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Brooke and Jeffrey: Second Date Update

Awkward Tuesday: My Brothers Wife Is A Bad Boss

Brooke and Jeffrey: Second Date Update

iHeartPodcasts

Relationships, Society & Culture, Comedy

4.52.3K Ratings

🗓️ 14 April 2026

⏱️ 18 minutes

🧾️ Download transcript

Summary

One of our listeners needs our advice on how to turn someone down. But it’s not just anyone… it’s someone in their own family! We’ll explain more in an Awkward Tuesday Phone Call!

See omnystudio.com/listener for privacy information.

Transcript

Click on a timestamp to play from that location

0:00.0

Hey, it's your second date podcast.

0:02.1

And if you're new to our podcast, welcome.

0:04.0

Yay.

0:04.5

You might be a little confused.

0:06.0

On Tuesdays, we actually don't do a second date.

0:08.3

We do what's called an awkward Tuesday phone call, which can be between any two people, right?

0:14.2

It could be a mother and a son.

0:15.8

It could be a coworker and a boss or whatever.

0:18.9

Also, if you're new here, I'm trying to make up something for the new people. We're naked. Oh. We're always naked all the time. That's why we don't do these on video. Yeah, that's fine. That'll get them, Brooke, a job. But yeah, though, this is just an awkward call. We give our advice and try to help one of our listeners out. And it's always pretty funny. So hope you enjoy this. It's Brooke and Jeffrey in the morning. Turning someone down without hurting their feelings. Yeah. That's almost impossible. Yeah. I think it is. But we've all been really proud of Brooke and how she's been able to get over my rejection and soldier on bravely here at work.

0:54.9

I know she hasn't cried what she's always smiling.

0:57.3

You're so strong, Brooke.

0:58.8

So let her be a beacon of hope for our listener on the line today.

1:03.1

You would never tell.

1:04.6

Yeah, no.

1:05.5

But he needs help to gently turn someone down.

1:09.3

The weird part though is person he's turning down is kind of in his family.

1:14.8

What?

1:15.0

Wait, what?

1:15.6

What the heck?

1:16.2

They're not like step siblings or blood-related at all.

1:19.2

Oh, thank God.

1:19.9

But you're going to understand why it's so weird and he needed our advice in your brand new Awkward Tuesday phone call.

...

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