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Scott Galloway's 4th Grade Crush Surprises Him

November 14, 2025 / 02:36

This episode features Scott Galloway and his fourth-grade girlfriend, Debbie Brewbaker, reminiscing about their childhood. They discuss their experiences in school, including being the smartest kids in their class and their past interactions.

Scott shares a humorous anecdote about his childhood crush on Debbie, who now identifies as a lesbian. Their playful banter highlights their long-lost connection and the passage of time since they last saw each other.

Debbie recounts how she learned about Scott's mention of her on the Pivot podcast, leading to her attendance at the event. The conversation is light-hearted, filled with laughter and nostalgia as they reflect on their younger selves.

The episode captures a unique moment of reconnection and showcases the warmth of childhood memories, making it a delightful listen for fans of both Scott and Debbie.

TLDR

Scott Galloway reunites with his fourth-grade girlfriend Debbie Brewbaker, sharing nostalgic stories and laughter about their childhood.

Episode

2:36

00:00:00

Let's show this clipping photo here. This is a picture of Scott Galloway as a kid doing Taekwondo.

00:00:07

Where did you get this? Exactly. Seriously, we didn't. So, let's bring the lights up, please,

00:00:12

so I can see where people are. So, hi. Hi. What's your name? Debbie Brewbaker. Jesus Christ. Really?

00:00:23

Hi, Scott. This is apparently or Scott thinks so. his fourth grade girlfriend. I I'm thinking so. Uh

00:00:40

that's her up there. He's right there. Just real quick, Gabby and I were the smartest kids in the third grade and

00:00:48

they used to send us to fifth grade for math and English and we used to hang out.

00:00:52

We did. And I I am thinking maybe you had a crush on me and maybe maybe I had a crush on you, but I am now on Carara's

00:01:00

team. I bat for the other side, but I haven't seen you in 50 years. Get back up here, Scott Gallery. Stop

00:01:26

making out with your third great girlfriend. Um, who is of course Scott's always like, "Everyone I went out with

00:01:31

became a lesbian. I'm I should have known. We spent the night in your dad's camper and you wouldn't

00:01:35

even kiss me. We're playing truth or dare." And you're like, "Nope. Nope." Okay. You have a really quick

00:01:39

question for us, Debbie? I'll just tell the quick story, but my my stepsister who's here uh is a huge

00:01:45

fan of both of you. She listens to Pivot every every podcast and she I guess heard you say something about me and

00:01:53

being the smartest girl in third grade and she texted me. I guess she almost got in an accident. She was driving and

00:01:59

she texted me immediately and said, "Do you know Scott Galloway from fourth grade?" And I said, "Yes, I do."

00:02:05

And uh that led to other things that got me here. And I I've never seen you bald

00:02:11

or tall. It's It's not a good look. Are you going to change back for him? Don't Maybe. I'd like to get to know you.

00:02:23

Anyway, Debbie, thank you so much. We really It's so good to see you, Debbie. That was

00:02:29

so nice. What a thrill.

Badges

This episode stands out for the following:

100
Best writing
Quality / Craft
70
Most heartwarming
65
Best overall
60
Most satisfying

Episode Highlights

Scott's Fourth Grade Crush
Scott reminisces about his childhood crush, revealing humorous and nostalgic moments.
“I am thinking maybe you had a crush on me and maybe maybe I had a crush on you.”
@ 00m 55s
November 14, 2025

Episode Quotes

Jesus Christ. Really?
Scott Galloway's 4th Grade Crush Surprises Him
It's not a good look.
Scott Galloway's 4th Grade Crush Surprises Him
I'd like to get to know you.
Scott Galloway's 4th Grade Crush Surprises Him

Key Moments

Childhood Memories00:04
Reunion Surprise00:20
Nostalgic Crush00:55
Unexpected Compliments02:11

Tension Over Time

Words per Minute Over Time

Vibes Breakdown