grow older.
• The cast highlights how these cash gifts start meaningful for children but become nostalgic, almost comical, as adults.

"When I was like 6, 10 bucks is a big deal to a 6-year-old... By the time I’m 18, doesn’t even really fill the gas tank…by 25, it’s almost like a joke. But you’re not even gonna say anything because it’s just something she’s been doing since you were four." — Kristin (04:02)

3. Traditions Beyond Money

• The crew mentions other quirky holiday requirements, like H (not present that morning) who still has to take Christmas photos with Santa for his grandparents at age 24.
• Birthday gifts often “cap” at a certain dollar value as the child grows, sticking as a tradition.

"Every Christmas, he has to go get his picture taken with Santa for his grandparents. And he’s 24 and his brother’s 21, and they still have to go do it." — Bert (05:40)

4. Listener Stories (08:25–19:10)

a. Danielle – The Sock & $5 Combo

• Danielle continues to receive $5 and a pair of socks every Christmas from her Aunt Connie—now extended to her fiancé. The logic: 'Everyone can use an extra pair of socks.'
• The cast sees wisdom in this practical tradition.

"Every year gives me $5 and a pair of socks. I’m 25. My brother’s 30. We get it every year. And I’m engaged now. And last Christmas, my fiancé got a pair of socks and $5, too." — Danielle (08:30)

b. Chris – The Eccentric Aunt

• Chris describes his 89-year-old Aunt Marie, who sends $5 for every birthday and Christmas. She is flamboyant, showing up in gold lamé pants and “bombs” (gin martinis).
• Chris realizes he’s not alone; the $5 gift is a widespread custom.

"She’ll come to Christmas dinner wearing gold lamé pants and a pink shiny shirt with about 4-inch pumps on. She drinks what she knows as her bombs, which are gin martinis. But apparently I’m not alone." — Chris (10:15)

c. Emily – Grandmother Checks

• Emily’s grandmother sends $5 for birthdays, sometimes requiring a relative to “chase” her with a checkbook, as the grandmother feels $5 is still significant.
• They acknowledge $5 was worth more in the past, and for a grandparent giving to many, it’s still meaningful.

"Her son has to chase us with a checkbook afterwards because she thinks that’s a lot of money still." — Emily (12:40)

d. Jennifer – The Taped Silver Dollar

• Jennifer's grandmother sends a silver dollar taped to a card every birthday—a fun tradition she now passes on to her daughter in her own way.

"Every birthday, I get a silver dollar taped to a card... No, usually they’re in my daughter’s piggy bank because my daughter actually gets cash for her birthday." — Jennifer (14:15)

e. Michael – McDonald’s Gift Cards

• Michael’s fiancée’s grandmother sends McDonald’s gift cards for every occasion ($5–$10 each).
• The cast agrees: as an adult, fast-food gift certificates could be unexpectedly useful.

"My fiancée’s grandmother sends gift cards to McDonald's every single occasion… $10 at McDonald's goes a long way, especially since I have a 4-year-old as well." — Michael (17:35)

5. Wider Reflections & Generational Differences

• Grandparents’ punctuality with gifts and cards is admired; cast jokes about their reliable timing.
• Cast discusses the superior penmanship of older generations and their love of “crisp bills.”
• Nostalgia about handwriting and how email/typing has replaced the tradition of letter writing.

"You ever notice how grandparents are never late either? I mean, that thing is gonna be there on time. They are never, ever, ever late." — Bert (15:56)

"Have you noticed that grandparents always have much better penmanship than either grandparents or our generation?... I always feel more pressure if I’m gonna write a, you know, if I address anything to an older relative." — Kristin (16:40)

Notable Quotes & Memorable Moments

• On evolving value:
  "Back in the day, $5 was a hell of a lot of money. And if she’s giving that to every grandchild… she’s divvying out however much, taking the Social Security check." — Kristin (13:05)

• On family quirks:
  "Sounds like my family drama. Oh, I got it. I’ll give it to my abuela… Aunt Liz will be jealous." — The Bert Show, playfully roleplaying family holiday scenarios (various)

• On the traditions' warmth:
  "It’s the sentimental, the whole thing…it's just something that’s been going on since you were four." — Bert (04:50)

Timestamps for Key Segments

• [03:15] Main topic introduction: Stacy’s “forever $5” holiday card story
• [04:02] Cast reminisces: childhood vs. adult significance of small cash gifts
• [05:40] Extended traditions: adult children still taking Santa photos
• [08:25] Listener Danielle: socks and $5 tradition
• [10:15] Listener Chris: the eccentric gift-giving aunt
• [12:40] Listener Emily: grandmother’s $5 and checkbook story
• [14:15] Listener Jennifer: silver dollar taped to every birthday card
• [15:56] Discussion: Grandparents’ reliability
• [16:40] Handwriting and generational changes
• [17:35] Listener Michael: McDonald’s gift cards from grandma

Episode Takeaways

• Small, thoughtful gifts from grandparents hold sentimental value, even as monetary worth diminishes.
• Such traditions are widespread and a source of nostalgia and laughter as families grow.
• Generational customs—be they crisp $5 bills, socks, silver dollars, or gift cards—create lasting memories and stories.
• The episode blends humor and warmth, highlighting the kind quirks that shape family identity.

For listeners with similar family traditions, this episode offers both a relatable laugh and a reminder of the simple joys in long-standing holiday customs.