Second Date Update: Burned By Beauties

Summary

Podcast Summary: Brooke and Jeffrey, Second Date Update - "Burned By Beauties"

Date: October 3, 2025
Podcast: Brooke and Jeffrey: Second Date Update
Host: Brooke and Jeffrey in the Morning (iHeartPodcasts)

---

Episode Overview

In this episode, the team helps Riley, a listener who hasn’t heard back from Dana after their promising first date. The segment playfully examines how past romantic disappointments, especially involving "beautiful people," can interfere with current relationships and lead to some truly awkward behavior. Brooke, Jeffrey, Jose, and several callers spotlight how baggage, trust issues, and even accidental matchmaking can derail romantic prospects—with plenty of humor, snark, and surprises.

---

Key Discussion Points & Insights

1. Meet-Cute at the Masked Art Event

• [04:31] Riley met Dana at an animal mask-themed art installation.
  • Riley: "The event we met at was an art installation, and the theme was animal mask."
  • Dana wore a flamingo mask with a matching dress; Riley had a crocodile mask, leading to playful banter ("I'm her natural predator").
• Both describe immediate chemistry, matching energies, and flirting.

2. First "Unmasked" Moments and a Rooftop Date

• [06:32] They saw each other's faces at the end of the event, with mutual relief ("We were both, oh, okay. I didn’t waste my time.").
• [06:48] Riley set up a second date—a rooftop evening—three or four days later.
• [07:03] Riley admits the date felt more "business-y" than romantic due to his skepticism of attractive women:
  • "I am skeptical of beautiful women. And this woman is beautiful. She is so stunning."
• He shares a backstory about being burned by a "klepto" ex who stole his laptop, shaping his current mistrust.

3. Riley’s Trust Issues Surface

• Riley confesses to interrogating Dana during the date ("my approach to the date was more like business-y and questiony"), fearing beautiful women can’t be both nice and honest.
• He worries he wasn’t "flirty enough" and ended things with just a small kiss, but still sensed positivity.
  • "I really feel like I wasn’t like flirty enough. I wasn’t cutesy, lovey-dovey." — Riley (08:29)

4. Why Dana Ghosted Riley—The Real Reveal

• Riley has tried to arrange another date, but Dana keeps making excuses.
• [13:17] Dana shares her side: after the date, she learned Riley "snooped around" her Instagram and went a big step further.
• [13:44] "He reached out to my ex and DM’d him." — Dana
  • Riley had contacted Dana’s ex on Instagram to ask if she was "trustworthy."
  • This behavior shocked Dana, who felt it was a major red flag and made her question Riley’s own trustworthiness.
  • "I feel like that's a red flag." — Dana (14:20)

5. The Confrontation, Riley’s Explanation, and More Surprises

• Riley claims he just wanted to protect himself from getting hurt again, so he solicited "references."
  • "I've been burned before, multiple times. And…it just so happens that these women…happen to be outrageously beautiful." — Riley (15:54)
• He reveals the unexpected: He and Dana’s ex "linked up, had a brew, had a conversation," and developed a budding friendship.
  • "We actually…had a really good him. And I'm kind. I…like, I heard a lot about you. I heard about your first kiss." — Riley (17:30)
  • "We're actually…we have plans tomorrow. We got basketball lined up, maybe a little train after." — Riley (17:57)

6. The Fallout and a Twist Ending

• Dana is taken aback and disturbed: "Y’all could just be friends at this point." — Dana (17:57)
• Riley seems more enthusiastic about his new “friend” than about a romance with Dana, even encouraging her to give her ex another shot:
  • "If it doesn't work out with us, I would still think you should probably give your ex another shot." — Riley (18:44)
• Dana, slightly amused but weirded out, admits she’s now considering reconnecting with her ex because “he never did anything like Riley did.”
  • "I'm thinking about deactivating my Instagram. Like, I'm just scared he's gonna reach out to somebody else and do an interview with them." — Dana (18:36)
• Riley transitions into accidental matchmaker—fine with the result, perhaps preferring his bromance with her ex!

---

Notable Quotes & Memorable Moments

• On Trust Issues:

  • "I am skeptical of beautiful women. And this woman is beautiful." — Riley (07:03)
  • "You don't typically ask for—like, at a job application you’d ask for references, but not necessarily in a dating situation." — Brooke (14:26)

• On Crossing the Line:

  • "He reached out to my ex and DM’d him." — Dana (13:44)

• On New Friendships:

  • "We linked up, had a brew, had a conversation kind of about life." — Riley (17:19)
  • "You're trying to get him back together?" — Legends.com Host (17:47)

• On Accidental Matchmaking:

  • "Would you consider going back out with your ex? … as a favor to Riley." — Legends.com Host (19:16)
  • "I don't think it was an accident. I think maybe I wanted this the whole time. I'm fine with that." — Riley (19:49)

---

Timeline of Important Segments

• [04:31] - [06:22]: Riley and Dana’s initial masked art event and playful flirting.
• [06:48] - [08:47]: The rooftop first date, Riley’s skepticism and (mis)approach.
• [13:17] - [14:33]: Dana details how Riley contacted her ex, why it felt like a violation.
• [15:10] - [18:10]: Riley justifies his actions and describes befriending Dana’s ex—surprising everyone.
• [18:36] - [19:49]: Dana warms to the idea of reconnecting with her ex; Riley passes the romantic baton.

---

Tone & Style Highlights

• Humorous and self-aware: The hosts joke throughout ("I’m definitely paperback"—Brooke [11:17]), gently roast Riley’s trust issues, and riff on the drama of dating.
• Playful but pointed: While the segment lampoons Riley’s paranoia about "pretty people," it also exposes toxic insecurities and how they impact genuine connection.
• Banter and empathy: The hosts encourage honesty but call out cringe moments, helping both Riley and Dana articulate their boundaries—and their bewilderment!

---

Episode Takeaways

• Trust issues from prior heartbreak can sabotage potentially good connections.
• Overstepping with "background checks" on dates is invasive and a surefire way to kill romantic interest.
• Occasionally, a second date disaster becomes a bromantic meet-cute instead—leaving the original couple single, but with a new (and weirdly supportive) friend dynamic.
• Sometimes, the funniest stories come from dating fails—and may even spark reunions no one anticipated.

---

For all Second Date Update episodes, search for "Brooke and Jeffrey" on Spotify, Apple, or wherever you find podcasts.

Transcript

[Mori Hair Care Announcer]

A life that's carefree needs hair that's worry free. Have both with Mori reduce shedding and thinning in as little as 12 weeks with clinically proven all natural Mori nourishing hair care products. Others containing sulfates, parabens and GMOs can actually weaken your hair over time. You can look great for holiday photos. Still not sure we get it. So right now purchase Mori at 50% off while it lasts and take a quiz for a custom hair care recommendation at M O e r I e.com results can vary. Mori is not a substitute for medical advice. See website for more.

[Legends.com Advertiser]

You need to check out legends.com today. Legends is a free to play social casino and sportsbook with all of the games that you know and love. They even have Plinko and live Blackjack and that's L E G e n d z.com whether you're a seasoned player or just starting out, their games are designed to entertain and thrill. The best part is you get free coins every day so you can play for free and redemption to your bank account is instant. It's legit and new players get an exclusive welcome bonus. Join thousands of players on Legends with a Z. No purchase necessary. Legends International Void we're prohibited by law. 18 plus terms and conditions apply.

[Jose from Brooke and Jeffrey in the Morning]

Hey Prime Big Deal Days is coming up soon. October 7th and 8th. Hey what's up? It's Jose from Brick and Jeffrey in the Morning and there are going to be some crazy big deals like up to 40% off. So it's the perfect chance to treat yourself. Now. I love a nice steak. Maybe during Prime Big Deal Days I could pick up some high end steak knives. Ooh, you can do the same thing. Find just the thing to treat yourself. Get ready. Prime Big Deal Days are coming soon. October 7th and 8th hey what's up?

[Mario Lopez]

It's Mario Lopez. Back to school is an exciting time, but it can also be overwhelming and kids may feel isolated, a vulnerability that human traffickers can exploit. Human trafficking doesn't always look like what you expect. Everyday moments can become opportunities for someone with bad intentions, whether you're a parent, teacher, coach or neighbor. Check in, ask questions, stay connected. Blue Campaign is a national awareness initiative that provides resources to help recognize suspected instances of human trafficking. Learn the signs and how to [e-mail] blue campaign.

[Josh Clark from Stuff You Should Know]

Hi there, this is Josh Clark from the Stuff youf Should Know podcast. If you've been thinking, man alive, I could go for some good true crime podcast episodes, then have we got good news for you. Stuff youf should know just released a playlist of 12 of our best true crime episodes of all time. There's a shootout in broad daylight, people using axes in really terrible ways. Disappearances, legendary heists, the whole nine yards. So check out the Stuff youf Should Know True Crime Playlist on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

[Brooke from Brooke and Jeffrey in the Morning]

Hey, it's a brand new episode of your second day podcast. Thanks for being here. It's Brooke and Jeffrey in the morning, and I feel like today's is really a lesson on how your past relationships can affect your current relationships. Yeah, in a pretty hysterical way here, but yeah, yeah, not always in the most healthy way, but you're gonna hear that in just first, we love to see your comments come in. Thank you so much for taking the time to leave them.

[Jeffrey from Brooke and Jeffrey in the Morning]

Yes, one person said. Hey, guys. Longtime listener. Listening to this show made me think of a drinking game. Every time Brooke snorts take a drink. Her snort is adorable. I would suggest Jose laughing, but then we wouldn't get through the full thing.

[Brooke from Brooke and Jeffrey in the Morning]

That's really funny.

[Jose from Brooke and Jeffrey in the Morning]

Yeah, it is a pretty good. You'll get at least like three to 10 shots throughout each show.

[Brooke from Brooke and Jeffrey in the Morning]

And do you know what's weird? I think it's genetic. My daughter does it. Oh, I don't know why. Yeah, I skipped my son, but my daughter does the same thing and I.

[Jose from Brooke and Jeffrey in the Morning]

We know which one's going to get bullied.

[Brooke from Brooke and Jeffrey in the Morning]

Yeah. Every time I'm like, oh, I'm sorry, honey. I'm really sorry.

[Jose from Brooke and Jeffrey in the Morning]

It's a true testament. You cannot control your laugh.

[Brooke from Brooke and Jeffrey in the Morning]

That is so true.

[Jeffrey from Brooke and Jeffrey in the Morning]

I don't know if there's a lot of snorts today, but get a drink ready in case anybody.

[Brooke from Brooke and Jeffrey in the Morning]

Here we go. Drink up. Your new episode starts right now.

[Legends.com Advertiser]

Second date update. When you've been single for a bit and your friends are telling you you need to get back out there and start dating again.

[Brooke from Brooke and Jeffrey in the Morning]

Y.

[Legends.com Advertiser]

If you're a little shy about it, maybe the best thing you could do is pop on a mask and leave the house with your head held high.

[Jose from Brooke and Jeffrey in the Morning]

A mask?

[Brooke from Brooke and Jeffrey in the Morning]

What kind of mask? Like, like a Pandemic era mask or like a full.

[Legends.com Advertiser]

Brooks certainly is interested in getting herself back out there and wanting to know exactly which type of mask to wear. Maybe that's a question we should ask to our listener, Riley, because that's what he did. And apparently it led him to a little love connection. So, Riley, welcome to the show.

[Riley (Caller)]

Hey, guys, thanks for having me.

[Brooke from Brooke and Jeffrey in the Morning]

Okay, your voice isn't muffled. That means you must be mask free right now.

[Riley (Caller)]

I'm sans mask at the moment. Yeah.

[Brooke from Brooke and Jeffrey in the Morning]

Okay.

[Legends.com Advertiser]

Okay.

[Brooke from Brooke and Jeffrey in the Morning]

All right.

[Legends.com Advertiser]

Now, Brooke wants to know what type of mask you wore, but I'm more curious about the girl that we're going to be calling here first. What's her name?

[Riley (Caller)]

So I met Dana while I was wearing an animal mask.

[Brooke from Brooke and Jeffrey in the Morning]

Why were you. Why were you wearing an animal mask? Y.

[Riley (Caller)]

So the event we met at was an art installation, and the theme was animal mask.

[Brooke from Brooke and Jeffrey in the Morning]

Oh, this makes sense.

[Legends.com Advertiser]

Everybody at the art installation was required to wear a mask in order to be there.

[Riley (Caller)]

Yeah, I think encouraged is more the term. There were a few people without masks.

[Brooke from Brooke and Jeffrey in the Morning]

Okay. Okay. So you're into art. Like, it was an art event that you were at?

[Riley (Caller)]

Very much so, yeah.

[Brooke from Brooke and Jeffrey in the Morning]

Cool. That's cool. And it sounds like she probably was too. Was she masked?

[Riley (Caller)]

Yeah, yeah. Her dress was beautiful, and it matched her flamingo mask.

[Legends.com Advertiser]

Okay.

[Riley (Caller)]

What were you.

[Jose from Brooke and Jeffrey in the Morning]

What animal were you.

[Brooke from Brooke and Jeffrey in the Morning]

Wait, we don't want to know if she was standing on one leg.

[Jose from Brooke and Jeffrey in the Morning]

No, sorry to move on.

[Legends.com Advertiser]

How in character was she?

[Brooke from Brooke and Jeffrey in the Morning]

I'm kidding.

[Riley (Caller)]

Well, she was hopping around on a leg for a little bit because we. We had our little inside joke, and the inside joke was because I had a crocodile mask on. Oh, I'm her natural predator.

[Brooke from Brooke and Jeffrey in the Morning]

I'm gonna get, like, Alexis's dream interaction. I'm joking.

[Legends.com Advertiser]

Okay.

[Jose from Brooke and Jeffrey in the Morning]

I was like, what?

[Jeffrey from Brooke and Jeffrey in the Morning]

I like animals.

[Brooke from Brooke and Jeffrey in the Morning]

Okay.

[Legends.com Advertiser]

Yeah, yeah. Animals attacking each other inside of an art gallery. That's really cute and romantic.

[Brooke from Brooke and Jeffrey in the Morning]

I mean, obviously it's flirting, right? Like, you guys are flirting with each other.

[Riley (Caller)]

Oh, yeah, very much. I mean, we really hit it off. The masks kind of did it, but sort of our energies matched, and I think our sense of humor matched too.

[Brooke from Brooke and Jeffrey in the Morning]

Okay.

[Jeffrey from Brooke and Jeffrey in the Morning]

You can't tell someone's cute with a mask on. Like, remember in Covid when people would wear them, and then as soon as they take them off, you're like, oh, you're a different person.

[Jose from Brooke and Jeffrey in the Morning]

Yeah.

[Brooke from Brooke and Jeffrey in the Morning]

When did you guys see each other's faces?

[Riley (Caller)]

We did at the end of the night. It was both, like, release. You know, we were both. Oh, okay.

[Jeffrey from Brooke and Jeffrey in the Morning]

Okay.

[Legends.com Advertiser]

I didn't waste my time. Okay.

[Brooke from Brooke and Jeffrey in the Morning]

All right.

[Jose from Brooke and Jeffrey in the Morning]

So there would have been awkward, too.

[Legends.com Advertiser]

To be like, oh, so this is just the first meetup. Was there a date after this?

[Riley (Caller)]

So I did ask her out, and, yes, we did go out. It was like three or four days later. We did a little rooftop scenario.

[Jose from Brooke and Jeffrey in the Morning]

Oh, the rooftop bar or something.

[Brooke from Brooke and Jeffrey in the Morning]

What was the vibe like then? Because you guys were so playful and everything the first time you met, the.

[Riley (Caller)]

Date was normal, and I stand by that. But here's my thing. I am skeptical of beautiful women. And this woman is beautiful. She is so stunning.

[Brooke from Brooke and Jeffrey in the Morning]

Why are you skeptical of beautiful women?

[Riley (Caller)]

Well, I dated a couple of beautiful women. One was a damn klepto. Friggin liar. Klepto. She stole my, my laptop.

[Brooke from Brooke and Jeffrey in the Morning]

I don't know that that speaks to all beautiful women. It speaks to her or your taste in woman.

[Legends.com Advertiser]

Why would you trigger him with a question like this? Look what you've done to this phone call.

[Brooke from Brooke and Jeffrey in the Morning]

So was she different than all the other stereotypes that you have in your head about pretty people?

[Riley (Caller)]

Well, I think I gave her the benefit of the doubt. But here's the thing though. I feel like my skepticism kind of bit me in the butt because my approach to the date was more like business y and questiony. Like, well, what do you do? What are your favorite things? And this and that.

[Brooke from Brooke and Jeffrey in the Morning]

Unless like you were basically trying to interrogate her and find out what's wrong with you. Yeah, you can't be beautiful and nice.

[Legends.com Advertiser]

Did you ever hold like your, your hand out with your watch on it and like see if maybe she would try, try and swipe it off of.

[Jeffrey from Brooke and Jeffrey in the Morning]

You, leave your wallet on the table and go to the bathroom?

[Jose from Brooke and Jeffrey in the Morning]

Ooh, a tester.

[Legends.com Advertiser]

Yeah, that didn't happen.

[Riley (Caller)]

No, she didn't steal the watch.

[Legends.com Advertiser]

Okay, well, she passed the klepto test.

[Jeffrey from Brooke and Jeffrey in the Morning]

Dang, that's big.

[Riley (Caller)]

Yeah, but really I do. I'm honestly like, I'm running this situation over my brain many times. I really feel like I wasn't like flirty enough. I wasn't cutesy, lovey dovey.

[Legends.com Advertiser]

Okay, well, you're admitting maybe it didn't go perfectly, but how did the date end?

[Riley (Caller)]

It did end well. We had a little kiss.

[Brooke from Brooke and Jeffrey in the Morning]

Oh, cute. That's great.

[Legends.com Advertiser]

Like a Hershey's kiss.

[Riley (Caller)]

It was a little peck, you know, like it wasn't anything outrageous. But then after that, I've asked her out a couple of times and she did at first seem keen on it, which I've also heard before. Which goes back to why I don't trust these pretty people. Because it's like there are other options on the other side.

[Jeffrey from Brooke and Jeffrey in the Morning]

Of course, I think everybody can have.

[Dana (Caller)]

A lot of options.

[Riley (Caller)]

You're right, anybody can. But let's be real, pretty people have more.

[Jose from Brooke and Jeffrey in the Morning]

Absolutely.

[Brooke from Brooke and Jeffrey in the Morning]

You feel very triggered by pretty people. It feels like.

[Riley (Caller)]

Well, you're not wrong.

[Brooke from Brooke and Jeffrey in the Morning]

Okay, so are you going to be able to be calm if we get her on the phone and she doesn't want to go out with you again? Or are you going To.

[Riley (Caller)]

Honestly, I think she already doesn't want to go out with me. She keeps kind of making up things to not go out on a second date. So if I had the opportunity to just to find out what it is instead of being iced out, like, I think that would go a long way. Not only between her and I, but, like, me moving forward.

[Brooke from Brooke and Jeffrey in the Morning]

Yeah. Pretty people in general.

[Legends.com Advertiser]

Well, you know, let's give him a little bit of credit for putting himself out of his comfort zone and being willing to date a beautiful person. That's. That's a big. That's a big move.

[Brooke from Brooke and Jeffrey in the Morning]

Must be hard, you know?

[Legends.com Advertiser]

And so we're going to try to reward that by doing our best with their second date update. When we come back, call Dana and try to get you some answers right after this second date update. Ugh. Beautiful people, right? We just can't be trusted. I mean, yeah, sure, we look nice on the outside, but inside, well, yeah, we're still beautiful.

[Jose from Brooke and Jeffrey in the Morning]

Yeah, it's pretty nice in there.

[Legends.com Advertiser]

It's genetic. Yeah. But some of us, a very small percentage, I'm sure sometimes will do bad stuff just because we can.

[Jose from Brooke and Jeffrey in the Morning]

No.

[Legends.com Advertiser]

And ugly people. Let us say that.

[Riley (Caller)]

So.

[Legends.com Advertiser]

And it sounds like our listener Riley has been burned by a bombshell before, and he's currently getting burned again by another beautiful woman who's not calling him back for a date.

[Riley (Caller)]

Yep.

[Jose from Brooke and Jeffrey in the Morning]

It happens when you go for the bombshell, brother.

[Riley (Caller)]

More than one.

[Brooke from Brooke and Jeffrey in the Morning]

Hype him up into this mindset. This is the mindset he needs to get out of.

[Riley (Caller)]

But he's not wrong.

[Legends.com Advertiser]

Yeah, exactly. Not wrong. That's why we're going to call and look this beauty right in the face and say, what gives?

[Brooke from Brooke and Jeffrey in the Morning]

Okay, wait, I thought it was like, don't judge a book by its cover. I mean, that's true for beautiful people. For ugly people, it doesn't matter. Matter.

[Legends.com Advertiser]

Brooke, you can't afford this book cover.

[Brooke from Brooke and Jeffrey in the Morning]

I'm definitely paperback.

[Legends.com Advertiser]

Riley, we're about to call Dana here. You feeling ready?

[Riley (Caller)]

As ready as I'm ever going to be. Thank you.

[Brooke from Brooke and Jeffrey in the Morning]

Okay, take deep breaths through this, okay?

[Legends.com Advertiser]

We're going to try and get you this bombshell back.

[Jose from Brooke and Jeffrey in the Morning]

Yeah.

[Brooke from Brooke and Jeffrey in the Morning]

Whether he wants or not, I can't quite say.

[Jeffrey from Brooke and Jeffrey in the Morning]

He hates him, but he loves him.

[Legends.com Advertiser]

Yeah, Everybody wants him. So here we go, my life. Let's dial this number.

[Dana (Caller)]

Hello?

[Legends.com Advertiser]

Hello? Is this Dana?

[Dana (Caller)]

Yes, it is. Who is this?

[Brooke from Brooke and Jeffrey in the Morning]

She does have a nice voice.

[Legends.com Advertiser]

I really. Yeah, you have a very nice, sultry voice, Dana.

[Jose from Brooke and Jeffrey in the Morning]

My name's Jose.

[Brooke from Brooke and Jeffrey in the Morning]

What? Don't mock her. She doesn't even know who we are.

[Legends.com Advertiser]

Sultry, you're probably noticing a lot of people on the phone right now. It's because you're on a radio show called Brooke and Jeffrey in the Morning.

[Jose from Brooke and Jeffrey in the Morning]

Hi. Good morning.

[Riley (Caller)]

Hello.

[Brooke from Brooke and Jeffrey in the Morning]

Hi.

[Legends.com Advertiser]

Hey.

[Dana (Caller)]

Did I win something or. What's going on?

[Legends.com Advertiser]

Besides the genetic lottery, maybe?

[Jeffrey from Brooke and Jeffrey in the Morning]

We heard you're beautiful.

[Brooke from Brooke and Jeffrey in the Morning]

That's what. That's what Jeff said is saying.

[Legends.com Advertiser]

The reason that we're calling is because one of our listeners gave us your number, asked us to reach out on his behalf. A guy named Riley that you went out with.

[Dana (Caller)]

Wow.

[Legends.com Advertiser]

Yeah. And we do this because it's part of a segment called A Second Date Update where we attempt to help out our listeners. If they're not getting a call back after a solid first date, we try to figure out the reason why. Okay, so Riley says, according to him, he's been trying to get a hold of you and he's not having any luck, so he feels like something must be up.

[Dana (Caller)]

Yeah. So. Okay. Sorry, you're just catching me off guard.

[Brooke from Brooke and Jeffrey in the Morning]

That's okay. You guys had quite the connection before your guys date started.

[Dana (Caller)]

Yeah, I mean, he was cool, but after our date, I found out that he snooped around my Instagram and found pictures of me and my ex.

[Riley (Caller)]

Huh.

[Dana (Caller)]

Yeah.

[Brooke from Brooke and Jeffrey in the Morning]

Okay, so. Well, hold on.

[Legends.com Advertiser]

You can't blame him for looking at your Instagram.

[Jeffrey from Brooke and Jeffrey in the Morning]

How do you know he did that is the problem.

[Legends.com Advertiser]

That is a good question actually. Yeah. How do you know?

[Brooke from Brooke and Jeffrey in the Morning]

Maybe he accidentally hit that like. Oh, God, that's terrible, isn't it?

[Dana (Caller)]

No, actually it's worse. He reached out to my ex and DM'd him.

[Jose from Brooke and Jeffrey in the Morning]

Oh.

[Brooke from Brooke and Jeffrey in the Morning]

Oh, no.

[Legends.com Advertiser]

Okay, that's. That's a step farther than.

[Jose from Brooke and Jeffrey in the Morning]

That's pretty cringe.

[Brooke from Brooke and Jeffrey in the Morning]

What did he. What did he say to your ex in a dm?

[Dana (Caller)]

Well, this is how I found out. My ex reached out to me and told me that apparently Riley was asking him if I was trustworthy and asking him for advice.

[Legends.com Advertiser]

Sorry, if you were what? Worthy?

[Brooke from Brooke and Jeffrey in the Morning]

Trustworthy.

[Riley (Caller)]

Trustworthy.

[Dana (Caller)]

Yeah.

[Legends.com Advertiser]

How does that make you feel, knowing that he reached out to your ex?

[Dana (Caller)]

Well, you know, I feel like he's not trustworthy because I feel like that's a red flag.

[Jose from Brooke and Jeffrey in the Morning]

It is a lot. Yeah.

[Brooke from Brooke and Jeffrey in the Morning]

You know, you don't typically ask for like at a job application you'd ask for references, but not necessarily a dating situation.

[Jose from Brooke and Jeffrey in the Morning]

And this is one date. It's like if they've been dating for maybe. Yeah, he's like, all right, I'm going to ask. Screaming my girlfriend. Still, it seems weird.

[Brooke from Brooke and Jeffrey in the Morning]

Yeah, that's a lot he didn't tell us that.

[Legends.com Advertiser]

Yeah, we did not know that.

[Brooke from Brooke and Jeffrey in the Morning]

And I bet he doesn't even know that you know that.

[Dana (Caller)]

I don't know what he knows. I mean, he's, you know, he knows a lot.

[Legends.com Advertiser]

We can find out exactly how much he knows because Riley is on the other line of this phone call, listening and waiting to talk to you.

[Dana (Caller)]

Oh, wow.

[Brooke from Brooke and Jeffrey in the Morning]

Oh, wow.

[Legends.com Advertiser]

She said so. Unlike him.

[Jose from Brooke and Jeffrey in the Morning]

It's romantic.

[Legends.com Advertiser]

He's got a lot of surprises up his sleeve. Riley, are you there?

[Riley (Caller)]

I'm here. Yep.

[Brooke from Brooke and Jeffrey in the Morning]

Oh, Riley, what are you doing for X Dog? Why does that tell us that?

[Riley (Caller)]

Well, at least the good news is you passed the test.

[Jeffrey from Brooke and Jeffrey in the Morning]

No, that's not the new test.

[Brooke from Brooke and Jeffrey in the Morning]

Nobody wants a test while they're dating.

[Riley (Caller)]

He wasn't supposed to find out. He promised he wouldn't say anything.

[Brooke from Brooke and Jeffrey in the Morning]

He must have been a pretty person. Can't trust them, right?

[Riley (Caller)]

Well, he sure wasn't ugly.

[Brooke from Brooke and Jeffrey in the Morning]

Okay, okay. Oh, his allegiance is obviously going to be to her, not to you, random.

[Jeffrey from Brooke and Jeffrey in the Morning]

Guy from the Internet dming him about a girl.

[Legends.com Advertiser]

Well, you know what? We really need to just step back so that you and Riley can talk this out, because this is something between the two of you. So go ahead.

[Riley (Caller)]

Okay, so here's the deal. I've been burned before, multiple times. And it just so happens that these women, also like yourself, happen to be outrageously beautiful. Now, I'm not saying that you're going to do those things, but I've been burned, and I'm just trying to make sure that I don't get burned again. And I was looking to get some background from your ex, who, by the way, seems like a pretty cool dude. Oh.

[Legends.com Advertiser]

Oh, you approve?

[Dana (Caller)]

It's just weird because we went on one day and then you reached out to him behind my back and it's like, why don't you get to know my friends and ask them some questions? Yeah.

[Jose from Brooke and Jeffrey in the Morning]

Yeah.

[Riley (Caller)]

All right, hear me out. I reached out to him, obviously for a specific reason. And if he had said anything that was like really bad, or if he was just a kind of a crazy ex, I wouldn't have one taken the information into professed it to the world on the radio station. Right.

[Jose from Brooke and Jeffrey in the Morning]

That's honest.

[Legends.com Advertiser]

It was a positive review of you, Dana, so.

[Dana (Caller)]

Yeah, but you shouldn't have done that.

[Riley (Caller)]

Yeah, but I think I should have. And also, I think I've kind of made a new friend in the meantime. Like he's a cool dude.

[Dana (Caller)]

That's insane.

[Legends.com Advertiser]

Friend is a really strong word there, Riley. You've had one conversation with him it.

[Riley (Caller)]

Might have been maybe more than that.

[Brooke from Brooke and Jeffrey in the Morning]

What do you mean?

[Legends.com Advertiser]

What?

[Jose from Brooke and Jeffrey in the Morning]

What?

[Riley (Caller)]

Well, we linked up, had a brew, had a conversation kind of about life.

[Brooke from Brooke and Jeffrey in the Morning]

Had a beer with her ex.

[Riley (Caller)]

Whoa.

[Dana (Caller)]

You did not meet with him. Come on, like, you're joking.

[Riley (Caller)]

No, I did. We actually, like, had a really good him. And I'm kind. I. Like, I heard a lot about you. I heard about your first kiss.

[Jose from Brooke and Jeffrey in the Morning]

Oh, my God.

[Dana (Caller)]

Oh, wow.

[Riley (Caller)]

I honestly can't believe you broke up with the guy. Like, he really seems like a genuine sweetheart.

[Dana (Caller)]

Yeah.

[Legends.com Advertiser]

You trying to get him back together?

[Riley (Caller)]

I honestly do like him. We're actually. We have plans tomorrow. We got basketball lined up, maybe a little train after.

[Dana (Caller)]

Y' all could just be friends at this point.

[Jose from Brooke and Jeffrey in the Morning]

Sounds like they are.

[Brooke from Brooke and Jeffrey in the Morning]

I don't know. We need more male friendship in this world.

[Dana (Caller)]

Yeah, but I just met the guy, and then he was, like, hanging out with my ex. Like, that's weird. Isn't it weird?

[Legends.com Advertiser]

Yeah.

[Jose from Brooke and Jeffrey in the Morning]

This did get worse.

[Riley (Caller)]

Guys, it's. It's actually not weird. Now I know a lot about her, and I'm actually just like your ex. Like, I really do think we'd be a good match.

[Brooke from Brooke and Jeffrey in the Morning]

Oh, the ex didn't work out for a reason.

[Legends.com Advertiser]

Yeah, well, it sounds like Riley ships the relationship. Dana's. Exactly. Even ships it. All we need is the final sign off from Dana to go out with Riley one more time and make this thing final.

[Dana (Caller)]

No. And I'm thinking about deactivating my Instagram. Like, I'm just scared he's gonna reach out to somebody else and do an interview with them.

[Brooke from Brooke and Jeffrey in the Morning]

Yeah.

[Riley (Caller)]

I gotta say, Dana, I've been single for a while, and, you know, if it doesn't work out with us, I would still think you should probably give your ex another shot. Wow.

[Jose from Brooke and Jeffrey in the Morning]

Are you waiting for him?

[Jeffrey from Brooke and Jeffrey in the Morning]

What a good friend.

[Dana (Caller)]

You know, Riley, what you should do is hang up this phone and we should never talk again.

[Legends.com Advertiser]

All right, she's not interested in Riley. But, Dana, I'm only gonna offer this once. Would you consider going back out with your ex? No. As a favor to Riley.

[Brooke from Brooke and Jeffrey in the Morning]

That's a different segment. We do.

[Legends.com Advertiser]

And we would pay for that. Everybody wants it to happen. Even Riley wants it.

[Riley (Caller)]

No, don't be foolish, Dana. He's a good guy.

[Legends.com Advertiser]

Okay, this is unprecedented on the.

[Dana (Caller)]

Well, maybe that's a good idea, because he never did anything like Riley did.

[Legends.com Advertiser]

So you're comparing them now?

[Dana (Caller)]

I'm open to it.

[Jose from Brooke and Jeffrey in the Morning]

Oh, my gosh.

[Dana (Caller)]

Yes.

[Riley (Caller)]

Now we're getting somewhere.

[Dana (Caller)]

Oh, my gosh.

[Legends.com Advertiser]

Riley, how do you feel about accidentally playing matchmaker?

[Dana (Caller)]

Yeah.

[Riley (Caller)]

You know, I don't think it was an accident. I think maybe I wanted this the whole time. I'm fine with that.

[Legends.com Advertiser]

Okay.

[Brooke from Brooke and Jeffrey in the Morning]

Does love your exact Brooke and Jeffrey in the morning.

[Jose from Brooke and Jeffrey in the Morning]

Hey, what's up?

[Mario Lopez]

It's Mario Lopez. Back to school is an exciting time, but it can also be overwhelming and kids may feel isolated. A vulnerability that human traffickers can exploit. Human trafficking doesn't always look like what you expect. Everyday moments can become opportunities for someone with bad intentions. Whether you're a parent, teacher, coach or neighbor. Check in, ask questions, stay connected. Blue Campaign is a national awareness initiative that provides resources to help recognize suspected instances of human trafficking. Learn the signs and how to [e-mail] blue campaign.

[Legends.com Advertiser]

You need to check out legends.com today. Legends is a free to play social casino and sportsbook with all of the games that you know and love. They even have Plinko and live blackjack and that's L, E G E N D Z. Whether you're a seasoned player or just starting out, their games are designed to entertain and thrill. The best part is you get free coins every day so you can play for free. And redemption to your bank account is instant. It's legit and new players get an exclusive welcome bonus. Join thousands of players on legends with a Z.com today. No purchase necessary Legends International Void we're prohibited by law. 18/ terms and conditions apply. Wow, what a weird turn of events.

[Brooke from Brooke and Jeffrey in the Morning]

Yeah, that.

[Legends.com Advertiser]

I mean wouldn't it be insane if Dana and her ex and ended up getting married after all of this? All cuz Riley stalked their instagrams and.

[Jose from Brooke and Jeffrey in the Morning]

Brought them back together.

[Brooke from Brooke and Jeffrey in the Morning]

Riley would definitely be the best man.

[Jose from Brooke and Jeffrey in the Morning]

Oh yeah.

[Legends.com Advertiser]

Either the best man or maybe even the officiant of the wedding.

[Brooke from Brooke and Jeffrey in the Morning]

I don't know.

[Jose from Brooke and Jeffrey in the Morning]

He's gonna cry too much.

[Brooke from Brooke and Jeffrey in the Morning]

I think Riley likes her ex more than she likes her ex.

[Legends.com Advertiser]

Maybe. I mean the only more bizarre than that would be if the ex boyfriend calls us two weeks from now for a second aid update. Because Dana's now not calling. Calling him back.

[Jose from Brooke and Jeffrey in the Morning]

Oh boy.

[Jeffrey from Brooke and Jeffrey in the Morning]

That might not be crazy. That might be expected.

[Brooke from Brooke and Jeffrey in the Morning]

Doesn't often work out with exes.

[Legends.com Advertiser]

We're still willing to try to help him out, right? We need the content. Make sure to go find all of our second dates up. They're on Spotify, Apple, wherever you get your podcast. Just search at Brooke and Jeffrey.

[Jose from Brooke and Jeffrey in the Morning]

Hey, what's up?

[Mario Lopez]

It's Mario Lopez. Back to school is an exciting time, but it can also be overwhelming and kids may feel isolated vulnerability that human traffickers can exploit. Human trafficking doesn't always look like what you expect. Everyday moments can become opportunities for someone with bad intentions. Whether you're a parent, teacher, coach, or neighbor. Check in, ask questions, stay connected. Blue Campaign is a national awareness initiative that provides resources to help recognize suspected instances of human trafficking. Learn the signs and how to [e-mail] blue campaign.

[Josh Clark from Stuff You Should Know]

Hi there, this is Josh Clark from the Stuff youf Should Know podcast. If you've been thinking, man alive, I could go for some good true crime podcast episodes, then have we got good news for you. Stuff youf Should Know just released a playlist of 12 of our best true crime episodes of all time. There's a shootout in broad daylight, people using axes in really terrible ways, disappearances, legendary heists, the whole nine yards. So check out the Stuff youf Should Know True Crime Playlist on the iHeartRadio app, app, Apple Podcasts or wherever you get your podcasts.

[Chris Pine from Cardiac Cowboys]

People called them murderers. Ten years later, they were gods. Today, no one knows their names. A group of maverick surgeons who took on the medical establishment who risked everything to invent open heart surgery. Welcome to the wild west of American medicine. I'm Chris Pine and this is Cardiac Cowboys. If you like medical drama, if you like heart pounding thrillers, you will love Cardiac Cowboys. Listen on the iHeartRadio app or wherever you listen to podcasts.

[Brooke from Brooke and Jeffrey in the Morning]

Sponsored by Jasper AI Built for marketers.

[Jose from Brooke and Jeffrey in the Morning]

I'm Jonathan Goldstein and on the new season of Heavyweight. And so I pointed the gun at him and said, this isn't a joke. A man who robbed a bank when he was 14 years old and a centenarian rediscovers a love lost 80 years ago.

[Riley (Caller)]

How can a 101-year-old woman fall in love again?

[Jose from Brooke and Jeffrey in the Morning]

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

[Jeffrey from Brooke and Jeffrey in the Morning]

The murder of an 18 year old girl in Graves County, Kentucky went unsolved for years until a local housewife, a journalist and a handful of girls came forward with a story.

[Josh Clark from Stuff You Should Know]

America, y' all better wake the hell up.

[Riley (Caller)]

Bad things happens to good people in small towns.

[Jeffrey from Brooke and Jeffrey in the Morning]

Listen to Graves county on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts and to binge the entire your season ad free. Subscribe to Lava for Good plus on Apple Podcasts.