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Brooke and Jeffrey: Second Date Update

Second Date Update: An Ex Walks Into A Bar

27 Mar 2026

Transcription

Chapter 1: What is the main topic discussed in this episode?

0.689 - 13.534 Jeff

I'm Lori Siegel, and on my new podcast, Mostly Human, I'll take you to some wild corners of the tech world. I'm about to go on a date with an AI companion at a real world cafe right here in New York City.

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14.455 - 19.966 Unknown

There's no playbook for what to do when an AI model hallucinates a story about you.

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20.387 - 23.693 Jeff

Mostly Human is your playbook for how tech can work for you.

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23.673 - 27.484 Unknown

Anyone can now be an entrepreneur. Anyone can build an app. And it's very empowering.

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27.785 - 33.16 Jeff

Listen to Mostly Human on the iHeart Radio app, Apple Podcasts, or wherever you listen to your favorite shows.

36.43 - 49.67 Brooke

On the CINO Show podcast, each episode invites you into a raw, unfiltered conversations about recovery, resilience, and redemption. On a recent episode, I sit down with actor, cultural icon, Danny Trejo to talk about addiction, transformation, and the power of second chances.

49.99 - 56.4 Brooke

The entire season two is now available to binge, featuring powerful conversations with guests like Tiffany Addish, Johnny Knoxville, and more.

56.42 - 60.306 Eric

I'm an alcoholic, and without this drug, I'm gonna die.

60.546 - 65.914 Brooke

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

Chapter 2: What distractions should you avoid on a first date?

542.974 - 566.086 Brooke

Yeah, totally. I mean, it's totally unfortunate. Do you think the date would have gone flawlessly if your ex hadn't walked into that restaurant? Yeah, it sucks that that happened, but it's out of my control right now. Yeah, that wasn't your fault. And as long as you didn't go home and post a long TikTok or Instagram post about seeing your ex and how great she looked, but you're past it now.

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566.247 - 577.676 Brooke

So that you look pathetic to two women, not just one? Exactly. As long as you didn't do that, then we might have a chance to save this for you. Please tell us you didn't do that. I didn't do that exactly.

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578.978 - 580.762 Unknown

Exactly. Oh, boy.

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580.782 - 591.782 Brooke

Oh, no. You posted on MySpace. This is going to be one of those where we find out something. Whatever damage you did to yourself, we're going to have to undo it when we come back and get you your second date update right after this.

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591.822 - 596.11 Jeff

Hold on.

597.136 - 621.945 Brooke

Let's recap Eric's first date for those of you just joining. Eric met a woman named Vanessa for dinner recently. She's in the beauty industry. And for the first 20 minutes, everything was great. It was perfect. Conversation was flowing. The connection was easy. It was all gravy until Eric's ex-girlfriend walked in and sat down with an eye shot. Dude, what are the odds?

621.925 - 626.831 Brooke

So vibes changed after that. And he had to admit that his ex was there.

627.031 - 627.312 Unknown

He did.

627.392 - 649.521 Brooke

He was so weird. He told Vanessa, not sure if that was a bad idea or a horrible idea, but he did it. I mean, he had no other choice. The worst idea is what happened after. It was on his mind. And that's why right before he left, he stopped by his ex's table and told her she has nice hair. And that's the bad part. So great date if it was just Eric and his ex.

Chapter 3: What unexpected event derailed Eric's date?

814.861 - 841.573 Brooke

Oh, so he even shared some crazy ex stories, huh? So is that what upset you? I'm not upset. Why do you keep asking that? I meant like why you're not calling him back. We're trying to figure out what's happened with you since the date with Eric. Yeah. I mean, so we said goodbye in the parking lot, but I stayed because I wanted to follow his ex home. Oh.

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843.055 - 845.721 Unknown

What do you mean?

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846.082 - 858.853 Brooke

Just to make sure she got home safe? Well, no, I wanted to make sure that what happened to Eric didn't happen to the guy that she was on a date with. Wait, what happened to Eric? What was his story?

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Chapter 4: How did Eric handle the situation with his ex at the restaurant?

859.323 - 864.588 Brooke

Well, it's his story, so I don't really want to share it, but, like, it sounds like she traumatized him.

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865.829 - 865.969 Unknown

Oh, no.

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866.049 - 882.165 Brooke

So what happened when you got back to where she was going? Well, he dropped her off, and she kissed him, but he did not go inside, and so I went up to talk to the guy when he went back to his car. Wait, wait, wait.

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882.185 - 882.405 Unknown

Whoa. Okay.

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882.425 - 905.8 Brooke

You parked, got out of your car, approached his car in the dark. Yeah, because I had to warn him. And I was like, what are you doing right now? Do you want to grab a drink with me? Wait, what? What's the goal by asking this guy out? Because I wanted to warn him. Because like Eric told me all these stories and I needed time. If they weren't stories, I could just tell them on the street.

905.78 - 928.783 Brooke

You just met Eric. You don't know what's true, what's not true. It's a one-sided story. Eric's still alive. It's not like you're saving someone's life. So what happened when you went out and talked to the other guy? I told him all the things about why they broke up and how she's a big-time manipulator. And he was kind of like, maybe I can kind of see those signs or whatever.

928.763 - 949 Brooke

This was, like, I think their second date, and I was like, okay. I mean, she's a bad person, I guess. But you don't know that. I mean, I've been talking to Eric for, like, a week or so before our date, and he seemed like a trustworthy guy, and I absolutely believed him. And so you've got to trust some people out there. Sure.

950.617 - 976.793 Brooke

For some reason, Brooke doesn't trust our own listener, who just happens to be on the line right now, quietly listening in on this phone call. I bet he is speechless right now. Because, yeah, he is there, actually, Vanessa, on the phone right now. Who is? Eric is. Yeah, I'm sorry. I didn't, like, sneak up on you, Vanessa. But, like, what? Why? Why did you? Why would you follow? What? What?

978.005 - 1000.387 Brooke

I mean, you know the stories you told me. I had to save this guy from going through what you went through. Wow. I didn't ask you to do that. No, you didn't. But I feel like I needed to give him the heads up. Well... I was trying to be honest with you, and now I feel like this could blow back on me. How?

Chapter 5: What was Vanessa's reaction to Eric's ex being present?

1006.795 - 1035.99 Brooke

No, he will not hear from her. I made him promise not to tell her anything. Maybe that's why he stopped going on dates with her. We trust everyone but the woman we've never spoken to. What did your ex do that was so awful? We're on the radio. I'm not going to say that. But, like, you telling me this stuff on our date is pretty much giving me permission to go and tell this guy. Oh, no. What is it?

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1036.03 - 1045.12 Brooke

It would be permission if you told me you were going to do that, and then I said yes. That would be permission. That's what permission is. You had already left, though. Yeah.

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1045.741 - 1063.168 Brooke

Superman doesn't ask for permission to save somebody's life when they're in danger. He just swoops in and saves them. Okay, but Eric, honestly, was this guy in any danger because of your ex? I don't think he was in danger. That's exactly what you said when you started to date her, bro.

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1063.228 - 1076.072 Brooke

Wouldn't it have been nice if at the start of your last bad relationship, Vanessa had come up to you on date number two and been like, look, this girl is bad news for you. She is going to hurt you. And she would have been right. I mean, maybe.

Chapter 6: Why didn't Eric and Vanessa change locations during the date?

1076.092 - 1084.864 Brooke

Yeah, it was a pretty bad ending, and I guess that could have been good. See? Nope. Clearly, she has a heart of gold and wants to save men from terrible women, but I think we're missing the point here.

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1084.884 - 1085.585 Unknown

Is that what she's doing?

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1085.645 - 1106.207 Brooke

If I'm just summarizing what I think I'm hearing. It's not like a glaring red flag that she's following strangers over the night with her car and interfering in relationships she knows nothing about? Okay, tomato, tomato, Brooke. I pretty much said the exact same thing. We're avoiding the main question here, and that's, Vanessa, why aren't you talking to Eric since that night?

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1106.272 - 1120.513 Brooke

Well, I was focusing on making sure that this guy was okay. The other guy. Have you gone on more than one hangout with this guy? Yeah, of course. He didn't believe me at the start. So, like, I went to go talk to him again during the daytime. Wait a second.

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Chapter 7: How did Eric try to maintain composure during the awkward encounter?

1120.533 - 1133.681 Brooke

So, you are seeing my ex-girlfriend's new boyfriend. Eric, they went on two dates. That's not a boyfriend. Yeah, don't be crazy. She ended it for him, remember?

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1133.701 - 1133.961 Unknown

That's right.

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1133.981 - 1157.16 Brooke

She's not seeing him. She's warning him. In fact, I'm seeing him again tonight, and I'm going to warn him for a third time. Wow. Oh, wait a minute. Sounds like he's enjoying the warning. This doesn't sound right. There's something off here. You know what? Go with your gut, Eric. You're right. The thing that's off is that I haven't offered to send you two out on another date.

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1157.34 - 1181.011 Brooke

Thank you for reminding me, Eric, because we would love to put up however much money it takes to get you two back together for one more meetup. I guess I should ask Vanessa, what do you think? Listen, Eric, my focus right now is in this other guy, and once he 100% believes me not to go out with your ex, then I will focus on you. I don't know. I don't know, Vanessa.

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1181.031 - 1203.534 Brooke

Well, we're out of time, and it's sounding like it's a no for Eric. So instead, the gift cards are going to Vanessa and the dude that she followed home to save from dating your ex-girlfriend. Emily! I don't think I've ever said those words in my entire life, but I'm glad that I get to today because at least it gives Jose hope that someday a woman might follow him home without asking.

1203.694 - 1207.998 Brooke

Oh, yeah, that has to be how it goes down. Oh, so romantic.

1208.018 - 1209.34 Jeff

Brooke and Jeffrey in the morning.

1209.4 - 1235.695 Unknown

Why hasn't a woman formally participated in a Formula One race weekend in over a decade? Think about how many skills they have to develop at such a young age. What can we learn from all of the new F1 romance novels suddenly popping up every year? He still smelled of podium champagne and expensive friction. And how did a 2023 event called Wagageddon change the paddock forever?

1236.116 - 1239.621 Unknown

That day is just seared into my memory.

Chapter 8: What did Eric say to his ex-girlfriend before leaving?

1240.763 - 1250.978 Unknown

I'm culture writer and F1 expert Lily Herman, and these are just a few of the questions I'm tackling on No Grip, a Formula One culture podcast that dives into the underexplored pockets of the sport.

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1250.958 - 1278.778 Unknown

In each episode, a different guest and I will go deeper into the wacky mishaps, scandals and sagas, both on the track and far away from it, that have made F1 a delightful, decadent dumpster fire for more than 75 years. Listen to No Grip on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts. I'm Bailey Taylor, and this is It Girl.

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1279.139 - 1295.308 Unknown

You may know me from my It Girl series I've done on the streets of New York over the years. Well, I've got good news. I am bringing those interviews and many more to this podcast. Yes, we will talk about the style and the success, but we are also talking about the pressure, the expectations, and the real work with the women shaping culture right now.

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1295.288 - 1308.538 Unknown

As a woman in the industry, you're always underestimated. So you have to work extra hard and you have to push the narrative in a way that doesn't compromise who you are and your integrity. You know, I like to say I was kind of like a silent ninja.

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1308.603 - 1321.583 Jeff

Each week, I have unfiltered conversations with female founders, creatives, and leaders to talk about ambition, visibility, and what it really takes to build something meaningful in the public eye. Because being an It Girl isn't about the spotlight. It's about owning it.

1322.004 - 1330.216 Brooke

I think the negatives need to be discussed and they need to be told to people who maybe don't do this every day just so they know what's really going on. I feel like pulling the curtain back is important.

1330.597 - 1336.686 Jeff

Listen to It Girl with Bailey Taylor on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

1340.125 - 1363.734 Brooke

I would not be surprised if Vanessa hangs around that woman's apartment all next week. She might even move into the building with her. Just to warn any future dudes that she stops by with, don't date her. She's crazy. Trust me, I would know. We never asked. She did sound busy when we first called her. Like, she could have just actually been in her car outside of her apartment. Yeah.

1363.755 - 1373.049 Brooke

Just scoping out the place, ready to save any dudes from their own demise. It could get worse. Like, if the other girl sees her, then she's going to start following her. Eventually, they're going to stalk each other.

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