Brooke and Jeffrey: Second Date Update - Second Date Update: The Best Listener Ever

Episode Date: March 20, 2026

James came on our show a few months ago and actually USED his previous experience to change for the better?? Hear how he’s worked to become a better DATER in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

Getting ready for a game means being ready for anything, like packing a spare stick. I like to be prepared. That's why I remember, 988 Canada's suicide crisis helpline. It's good to know, just in case. Anyone can call or text for free confidential support from a train responder anytime. 988 suicide crisis helpline is funded by the government in Canada. In the middle of the night, Saskia awoke in a haze. Her husband, Mike, was on his laptop.

What was on his screen would change. Soski's life forever. I said, I need you to tell me exactly what you're doing. And immediately, the mask came off. You're supposed to be safe. That's your home. That's your husband. Listen to Betrayal Season 5 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

I'm Nancy Glass, host of the Burden of Guilt Season 2 podcast. This is a story about a horrendous lie that destroyed two families. Late one night, Bobby Gumpbright became the victim of a random crime. The perpetrator was sentenced to 99 years until a confession changed everything. I was a monster. Listen to Burden of Guilt Season 2 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Good people. What's up? What's up? It's Questlove. So recently, I had the incredible opportunity to have a real conversation with actors and producer Jamie Lee Curtis from routines to recovery, true lies, and a certain Jermaine Jackson music video.

Jamie's real and raw. And it's something I really admire about her. I am so happy that I'm the head bitch in charge at 67, that I have the perspective that I have at my age to really be able to put all of this into context. Listen to the Questlove show on the Iheart radio 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.

Join me, Lily Herman, as we dive into the under-explored pockets of F-1, including the story of the woman who last participated in a Formula One race weekend, the recent uptick in F-1 romance novels, and plenty of mishap scandals and sagas that have made Formula One a delightful, decadent dumpster fire for more than 75 years. Listen to No Grip on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Well, this is definitely a first. Someone who was previously on a second date update, use that experience to better themselves.

Yeah. What? Learning? I know. I know. We were all as shocked as you. I know. 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. My brain is glitchy. We'll say it one more time. Yeah, brand new second date update. Yes. But first comments, but first comments. I'm kidding.

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. One of our listeners, Dead School, was binging old ones. And was back to like 2020 and found the first second date update I ever did. And commented, this is Alexis's first second date update. And it was one about someone living hashtag van life. Oh, I was like, what it?

I don't remember that. Yeah, you probably wouldn't like to listen to it. No, I refuse. I hate to listen to my early things. No, but I'm like, what a good one. You guys threw me in on band life. There you go. There you go.

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

Yeah. 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 want her help. Yeah, it's true. 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. Okay. And James says he's learned his lesson and fixed all of his. personal flaws. Oh, wow. All of them. That's exciting to hear. So James, welcome back. Hey, guys. Thanks for having me. James. How does it like to be perfect now? I'm trying.

Okay. 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. Yeah, yeah. So I've been taking free class online through this website named YouTube. You might have heard of it. Oh. YouTube is so helpful for anything. What are the classes about?

They're listening classes. Oh. How many times do you like 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. That's awesome.

Like actively. Yeah. I mean, truly it is a skill. Yeah. What's happened since then? Tell us. 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. I mean, it feels weird. It's a little awkward. Yeah. How did your mock date with your brother's wife go?

I think it actually went pretty well. Okay, so she gave me like a solid B minus, which is actually pretty good because I don't think she even likes me. 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. He's like, yeah, I don't get it. Now you don't respond to my midnight text. Well, just because you're married to my brother, that's it? No, actually, it's not her. Okay. It's a woman named Audrey.

She's a high school teacher. Cute. Oh, nice. How did you meet Audrey? Through the apps. Okay. She's super sweet and cute. She's not really hot, really.

Okay, let's not say that again when she's on the phone. Well, I appreciate getting a full, like, mental image of what she looks like. I mean, I think that's okay. Like, you can be really attractive and not be your stereotypical hot, I think, is what you mean. Yeah. Right. And I actually mean it in a good way. Like, that's not really what I need right now.

Okay. And we grabbed drinks together. It was cool. It was good vibe. So, honestly, I have no idea why she's not calling me back. All right. And, wait. How was your conversation skills?

Like, you asked her a lot of questions, right? Yeah, yeah, I asked her questions. I was actively listening. I was doing all the things. Yeah, I even wrote down a few notes about the date afterwards so that I could like ask you guys about it. Oh, wow, you came prepared. What notes did you take?

Okay, so one of the things is I started off the date with like a little humor. You know, I walked in and as a joke, I sat down at the table next to her with a different woman. And I loudly was like, oh, hi, you must be my date, Audrey. And I thought it would be kind of funny Oh, there was already a woman sitting next to her. You said that you didn't bring another woman. Okay, you either confused two women at the same time

Or made them both laugh. How did Audrey react to that? Yeah, please be laughed. I mean, I think it was good. She waved and she was like, hey, I think you mean me. Oh, that's cute. Well, at least one of you laughed, even if it's you laughing at your own joke. Neither of the woman in the room.

But he's fine. He's attempting to break the ice and make things more play. right from the beginning. Yeah, I think it did help break the ice. Okay. I was trying to find places like pepper and some humor, you know, but I got really quiet when the bill came. And I said, like, oh, it's kind of cool that this whole meal was free tonight.

And she's like, what do you mean? And I said, we're going to go to the car. Follow me. Three, two, one. Oh. Oh. But you stayed and paid, right? No, I stood up and bolted.

No, I actually did pay. How did Audrey react to your suggestion that you dine and dash, like before she realized it was a joke? Yeah. Well, her eyes that looked super big. She was really concerned. Oh, she thought it was real. Uh-oh, that's not good. That's funny.

Yeah. But she kind of smiled and maybe laughed a little. Oh, yeah. She wasn't feeling that joke. I wonder if it's just maybe first aid energy or your senses of humor aren't meshing. Or as a comedian, you had what we call a tough crowd. Right? That old restaurant seemed pretty stiff to me, brother.

Yeah. Come on now. Everyone should have been like in hysterics. I know. The waiter even. I mean, that's how I feel too. But I'm still not getting to solve that. Okay.

It's not me. It's you. Yeah. Like what was the last interaction that you and Audrey had at dinner? Well, I paid the bill and then we hug goodbye in the parking lot. Okay. Did you at that point feel like you were going to get another date? Yeah.

I felt like I was on point. All right. All right. And at no point did you interrupt her when she was telling a story about her grandparents dying, right? Like, that never happened? No, this time I listened to all her death stories all the way through. Ew.

There we go. He's like, do you have another death story? Yeah. Had your great-great-grandfather die. Okay, good. I feel like there's a lot of improvement here. Yeah. I just think you get another chance just for the effort.

Totally. Well, that's all I feel, too, but like she doesn't know that, guys. Oh, that's true. Yeah. She doesn't know where you started. Maybe it's just a situation. Like, she's intimidated by just. just how funny and hilarious and witty you are all the time.

And she feels like she can't match your energy. Intimidating. I don't know that I was going with that. But let's find out. We're going to come back, call Audrey, and try and get you your second date update with extra good listening right after this. Thank you so much, Ted. Yeah, hold on. Brooke and Jeffrey in the morning.

Second date update. We may be witnessing a true success story here with our listener, James. I just can't believe it. Because he's made some major strides since the last time he came on our show. He's been taking free classes on YouTube to become a better listener. He's been taking his sister-in-law out on mock dates to test his communication skills and improve his under-the-table footsy game. Hey, practice means progress. Exactly.

All that work finally paid off when he went out with a new woman named Audrey because he didn't interrupt any of her stories. He injected playful humor. throughout the date. So we're all wondering why Audrey wouldn't be calling him back. I mean, maybe she's been mock dating her brother-in-law to try to improve herself for you, James. Have you ever thought about that? Oh, wow. That ain't crossed my mind.

The only thing I could thank for you, James, is maybe you were so in your head about all these tips and tricks that you've learned that you forgot just about like, I don't know, the chemistry, right? Yeah, let it just take over. Yeah, I guess so. I mean, I thought there was chemistry, but maybe I just missed it. I need to practice more. I think it's legit. Okay. Well, we'll call your sister-in-law up after this if it doesn't work out.

Well, she did only give him a B-minus. That's true. But that was good because she doesn't like him. Right. Still, room for improvement. But let's reach out to Audrey first. We'll see what she has to say. I'm going to dial her number right now.

Here we go. Hello? Hey, Audrey. This is Brooke and Jeffrey in the morning, the radio show. Hi. Hi. Hi. Hey, welcome to the show.

Um, you do what's up? Yeah. Yeah. Thanks for answering. We're doing a segment right now. It's called a second date update. And one of our listeners has asked us to get a hold of you. Okay.

So I don't know if you're familiar with that segment, but basically we know that you went out on a date with this guy named James. Yeah. James. Yes. Yeah. We spoke to him and heard about your date a lot. little bit. He's a little bit confused about why there hasn't been a second meetup. I'm confused about this phone call. Let me just say that.

Okay. I think that's fair. We're just trying to get a sense of where your head is at when it comes to James. James is very funny, like cute, but just like for being honest here and I have to do this. He's just a little too fast for me. Fast? Oh, I would have thought the other way. Fast in what way? So, I mean, this just really got to me, like, stood out to me on the date. But I was kind of complaining because, like, I own my own house. He runs an apartment, but I have my own house. Isn't that a little humble brag?

I mean, listen, I work really hard. Yeah, yeah, good for you. I'm just plain. That's awesome. Well, thank you. So I was just kind of complaining. I was, like, expensive. Like, I just dealt with a leaky roof.

Yeah. And my seating system and cooling system just got messed up last year. and I put out a ton of money. So I was just complaining, and he, like, the first sentence inside of his mouth was, well, why don't we just buy a property together? Oh, my gosh. Yeah, so literally, that was me. I'm like, what do you mean?

And he's like, well, I'm really, really handy. I learned a lot from my dad. He was an electrician. You know, I'm a two-bath, three-bed kind of guy. Like, we should do it. I got to say. Handymands are good to have. And hard to come by these days.

Yeah, totally. You know, like, I understand where that. might fail fast, but it also might be a good investment for you. Oh, so Brooke, that's okay that he said that? No, no, I'm joking. That's okay. But I would assume he was being lighthearted in that part of the conversation. Yeah, we heard that he's a very humorous type of guy.

I mean, he seemed serious in the moment, but I mean, I could have read him wrong. Maybe I misunderstood. I mean, he didn't pull out like Zillow or Redfin on his phone and like start searching for properties right there, right? He's one, two blocks away. You want to go to open house? No, but just to say that on a first date felt really awkward. Yeah, I could see that. I don't know if it's a reason to, like, never see him again.

But we can understand you were a little scared by it, a little intimidated. It was a lot all at once on a first date. That's what you're saying. Absolutely. Okay. Well, if you feel like he's serious, there's a good way to find out because actually, James is on the other line of this phone call listening in waiting to talk to you. Oh, gosh.

Really? Yeah, really. Come on. I'm sorry, that's how this works. James, are you there? Hey, Audrey. Oh. All right.

Hi, James. Hey, it's so good to hear your voice, first of all. Good. But, hey, I want to be clear. Like, I actually wasn't joking when I said the idea about the house and moving in, because I thought I could be helpful. What? Moving in.

What, James. Wait. Wait, you went from buying a place with her to just. just moving into the place she already bought? No, but in my defense, like, I don't mean right away. I'm not trying to, like, jump into that right now. Oh, that does help a little bit, actually. Yeah, I mean, like, far in the future, like a month or two from now.

What? Oh, no. No, that's not far in the future. That's a lot. No, that's a lot to handle. I appreciate it. You're really nice. But if I need a handyman, I'll just call somebody.

I don't need them to move in with me. Yeah. Let her call you over when she. she needs something and they'll make a date out of it. She'll literally just hire your dad as an actual electrician. So Audrey, you're saying I made a mistake on the date. I'm saying you should not have said that to me, even if you were thinking of it. I appreciate it.

I guess it seems like your heart's in the right place, but like... But you're saying I made a mistake, though. Yes, you made a mistake. You're talking about moving in with me. Like, we don't even know each other. Why do you keep asking her about you making a mistake? I'm just writing this down. I'm trying to learn.

God. Oh, yeah, that is kind of... His self-improvement journey. Self-improvement journey? I don't know anything about that. Oh, boy. Oh, yeah. I think that could be a positive.

It's could be more attractive. Tell her, James. Tell her what you've been doing. Go for it, James. Okay, wow. Okay, we're doing that. Okay, well, I went out with my brother's wife. No, go, go.

No, no. No, James. Don't start dating. Go on. No, no. Guys, he's dating his brother's wife. No, no, no, no, no, no. James, go back before your brother's wife.

Go to the listening part, James. Oh. I don't want to go to another place. He just said he's dating his brother's wife. No. It was. No. James, you need to explain that to her.

Uh, well, I, uh, I asked her to you. No. James. Tell her about the practice. Just use the words mock date. Yes. Mock date. Right.

Right. A mock date. Right. Oh, my God. And so she could critique me so that all the stupid things I do, she could be like, hey, you're an idiot. Don't do those things. And then maybe I'll learn.

It was just to be a better dater, basically. And she doesn't even really like me, but she gave me a pretty good story. Wow. But he did well. He passed. I think, Audrey, what he's trying to say is he really, truly is actively trying to improve who he is. And, Audrey, you don't even know this, but I actually called the show before because I talked over a lady

when she was trying to tell me about her pet dying. This is a joke. I think the next step on your journey, James, is to find a YouTube class about not oversharing during a first date. Because there may have been too much information there. Okay, fine, hold on. Let me write that down.

Okay, all right. Audrey, honestly, I'm still rooting for this guy. I still think you should give him another chance. He is. We all are team James, though, Audrey. He's definitely been trying to work on himself. and be a better guy, a better date or so. He might not be perfect right now, but maybe down the road.

Three dates from now, five dates, a month when you move in together. Okay, stop a job. Audrey, he's not lying. I actually really will be better, like, a couple months from now. I'm really sorry that I brought up the move-in thing. Maybe we don't do that. We can just go on vacation together, and that will alleviate you from having to be around on the deep to pipe.

That's a good idea. Is that better? Did you just say no, Audrey? And let's pump the brakes. Let's pump the break. Okay. No vacations just yet. Like, I think, James, you're a great guy.

I have to be honest. I've been dating quite a lot more than I'd like to right now. And most guys are not admitting their flaws and faults. So in a way, I like that you overshare and you're honest about who you are. Like, it takes a lot to do this. And I mean, you are funny. Like, the Dyn and Dash thing kind of got me by surprise. All that hit.

Oh, okay. Hey, do you guys hear that? She thinks I'm funny. Hold, let me write that down. Okay. All right, well, sure. You write that down, and in the meantime, we need to ask Audrey if you'll consider going out on one more date with James, and we would pay for that. Okay.

Two conditions. We're not buying a property together, and we're not going on vacation. Okay. You set down pretty strict terms. James, are you willing to bend and abide by those rules? Wait, yeah. Does she mean it ever? because I kind of do want to go on vacation at some point.

Of course. Just be before the second date, James. Yeah. All right, yeah. I mean, just don't slam that door, I guess. The whole thing is. I don't know. I guess I can do it.

That's a motivational quote that didn't make sense. Yeah, I think you're written down. Yeah. So, yes, you're going out again. Pizza. Let's go for pizza. Let's keep it casual. But I'm definitely willing to go out with you again, James.

Okay. All right. I'm just going to do one more mock date with my brother's wife and then we'll do it. Okay. I just feel bad for the brother's wife at this point. It's like five dates in. She's like, what is going on?

Yeah, you better be paying for dinner. Brooke and Jeffrey in the morning. Getting ready for a game means being ready for anything. Like packing a spare stick. I like to be prepared. That's why I remember 988, Canada's suicide crisis helpline. It's good to know just in case. Anyone can call or text for free confidential support from a train responder anytime.

988 suicide crisis helpline is funded by the government in Canada. In the middle of the night, Sasquia awoke in a haze. Her husband, Mike, was on his laptop. What was on his screen would change Saskia's life forever. I said, I need you to tell me exactly what you're doing. And immediately, the mask came off. You're supposed to be safe.

That's your home. That's your husband. So keep this secret for so many years. He's like a seasoned pro. This is a story about the end of a marriage. But it's also the story of one woman who was done living in the dark. You're a dangerous person who prays

on vulnerable and trusting people. You're a predator, Michael. I've been good. Listen to Betrayal Season 5 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. James has a lot of homework to do before his next date. Well, he's been taking notes. That's the thing. He's got to go back and review his notes, book another hangout with his brother's wife,

probably listen back to this podcast and the old one that he did before, which you can too, by the way, Spotify, Apple, IHeart, wherever you get your podcast. Yeah, you should study. Notes for those, huh? Yeah, but overall, he's one of the few guys who's ever been on this show who actually seems like he's really putting in the effort to find a suitable mate for himself. You're not just guys, just person. People. Like, I'm really, I hope we get an update from them.

Me too. I hope we get an update from him and Audrey or from him and his sister-in-law, whoever. He deserves to end up with somebody. We're going to get an awkward Tuesday phone call from her. Like, can we tell my brother-in-law to stop asking me out? And we would do that. But either way, we are pro James at the moment. And you could be pro James by just subscribing to the podcast.

Hit that follow button. In the middle of the night, Saskia awoke in a haze. Her husband, Mike, was on his laptop. What was on his screen would change Saskia's life forever. I said, I need you to tell me exactly what you're doing. And immediately, the mask came off. You're supposed to be safe. That's your home.

That's your husband. Listen to Betrayal Season 5 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Nancy Glass, host of the Burden of Guilt Season 2 podcast. This is a story about a horrendous lie that destroyed two families. Late one night, Bobby Gumpbright became the victim of a random crime. The perpetrator was sentenced to 99 years. until a confession changed everything. I was a monster.

Listen to Burden of Guilt Season 2 on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Good people, what's up, what's up? It's Questlove. So recently, I had the incredible opportunity to have a real conversation with an actress and producer,

Jamie Lee Curtis, from routines to recovery, true lies, and a certain Jermaine Jackson music video. Jamie's surreal and raw. and something I really admire about her. I am so happy that I'm the head bitch in charge at 67, that I have the perspective that I have at my age to really be able to put all of this into context.

Listen to the Questlove show on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Bailey Taylor, and this is It Girl. This podcast is all about going deeper with the women-shaping culture right now. Yes, we will talk about the style and the success, but we are also talking about the pressure, the expectations, and the real work behind it all. As a woman in the industry, you're always underestimated. So you have to work extra hard in a way that doesn't compromise who you are in your integrity. You know, I like to say I was kind of like a silent ninja. Listen to It Girl with

Bailey Taylor on the IHeart Radio 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. Join me, Lily Herman, as we dive into the under-explored pockets of F-1, 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. Listen to No Grip on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.