Say Yes to the Ex: Unlucky Number 13

Summary

Podcast Summary: Brooke and Jeffrey – "Say Yes to the Ex: Unlucky Number 13"

Episode Title: Say Yes to the Ex: Unlucky Number 13
Release Date: June 1, 2025
Podcast: Brooke and Jeffrey: Second Date Update
Host/Author: iHeartPodcasts

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Introduction to the Episode

In this episode of Brooke and Jeffrey: Second Date Update, the hosts delve into the intricate and often tumultuous journey of rekindling past relationships. Titled "Say Yes to the Ex: Unlucky Number 13," the episode centers around Natalie, a returning listener seeking a second chance with her ex-boyfriend, Caleb. The discussion navigates themes of trust, forgiveness, and personal growth following a tumultuous breakup marked by infidelity.

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The "Say Yes to the Ex" Segment

Introduction of Natalie: The segment begins with Brooke introducing Natalie, who previously appeared on the show regarding a disturbing second date experience at a red envelope party. Natalie now returns with a desire to reconnect with her ex, Caleb, whom she dated three years prior for six to seven months.

Natalie's Background: Natalie candidly shares her past mistakes, revealing that she was unfaithful during her relationship with Caleb. She admits, “I was unfaithful and I got caught. Yeah, and I totally deserved him breaking up with me” (07:16). Despite this, she expresses heartfelt remorse and confidence in her personal growth, stating, “I'm not that person anymore. And I just know he's a solid person that doesn't have neon signs and giant arrows in his bedroom” (07:44).

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Attempting Reconciliation with Caleb

Reaching Out: After reflecting on Natalie's desire to reconnect, the hosts discuss whether it's possible to mend a relationship after such a breach of trust. Jeff poses the question to the audience, “Can you come back from a cheating scandal?” (08:21), sparking a broader conversation about forgiveness and the possibility of second chances.

The Live Call: To facilitate Natalie's request, the producers successfully contact Caleb, who is placed on hold unaware of the segment's purpose. Natalie prepares nervously, contemplating the potential outcomes. When Caleb joins the call, the tension is palpable.

Confronting the Past: Natalie's confession during the call is both candid and humorous. She reveals the extent of her infidelity, saying, “It wasn't once she cheated with 13 people” (15:03), including unconventional individuals like an escape room instructor. Caleb's reaction is one of disbelief and hurt, exclaiming, “You told me 13 different dudes... it was a lot of people, and I knew most of them, so” (15:55).

Resolution: Despite Natalie's earnest attempts to demonstrate her change, Caleb remains firm in his stance. He agrees to meet for coffee but makes it clear that trust has been irreparably damaged: “There is zero chance of me ever trusting you again or being in any kind of relationships” (19:29).

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Hosts’ Perspectives and Discussion

Brooke and Jeffrey's Take: Throughout the episode, Brooke and Jeffrey offer insightful commentary on the complexities of rebuilding trust after infidelity. Jeff emphasizes his belief in forgiveness, stating, “Personally, I believe in forgiveness, and in certain situations, maybe this is one of them” (11:26). However, Brooke maintains a more cautious viewpoint, questioning the practicality of giving second chances in such scenarios.

Balancing Humor and Seriousness: The hosts adeptly balance humor with the serious nature of Natalie's situation. Instances like Caleb referencing his "arena" bedroom (06:03) and the playful banter about escape rooms add levity to the discussion, making the episode engaging while addressing deep emotional issues.

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Conclusion and Takeaways

The episode culminates with a reflection on the challenges of rekindling past relationships fraught with betrayal. While Natalie's attempt to reconnect with Caleb highlights the desire for redemption and growth, Caleb's resolute stance underscores the lasting impact of broken trust. Brooke and Jeffrey leave listeners contemplating the delicate balance between forgiveness and self-respect in the realm of second chances.

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Notable Quotes with Timestamps

• Natalie on Personal Growth:
  “I'm not that person anymore. And I just know he's a solid person that doesn't have neon signs and giant arrows in his bedroom.” (07:44)

• Jeff on Forgiveness:
  “Personally, I believe in forgiveness, and in certain situations, maybe this is one of them.” (11:26)

• Caleb's Firm Stance:
  “There is zero chance of me ever trusting you again or being in any kind of relationships.” (19:29)

• Brooke on Second Chances:
  “It doesn't sound like you were really into the relationship to begin with.” (08:44)

• Natalie’s Admission:
  “I was unfaithful and I got caught. Yeah, and I totally deserved him breaking up with me.” (07:16)

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Timestamps

• 07:16 – Natalie admits to being unfaithful.
• 07:44 – Natalie expresses personal growth.
• 08:21 – Jeff questions the possibility of reconciliation after cheating.
• 11:26 – Jeff discusses his belief in forgiveness.
• 15:03 – Natalie reveals the extent of her infidelity.
• 19:29 – Caleb states he cannot trust Natalie again.

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This episode of Brooke and Jeffrey: Second Date Update offers a compelling exploration of the possibility and pitfalls of rekindling past relationships marred by infidelity. Through Natalie's heartfelt journey and the hosts' balanced perspectives, listeners gain valuable insights into the complexities of love, trust, and forgiveness.

Transcript

[Brooke]

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[Alexis]

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[Brooke]

All right, you were in for a Sunday treat, my friends. You have found the second Aid Update podcast. It's Brooke and Jeffrey in the morning. And Sunday is where we introduce you to something new.

[Jose]

Yeah.

[Brooke]

Something different that we do on our show because we do do a full hour podcast over on our main feed. And this one is a segment called say yes to the X. Alexis, have we run this in the second day?

[Jose]

I think so. You guys might have heard it once or twice.

[Brooke]

Okay. Ye. It's where. I mean, it's pretty obvious, right? You want to get back together with your ex and we help facilitate that. This one's going to be a big discussion about cheating. Yeah. And if. If once a cheater, always a cheater, I think is going to be the comment section for sure. But before we start the podcast, Alexis, let's highlight some of the great comments that people are leaving.

[Jose]

I saw one from Keegan Barnett who said that point when you wake up from a tonsillectomy, go to the recovery room and the first thing you ask for is your phone and headphones to listen to your daily Brooke and Jeffrey episode. I think I have problem.

[Brooke]

I think. I think we're better after any sort of anesthesia surgery. Totally. Well, thanks for being with us. And hey, if you got a great comment, please leave it. We love to highlight them, like subscribe and sit back and enjoy.

[Ryan Seacrest]

Yes.

[Jeff]

There's a lot of things that you'd happily say yes to without even thinking about it.

[Brooke]

Ooh, okay.

[Jeff]

Yeah. Like yes to free Costco samples.

[Brooke]

Yes, Duh.

[Jeff]

Yes to concert tickets for. For a band I don't even like.

[Brooke]

God, yes.

[Jeff]

I'd even say yes to a free trip to Mexico with the stipulation I'd have to hide balloons somewhere on my body.

[Listener]

Whoa, wait a minute.

[Brooke]

Can't be that bad, right?

[Jeff]

Nothing's free in this world.

[Listener]

Are you listening to drug mules?

[Jeff]

But it's much harder to say yes to your ex. Oh, yeah, that's what one of our listeners is hoping for today. And all I know is this. After today's call, I will never look at escape rooms in the same way ever again.

[Brooke]

You're not wrong.

[Jeff]

You're going to understand why when you hear it in a brand new say yes to the X right after this, it's Brooke and Jeffrey in the morning. And it's time for another charming edition. Say yes to the X. Oh, my gosh.

[Brooke]

This is what we're doing where we.

[Jeff]

Try to help a listener reconnect with an old fling to see if there's any chemistry or desire lingering there that's hoping to be explored.

[Brooke]

And you know what? It's worked once. This.

[Jeff]

Yep, that's not a high success rate.

[Brooke]

But it's better than before that time.

[Jeff]

It worked. Yes, a success rate is there. And today's caller has actually been on the show with us before. You might remember one of the more disturbing second date calls we did last year involving two people going to a red envelope party, where after midnight, the party turns from nice to super naughty.

[Brooke]

Yes, I do remember red envelope. Why did they end up dating?

[Jeff]

So Natalie was the woman that we called that day. Yeah, she said yes to our offer of a second date, but now she's back. This time for say yes to the Ex. I think not the same guy that we hooked her up with that time on the show. But first, Natalie, we want to welcome you back. Thanks for being on again.

[Natalie]

Thanks for having me.

[Listener]

I thought not saying yes to this relationship that just happened like a month or two ago.

[Natalie]

Oh, you mean Alvin?

[Jeff]

Yeah. What happened with that guy in the red envelope party?

[Natalie]

You're not going to believe this, but he turned out to be kind of a freak.

[Brooke]

No, that is literally the least shocking thing that you could have said.

[Listener]

Freak out, A freak off.

[Jeff]

No way.

[Natalie]

You're right. I probably should have known. But it really sunk in when he started referring to his bedroom as the arena. Like he had an actual neon sign above his bed that says the arena.

[Jeff]

Okay, well, hold on. Now he's starting to sound like he's kind of a good guy. Are you sure that you should have ditched him?

[Brooke]

A neon sign?

[Listener]

Oh, my God. Welcome to the arena dedication.

[Brooke]

Which is worse, that he's single, which means he's bringing new ladies into that place.

[Jeff]

Okay, but apparently this isn't about Alvin and his arena. We're focused on a new old guy. Yeah, tell us about your new old fling.

[Natalie]

Okay, so we dated like three years ago. And we dated for like six to seven months.

[Jeff]

Okay, what's his name?

[Natalie]

His name's Caleb.

[Jeff]

Caleb.

[Brooke]

And what made you start thinking about him again? Is it just by comparison to Alvin? Everybody. He's the only one that seems normal.

[Jose]

No neon signs.

[Natalie]

Yeah, yeah, that's part of it. But this guy was so sweet and I just. I have, like, really good Memories of him. And I was the one who sort of messed it up.

[Listener]

And that is something people say. It's all about timing.

[Brooke]

Can we know how you messed it up? Yeah.

[Natalie]

I mean, I was unfaith. I was unfaithful and I got caught. Yeah.

[Brooke]

Do you say, you know, you.

[Jeff]

You got caught?

[Natalie]

Yeah, and I totally deserved him breaking up with me. But the thing is, I'm. I'm not that person anymore. And I just know he's a solid person that doesn't have neon signs and giant arrows in his bedroom.

[Jeff]

Oh, there's arrows, too?

[Brooke]

Oh, man.

[Jeff]

Yeah. Okay. I like a map to follow. I mean, wait, hold on.

[Brooke]

Us?

[Listener]

Yeah.

[Brooke]

Like, why would he want to take you back? I know that, you know, you're a change person, but why do you deserve a second chance?

[Natalie]

I mean, I've done the work to improve myself and, like, be a better partner for him. And I just know that if you do get him on the phone, I'm sure the questions of trust will definitely come up because that was kind of a big thing.

[Jeff]

I mean, that is a good question. What do you guys think? Can you come back from a cheating scandal?

[Listener]

It depends on the person. I would never.

[Jeff]

But, like, how hot they are.

[Brooke]

You mean, if you're already cheating six months into a relationship, it doesn't feel like you're cheating? You're fully. I mean, I don't think. Yeah, you know, I don't think once a cheater, always a cheater. Just doesn't sound like you were fully into him.

[Jose]

Yeah.

[Brooke]

You know, marriage, you can maybe try.

[Jose]

To work out, but you're just dating. Like, just break up and find someone else.

[Brooke]

Like, it doesn't sound like you were. You're really into the relationship to begin with.

[Natalie]

I mean, I was. I just think that I've changed and I've done a lot of work on myself, and I'm just a better person than I was when we were dating.

[Listener]

Well, that's in general, whether he takes you back or not.

[Brooke]

Right.

[Jeff]

A lot of the grass is greener on the other side type of thinking. But in the last three years since you broke up, have you had any contact with your ex, like, at all?

[Natalie]

I tried. You know, I tried in that first year. I reached out more than a few times, and he made it clear he needed more time and space, and he's gotten that. Now it's been three years.

[Jeff]

So, yeah, if he can't get over cheating in three years, then he's the one that has the problem.

[Brooke]

Oh, man. Do you know. Do you know, is Caleb single right now?

[Natalie]

I don't know, honestly. And I. And I. I, like, I don't expect him to be, like, jumping at the chance to get back with me, but I would like to just grab a coffee and see if we have that same, like, comfortable, fun vibe between us.

[Brooke]

Okay. Okay.

[Jeff]

And invite him back into your arena Possibly. If this goes really well.

[Brooke]

Maybe it's the Coliseum.

[Jose]

What?

[Brooke]

I don't know. He's coming up with a new name.

[Jeff]

It's a bigger arena with people watching.

[Listener]

Madison Square Garden.

[Brooke]

That's right.

[Jeff]

Yeah. So obviously, Natalie, you know how this works. We had our producer reach out to your ex, Caleb, and was able to get him on the phone. He is waiting on hold right now. Just doesn't know who he's about to be talking to.

[Natalie]

Oh, my gosh. Okay.

[Jeff]

Are you ready to talk to your ex from three years ago and see if he's willing to say yes to the ex?

[Natalie]

I think I'm ready. I'm ready.

[Brooke]

I can do this. Is. What if he hangs up?

[Jose]

I mean, it's a tough one.

[Jeff]

It's understandable.

[Brooke]

Yes, that's what I'm saying.

[Listener]

But at least say, oh, yeah, you know why I'm hanging up.

[Brooke]

Yeah. Maybe he's up into it, though. Maybe we're wrong.

[Jeff]

I mean, she claims that she's changed a lot in that time, so we'll find out if that's enough when we come back and put them together for say yes to the Ex right after this.

[Natalie]

Thank you so much.

[Jeff]

Yeah. Hold on. If you're just joining us, we're in the middle of say yes to the Ex with Natalie.

[Brooke]

Spicy one, too.

[Jeff]

She's attempting to reconnect with a guy that she dated three years ago. She told us that they had a fun, casual vibe together, but admits the biggest issue in their relationship was her unfaithfulness.

[Listener]

Yeah, a little bit of an issue.

[Jeff]

A little problem. She was caught, admitted it to the guy, regrets it, and since then has taken accountability for her actions, chose to move on and work on herself and like to know if there's any chance at a second go around with this guy.

[Listener]

Yeah, you make that sound great because most cheaters won't admit it and fall on the sword and be the bigger person. I guess you're right.

[Jeff]

Well, it's because personally, I believe in forgiveness, and in certain situations, maybe this is one of them. I'm hoping that enough time has passed that Caleb could find it in his heart to at least sit down and have a cup of coffee with Her.

[Brooke]

Jeff, you've never. You've never been cheated on, have you?

[Jeff]

I have not been cheated on. And I believe that there is goodness.

[Brooke]

I mean. I mean, I do think that people can grow and change and make different choices, but. Doesn't mean that's not on Caleb, though, you know, that's on her.

[Listener]

You go have fun with your new life.

[Jeff]

It doesn't seem like too much to ask for him to come sit down for coffee, right, Natalie?

[Listener]

You're right about that.

[Jeff]

Natalie, you would agree.

[Natalie]

Yeah, I. That's all I'm asking for. Like, just a coffee.

[Listener]

It doesn't mean he owes you that, but it would be a kind gesture if you could meet in the middle.

[Jeff]

Yeah, but he should pay for the coffee.

[Listener]

No, now you're really.

[Jeff]

Now you're asking for it.

[Brooke]

Last time you talked to him, on a scale of one to, like, super angry being 10, where was he at?

[Natalie]

Oh, I would probably say 10.

[Jeff]

Okay, so she said that she tried texting him, but he was like, I don't want to talk to you. I need more time.

[Brooke]

Yeah, but that's not three years. My 10 sounds a lot more vulgar than that.

[Jeff]

Well, let's see what. What number he's at, because he is. Remember, waiting on hold. Has not heard this segment happen up to this point, does not know the reason that he has been called by a radio station. I don't know. I feel like he might not be a full 10. Let's find out. I'm gonna punch him up. Unless producer Boyd really riled him up before putting him on the phone.

[Listener]

You know, Boyd can really get under your skin sometimes.

[Jeff]

He does that. But here, we're gonna talk to him a little bit, and then we'll tell him that you're there. Okay, Natalie?

[Natalie]

Okay. Thank you.

[Jeff]

Okay, so here we go.

[Listener]

Everyone duck.

[Brooke]

I know.

[Jeff]

Hello? Caleb, you there?

[Listener]

Hello?

[Brooke]

Hey, hey, hey. Welcome to the show, Caleb.

[Listener]

Good morning.

[Caleb]

Hey, good morning. How are you guys?

[Jeff]

Thanks for being on the show with us. I know you don't know the reason why you're here yet. Yeah, yeah.

[Caleb]

It's all mysterious. What's going on?

[Brooke]

Yeah, that's awesome. It could be really fun. The reason.

[Jeff]

Yeah, it could be.

[Caleb]

What is it?

[Jeff]

This is a segment we do. It's called say yes to the X, where somebody from your past who you've dated before, wants to know if there is any shot of a second chance with you. I know. We don't even know, like, what your situation is, if you're single or what you've got going on in Your life right now.

[Brooke]

Yeah.

[Listener]

If you are taken. We're not trying to disrespect.

[Jeff]

Right.

[Caleb]

Yeah.

[Jeff]

Yeah.

[Caleb]

I am single.

[Listener]

Okay, that's a good thing.

[Caleb]

I'm not sure if I want to talk to this person unless I know who it is.

[Brooke]

Yeah, that's a valid request.

[Jeff]

Oh, really? Okay, here we go.

[Brooke]

Drop that bomb.

[Jeff]

Well, normally. Okay, normally, I wouldn't do this. Normally, I just put you on the phone with them. But I can tell you it's somebody you dated for about half a year, and her name is Natalie. Yeah.

[Caleb]

Are you kidding me?

[Jeff]

I'm not.

[Brooke]

No, I was like, are you kidding me?

[Caleb]

No, that's. This isn't gonna be a thing. I don't. I don't want to talk to her.

[Brooke]

Well, maybe. Hey, she did come with a lot of regret for her actions, and you may just want to hear her out.

[Jeff]

Yeah, because I'm assuming you're hesitant because of the whole infidelity thing.

[Caleb]

You're. You're gonna have to make that plural. My guy infidelity.

[Brooke]

Oh, my God.

[Jeff]

Yeah.

[Caleb]

It wasn't Once she cheated with 13 people.

[Brooke]

That is some work.

[Jeff]

But it sounds. You guys only dated for six months.

[Caleb]

Yeah, that's what she told me when the truth came out. When I caught her.

[Listener]

Wait.

[Brooke]

Yeah.

[Jeff]

Oh, my God.

[Natalie]

Hi, Caleb. Caleb. Hi. We don't need to tell them all that.

[Brooke]

Well, how would you now we do.

[Caleb]

You told me 13 different dudes. The landlord, the propane guy, and my brother.

[Natalie]

Okay, no, no, no, no, no, no, no. Your frat brother. That. That's. It's not like you're related.

[Jeff]

No. Wait, what. What brother?

[Natalie]

His frat brother.

[Jeff]

Oh, fraternity bro.

[Brooke]

It doesn't count.

[Jose]

No.

[Jeff]

They're not even real people.

[Listener]

Right, bro? That's right.

[Brooke]

I mean, it counts. It just doesn't count as a bro.

[Caleb]

It was a lot of people, and I knew most of them, so.

[Natalie]

Listen. No, here's the difference. Back then, I was unhappy with myself, and that had nothing to do with.

[Caleb]

You except that we were together and.

[Jeff]

You were cheating on him.

[Natalie]

Hey. Right. But I was honest with you about it. I didn't hide it. I told you what was going on.

[Caleb]

It took a while until I found out with guy number 13.

[Natalie]

She came clean eventually, and that's my karma and something I dealt with, and I'm over it now. I'm so much better. Oh, sorry.

[Caleb]

I'm not over it.

[Listener]

Yeah.

[Brooke]

Natalie, did you really think. Like, you didn't tell us? I had just assumed that it was.

[Natalie]

One time, you know, I said that I Was unfaithful. You didn't ask for like a specific number.

[Brooke]

I feel like we just caught her cheating.

[Jeff]

Well, it's fair. We need to be better at asking questions when we're doing these segments. Let's keep that in mind.

[Brooke]

Did you cheat in any relationships after him?

[Jeff]

Well, that doesn't matter about that.

[Brooke]

It does, because she says she's grown.

[Jeff]

And changed, but we're not worried about her other relationships. We're worried about this relationship with Caleb. Caleb. She's done the work. She's moved past it. Are you ready to move past it yet?

[Listener]

That was well done. But wild question.

[Brooke]

Yeah.

[Caleb]

Like, yeah, here's the deal. It's like I still live in the same building and I still have the same landlord who occasionally looks at me.

[Jeff]

In that weird way.

[Brooke]

Pretty messed up that you didn't get a rent discount.

[Caleb]

It's not just the landlord. I mean, she slept with the freaking escape room instructor.

[Brooke]

What?

[Natalie]

Okay, okay, that was not my fault.

[Brooke]

I need to hear this.

[Natalie]

It just kind of happened. We were locked in separate rooms. He was a team leader. You do what the team leader says.

[Jeff]

Oh, my God.

[Caleb]

You are insane.

[Jeff]

Natalie, we have to get out of this room. Everyone take their pants off.

[Listener]

Yeah.

[Brooke]

Is there an escape room employee that isn't a 20 year old D and D guy?

[Caleb]

Okay, you guys can see why we're not together now, right?

[Listener]

Yeah.

[Brooke]

She slept with a guy in the middle of your date.

[Jose]

Of course together.

[Listener]

So I don't want to say anything, but I think her and Jeff were fooling around a little when she was on hold.

[Brooke]

Yeah.

[Jeff]

By the way, team leader, you have to listen to the team.

[Natalie]

So don't appreciate that you guys are not helping.

[Brooke]

Why would you ever think that he would move past this? Like, why would you ask this question? You just need to move on and give up.

[Jeff]

Brooke, what you're forgetting is this is all past stuff.

[Brooke]

That's great.

[Jeff]

We're talking three years ago. And I would hope that, Caleb, you could find it somewhere in your heart to say yes, because this girl deserves a 14th chance.

[Brooke]

As of today, she hasn't cheated on you. Know what the saying is? Fool me once, shame on you. Fool me 14 times, shame on the landlord.

[Natalie]

Okay, you guys are making such a big deal about the number of people and the truth is like, I've changed and I just want a cup of coffee.

[Brooke]

Okay, Okay, I think that's fine. But just maybe do it with a.

[Jose]

New guy or sleep with the barista. Then you get free coffee.

[Jeff]

That's before we even do that we need to ask. The whole purpose of this segment is Caleb, we. She wants it, Brooke. She's begging us for the coffee with Caleb.

[Brooke]

So Caleb, just like that team leader in that escape room, Caleb, would you.

[Jeff]

Be willing to say yes to the ex and meet up with Natalie for coffee?

[Caleb]

You know what? I think I actually have a thing or two of yours still at this apartment. So yeah, I can mew up the coffee, but just so you know, there is zero chance of me ever trusting you again or being in any kind of relationships.

[Brooke]

Okay, so you're gonna hook up over coffee as well? Yeah.

[Jeff]

I hear there's a coffee themed escape room that they just started downtown.

[Natalie]

I am Julia, new woman. So you'll see the new me. It's gonna be great.

[Listener]

Well, go let yourself shine. Let him see this new woman.

[Brooke]

And we're proud of you for that. Yeah, we really are.

[Jeff]

Just go to Co Coffee, bring your landlord and let's squash old qualms. You know What? Bring all 13 of those other guys back and we'll hash this out.

[Listener]

What is this? The Bachelor?

[Ryan Seacrest]

I don't.

[Brooke]

Brooke and Jeffrey in the morning.

[Ryan Seacrest]

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[Jenny Garth]

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[Ryan Seacrest]

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[Jeff]

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[Advertiser]

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[Alexis]

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