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Brooke and Jeffrey: Second Date Update

Second Date Update: The Best Listener Ever

20 Mar 2026

Transcription

Chapter 1: What improvements has James made since his last date?

0.689 - 13.534 Lori Siegel

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 - 33.16 Lori Siegel

Mostly Human is your playbook for how tech can work for you. Anyone can now be an entrepreneur. Anyone can build an app. And it's very empowering. Listen to Mostly Human on the iHeart Radio app, Apple Podcasts, or wherever you listen to your favorite shows.

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36.228 - 40.135 James

I became a millionaire overnight and lost everything that actually mattered.

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40.155 - 43.902 Lori Siegel

Hold on, Sophia. Did you just say they lost everything after becoming a millionaire?

43.922 - 56.785 James

That's right. And it gets worse. It's inheriting too much drama week on the OK Storytime podcast, so we'll find out soon. This person writes, I just inherited a fortune after losing my mom, and now my girlfriend's entire family is coming out of nowhere with their hands out.

Chapter 2: How did James prepare for his mock date experience?

56.765 - 62.953 Lori Siegel

And my girlfriend is already giving my money away. So the girl he wants to marry is already sending money out the door.

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62.973 - 69.721 James

To find out how it ends, listen to the OK Storytime podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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72.885 - 73.746 Brooke

Ten, ten shots fired in City Hall building.

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73.766 - 75.048 James

How could this have happened in City Hall?

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75.468 - 95.12 Lori Siegel

Somebody tell me that. A shocking public murder. This is one of the most dramatic events that really ever happened in New York City politics. I screamed, get down, get down. Those are shots. A tragedy that's now forgotten. And a mystery. That may or may not have been political. That may have been about sex.

95.702 - 102.415 Lori Siegel

Listen to Rorschach, Murder at City Hall on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Chapter 3: What did James learn about being a better listener?

104.808 - 111.785 Lori Siegel

In 2023, Bachelor star Clayton Eckerd was accused of fathering twins, but the pregnancy appeared to be a hoax.

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112.066 - 116.777 Unknown

You doctored this particular test twice, Ms. Owens, correct? I doctored the test once.

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117.419 - 124.255 Lori Siegel

It took an army of internet detectives to uncover a disturbing pattern. Two more men who'd been through the same thing.

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124.515 - 126.517 Unknown

Greg Gillespie and Michael Marancini.

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126.537 - 136.63 Lori Siegel

My mind was blown. I'm Stephanie Young. This is Love Trapped. Laura, Scottsdale Police. As the season continues, Laura Owens finally faces consequences.

137.391 - 150.776 James

Listen to Love Trapped podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Ready for a different take on Formula One? Look no further than No Grip, a new podcast tackling the culture of motor racing's most coveted series.

Chapter 4: What humorous moments occurred during James's date with Audrey?

151.317 - 167.862 James

Join me, Lily Herman, as we dive into the underexplored pockets of F1, including the story of the woman who last participated in a Formula One race weekend, the recent uptick in F1 romance novels, and plenty of mishap scandals and sagas that have made Formula One a delightful, decadent dumpster fire for more than 75 years.

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168.563 - 173.07 James

Listen to No Grip on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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173.995 - 183.292 Lori Siegel

Well, this is definitely a first. Someone who was previously on a second date update. Use that experience to better themselves. Yeah. What?

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183.392 - 183.893 Brooke

Learning?

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184.074 - 186.558 Lori Siegel

I know. I know. We were all as shocked as you.

186.618 - 187.059 Unknown

I know.

187.099 - 193.371 Lori Siegel

But this guy put the work in and you're going to hear what happened in a brand new, brand new second date update. Did I say brand new twice? Yeah, you did.

Chapter 5: Why did Audrey feel overwhelmed during the date?

193.351 - 209.175 Lori Siegel

My brain is glitchy. We'll say it one more time. Yeah. Brand new second date update. Yes. But first comments. But first comments. Yes. I'm kidding. Okay. I was like, is Brooke okay? Do we need to check on her? I love how maybe I'm just personally going to find this funny.

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209.575 - 212.019 Lori Siegel

One of our listeners, Dead Skull, was binging old ones.

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Chapter 6: What feedback did Audrey give about James's dating approach?

212.099 - 227.698 Lori Siegel

Yes. And was back to like 2020 and found the first second date update I ever did. Oh. And commented, this is Alexis' first second date update, and it was one about someone living hashtag van life. Oh. Interesting. I don't remember that, but you probably wouldn't like to listen to it.

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227.718 - 228.099 Unknown

No, I refuse.

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228.119 - 232.724 Lori Siegel

I hate to listen to my early things. No. But I'm like, what a good one you guys threw me in on, van life.

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232.744 - 233.685 Unknown

There you go.

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233.705 - 238.39 Lori Siegel

There you go. I love it. Well, thank you for binging all of it, and hope you enjoy this new one.

Chapter 7: How did James's past experiences shape his current dating style?

238.51 - 259.065 Lori Siegel

Yeah. Starts right now. Brooke and Jeffrey in the morning. Second date update. We always welcome with open arms and open mouths returning second daters who've been on this segment before and today is no exception. One of our listeners, James, is back. Yeah, because it's always shocking to us that you still

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260.159 - 282.452 Lori Siegel

last time he was on james got turned down by a woman who said he's not a great listener only because she was telling him the story of how her dog passed away and he interrupted her to say no yeah yeah you've already told me this before when are we going to go back to my place Oh, no. But that was then. This is now.

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282.673 - 283.114 Brooke

Okay.

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283.134 - 289.205 Lori Siegel

And James says he's learned his lesson and fixed all of his personal flaws. Oh, wow. All of them.

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Chapter 8: What are the next steps for James and Audrey after this call?

289.365 - 294.655 Lori Siegel

All of them. That's exciting to hear. So, James, welcome back. Hey, guys. Thanks for having me.

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294.855 - 294.935 Jeffrey

Wow.

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294.955 - 313.168 Lori Siegel

James would like to be perfect now. I'm trying. That actually sounds like a growth response. And I like that, James. Kind of a perfect answer. But even before we get to your date, what have you done specifically since then to work on yourself? Because that's what your email said you did.

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313.869 - 322.658 Jeffrey

Yeah, yeah. So I've been taking free classes online through this website named YouTube. You might have heard of it.

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322.698 - 344.065 Lori Siegel

YouTube is so helpful for anything. What are the classes about? They're listening classes. How many times do you pause the video and take a break? Rewind, like what did they say? On how to be a better listener. Yeah, yeah. That's awesome. How to listen actively. Yeah, I mean, truly, it is a skill. What's happened since then? Tell us.

344.298 - 364.717 Lori Siegel

Okay, so I'm trying to put it in practice and I asked my brother's wife out on like a mock date just to like test me out. That is awesome. That's really funny. Okay. It's a little awkward. Yeah. How did your mock date with your brother's wife go? I think it actually went pretty well.

364.817 - 371.343 Jeffrey

Okay. So she gave me like a solid B minus, which is actually pretty good because I don't think she even likes me.

371.563 - 395.405 Lori Siegel

That's great. I honestly, I applaud you. It actually does sound like you really did do some work on yourself. So that's good, but you're not getting a call back. So that's the not good part. Is it from your brother's wife? Yeah. Tell me we're not calling her. Yeah, I don't get it. Well, just because you're married to my brother. That's it. No, actually, it's not her.

395.685 - 396.206 Brooke

Okay.

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