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Brooke and Jeffrey

Masked Speaker: Donation Recognition

Brooke and Jeffrey

iHeartPodcasts

Comedy, Society & Culture, Relationships

4.71.9K Ratings

🗓️ 2 October 2025

⏱️ 9 minutes

🧾️ Download transcript

Summary

One of our listeners says her BIGGEST REGRET... was a selfless act of charity she did 20 years ago, and it haunts her every single day! She'll confess in your Masked Speaker podcast!

See omnystudio.com/listener for privacy information.

Transcript

Click on a timestamp to play from that location

0:00.0

Hey, I'm Jay Shetty and I'm the host of the On Purpose podcast.

0:03.6

Recently, I had a conversation with the one and only Madonna.

0:07.8

When I was broke and I had no friends, nowhere to live, I was held up at gunpoint, I was robbed.

0:13.9

Always horrendous things happened to me.

0:15.7

I had such an unhappy childhood that whatever happened to me in New York is better than what my life was,

0:21.4

so I'm not going back.

0:23.3

Listen to On Purpose with Jay Shetty on the Iheart Radio app, Apple Podcasts, or wherever

0:28.5

you get your podcasts.

0:30.2

The NFL is rolling.

0:32.0

That's right.

0:32.8

And you should be listening to NFL Daily as we march along to Super Bowl 60.

0:37.4

It's in the name, NFL Daily. So you'll

0:39.8

have fresh content in your feed all season long. Join me, Greg Rosenthal, in an all-star cast

0:45.0

of co-hosts for previews and recaps of every single game. NFL Daily will keep you up to date

0:50.5

with everything you need to know so you can sound smarter than all your friends. Listen to NFL Daily on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. No purchase necessary. Voidware prohibited. Ends 2826. Open to legal residents of the 50 U.S. States and D.C. 18 and over. For complete details, how to enter, prizes and official official rules, visit Toyotas gameday giveaways.com.

1:13.7

You don't know me.

1:16.1

A confession I can't take back.

1:18.7

I am.

1:21.3

The masked speaker.

1:24.4

Text to 78592 says, at the bar, I was carrying three beers when my buddy came up behind me and pulled my pants down. Oh, my gosh. Good timing. Underware came down too. Oh, no. And a huge roar of laughter went up. Oh. So a few weeks later, I spotted him filling up at the gas station, snuck up behind him and pulled

1:45.2

his shorts down.

1:46.3

Yes.

...

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