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Brooke and Jeffrey

Awkward Tuesday: Proposal Sabotage

Brooke and Jeffrey

iHeartPodcasts

Relationships, Comedy, Society & Culture

4.72K Ratings

🗓️ 30 September 2025

⏱️ 20 minutes

🧾️ Download transcript

Summary

The guy in today’s Awkward Tuesday Phone Call has had THREE FAILED PROPOSALS. He wants out help finding out what he’s doing wrong… or if there’s another explanation…

See omnystudio.com/listener for privacy information.

Transcript

Click on a timestamp to play from that location

0:00.0

The NFL is rolling.

0:01.9

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0:02.6

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

0:07.3

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0:09.4

So you'll have fresh content in your feed all season long.

0:12.3

Join me, Greg Rosenthal, in an all-star cast of co-hosts for previews and recaps of every single game.

0:18.6

NFL Daily will keep you up to date with everything you need to know so you can sound smarter than all your friends. Listen to NFL Daily on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

0:29.6

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0:43.6

I've looked at social media once or twice, and I've learned the only thing that goes more viral than a sweet, happy marriage proposal is a messy, awkward marriage proposal gone horribly wrong.

0:57.0

That's so true.

0:58.1

And that's why when I saw our listener's email today, I knew we had to talk to him because he hasn't had just one failed proposal, but three in a row.

1:07.6

And he needs our help to figure out, am I doing something wrong here?

1:12.1

Yeah.

1:12.6

Or is there another explanation?

1:15.4

You're going to hear it in your brand new Awkward Tuesday phone call.

1:18.7

Next.

1:20.4

It's awkward.

1:21.7

It's Tuesday.

1:23.2

It's awkward Tuesday phone call.

1:25.9

Some people in relationships believe there's cosmic signs that show you're meant to be together.

1:32.9

Okay.

1:33.7

Like when you start finishing each other's sentences.

...

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