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Brooke
Alright, if you live in a stupid area that changed the time who you're dumb. Yeah, we're with you.
Jeffrey
Your area is dumb.
Brooke
No, we live in that area.
Jeffrey
I'm dumb.
Brooke
Yeah, it's Brick and Jeffrey. Thank you for coming to the Second Date podcast and we are definitely feeling it this week. So we're going to get through this all together with a brand new awkward Tuesday phone call.
Jeffrey
I also think Mercury's in Gatorade, too.
Brooke
Yeah, I hate that. Especially when it's red Gatorade.
Jeffrey
Gosh, I'm all off.
Alexis
Sorry.
Jeffrey
Go ahead, Alexis.
Scott
Yeah.
Brooke
What do you got for comments? Oh, my gosh. Pace and Eddie said I just got done with a 15 mile walk. Whoa. Also, love to show you guys.
Announcer
Keep it up.
Jeffrey
Did you listen to us the whole time?
Brooke
I don't know.
Jeffrey
That's a long time. That's got to be like an hour. At least two hours. I don't know.
Scott
I don't. Yeah.
Brooke
All right, here we go. Brand new awkward Tuesday phone call starts right now.
Alexis
What's the biggest favor you've ever asked someone to borrow their car, loan you money?
Brooke
Yeah.
Alexis
Rent out their husband for a night.
Brooke
Oh, wow. I mean, how do you get the money to loan someone?
Alexis
One of our listeners has the most important request she's ever asked of anybody. Whoa. And honestly, probably 99% of people would laugh and just say no to this immediately.
Jeffrey
What, you want a kidney?
Alexis
No. But how can we somehow give her advice that's so good, she will fall into the 1% that actually gets a yes.
Brooke
That's a challenge, that is.
Alexis
We're going to find out if we can pull it off in your brand new awkward Tuesday phone call. Next.
Jeffrey
It's awkward.
Brooke
It's Tuesday.
Jeffrey
It's awkward Tuesday phone call.
Announcer
Call.
Alexis
How does a woman get a man to do what she wants? Oh, Brooke, what's your secret?
Brooke
I've never figured it out. That's why I just dump them and move on if it doesn't work.
Lily
Oh, wow.
Alexis
Okay.
Brooke
Feed them.
Alexis
Oh, oh, okay.
Lily
I don't know.
Alexis
I mean, 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.
Brooke
Oh, that's nice. That just sounds like getting someone to compromise with you.
Announcer
I mean, that's.
Alexis
That's the healthy, boring way to get what you want. But who wants to do that, right? Right, Alexis?
Brooke
Yeah, I stopped listening.
Announcer
Good. Yeah.
Alexis
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. Oh. And she's come to us seeking advice. So, Lily, welcome to the show.
Lily
Hi.
Brooke
Okay, I'm curious what your favor is.
Alexis
Yeah. What's going on?
Lily
So I'm moving across the country from Miami to Scottsdale. Of all Places.
Brooke
Okay, he cannot drive a moving van that far, I don't think.
Lily
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.
Jeffrey
Got it. You'd rather pay a moving company? You fly, they ship it.
Lily
Not exactly.
Alexis
Oh, you're sleeping. 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.
Brooke
And I'm gonna 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 always there, and you're long for the days of just being by yourself in a car.
Alexis
All right, Brook's message of the day to all the single ladies. Get out on the roads by yourself.
Commercial Voice
Dude.
Brooke
Seriously.
Alexis
Okay.
Jeffrey
Start taking the scenic route.
Alexis
Interesting. But, Lily, you said you're not interested in that route. What's going on? What's in your mind?
Lily
Yeah, I have a dog that has anxiety.
Brooke
Oh, a dog with anxiety. I am confused how all these pieces go together.
Lily
Okay, you. You can stop. I. I don't actually have a dog.
Brooke
What?
Alexis
What?
Lily
I actually just wanted to see if that would work, because I think. I think I'm going to use that as a way to get somebody to take me.
Brooke
Take you where?
Alexis
Yeah. What are you talking about? You're gonna have to be much more clear with us here.
Lily
So I'm. 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.
Brooke
A PJ Private jet.
Alexis
Oh, yeah.
Brooke
I thought it was, like, PT Cruiser or something. Okay, you met a guy at a club that claims to have a private jet. Yeah, that's a good point.
Lily
He has dogs. And so I made up my dog like he doesn't exist. But I said that I have a dog because.
Commercial Voice
I see.
Announcer
Yes.
Lily
Okay, so I didn't feel like it was right time to ask him, since I just met, if he would find me on his PJ to Arizona girl.
Alexis
Yeah, that's your question. For sure.
Brooke
You're going to show up to his plane even if he says yes, claiming you had a dog with no dog.
Announcer
Yeah.
Alexis
Sounds like she's just trying to get the yes for the private jet.
Commercial Voice
Yeah.
Alexis
At whatever cost. Reading that right.
Jeffrey
Will fall after.
Alexis
Yeah.
Lily
Yeah. I don't want to fly commercial. It's just kind of gross.
Alexis
What?
Jeffrey
Not even like, first class.
Brooke
Do you want this guy to spend whatever it costs? Like 30 grand, dude, or whatever.
Jeffrey
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
Brooke
cost, but you've met him once. Yeah, Yeah, I had so much money,
Lily
it was just once, and I didn't feel like I was comfortable asking after this meeting.
Scott
Once.
Alexis
That's so respectable. Thank you so much.
Brooke
It's just such a wild request. Like, I wouldn't even say yes to driving someone to an airport if I had only met them once.
Alexis
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 jealous.
Lily
Thank you.
Brooke
I'm not against scamming super rich people with private jets. Yeah, I mean, I will say that.
Jeffrey
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.
Alexis
It's a win win. You're right. So, but can we ask, do you have any actual romantic interest in this man? Oh, yeah.
Lily
I mean, maybe I would go on a date if he was going to bring me on the private jet.
Brooke
I think that will be your date
Jeffrey
served on the private jet.
Alexis
I like that you have standards set for. And there's lines that you definitely won't cross. Not sure where they are, but yes, you have them.
Brooke
Can I just ask, does he know anything about your move? Because that piece of this plan is kind of unsexy.
Lily
No, he doesn't.
Jeffrey
Oh, so you just show up with like 200 pieces of luggage?
Announcer
Oh, yeah.
Brooke
Wait, you're not moving your stuff on the plane too, are you?
Lily
As much as I can.
Alexis
That is.
Brooke
I thought it was a. Oh.
Lily
If it goes well, then maybe we can do more trips.
Alexis
Oh, that's nice. She has a bed frame in the
Jeffrey
middle of the pj.
Alexis
It's faster, it's nicer. You get to have company along the way that you don't hate. I love that.
Lily
I think that would be perfect.
Alexis
Okay, so what is the advice that you're looking to get from us then, with this call?
Lily
So, like, how do I ask him? Yeah, what do I say? Well, we Might say yes.
Alexis
He might. But we do have our work cut out for us. Alexis may even need to be a part of this advice giving session. Call me crazy, but she might actually be helpful here. Because when we come back, we're gonna 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.
Brooke
Boxes even.
Alexis
That's what this segment has come to.
Commercial Voice
Look at us.
Alexis
It's your awkward Tuesday phone call, and we're gonna do it right after this. Hold on.
Jeffrey
It's awkward?
Brooke
It's Tuesday.
Jeffrey
It's awkward Tuesday phone call.
Alexis
Never in the history of this show have we had a more dramatic request.
Jeffrey
I mean, you're actually right.
Alexis
Our listener Lily, says she desperately needs our advice. And if it doesn't work, sadly, she'll have to fly commercial.
Jeffrey
We got so many texts in about this.
Brooke
I bet people are screaming in their car right now in horror.
Alexis
As they should be. But what is she asking? 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.
Brooke
Hitch a ride with all her stuff.
Jeffrey
Yeah, as much as she can bring.
Alexis
They're already flying, so what's the difference? I should mention, in their initial conversation, they bonded over their dogs. His is real. Hers she made up. Yeah, and this all happened just a few days ago. So how do we get Lily on that plane? What's your advice?
Brooke
Well, I feel like you and this guy bonded over the dog, and your. Your only solution is to lean harder into the sob story about your dog's anxiety.
Announcer
Yeah.
Brooke
You know, make it sound really sad and pathetic 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 do.
Lily
I can be a damsel in distress.
Alexis
Okay.
Announcer
Okay.
Alexis
We might have to lean into that. Jose, what do you think?
Jeffrey
You said make the dog sound pathetic. Yeah, we can do that. Do you not realize we are at a radio station? We can play dog sounds throughout the call to make the dog sound real.
Brooke
Do we have any right now?
Jeffrey
Do we have any, Jeff?
Alexis
Oh, we have this one.
Brooke
It's not a dog. I want to plane with me anxious dog.
Alexis
I thought that's kind of a crazy idea.
Lily
But that's so perfect.
Jeffrey
You like that?
Alexis
Of course we more.
Jeffrey
Hold on.
Brooke
No, scary. All the dogs are gonna attack us.
Lily
Yeah, that does sound like a big scary dog, but it's a dog.
Jeffrey
Okay, well, okay, if we need to prove your job, since we have something.
Alexis
Yeah, yeah. All right. We'll have the dog sounds loaded up just in case you need them. But you have our advice, Lily. We're gonna step away and let you call this.
Brooke
What's His Name.
Alexis
I don't think we got his name. What is his name?
Lily
My dog is Princess.
Brooke
No, no, that bark does not fit a Princess. That's what's funny about it.
Alexis
The guy with the jet, what's his name?
Lily
Scott.
Brooke
Scott. Sounds like a rich guy.
Jeffrey
Yeah, Scott going to Scottsdale.
Alexis
All right, well, we're gonna dial Scott and we'll see if he answers. And hopefully you can get a free ride on a PJ to beautiful Arizona.
Scott
Oh, man.
Alexis
All right, here we go.
Scott
Hello.
Lily
Hey. Hey. How's it going? This is Lily.
Scott
I'm sorry, do I know you?
Lily
Yeah, yeah, we met at the club last Saturday.
Scott
Okay, cool. I'm sorry, you're gonna have to be a little more specific.
Lily
Remember, I was with a big group of women and we were at your table. We all hung out and just kind of hung out with you and your friends.
Scott
Oh. Oh, yeah. You're the one who left her bathing suit at my house.
Announcer
Oh.
Alexis
What?
Lily
No, that wasn't me.
Scott
Okay, sorry. Yeah, I, you know, I meet a lot of people, so.
Lily
Yeah, I get that. No, we talked about our dogs, and you told me about your Black Lab, and you told me how cute he was and everything, and you showed me a picture, and then I told you about my dog who has anxiety.
Scott
Oh, yeah. Okay, so what was your name again?
Lily
Lily. There's Lily.
Announcer
Lily. Lily.
Scott
Yeah, got it. Okay.
Announcer
I don't.
Scott
You know what? I. I think I met more than one Lily that night, but all good.
Brooke
Princess.
Alexis
Stop.
Lily
Princess.
Scott
Sorry, what's going on?
Lily
Oh, sorry. That's Princess. I think she heard your voice and I think she likes you.
Scott
Yeah. Okay. Well, that's fun.
Lily
Yeah.
Brooke
Yeah.
Announcer
So.
Lily
Hey, look, she likes your voice.
Scott
This is cool you called. I gotta run. I'm in the middle of kind of a commercial property deal here, so, I don't know, maybe we'll catch up. Maybe I'll see you at the club next weekend.
Lily
Yeah, well, actually, that's the problem. I'm not gonna be here anymore.
Scott
What do you mean?
Lily
I got a new job as a dancer in Scottsdale.
Scott
Oh, yeah? I love Scottsdale. Do you?
Lily
That's awesome. Oh, Princess, down. Stop.
Announcer
Stop.
Lily
Oh, gosh. She loves Scottsdale, too. Every time I Mention Scottsdale. She loves it.
Scott
Okay, well, hey, good luck. I mean, I'm sure we're gonna chat down the line.
Lily
Hold on.
Announcer
Wait.
Lily
Do you remember when I told you the Princess has anxiety?
Announcer
Sorry.
Lily
She gets embarrassed when I talk about it. Okay, so she can't make that long drive, you know, from Florida all the way to Scottsdale. So. And there's no way she can ride commercial. And her anxiety would just be crazy, you know? Yeah, she. Look at that. Every time I talk about. About her anxiety, she just. Yeah, she doesn't want to fly commercial.
Scott
It sounds like she's kind of wild.
Lily
Yeah, no, she just gets anxious when I talk about anxiety. And I know that you mentioned you have a private jet.
Scott
I did?
Lily
Well, you were in a conversation about it with somebody else and I just overheard it at the table.
Scott
So where are you going with this?
Lily
Well, I was hoping that maybe because of Princess's anxiety that we could catch a ride with you.
Scott
Wait, you really thought I had a private jet?
Announcer
Awkward.
Alexis
Oh, no, you made it up.
Brooke
What is dodge happening?
Announcer
Stop.
Jeffrey
Guys at the club in Miami making stuff up.
Brooke
Yeah, nobody else made up anything on this call. Yeah.
Scott
Okay, can somebody tell me what the heck's going on here?
Jeffrey
Oh, hi.
Lily
Just hang up on him. He's lying.
Alexis
Hold on. First, Scott asked a question. He wants to know what's going on. You're on the radio, Scott, with a show called Brooke and Jeffrey in the Morning.
Scott
Okay, and why?
Brooke
That is a hard one to answer.
Alexis
You have a lot of good questions, Scott, but basically this is called an awkward Tuesday phone call. Lily is a listener and needed our help having a difficult conversation with you about cross country travel.
Commercial Voice
Yes.
Brooke
You know, she was hoping to use your pj.
Alexis
Yeah.
Lily
You guys, it doesn't matter anymore. It sounds like he doesn't even have a private jet.
Alexis
Well, hold on.
Commercial Voice
Lily.
Alexis
Lily, let's not forget you weren't necessarily 100% truthful with him either. Princess down. Talking to your owner right now.
Lily
There's no Princess. I mean, I don't even have a dog.
Brooke
Oh, you're just going to tell him you don't even care.
Alexis
So wild to me so all of
Brooke
this and you're just like, I don't. I lied to you.
Jeffrey
What if his friend is a private. Yeah, talking about one.
Lily
No.
Scott
I am so confused right now.
Alexis
Okay, listen, we were under the impression, all of us were, that you had a private jet. And Lilly was hoping that you could take her and help her move from Florida to Arizona, make it a little easier on her.
Brooke
She wanted she wanted to use your private jet as u haul.
Commercial Voice
Yeah.
Scott
That is so messed up.
Brooke
Yeah.
Alexis
Wow.
Lily
No, you're not even. You're lying. You just lied to everybody at the club. Like, you're not even who you say you are. Like how? Why would you lie about that?
Scott
You lied about having a dog. That's worse than lying about having a Jack.
Lily
No, it's not, Princess.
Brooke
See, Scott, there's a dog. Didn't you hear it?
Lily
Yeah, those are sound effects. I don't have a dog.
Alexis
Fully blow it. All right, well, listen, Lily, I don't think this guy can help you with what you're looking for.
Lily
No.
Jeffrey
Is Broadway rich? Like, were you on vacation or what?
Scott
Like, you know what? I don't have to tell you.
Brooke
Yeah.
Alexis
All right, Scott, I'm sorry that we did this to you. Lily, this isn't going to work out. But if you do find another dude in the next few days who says he has a private jet, contact us.
Lily
I definitely will.
Alexis
Brooke would love nothing more than to help you get on some other guy's pj.
Lily
Oh, thank you guys so much. I would love that.
Brooke
Private jet after private jet. That's what we're here for.
Jeffrey
Text in. This may work really well. Text and do you have a private jet?
Alexis
Yes.
Brooke
78592. Have your assistant text in
Announcer
Brooke and
Lily
Jeffrey in the morning.
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Lily
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Commercial Voice
Next Monday, our 2026 iHeart Podcast Awards are happening live at south by Southwest.
Alexis
This is the biggest night In Podcasting
Commercial Voice
will honor the very best in podcasting from the past year and celebrate the most innovative talent and creators in the industry.
Brooke
And the winner is.
Commercial Voice
Creativity, knowledge and passion will all be on full display.
Lily
Thank you so much, iheartradio. Thank you to all the other nominees. You guys are awesome.
Commercial Voice
Watch live next Monday at 8pm Eastern, 5pm Pacific free@veeps.com or the Veeps app.
Alexis
It's amazing how quickly you can go from, I think I really like him and might even consider dating him to hang up on the guy. He's a liar and he's dead to me.
Jeffrey
I mean, sound effects.
Brooke
I don't know if she ever said she really liked him. Yeah, that's an exaggeration. Yeah, I couldn't even fake that. Yeah, she was pretty forthright in liking just the opportunity to use his private jet.
Alexis
Yeah, well, yeah, so it didn't work out. I do hope that she does find a ride, though, on a jet or on a yacht or some fancy mode of transportation that doesn't get her and her fake dog all anxious again.
Jeffrey
I want to know more about him, too, because he was all fake, too. Like, they may have been a perfect couple.
Brooke
You guys, she is going to be in a U haul. Listening to this podcast for hours is what's going to end up happening.
Jeffrey
Some poor other guys driving.
Alexis
No, no, she's going to be driving herself.
Brooke
It's your time to shine, girl. You can do this.
Alexis
Yeah, you got this, Lily. But honestly, you should probably get princess into some obedience classes because she was not acting very princess like during the call.
Jeffrey
You had to make a lot of stops on that road trip.
Brooke
You're real heavy with that sound effect.
Announcer
Yeah.
Alexis
Try to make it believable, maybe. Yeah, maybe we went overboard.
Jeffrey
We could have done a smaller dog.
Alexis
Yeah, probably. We have what we worked with. Those are the sound effects in our system. But you know what? We can always try to help out any listeners with their fake pets. Email the show. We'll load up the sound effects and help you call whoever you need to call. With an awkward Tuesday, make sure to hit subscribe to that podcast. Brooke and Jeffrey in the morning.
Podcast: Brooke and Jeffrey: Second Date Update
Episode: Awkward Tuesday: Private Jet For My Nervous Pet
Date: March 10, 2026
Host: iHeartPodcasts
In this installment of “Awkward Tuesday Phone Call,” the Brooke and Jeffrey crew take on one of their most outrageous listener requests yet. Lily, a listener preparing to move from Miami to Scottsdale, seeks advice on how to ask a man she just met to fly her (and her imaginary anxious dog!) to Arizona on his private jet. What follows is a hilarious, cringeworthy, and totally on-brand journey to get to the bottom of outrageous favor-asking, private jet pretenders, and fake pets.
The tone is classic Brooke and Jeffrey—sarcastic, playful, sometimes incredulous, but always looking for the comedic gold in awkward situations. The episode is high-energy, mocking the absurd expectations people sometimes have in dating (and favor-asking), while exposing what happens when two people “catfish lite” each other with status symbols and emotions.
Listeners walk away entertained, probably a little shocked at the audacity, and reminded that faking dogs and jets rarely leads to jet-setting success—but always delivers hilarity for everyone else.
Summary by PodcastAI
For more recaps or to submit your own awkward story, subscribe and contact the show at Brooke and Jeffrey in the Morning.