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Brooke
The Pumpkin Spice Latte is back at Starbucks. Crafted with our signature espresso and real pumpkin sauce, then topped with whipped cream, cinnamon and nutmeg, the psl get it while it's hot or iced. Only at Starbucks. You can make a difference in someone's life, including your own with a job in home care. These jobs offer flexible schedules, health care, retirement options and free training. They also provide paid time off and opportunities for overtime. Visit oregonhomecarejobs.com to learn more and apply. That's oregonhomecarejobs.com.
Jeffrey
Hey, it's Ryan Reynolds here.
Brooke
For Mint Mobile now.
Jeffrey
I was looking for fun ways to tell you that Mint's offer of unlimited Premium Wireless for $15 a month is back. So I thought it would be fun.
Derek
If we made $15 bills, but it.
Jeffrey
Turns out that's very ille. So there goes my big idea for the commercial. Give it a try@mintmobile.com Switch upfront payment.
Brooke
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Jeffrey
Hey it's Ryan Seacrest for Albertsons and Safeway. Now through August 26th it's back to deals time where you can enjoy storewide deals and earn four times points. Look for in store tags to earn on eligible items from Black Label Bacon, Pop Tarts, Quaker Activia, Lunchables, Frito Lay, Goldfish and Jack Links. Then clip the offer in the app for automatic event long savings. Shop in store or online for easy drive up and go pickup or delivery subject to availability restrictions apply. Visit Albertsons or Safeway.com for more details.
Brooke
Hey it's Brooke and Jeffrey and this is the second Day podcast. We got a brand new awkward Tuesday phone call for you coming up. But first a lot of feelings, a lot of big feelings on yesterday's second date. The lengths that that woman went through to get revenge for her friend were a lot. Yeah. I don't know that I would commit 10 hours just to get back at a guy that goes to my friends. I know, but some people were actually on her side. Yeah. They said, I don't know. I like her and her friend. Good for her. Guys who ghost deserve that. I don't really think it was hate for the guy. She was just defending her friend and upset that she got hurt, which makes total sense. Yeah. Yeah. So it's just so much time. I mean, it would be more fun to just take your girlfriend out and be like, hey, let's get over this guy.
Jeffrey
Also, this wouldn't work for guys because we would just, like, try to get the other girl back, like, and they just wouldn't respond.
Brooke
Yeah, I see. Like, different.
Jeffrey
I'll totally date your ex. Don't worry.
Brooke
Yeah. Yeah.
Derek
All right.
Jeffrey
That didn't work, so.
Derek
Yeah.
Brooke
Didn't work. Sorry. All right, well, thank you so much for commenting.
Derek
Always.
Brooke
We'd love to hear your thoughts about what happens during these episodes. And today we've got an awkward Tuesday that is, you know, gonna be fun for you. Yeah. So here it goes. Brand new starts right now.
Jeffrey
We've done a fair amount of these phone calls where we help out listeners, and then our reaction is, whoa. Did not expect that.
Brooke
Yeah.
Jeffrey
Yeah. Well, today we got a huge whoa. I definitely was not expecting that. Oh, wow. Jeff. Maybe one of the biggest of the entire year. I've never seen Jeff that animated before.
Brooke
The biggest woe of the entire year.
Jeffrey
Not expecting it. So, man, someone clip this. The whole show didn't even know what to say when the truth came out. So you'll be happy to know it gets extra awkward in your brand new awkward Tuesday phone call. Don't miss it. It's next. It's awkward.
Brooke
It's Tuesday.
Jeffrey
It's awkward Tuesday phone call. It's not necessarily the most fun, fun part of our jobs, but occasionally we have to do it.
Brooke
What is it?
Jeffrey
Help out a listener who's worried about possible cheating in their relationship.
Brooke
Yikes.
Jeffrey
No, we may not be private eyes, but we do know about eyeing privates, and that was close enough for a guy named Derek to reach out for help today. So, Derek, man, I'm sorry that we're meeting under these circumstances, but, hey, thanks for being on. Welcome to the show, dude.
Derek
Thank you, man. I appreciate it.
Brooke
My eyes are on your privates right now. Oh, is that supposed to be Helpful. No, I meant private life. Yeah, no, Jeff started it, man. I was just trying to finish it.
Jeffrey
You're a little more direct. I hinted at it and you went right for it. That's okay.
Brooke
Sorry.
Jeffrey
Derek, why don't you tell us about the reason that you emailed us for help? What makes you think that your girlfriend is cheating on you?
Derek
Yeah, so my girlfriend and I, we've been dating for a very long time. And. Okay, something weird has been happening, and it's been kind of happening over the past couple days, but, like, specifically the other day.
Brooke
Oh, so this is super recent.
Derek
Yeah, so I was over at her place, and every morning she takes a little run. Like, she does this all the time. Like, that's her. Her thing.
Jeffrey
Okay.
Brooke
I bet she wouldn't like it if you called it little. I mean, I'm sure it's a great run.
Jeffrey
Maybe he's a short run.
Derek
And so, you know, she brings her phone with her. She listens to music. So I was just doing some work, and I needed to go get a pen to write something down, right? And I went to her desk drawer, and underneath her notebook, I find a cell phone. And at first I was just like, oh, you know, it's just an old phone. But, like, as I'm looking at the cell phone, like, it looks brand new. Like the newest iPhone type of new.
Brooke
Oh, did she maybe buy one and not activate it yet?
Derek
That's what I thought at first. I was like, okay, like, maybe she needed new phones. We've been talking about that. Like, how we both wanted to get new phones recently, but both of us know each other's passwords. So I opened it, and there's one contact and a guy named Brian.
Brooke
Oh, no.
Derek
And I don't know any Brian. So I'm sitting there, I'm like, what the is this?
Brooke
Yeah, I would be freaking out.
Derek
So I found out from this person recently that you can Google somebody's phone number and, like, figure out who they are. Yeah, yeah, I did that. And it turns out he's from out of state. Couldn't find any pictures of him or anything.
Brooke
Oh, do you need Alexis to get on it? Because she could have those for you in, what, 30 seconds?
Jeffrey
Yeah, she may already have his number.
Derek
Yeah, I mean, yeah, that might. That might be helpful. So, like, I'm thinking she's hiding this for me, right? And, like, she has been acting, like, kind of strange.
Brooke
Oh, man.
Derek
Like, she'll go and she'll be like, I'm going to go run some errands and Then she'll be gone for 30 minutes and she'll come back extremely happy. And there's times where she'll come back, no, like, bags at all, no nothing. It's all generic.
Jeffrey
And the fact that she's coming back super happy from her 30 minute errand is also kind of.
Brooke
You said the guy was out of state.
Derek
For all I know, he could be nearby and just have an out of state phone number.
Jeffrey
Yeah.
Brooke
Do you ever check when she's gone? Like, if she takes. Takes that extra phone with her or if it's like, still in the drawer?
Derek
So I put it back the other day and I went to check it this morning and it was gone.
Jeffrey
Alexis, what does that mean?
Brooke
Not good things, Jeff.
Derek
Not good things.
Brooke
Oh, no.
Jeffrey
Okay. You always keep your secret boyfriend phone in the same spot every single day, except when it's moved. Then you know you're up to no good point.
Brooke
It's not an old phone. Like, she's actively taking it.
Jeffrey
But that's what I was gonna say. Why would you leave like, a cheater burner phone, like, out and around your boyfriend?
Derek
Ye.
Brooke
It was in a drawer underneath a notebook.
Jeffrey
Yeah. How much. How much more hidden does it have to be?
Brooke
I mean, I could think of a lot better spots to hide it if it's been going on for a long time. You get lazy with that stuff, you know? Yeah. I mean, could there be any other reason for it? Have you thought of.
Derek
Not that I can really think of.
Brooke
Okay.
Derek
But dang. I tried something really stupid, so I tried to, like, weave his name into conversations. Oh.
Jeffrey
Because I was going to ask have, like, why haven't you brought this up and confronted her about it? But you've tried to do it in a sneaky way.
Derek
Yeah, I'm extremely nervous. Like, I've been with this girl for so long that it to the point where it's like, I don't want to believe it's true, you know?
Brooke
How did you weave Brian into conversation?
Derek
I was telling a story when I went to go get my oil change and I was saying, oh, yeah, like the guy Brian, like, was talking about this and I was like, you know, like, I know a lot of Brian's. Like, don't you know Brian? Like, you know what I'm saying?
Jeffrey
Brian's such a cool man. I mean, you must know tons of Brian.
Derek
You know, Brian's.
Brooke
Honey, how attractive do you find Brian?
Derek
Yeah. Yeah.
Brooke
What was her response?
Derek
She got, like, really adamant, like, no, no, not really. And then again after that, that was when the phone Kind of disappeared, and I don't know what else to do. Like, I'm afraid of how this conversation is going to go, and I don't know how to bring it up.
Brooke
Yeah, it sounds like up until this point, you thought you were in a happy relationship.
Derek
Yeah. Like, it's been so great, I thought.
Brooke
Yeah.
Jeffrey
Okay.
Brooke
That's so hard. I'm sorry.
Jeffrey
And so we never call. What was your girlfriend's name?
Derek
Annie.
Brooke
Annie.
Jeffrey
Annie. Okay.
Brooke
It sounds like such a nice name, too.
Derek
No, it does.
Jeffrey
With your awkward call. Are we reaching out to Annie here, or are we calling this guy Brian and trying to figure out. We're starting with the first B. Brian Anderson. You better be ready.
Derek
I really don't care about the guy. I want to hear it from her.
Brooke
Yeah, that's the right place to put your energy. Oh, it's not bad. I would have for sure called him. I mean, he may not even know, you know, that she's in a relationship.
Jeffrey
Yeah. So we need to really figure out what is our advice going to be to help you with this and get.
Brooke
Her to confess, if that's what's happening.
Jeffrey
Seriously, Derek, you deserve some answers when we come back and let you make your awkward Tuesday phone call to find out if your girlfriend is being unfaithful with some dude named Brian. It's coming up right after this. Hold on. It's awkward.
Brooke
It's Tuesday.
Jeffrey
It's awkward Tuesday phone call. I think most people have one drawer in their house with, like, 10 different random phones in there and a bunch of old charger cables.
Derek
Dude.
Jeffrey
Yes, Just old devices you never turned in or threw out. Cause maybe you're open to reminisce when one day and look back at all the old naughty photos of yourself 10, 15 years ago. You think that. But I just found those phones recently, and I was like, why do I have these? I never even turned them on again.
Derek
Exactly.
Jeffrey
But that's different than the phone our listener Derek found in his girlfriend's desk recently, which was brand new with only one contact in it and no naughty pictures, unfortunately.
Brooke
Right, Jeff?
Jeffrey
Not that he could find. At least the contact was a random guy named Brian from out of state who he's never even heard of before. So naturally, he's thinking, oh, God, this is my girlfriend's burner phone that she's using to sneak around on me with.
Brooke
Yeah, and the more we got into it, the more we felt the exact same thing.
Jeffrey
Right. Hasn't been able to confirm that officially, though. So that's what he's trying to do once and for all with his awkward Tuesday phone call. Or hopefully just find out that he's totally wrong and there's some other explanation for it. First, he needs advice. So, Brooke, what do you have for him?
Brooke
I think the first thing you need to do is like, remind her you're a person with feelings that she actually cares about.
Jeffrey
Derek, can you confirm that you are an actual person with real feelings?
Derek
That I can. That I can.
Brooke
Yes. And I think you need to lay it out there. You need to say, look, I found this phone. It's got a contact Brian on it. You need to explain.
Derek
It's going to be kind of hard for me to do, but I'm a definitely try.
Brooke
I know. We're here for you, though. You know, we got your back. I can't even imagine being in your position.
Jeffrey
Or is it hard for him to do because he's not a real person? We don't know. So, Jose, what's your advice for Derek here? Look, there's a lot of ways this conversation can go to put her on.
Derek
The defensive, and we don't want to do that. So suggest that we need to get new phones. Honey.
Brooke
What?
Jeffrey
And then that way, the rest of the story may come out. She. Oh, I just have a new phone. Oh, I see. You're trying to get her to admit that she has a second phone without accusing her of it. Yeah, I already got one in the drawer. Okay, that's. It's interesting. It's totally conflicting advice than what Brooke said, which was to directly bring it up.
Brooke
He already. He already tried the whole slip Brian into a conversation, and it didn't work.
Jeffrey
That's true. So, I mean, at the end of the day, Derek, it's going to be up to you to decide which piece of advice you feel like fits best for you. But no matter what, we're going to be waiting here ready to support you on the other line.
Derek
Okay.
Brooke
And you also remember that you are a person to be loved and cherished. And if someone's not doing that for you, then it's time to move on.
Jeffrey
Wow.
Derek
Thank you, guys. A lot. It means a lot.
Jeffrey
Hey, man, you got this, brother. Really trying to sell the human aspect there.
Derek
Okay.
Brooke
Jeff's attached.
Jeffrey
I'm not sure still, but maybe things will clear up when you make this call. I'm gonna dial your girlfriend Annie here. You gave me her number, and hopefully she picks up, but here we go, man. Good luck.
Derek
Hello? Hey, babe. Oh, hi. Hi. How are you? I'm doing okay. Just my standard routine. Just didn't expect call from you. Not from your number. Oh, you know, I was just in the process of maybe getting a new phone. You know, just trying to figure that whole thing out. Because, you know, I think we're both kind of due for new phones, don't you think? Yeah. Yeah. But good try. You know that I love you a lot. Yes. And I would hope that feeling is reciprocated. Of course. Of course. Okay. Yeah. Yeah. Because, you know, as a fellow human being, you know, I feel like we all have feelings that should be cherished. What's going on? Are you on something right now? No. Are you possibly on something called Brian Bishop? You asked me about the same thing the other day. I don't know anyone named Brian, so please stop asking me. I mean, it's kind of hard to think that when I found another phone in our room with the contact Brian. I don't know what you're talking about. So we're just gonna pretend that there wasn't a phone underneath your notebook with a contact named Brian that just magically disappeared the day after I mentioned the name Brian? That was my drawer. It's not yours. You're snooping in places that you should not. No one was snooping. I literally just to go get a pencil and I saw the phone. So let's not beat around the bush here and try to act like the phone wasn't found. Trust me, I am not interested in any other guy. What do you mean? Nah, nah, nah, nah, nah, nah. You're telling me about this phone like. No, put yourself in my dude for a second. Like, this is crazy. You're never, ever going to meet him. What does that even mean?
Jeffrey
What?
Derek
Awkward.
Jeffrey
Oh, no. What is happening here?
Brooke
What do you mean you're never gonna meet him? He doesn't want to meet your sight.
Jeffrey
Yeah.
Derek
Wait, what's happening? Who are those people?
Jeffrey
That's our question. Yeah, these people. You're talking about us. We're a radio show. We're called Brooke and Jeffrey in the Morning.
Derek
Hi. Good morning.
Jeffrey
You're on a segment that we do called the Awkward Tuesday Phone Call.
Brooke
Oh, man.
Derek
I don't want to talk about this with you guys. You're going to talk to them about it.
Jeffrey
Listen, and the reason that we're on the phone with your boyfriend Derek here is because we're trying to help him. After the phone that he found, he didn't know the right way to handle this situation with you. He was going through us to get a little bit of advice.
Derek
Derek, you're going to make me freaking blow your surprise. What are you talking about right now?
Brooke
What surprise?
Jeffrey
Surprise.
Derek
Look, this is really embarrassing to admit, but I am not cheating on you whatsoever.
Jeffrey
Okay, but you're saying things like, don't worry, you're never gonna meet the other guy. Like, who are you. What are you even talking about there?
Derek
Okay, well, I meet guys on a certain website, and I engage them in, like, a friendly conversation.
Brooke
All right, Are you talking about, like, only fans or something? Are you doing video stuff?
Derek
No, they just pay for things, so I ask them for a new phone.
Brooke
What?
Jeffrey
We're still a little unclear here, Annie. I don't understand. How is this, like, not as bad as it sounds?
Brooke
It sounds worse, to be honest.
Derek
Well, so far, I've gotten 40 phones and soldiers, most of them all to pay for our car.
Brooke
What? So you're trying to make this, like, altruistic? Like you're talking to other men for the betterment of a new car for you guys?
Derek
Wait, wait, wait, wait, wait, wait, wait, wait. After all the crime documentaries that we've watched, do you think that's smart?
Brooke
Wait, you're worried about crime? I mean, out of 40 phones, there's no way you're not gonna have to do something exchanged one of those guys? No, there's no way.
Derek
And again, the guys who are are probably the ones that are going to stalk us afterwards.
Brooke
Yes, you're not wrong.
Jeffrey
Well, if your car's fast enough, they won't be able to catch.
Derek
I mean, it goes to a P.O. box, so they'll never know what our address is.
Jeffrey
Oh, that's kind of smart. But still, it doesn't feel.
Brooke
Dude. Derek, do you feel better or worse? Like, where are you at?
Derek
How cool of a car are we talking? Whoa.
Jeffrey
Is the juice worth the squeeze is what he's asking.
Derek
I mean, some surprises need to be kept secret. I'm not saying that yet. O luxury.
Brooke
I put resale markets. That good?
Jeffrey
Yeah, or it's like, blow the anniversary gift.
Brooke
Or this is all just a big lie to cover up your actual cheating. Like, it's. Why wouldn't you tell them what kind of call.
Jeffrey
Wait a minute. I was done with the cheating part.
Derek
When we're home tonight, I can show you all of the books, and you can see how much money that I've made through this business.
Jeffrey
Oh, you track everything, Mark, you need.
Brooke
To read those chat messages, I think.
Jeffrey
Or if there's none, that's also saying a lot. They're all deleted. And Annie, Alexis wants the website that you're meeting these scammable. Guys on. So if you could forward that to Brooke and Jeffrey in the morning, full of those guys for Alexis.
Derek
We're fine.
Jeffrey
Okay, never mind. We're good. You keep scamming.
Derek
If this is real, I will say next time you can keep what you're getting me a secret, but still wrote me into this little plan of yours that might make me seem a little less likely to think that you're cheating.
Jeffrey
He's what? He wants Jet skis, Annie. He's asking for jet skis next time. Okay, There you go. You enjoy your anniversary.
Brooke
Brooke and Jeffrey in the morning. You can make a difference in someone's life, including your own, with a job in home care. These jobs offer flexible schedules, health care, retirement options, and free training. They also provide paid time off and opportunities for overtime. Visit oregonhomecarejobs.com to learn more and apply. That's oregonhomecarejobs.com.
Jeffrey
Hey, it's Ryan Seacrest for Albertsons and Safeway. Now through August 26th, it's back to deals time, where you can enjoy storewide deals and earn four times points. Look for in store tags to earn on eligible items from Black Label Bacon Pop Tarts, Quaker Activia, Lunchables, Frito Lay, Goldfish, and Jack Links. Then clip the offer in the app for automatic event long savings. Shop in store or online for easy drive up and go pickup or delivery subject to availability restrictions. Apply. Visit Albertsons or Safeway.com for more details. You hear of couples embracing the side hustle now more than ever. True, this one's a little bit different, but I think still falls underneath that umbrella, right?
Brooke
I mean, if you could keep one box from interfering with the other box. But it's all going to get messy.
Jeffrey
I don't know. What if he does the same? What if he starts, you know, doing the thing for ladies that balances it out?
Brooke
Sure, sure. And I'm sure none of these people giving money will ever expect anything else than a friendly conversation. Send something that they weren't asked for.
Jeffrey
Oh, thanks for saying Hi back. Here's $1,000. Okay. That's all I wanted.
Brooke
Totally how it works, Jeff.
Jeffrey
All right, you bring up some fair points. I'm gonna have to request some of the transcripts of these conversations before we can fully endorse it to our listeners. Listeners going forward. I don't know if you want to see them, dude.
Brooke
You may be able to sell those.
Jeffrey
Yeah. One thing I can endorse fully is subscribing to our show. And yes, I am getting paid to say that. Okay, full admission. Getting paid for not a lot though.
Brooke
You mean this is your job?
Jeffrey
Yeah, this is my job. Exactly. It's sadder the more I say it, but if you haven't subscribe at Brooke and Jeffrey hey, it's Ryan Seacrest for Albertsons and Safeway. Now through August 26th, it's back to Deals time, where you can enjoy storewide deals and earn four times points. Look for in store tags to earn on eligible items from Lindor, Oreo Lays, Celsius, Cottonelle and Snapple. Then clip the offer in the app for automatic event long savings. Shop in store or online for easy drive up and go pickup or delivery subject to availability restrictions apply. Visit Albertsons or Safeway.com for more details.
Brooke
Every business has an ambition. PayPal Open is the platform designed to help you grow into yours with business loans so you can expand and access to hundreds of millions of PayPal customers worldwide. And your customers can pay all the ways they want with PayPal, Venmo, pay later and all major cards so you can focus on scaling up when it's time to get growing. There's one platform for all business PayPal open grow today at paypalopen.com loans subject to approval in available locations. Untold Stories Life with a Severe Autoimmune Condition, a production from Ruby Studio in partnership with Argenics, is back with Season four. Join me, Martine Hackett, as we explore the realities of life with Myasthenia gravis or MG and chronic Inflammatory demyelinating polyneuropathy, or cidp. We'll uncover the stories of resilience and self advocacy in the face of uncertainty. From overcoming misdiagnosis to finding empowerment in small victories, these are moments that change us. Here's a glimpse of what's in store. Whenever I go to my specialist, he mentions the R word. Remission. Is it possible? Like, is it over? But also knowing it's never really over, but just being able to say, hey, there's light at the end of the tunnel. Stay the course. Don't give up on yourself. Every single person living with the autoimmune illness has a life worth living, and it's up to you to define that, to capture that, and to go guns blazing. Follow and listen to Untold Stories on the iHeartRadio app or wherever you get your podcasts. At Hills Pet Nutrition, we know that pet parent guilt is real. Leaving too long, playing too little. New homes, new babies, Waking them up when they look so comfy. Running out of patience, Running out of treats.
Derek
Running the vacuum.
Brooke
You can only do so much. That's why there's hills. Science led nutrition to help you give more love than humanly possible. Because you're only human. There's hills. Find the right food@hillspet.com Science does more.
Jeffrey
Talk about stepping up. It's time to level up your game.
Derek
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Podcast: Brooke and Jeffrey: Second Date Update
Episode Air Date: August 26, 2025
Episode Theme: A boyfriend suspects his girlfriend is cheating after finding a mysterious burner phone—and gets much more than he bargained for on the Awkward Tuesday Phone Call.
This episode centers around Derek, a listener suspicious that his long-term girlfriend, Annie, is hiding something after he discovers a new phone with a lone male contact ("Brian") hidden in her drawer. With suspicion mounting, Derek turns to the Brooke and Jeffrey team for help confronting Annie in a high-stakes, live on-air conversation. What starts as a potential infidelity drama takes an unexpected detour into the world of side hustles, online suitors, and car fundraisers.
(Begins ~13:59)
Annie’s Secret Hustle:
Hosts’ Reactions: Both shocked and bemused, the hosts press Annie for details. They voice skepticism, particularly about the risks and the true nature of the ‘friendly’ arrangement.
Safety Concerns: Derek and the hosts express concern about the dangers of Annie’s side hustle and speculate about expectations from the men involved.
Derek’s Response: Shock turns to disbelief, then playful acceptance.
Hosts’ Final Thoughts:
Light-hearted, irreverent, and packed with sarcasm, even in tense moments. Brooke and Jeffrey’s banter keeps the mood playful, balancing concern and comedy. Despite the real emotional stakes for Derek, the bizarre twist transforms the episode from cheating drama to wacky relationship economics.
If you love relationship mysteries with a side of wild, unexpected twists and comedic commentary, this is a prime “Awkward Tuesday” segment. The episode takes listeners through jealousy and suspicion, only to end in baffled laughter and a unique look at the extremes some couples will go for their shared goals. A cautionary (and comedic) tale for anyone who thinks a hidden phone always equals cheating—it might just be a hustle. Or, as Jeffrey sums up, at least make sure you get jet skis next time.