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Brooke and Jeffrey: Second Date Update

Awkward Tuesday: From Ferrari To Friendzone

31 Mar 2026

Transcription

Transcript generated automatically by AI and may contain errors.

Chapter 1: What is the premise of today's Awkward Tuesday Phone Call?

0.031 - 2.734 Jose

Hey there, folks. Amy Robach and TJ Holmes here.

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2.954 - 15.145 Unknown

And we know there is a lot of news coming at you these days, from the war with Iran to the ongoing Epstein fallout, government shutdowns, high-profile trials, and what the hell is that Blake Lively thing about anyway?

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15.545 - 17.768 Jose

We are on it every day, all day.

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17.968 - 21.011 Unknown

Follow us, Amy and TJ, for news updates throughout the day.

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21.391 - 26.916 Jose

Listen to Amy and TJ on the iHeartRadio app, Apple Podcasts, or wherever you listen to podcasts.

30.17 - 38.519 Unknown

This Women's History Month, the podcast Keep It Positive, Sweetie, celebrates the power of women choosing healing, purpose, and faith, even when life gets messy.

38.899 - 41.522 Brooke

Love is not a destination. You have to work on it every day.

41.702 - 59.181 Unknown

Keep It Positive, Sweetie creates space for honest conversations on self-worth, love, growth, and navigating life with grace and grit, led by women who uplift, inspire, and tell the truth out loud. I have several conversations with God, and I know why it took 20 years.

59.212 - 77.001 Unknown

To hear this and more, listen to Keep It Positive, Sweetie on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. It's the new me and it's the old them. This Women's History Month, the podcast, If You Knew Better with Amber Grimes, spotlights women who turn missteps into momentum and lessons into power.

Chapter 2: What compliment did Kate give that led to her regret?

712.286 - 725.637 Jose

Dude, they were four to five dates in. That's like almost the start of like a relationship. I mean, like that's where you start to decide, like, are we doing this? We're dating. Yeah, but his nerves were getting the best of him being back in the dating scene, so she tried to lift him up and be positive.

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725.677 - 725.937 Unknown

Yep.

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726.118 - 729.064 Jose

And her encouraging words were a little too encouraging.

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729.084 - 729.264 Unknown

Yep.

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729.605 - 744.434 Jose

Because now he's lined up 15 new dates for himself, one of which happens tonight, and Kate wants to try to change his mind. Mm-mm. So she needs our help on how to do that. Brooke, what's your advice? This is hard. You don't want to come off desperate. I think what I would do.

744.754 - 747.159 Unknown

No, you don't. You don't. You don't.

747.179 - 748.962 Jose

You want to be a catch, right? Yeah.

Chapter 3: How did Kate's compliment affect her relationship with Jim?

749.022 - 767.469 Jose

Especially for a guy like this. That's why you fight fire with fire, Kate. You tell him you have a date tonight with someone super hot. Oh, that is good. I was expecting more mature advice from Brooke. I was thinking about it. I thought about, like, be honest with your feelings. But then that just comes off as clingy, okay?

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767.589 - 773.194 Kate

I don't know about that one. That seems like that could just be the end of anything.

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773.234 - 794.279 Jose

No, listen. In high school, I used to tell these boys that I liked that other boys from another school were taking me out. When really, I was just eating banana cream pie with my best friend. And you know what? I eventually dated that guy that I lied to. That is a good one. That's one tool in your tool bag that you could use. Jose, what's your advice? You need to get out of the friend zone.

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794.299 - 821.642 Jose

And the best way that you can do this is to bring up that it's great you got to experience dates with you, but we never finished our lesson. Kissing is next. What? Are you regretting calling into this show for advice? It sounds like a friend right now that I'm talking to. Do you want to kiss him or not? I do want to kiss him, but I don't want to be like, I don't know, like a lesson.

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821.662 - 845.17 Jose

Maybe you haven't kissed after four to five dates. Not yet. Oh, super friend zones. This is worse than I thought. This is bleak. She said that he's nervous about getting back in the dating world. I'm sure he's trying to take it slow, too. Yeah, so did my husband. Slow, whatever. Did you just say my husband and then air in the same sentence? He tried to take it slow, too.

845.35 - 860.108 Jose

How did that work out with him? Okay. Well, we're running out of time here, Kate, so we got to make this call. I'm going to dial this guy Jim for you and see if you can convince him to cancel his date plans tonight and choose you instead. Okay. And kiss you. Finally. Oh, my gosh.

860.128 - 860.568 Brooke

We'll see.

860.608 - 897.137 Jose

It's up to you how you want to do it, but we're going to be behind you in your corner ready to jump in when you need help. All right? You ready? Yeah, thanks. All right. Oh, this is going to be so awkward. Let's see how it goes. Hello? Hey. Hi. Hello? It's Kate. Yikes. Oh. Oh. Oh. Oh. I'm sorry. Why didn't you call me from your number?

898.979 - 900.941 Kate

Huh? Oh.

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