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Brooke and Jeffrey: Second Date Update

Awkward Tuesday: Private Jet For My Nervous Pet

10 Mar 2026

Transcription

Transcript generated automatically by AI and may contain errors.

Chapter 1: What is the listener's unique request for help?

0.031 - 18.031 Unknown

In the middle of the night, Saskia awoke in a haze. Her husband, Mike, was on his laptop. What was on his screen would change Saskia's life forever. I said, I need you to tell me exactly what you're doing. And immediately, the mask came off.

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18.732 - 22.596 Jeff

You're supposed to be safe. That's your home. That's your husband.

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23.791 - 46.993 Unknown

Listen to Betrayal Season 5 on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hi, it's Jill Winterstein, host of the Spirit Daughter podcast, where we talk about astrology, natal charts, and how to step into your most vibrant life. And today I'm talking with my dear friend, Krista Williams. It can change you in the best way possible. Dance with the change.

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47.113 - 64.294 Unknown

Dance with the breakdowns. The embodiment of Pisces intuition with Capricorn power moves. So I'm like delusionally proud of my chart. Listen to the Spirit Daughter podcast starting on February 24th on the iHeartRadio app, Apple Podcasts, or wherever you listen to your podcasts.

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65.152 - 86.94 Nancy Glass

I'm Nancy Glass, host of the Burden of Guilt Season 2 podcast. This is a story about a horrendous lie that destroyed two families. Late one night, Bobby Gumpright became the victim of a random crime. The perpetrator was sentenced to 99 years until a confession changed everything. I was a monster.

87.646 - 96.276 Nancy Glass

Listen to Burden of Guilt Season 2 on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

96.296 - 115.138 Jeff

Good people, what's up, what's up? It's Questlove. So recently I had the incredible opportunity to have a real conversation with actress and producer Jamie Lee Curtis from Routines to Recovery, True Lies, and a certain Jermaine Jackson music video. Jamie's real and raw, and it's something I really admire about her.

115.118 - 130.026 Unknown

I am so happy that I'm the head in charge at 67, that I have the perspective that I have at my age to really be able to put all of this into context.

130.307 - 136.418 Alexis

Listen to The Questlove Show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Chapter 2: How does the listener plan to leverage a private jet for her move?

139.171 - 144.157 Lily Herman

Look no further than No Grip, a new podcast tackling the culture of motor racing's most coveted series.

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144.718 - 161.239 Lily Herman

Join me, Lily Herman, as we dive into the underexplored pockets of F1, including the story of the woman who last participated in a Formula One race weekend, the recent uptick in F1 romance novels, and plenty of mishap scandals and sagas that have made Formula One a delightful, decadent dumpster fire for more than 75 years.

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161.96 - 166.506 Lily Herman

Listen to No Grip on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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167.448 - 171.173 Jeff

All right, if you live in a stupid area that changed the time, whew.

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171.213 - 172.695 Lily Herman

You're dumb. Yeah, we're with you.

172.715 - 190.84 Jeff

Your area's dumb. No, we live in that area, too. Yeah, I'm dumb. Yeah, it's Brick and Jeffrey. Thank you for coming to the Second Date Podcast. And we're definitely feeling it this week. So we're going to get through this all together with a brand new Awkward Tuesday phone call. I also think Mercury's in Gatorade, too. Yeah, I hate that, especially when it's Red Gatorade. Oh my gosh, I'm all off.

190.86 - 191.861 Alexis

Sorry, go ahead, Alexis.

191.881 - 193.143 Jeff

Yeah, what do you got for comments?

193.383 - 199.49 Alexis

Oh my gosh, Payson Eddie said, I just got done with a 15-mile walk. Also, love the show, you guys. Keep it up.

Chapter 3: What challenges does the listener face with her request?

211.947 - 239.22 Jeff

What's the biggest favor you've ever asked someone? To borrow their car? Loan you money? Rent out their husband for a night? I mean, how do you get the money to loan someone? One of our listeners has the most important request she's ever asked of anybody. And honestly, probably 99% of people would laugh and just say no to this immediately. What, you want a kidney?

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239.2 - 258.087 Jeff

No, but how can we somehow give her advice that's so good she will fall into the 1% that actually gets a yes? That's a challenge, Jeff. That is. We're going to find out if we can pull it off in your brand new Awkward Tuesday phone call next. It's awkward.

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258.327 - 259.95 Alexis

It's Tuesday.

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259.97 - 268.757 Jeff

It's Awkward Tuesday phone call. How does a woman get a man to do what she wants? Brooke, what's your secret?

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270.039 - 270.92 Unknown

I've never figured it out.

270.96 - 293.052 Jeff

That's why I just dump them and move on if it doesn't work. Oh, wow. No? Feed them? Oh. Okay. I don't know. Maybe. Yeah, bribe them with food. The internet, because I looked this up, the internet suggests, quote, build him up through appreciation, respect, and clear communication. Oh, that's nice. That just sounds like getting someone to compromise with you.

Chapter 4: How do the hosts react to the listener's plan?

293.173 - 299.801 Jeff

I mean, that's the healthy, boring way to get what you want. But who wants to do that, right? Right, Alexis?

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299.821 - 300.942 Brooke

Yeah, I stopped listening. Good.

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301.883 - 328.344 Jeff

But our listener, Lily, is at a crossroads right now where she's running out of time and needs a guy, specifically one man, to do her a huge favor. And she's come to us seeking advice. So, Lily, welcome to the show. Hi. Hey. Okay, I'm curious what your favor is. Yeah, what's going on? So, I'm moving across the country from Miami to Scottsdale, of all places.

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328.364 - 344.908 Jeff

Okay, he cannot drive a moving van that far, I don't think. No, and I don't want to drive. It's expensive. I'm a single female. I don't want to stay at a bunch of roadside motels. I just don't feel comfortable with that. Got it. You'd rather pay a moving company, you fly, they ship it.

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345.361 - 346.523 Unknown

Not exactly.

346.563 - 366.277 Jeff

You're sleeping on the idea of roadside motels, by the way. They're actually way more fun than they get portrayed in the media. And I'm going to tell you, driving around as a single woman is really a great time. Oh, really? There'll be a point in your life where you have no alone time, where you have kids and a husband and they're all there.

366.297 - 371.905 Jeff

And you'll long for the days of just being by yourself in a car. All right. Brooke's message of the day to all the single ladies.

Chapter 5: What advice do the hosts give about asking for favors?

372.185 - 381.818 Jeff

Get out on the roads by yourself. Dude, seriously. Okay. Interesting. But Lily, you said you're not interested in that route. What's going on? What's in your mind?

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382.158 - 384.261 Unknown

Yeah, I have a dog that has anxiety.

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385.068 - 389.372 Alexis

A dog with anxiety. I am confused how all these pieces go together.

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389.572 - 392.936 Unknown

Okay, you can stop. I don't actually have a dog.

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394.097 - 394.357 Jeff

What?

394.817 - 402.405 Unknown

I actually just wanted to see if that would work because I think I'm going to use that as a way to get somebody to take me.

402.425 - 408.07 Jeff

Take you where? Yeah, what are you talking about? You're going to have to be much more clear with us here.

408.09 - 414.957 Unknown

So I'm stressed about the move and last weekend I was out at a club with my girls and we met this guy and he's got a PJ.

415.223 - 416.284 Alexis

A private jet.

Chapter 6: How does the listener justify her request involving a fake dog?

442.561 - 463.451 Jeff

If he would fly me on his PJ to Arizona. Girl. Yeah, that's definitely a No. 2 question for sure. You're going to show up to his plane even if he says yes, claiming you had a dog with no dog. Yeah. Sounds like she's just trying to get the yes for the private jet. Yeah. At whatever cost. Am I reading that right? Dominoes will fall after.

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463.511 - 463.891 Unknown

Yeah.

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464.272 - 473.465 Jeff

Yeah, I don't want to fly commercial because it's just kind of gross. What? Not even like first class? So you want this guy to spend whatever it costs, like 30 grand.

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473.505 - 473.986 Unknown

Dude.

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474.006 - 486.696 Jeff

Or whatever. I saw T-Pain show the world that it costs over 100 grand to get a private jet from like Atlanta to Scottsdale. That was one day. I don't know how much they normally cost, but. You've met him once. Yeah.

487.217 - 487.317

Yeah.

487.297 - 503.668 Jeff

That's so much money. It was just once, and I didn't feel like I was comfortable asking after just meeting once. That's so respectable. Thank you so much. It's just such a wild request. I wouldn't even say yes to driving someone to an airport if I had only met them once.

Chapter 7: What unexpected twist occurs during the call with the listener?

504.307 - 523.959 Jeff

But, Brooke, we're obligated to help out our listeners in this segment, no matter if it's with a really serious issue or with a total scam. We're here for the people. And that includes hot, selfish girls, too. So let's not be jelly. Thank you. I'm not against scamming super rich people with private checks. I mean, I will say that.

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524.039 - 532.272 Jeff

Plus, if we're humoring this, he may literally have a property in Arizona and go, oh, yeah, I haven't checked on my vacation home in a while. Let's do it. It's a win-win. You're right.

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532.292 - 532.693 Unknown

It could happen.

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532.773 - 556.834 Jeff

Can we ask, do you have any actual romantic interest in this man? Oh, yeah. I mean, maybe I would go on a date if he was going to bring me on the private jet. I think that will be your date. I like that you have standards set for yourself, and there's lines that you definitely won't cross. I'm not sure where they are, but yes, you have them. Can I just ask, does he know anything about your move?

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556.854 - 570.072 Jeff

Because that piece of this plan is kind of unsexy. No, he doesn't. Oh, so when you show up with like 200 pieces of luggage, he's not going to think something's wrong? Yeah. Wait, you're not moving your stuff on the plane too, are you?

570.507 - 571.528 Unknown

As much as I can.

571.548 - 576.592 Jeff

Oh, that is smart. I thought it was a shit.

576.612 - 580.395 Unknown

Oh, if it goes well, then maybe we can do more trips.

580.415 - 583.798 Jeff

Oh, that's nice. She just has a bed frame in the middle of a PJ.

Chapter 8: What are the final thoughts on the listener's situation?

583.818 - 615.367 Jeff

It's faster. It's nicer. You get to have company along the way that you don't hate. I love that. I think that would be perfect. Okay. So what is the advice that you're looking to get from us then with this call? So, like, how do I ask him? What do I say? I think he might say yes. He might, but we do have our work cut out for us. Alexis may even need to be a part of this advice-giving sesh.

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615.387 - 645.402 Jeff

Call me crazy, but she might actually be helpful here because when we come back, we're going to try to help Lily hitch a ride on a guy's private jet, bringing along multiple suitcases so she can move to Scottsdale without driving there. Boxes even. That's what this segment has come to. Look at us. It's your Awkward Tuesday phone call, and we're going to do it right after this. Hold on.

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645.668 - 670.397 Jeff

Never in the history of this show have we had a more dramatic request. I mean, you're actually right. Our listener, Lily, says she desperately needs our advice. And if it doesn't work, sadly, she'll have to fly commercial. I bet people are screaming in their car right now in horror. As they should be. But what is she asking?

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670.857 - 693.12 Jeff

Well, she's moving from Miami to Scottsdale and does not want to drive cross-country. Doesn't want to fly with the normies on Southwest either. So instead, she wants to hitch a ride on the private jet of a dude that she just met. Hitch a ride with all her stuff. Yeah. As much as she can bring. They're already flying, so what's the difference?

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693.16 - 706.033 Jeff

I should mention, in their initial conversation, they bonded over their dogs. His is real, hers she made up. And this all happened just a few days ago, so how do we get Lily on that plane?

706.053 - 706.974 Brooke

Brooke, what's your advice?

707.154 - 732.606 Jeff

Well, I feel like you and this guy bonded over the dog, and your only solution is to lean harder into the sob story about your dog's anxiety. You know, make it sound really sad and pathetic, and... And let him be your knight in shining armor who comes up with the idea to fly you on a private jet to save you and your dog. I can be a damsel in distress.

732.626 - 732.726 Unknown

Okay.

732.746 - 740.257 Jeff

Okay. We might have to lean into that. Jose, what do you think? You said make the dog sound pathetic. Yeah. We can do that. Do you not realize we are at a radio station?

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