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Jon Stewart
Jon Stewart is back in the host chair at the Daily show, which means he's also back in our ears on the Daily Show Ears Edition podcast. Join late night legend Jon Stewart and the best news team for today's biggest headlines, exclusive extended interviews and more. Now, this is the second term we can all get behind. Listen to the Daily Show Ears edition on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
AJ Stephens
$1.4 billion in NFL quarterback contracts the untold stories behind the biggest deals in football history. I'm AJ Stephens, Vice President of Client strategy at Athletes first, introducing the Athletes First Family podcast, the Quarterback Series. My co host Brian Murphy, Athletes First CEO and I are sitting down with the agents who have negotiated contracts for Justin Herbert, Deshaun Watson, Dak Prescott, K. Tua, Tonga Wailoa and Jordan Love. Listen to Athletes First Family podcast on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
Erica and Mila
The OGs of uncensored motherhood are back and badder than ever. I'm Erica. And I'm Mila and we're the hosts of the Good Moms Bad Choices podcast brought to you by the Black Effect Podcast Network every Wednesday. Yeah, we're moms, but not your mommy. Historically, men talk too much and women have quietly listened. And all that stops here. If you like witty women, then this is your choice. Listen to the Good Mom's Bad Choices PODC every Wednesday on the Black Effect Podcast Network, the iHeartRadio app, Apple Podcast or wherever you go to find your podcast.
Ad Council
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Brooke
Hey, you made it to the podcast. Welcome. And we tried a thing in December. Yeah, we did right what we do, Alexis. We started putting awkward Tuesdays on a Sunday. Totally makes sense.
Jeff
Oh yeah, it's not awkward for that day.
Brooke
And we asked you, do you like it? Do you want us to keep doing it? Overwhelmingly, people commented on our Spotify page that yes, please keep doing them. Definitely keep it up. I could binge this all day and one person Even said this is pretty mid. I love a pretty mid comment.
Jeff
Hey, Jeff is commenting. I'm glad.
Brooke
So listen, you're stuck with your awkward Tuesdays on Sunday. Yeah. And if you want to hear a full hour of our show, we do a brand new show every day, Monday through Friday. Just go to the Brook and Jeffrey main feed. But for now, let's make things a little weird and get awkward.
Jose
They say no good deed goes unpunished. Well, one of our listeners tried a good deed to help out his old high school crush, and now he thinks he may have ruined it forever.
Brooke
Oh, no.
Jose
That's why it's Brooke and Jeffrey to the rescue. Can we swoop in and save him from the bonehead mistake he made while driving a bakery store delivery truck?
Dave
Oh, wow.
Brooke
What?
Jose
Once you hear it, you'll understand why his old crush is so angry at him in your brand new awkward Tuesday phone call right now. It's awkward.
Erica and Mila
It's Tuesday.
Jose
It's awkward Tuesday phone call. What I love about classic Hallmark movies is how realistic and relatable they are.
Brooke
Oh, totally, J.
Jose
Because who hasn't taken a trip to a small town and fallen in love with the hunky widower who runs the local reindeer farm?
Brooke
I mean, not to mention all the in game keepers. I know.
Jeff
So many inkeepers, and all the business is going out of business.
Brooke
They need help, Jeff.
Jose
But they're all ripped, too. I mean, they're in touch with nature, but in between dumbbell curls, they will take a pause to connect with you.
Brooke
I got to tell you, as someone from an actual small town, so many hotties.
Jose
Just so realistic and so relatable. Tractors. We've all been there, at least in our minds. But one of our listeners has literally been there because he describes his life as a failed Hallmark film.
Brooke
What?
Jose
And needs our help on finally getting his happy ending. So let's talk to Dave. Dave, welcome to the show.
Dave
Hey. Hey, how's it going?
Brooke
Dave, if you don't have a six pack or at least a four pack, hang up. Yeah, we should make that roll all the time.
Dave
Oh, I got eight. I got eight.
Jose
He's got an eight pack.
Brooke
Okay, okay.
Jose
All right. We will accept you into our arms and try and help you out. But you mentioned that your life isn't going quite the way that you thought it was going to be going. Tell us about it.
Dave
Yeah, I mean, at least this aspect of it. Like, so there's this girl that I used to have a crush on in high school.
Jose
What's her name?
Dave
Her name's Chloe, which I think is such a. Such a pretty name.
Brooke
Oh, you still have a crush.
Dave
This was back when I was, like, really dorky. So I, like, didn't really do anything about it in high school.
Brooke
Okay.
Dave
But then years later, like, more recently, I randomly run into her on a ski trip.
Brooke
Ooh.
Dave
And we hit it off. We're, like, racing each other down the slope.
Brooke
Wait, did you recognize her? Immediately.
Dave
Right away. And it, you know, it took her a second to recognize me because I look a lot different. She was like, wait, Dave from high school?
Jeff
Oh, she remembered your name, too. That's good. I don't remember anybody's names ever, so.
Brooke
Oh, wow.
Jose
Ski slopes.
Brooke
That is very hallmarky. Yeah.
Dave
I mean.
Jose
Yeah.
Dave
So we got to talking, and it turns out she's still in our hometown, and she, like, owns a bakery there, which is extremely charming.
Jeff
Oh, my gosh.
Jose
Hallmark cliche.
Brooke
Oh, my God. Is she going to get frosting on her face and you're going to have to wipe it off and then kiss her?
Dave
Oh, my gosh.
Brooke
That is actually adorable.
Dave
Yeah, it's like, the perfect meet cute. You know, it's like, all happening organically.
Jose
Were you able to, like, finagle another meetup?
Dave
Yeah. So I told her that I'm actually going back home to our hometown for the holidays to see my folks.
Brooke
Okay.
Dave
So it's a couple weeks later, I go to the bakery. She's there. It's. The energy is just like before. But I asked her out for dinner. She said yes. And so we go out, and I can tell she's, like, really stressed out.
Brooke
Is she nervous at dinner? She's stressed, yeah.
Dave
Well, I was wondering if she was nervous or whatever, but then she tells me that her delivery driver quit, so she has all these orders to fulfill, and she can't physically do it.
Brooke
There's the plot.
Jeff
Oh, my God. There's the plot. Oh, my God.
Brooke
You jumped in and saved the day. You better have.
Dave
So I told her. I was like, I can drive the truck for you. I've got nothing else to do. I'm just, like, hanging out with my family, so.
Brooke
So did she take you up on it?
Dave
Yes, she lets me help, and she's really grateful for the offer. And we did kiss that night.
Brooke
And then you got to spend days with each other because now you're helping her out at the bakery.
Jose
Although you're not supposed to kiss the people that you work for. Yeah.
Jeff
Also, how much is she paying to get the benefits here?
Brooke
That's not necessarily true, Jeff. I've kissed a lot of people I worked with.
Jose
I know. Look how your career has turned out.
Dave
No, I mean, that's generally the rule, but, yeah, it's like, kind of a different situation. Right. So, like, I show up in the morning really early, I get the truck, and I'm doing deliveries for her, and it's, like, actually fun. I'm driving around just, like, dropping off baked goods to people. People are really happy.
Brooke
That's amazing.
Jeff
So you're spreading joy. You're making her happy. Everything sounds whimsical.
Jose
I know nothing sounds awkward to this point.
Jeff
It sounds beautiful.
Dave
Well, there's this big hill in our hometown, and it's this, like, notorious kind of hill, and I should have known better, but I parked on the hill, and I don't think I put the parking brake on or the parking brake was faulty, but it doesn't matter. Like, it rolled down and it crashed.
Brooke
You crashed her van?
Dave
Yeah, I wasn't even in it, you know, it just rolled down.
Jose
Oh, dude.
Jeff
No.
Dave
It just hit this big cement wall.
Brooke
Oh, my God.
Jeff
Is the wall wall.
Brooke
Okay, you guys, small businesses can't take on expensive expenses like that.
Jose
How did Chloe react when you told her?
Dave
She couldn't believe it. It was such a, like, massive. I mean, like, disappointment for her because I'm like. I offered to help out, and then I messed it up. I feel, like, terrible. And, you know, I offered to, like, pay for damages to the truck and everything, but you don't want to do that.
Brooke
That's a lot of money.
Dave
It's been a few weeks, and, yeah, she's not talking to me, so I know this is an awkward conversation to have, but, you know, I'm trying to convince her to forgive my mistake, give me a second chance, and just seeing each other again, like, at least, like, one more time.
Brooke
Yeah, I mean, what was the last thing she said to you?
Dave
Well, honestly, I'm not sure if I can say it on the radio because there were a lot of words that probably wouldn't be okay for the radio.
Jose
Oh, yeah, let's try one of them. Let's see how it goes. Just say one.
Erica and Mila
She's passed.
Jose
Okay.
Jeff
Thing is, you haven't talked to her since, so hopefully she's had some time to calm down and process.
Brooke
Yeah, I just say, get the dump button ready, Jeff.
Jose
Swearing fireworks might happen when we come back and try and call the girl you used to have a crush on in high school and tell her, hey, sorry for crashing your bakery delivery truck into a cement wall.
Jeff
You want to hang out Sometime.
Jose
But you're calm now, right? We're going to do it with your awkward Tuesday phone call right after this. It's awkward.
Erica and Mila
It's Tuesday.
Jose
It's awkward Tuesday phone call. Today we're dealing with the case of Hallmark movie gone wrong, featuring our listener Dave, with his chiseled eight pack, who ran into his old high school crush while on a ski trip recently. They reconnected, and he found out she worked at a bakery back in their.
Jeff
Hometown, which we laughed because that's, like, literally a Hallmark cliche.
Jose
And she didn't have a delivery driver to fill all of her orders.
Brooke
Oh, no.
Jeff
He quit days before Christmas.
Jose
So Dave boldly volunteered to step in and accidentally crashed her delivery truck into a cement wall, ruining not just the orders, but their chance at a true Hallmark love, in his defense.
Jeff
And wasn't inside when it crashed.
Brooke
Her business, Jeff.
Jeff
That's the whole business.
Jose
Yeah, I mentioned he ruined the orders.
Brooke
Yeah, probably a little bit more than that.
Jose
Okay, if you want to find, like, the sad part about it, we can really focus in on that. But the thing is, now he wants our help to make things right with Chloe. Just needs a little bit of advice on how to get back into her good graces. So, Brooke and Jose, what do you guys think?
Brooke
Wait, have you talked to her since she was, you know, cussing and super in the moment?
Dave
I've only been texting, but we haven't actually gotten on the phone to talk.
Brooke
Okay, so this is your first opportunity for a real apology, like a calm one. After the emotions have died down, you need to just tell her how sorry you are.
Jeff
Yeah. Grovel and the sword.
Brooke
And if, you know, you already offered to pay for a van, what you need to do is if she doesn't take you up on that again, then you say, all right, I've got to make this right. Please let me take you skiing.
Jose
Yeah.
Brooke
Bam. Suddenly, you're on a date together on the ski hill.
Jose
Yes.
Jeff
And then offer to pay for, like, six more vans.
Jose
All right, so Brook's advice, like it always is, is have the man apologize.
Brooke
But crash the band.
Jose
It's always the guy's fault. So what do you think, Dave? Is that. Is that helpful?
Dave
Yeah. Yeah, no, that's helpful. I mean, now that the emotions have died down a little bit, if I say sorry now, you know, maybe it'll resonate with her a little bit more.
Brooke
Yeah.
Jose
Okay. But you can't just say it. You have to sound it.
Jeff
Yeah, well, you are sorry, so it will be.
Jose
Oh, then what was the advice that's the advice.
Brooke
Just be sincere, apologize. Therapy brought him to this advice right here. Try to make it up to her.
Jeff
There's no trick to this one. It's like, okay, just gotta go.
Dave
You're right. All right.
Chloe
And ask her to go skiing.
Jeff
Yeah, yeah, end it with that. That's going to be a nice touch.
Jose
All right, and then Brooke will offer to pay for the truck if it goes well. So here we go. I'm going to dial Chloe's number and let you make your awkward Tuesday phone call.
Dave
All right.
Jose
All right, we'll jump in if you feel like you need a little bit of help. But here we go.
Chloe
Hello?
Dave
Chloe, hey, it's Dave.
Chloe
Oh, my God. What do you want?
Dave
Hey, it's really good to hear your voice. You know, I know I've apologized before, but I just wanted to say again how sorry I am for everything that happened. And I just wanted to check in with you and see how you're doing.
Chloe
You mean since you've crashed my delivery truck and threw a giant wrench in my business? I'm doing great, Dave. I'm doing so great.
Dave
You're great. Okay, well, that's actually really, really good to hear.
Chloe
I was being sarcastic. Why are you calling me?
Dave
Look, I just need to know how I can make it up to you. Like, you know, I offered to pay for the truck even though the accident. Accident wasn't 100% my fault? I think not. You know, I'm sorry.
Chloe
It wasn't your fault. You crashed my truck.
Dave
Well, yeah, but that could have happened to anybody. I mean, the truck seemed like it needed.
Chloe
No, because after it happened, you then ate all of the cupcakes from one of the orders.
Dave
Okay, well, they weren't gonna get there in time. And I'm, like, not gonna wait forever for the cops to show up. I was hungry. That was the only thing around.
Chloe
The heat ate the product. Dave. Do you realize I had to rebake the entire order?
Dave
Look, I'm just letting you know, like, regardless of who ate what, you were.
Chloe
The one who ate everything. So it's not a question of who. It is you that ate everything.
Dave
Look, this has affected me just as much as you. I mean, I've been going to therapy to, like, cope with my feelings about.
Erica and Mila
You Told me you went out to.
Chloe
The desert and did ayahuasca for two days.
Dave
It was just soul searching, you know, it's the kind of therapy.
Chloe
It's not therapy. It's doing drugs, Dave.
Dave
Okay, this isn't going like I thought.
Chloe
It would yeah, you think? I don't really know what your purpose is of calling me.
Dave
Well, I've been doing a lot of work on myself, obviously, and I think I'm doing better. And I'm just wondering if there's any chance you'll get over it and we can. We can go out again. I'll take the ski.
Jose
Awkward. You'll get old Chance.
Jeff
He offered to pay for skiing.
Brooke
Wow.
Chloe
That was painful. What's going on?
Jose
Hey.
Jeff
What's going on with you?
Brooke
We just witnessed the worst apology we may have ever heard.
Jose
There was some apologies in there, but, Chloe, you're on the radio right now with a show called Brooke and Jeffrey in the Morning.
Chloe
Are you serious?
Jose
Yeah, yeah, yeah. This is a segment that we do. It's called the Awkward Tuesday Phone Call, which it's like.
Chloe
It can't get worse, to be honest.
Jose
Yeah.
Brooke
I mean, it could be, like, free promotion for your bakery business. So that's good.
Dave
I mean, I'm not good at these things. I really needed help. I don't know.
Jose
We could tell. So, look, Chloe, we're trying to help Dave make his apology sound more sincere, because he really does feel bad.
Brooke
And it's so crazy, Chloe, because when he talked to us before we called you, he was so sincere and so just regretful of what had happened, and he felt like an idiot and he wished he could take it back.
Chloe
He also didn't mention the cupcakes.
Jose
Yeah, yeah, that part was new to us. We didn't hear about that.
Jeff
You ate the product, bro.
Dave
Listen, the cupcakes were, like, not an important part of it. You know, the van, obviously, was the main thing. And the main, main thing is that I feel really, really bad about everything that happened.
Jose
Yeah, you feel bad because you're coming down off of your ayahuasca trip. Look, we didn't realize that this was the scenario, Chloe, but, yeah, there's more.
Jeff
Layers than we knew.
Jose
Clearly, we missed some parts. He absolutely did screw up. He is very sorry.
Jeff
He admits that.
Jose
Is there any chance that maybe you're being just, like, a little bit harsh with the judgment? Because I'm just saying, maybe I want to hear from Chloe.
Chloe
I'm not. I'm assuming that he probably failed to mention that he was two hours late to start the delivery. And also, he smelled like rum.
Brooke
Oh, man, rum goes great with cake and.
Jeff
Hia.
Dave
No, that was just my cologne. That was just my cologne.
Brooke
Oh, I see. Captain Morgan's. That's the one that you got.
Dave
I was on vacation, and I, like, offered to show up. And honestly, she's lucky I, like, agreed to deliver for her at all.
Brooke
See? Okay, listen, listen. I think this is where you both went wrong. You shouldn't have mixed love and business. If you would have never volunteered, none of this bad stuff would have happened.
Jose
That's actually a really good point, Brooke. Never ask anybody you know personally to help you during the holiday season.
Chloe
I didn't ask him to help me. I offered to pay him, and he made me pay him up front.
Jeff
Wait, was you boss here paid?
Dave
Okay, but she didn't tip me.
Brooke
Dave, Dave, Dave. You crashed the car and ate the cupcake.
Jose
And you made it sound like this whole thing was out of, like, generosity and the kindness of your heart. You didn't say that you were getting paid to do this.
Brooke
You got a side job while you're.
Dave
Home for the year.
Brooke
It's like the cupcake swindler came back to town.
Dave
I mean, it was minimum wage. I didn't ask for anything more than that. And I thought it would be weird if she didn't pay me.
Brooke
You didn't even deserve that much money.
Jose
Dave, you probably need to honestly give this a little bit more time before you start asking for forgiveness.
Brooke
No, no, I think that he just needs to be done. There, done.
Jose
I say give it a few years. Check in with her. Chloe, when would you like him to check back in with you to see if he'll forgive him?
Chloe
He can lose my number completely. I'm not interested in seeing Dave ever again.
Brooke
There we go. I think he just got banned from a cupcake shop.
Chloe
Banned from the bakery title.
Jeff
Yeah, probably the only bakery in that whole town, too. He's like, no more baked goods for him.
Dave
Yeah, well, there was one thing that. That I haven't said yet, which I was hoping would be like, an exciting piece of news, but I. I lost my job in the city just so. I'm moving back home, actually.
Jose
Chloe, he needs a place to live. Can he live with you?
Chloe
I'm hanging up.
Jose
Okay, well, happy holidays. Yeah.
Brooke
Brooke and Jeffrey in the morning.
Jon Stewart
Jon Stewart is back in the host chair at the Daily show, which means he's also back in our ears on the Daily Show Ears Edition podcast. Join late night legend Jon Stewart and the best news team for today's biggest headlines, exclusive extended interviews and more. Now, this is the second term we can all get behind. Listen to the Daily show ears edition on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
AJ Stephens
$1.4 billion in NFL quarterback contracts. The untold stories behind the biggest deals in football history Story I'm AJ Stephens, Vice President of Client Strategy at Athletes first, introducing the Athletes First Family Podcast, the Quarterback Series. My co host Brian Murphy, Athletes First CEO and I are sitting down with the agents who have negotiated contracts for Justin Herbert, Deshaun Watson, Dak Prescott, Tuathailoa and Jordan Love. Listen to Athletes First Family Podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast.
Erica and Mila
Podcasts the OGs of Uncensored Motherhood are back and badder than ever. I'm Erica. And I'm Mila, and we're the hosts of the Good Mom's Bad Choices Podcast brought to you by the Black Effect Podcast Network every Wednesday. Yeah, we're moms, but not your mommy. Historically, men talk too much and women have quietly listened. And all that stops here. If you like witty women, then this is your try. Listen to the Good Moms Bad Choices Podcast every Wednesday on the Black Effect podcast network, the iHeartRadio app, Apple podcast, or wherever you go to find your podcast.
Ad Council
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Episode: Awkward Tuesday: Hallmark Movie Fail
Release Date: January 19, 2025
Hosts: Brooke and Jeffrey
Platform: iHeartPodcasts
The episode kicks off with Brooke and Jeffrey discussing a recent experiment where they shifted their "Awkward Tuesday" segment to Sundays. Receiving mixed feedback from listeners, the hosts humorously acknowledge comments ranging from enthusiastic support to critiques like "this is pretty mid" (02:16). Embracing the positive responses, they announce the continuation of this quirky segment aimed at resolving awkward dating scenarios.
Dave's Story:
A listener named Dave reaches out for help with an awkward situation resembling a Hallmark movie plot gone wrong (02:49). Dave reconnects with his high school crush, Chloe, during a ski trip. Sparks fly as they reminisce and bond over shared memories, leading Dave to offer assistance with Chloe's bakery deliveries after her delivery driver quit (04:37).
Key Events:
Reconnection and Romance:
Disaster Strikes:
Aftermath:
Brooke and Jose's Guidance:
Brooke and Jose dissect Dave's predicament, offering pragmatic yet humorous advice:
Sincere Apologies: Emphasize the importance of a heartfelt apology after emotions have settled (11:08).
Brooke (11:17): "Just be sincere, apologize. Therapy brought him to this advice right here."
Rebuilding Trust: Suggest practical steps like rekindling shared interests (e.g., skiing) to mend the fractured relationship (11:29 - 12:00).
Authenticity Over Tactics: Caution against overcomplicating apologies with grand gestures, advocating for genuine expressions of remorse instead (12:00 - 12:28).
Jeff's Interjections:
Jeff adds comedic relief by highlighting the pitfalls of Dave's approach, such as offering to pay for multiple vans humorously (11:29 - 11:43).
Jeff (11:33): "Grovel and the sword."
In a bold move, Brooke and Jose decide to broadcast Dave's attempt to apologize live, leading to an excruciatingly awkward conversation between Dave and Chloe (12:32 - 19:01).
Highlights of the Call:
Chloe's Initial Reaction: Chloe is irate, expressing frustration over the truck accident and the ruined cupcake orders (13:10 - 14:17).
Chloe (13:27): "What do you want?"
Dave (13:39): "I'm sorry."
Escalating Tension: Dave's attempts at reconciliation fall flat as Chloe confronts him about the mishaps, including his unprofessional behavior and personal missteps (14:04 - 17:22).
Chloe (16:12): "It's not therapy. It's doing drugs, Dave."
Final Blow: Chloe unequivocally rejects Dave's apologies and ends the call, firmly severing ties (18:36 - 19:01).
Chloe (18:27): "He can lose my number completely. I'm not interested in seeing Dave ever again."
Hosts' Reflection:
Brooke and Jose express regret over the call's outcome, acknowledging Dave's genuine remorse but recognizing that some situations may not be salvageable (15:22 - 19:01).
Brooke (17:32): "You shouldn't have mixed love and business."
The episode serves as a cautionary tale about intertwining personal relationships with professional assistance, especially during emotionally charged times. Brooke and Jeffrey use Dave's story to highlight common pitfalls in dating and the importance of clear boundaries and effective communication.
Notable Quotes:
Brooke (04:26): "Dave, if you don't have a six pack or at least a four pack, hang up."
Dave (07:02): "I'm just, like, hanging out with my family, so."
Chloe (16:12): "It's not therapy. It's doing drugs, Dave."
Listeners are encouraged to reflect on Dave's experience, understanding that while good intentions are commendable, professionalism and clear communication are crucial in both personal and business endeavors.
For more engaging stories and relationship insights, tune into Brooke and Jeffrey's daily segments available on iHeartRadio, Apple Podcasts, and Spotify.