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Scott Galloway's 4th Grade Crush Surprises Him

November 14, 2025 / 02:36

This episode features Scott Galloway and Debbie Brewbaker discussing their childhood memories, including a humorous reunion after 50 years.

Scott shares a nostalgic moment with Debbie, who was his fourth-grade girlfriend. They reminisce about their time in school, including being sent to higher grades for their academic abilities.

Debbie recounts how she learned about Scott's mention of her on the podcast, leading to her attendance at the event. Their light-hearted banter includes jokes about Scott's appearance and their past interactions.

The conversation highlights the joy of reconnecting with old friends and the impact of shared memories from childhood.

TL;DR

Scott Galloway reunites with fourth-grade girlfriend Debbie Brewbaker, sharing humorous childhood memories and their academic experiences.

Episode

2:36
00:00:00
Let's show this clipping photo here.
00:00:02
This is a picture of Scott Galloway as a
00:00:04
kid doing Taekwondo.
00:00:07
Where did you get this?
00:00:09
Exactly.
00:00:09
Seriously, we didn't.
00:00:10
So, let's bring the lights up, please,
00:00:12
so I can see where people are. So, hi.
00:00:15
Hi.
00:00:16
What's your name?
00:00:18
Debbie Brewbaker.
00:00:20
Jesus Christ. Really?
00:00:23
Hi, Scott.
00:00:26
This is apparently or Scott thinks so.
00:00:28
his fourth grade girlfriend.
00:00:31
I I'm thinking so. Uh
00:00:40
that's her up there. He's right there.
00:00:44
Just real quick, Gabby and I were the
00:00:46
smartest kids in the third grade and
00:00:48
they used to send us to fifth grade for
00:00:49
math and English and we used to hang
00:00:51
out.
00:00:52
We did. And I I am thinking maybe you
00:00:55
had a crush on me and maybe maybe I had
00:00:58
a crush on you, but I am now on Carara's
00:01:00
team. I bat for the other side,
00:01:06
but I haven't seen you in 50 years.
00:01:24
Get back up here, Scott Gallery. Stop
00:01:26
making out with your third great
00:01:27
girlfriend. Um, who is of course Scott's
00:01:30
always like, "Everyone I went out with
00:01:31
became a lesbian. I'm
00:01:32
I should have known. We spent the night
00:01:33
in your dad's camper and you wouldn't
00:01:35
even kiss me. We're playing truth or
00:01:36
dare." And you're like, "Nope.
00:01:37
Nope." Okay. You have a really quick
00:01:39
question for us, Debbie?
00:01:40
I'll just tell the quick story, but my
00:01:42
my stepsister who's here uh is a huge
00:01:45
fan of both of you. She listens to Pivot
00:01:47
every every podcast and she I guess
00:01:50
heard you say something about me and
00:01:53
being the smartest girl in third grade
00:01:55
and she texted me. I guess she almost
00:01:57
got in an accident. She was driving and
00:01:59
she texted me immediately and said, "Do
00:02:01
you know Scott Galloway from fourth
00:02:03
grade?" And I said, "Yes, I do."
00:02:05
And uh that led to other things that got
00:02:08
me here. And I I've never seen you bald
00:02:11
or tall.
00:02:14
It's It's not a good look.
00:02:16
Are you going to change back for him?
00:02:18
Don't
00:02:18
Maybe. I'd like to get to know you.
00:02:23
Anyway, Debbie, thank you so much. We
00:02:25
really It's
00:02:26
so good to see you, Debbie.
00:02:29
That was
00:02:29
so nice. What a thrill.

Episode Highlights

  • Reconnecting After 50 Years
    Scott and Debbie reminisce about their childhood crushes and shared memories.
    “I haven't seen you in 50 years.”
    @ 01m 06s
    November 14, 2025
  • A Surprising Encounter
    Debbie shares a story about her stepsister's admiration for Scott.
    “Do you know Scott Galloway from fourth grade?”
    @ 02m 01s
    November 14, 2025

Episode Quotes

Key Moments

  • Childhood Memories00:04
  • Unexpected Reunion01:06
  • Humorous Reflection02:14

Words per Minute Over Time

Vibes Breakdown

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