Brooke and Jeffrey: Second Date Update - Second Date Update: Mother's Dayte

Episode Date: September 12, 2025

The guy in today’s Second Date Update decided he would surprise his date with an unexpected guest during their dinner… Hear who it was in the podcast!See omnystudio.com/listener for privacy information.

I just normally do straight stand-up, but this is a bit different. What do you get when a true crime producer walks into a comedy club? Answer, a new podcast called Wisecrack, where a comedian finds himself at the center of a chilling true crime story. Does anyone know what show they've come to see? It's a story. It's about the scariest night of my life. This is Wisecrack, available now.

Listen to Wisecrack on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hi, my name is Enya Umanzor. And I'm Drew Phillips. And we run a podcast called Emergency Intercom. If you're a crime junkie and you love crimes, we're not the podcast for you. But if you have unmedicated ADHD... Oh my God, perfect.

And want to hear people with mental illness, psycho babble. Yes, yes. Then Emergency Intercom is the podcast for you. Open your free IHeartRadio app. Search Emergency Intercom and listen now. What would you do if one bad decision forced you to choose between a maximum security prison or the most brutal boot camp designed to be hell on earth? Unfortunately for Mark Lombardo, this was the choice he faced. He said, you are a number, a New York State number, and we own you.

Listen to shock incarceration on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Every case that is a cold case that has DNA right now in a backlog will be identified in our lifetime. On the new podcast, America's Crime Lab, every case has a story to tell, and the DNA holds the truth. He never thought he was going to get caught, and I just looked at my computer screen. I was just like, ah, gotcha. This technology's already solving so many cases. Listen to America's Crime Lab on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hi, it's Gemma Spag, host of the psychology of your 20s. This September at the psychology

of your 20s, we're breaking down the very interesting ways psychology applies to real life, like why we crave external validation. I find it so interesting that we are so quick to believe others' judgments of us and not our own judgment of ourselves. So according to this study, not being liked actually creates similar pain levels as real life physical pain. Learn more about the psychology of everyday life and of course, your 20s this September, Listen to the psychology of your 20s on the IHart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, it's your brand new second date update. Where are you laughing already, Brooke?

Where are you started? Because, yeah, one of our listeners brought a surprise guest, we'll say, on the date. And who he brought is a little shocking. So you're going to hear it coming up. I know people are going to have some strong reactions to this one. But first, let's go over some comments, Alexis. Yeah, Turkey said, my only problem is Brooke and Alexis sound the same. Really?

Yeah, so let's, okay, this is Alexis. This is Brooke. No, you're copying me now. Bro, you're copying me now. Stop here, dude. She's moving her hands like me. Nobody can see her. Nobody can see her.

Come on. I can help. This is how you tell the difference is Brooke is the one who snorts when she laughs. Yeah, Brooke is a snorter. And Alexis just has like a honk, like a huon, when she laughs. Oh, wow. I don't know that. Yeah, there you go.

Oh, yeah. I've never been told that in my life. Oh, it's great. I study it. I've never been told that in my life. Hey. All right, we'll keep you guessing. All right, we'll keep you guessing.

Your brand new second date starts right now. Right now. Second date update. We get a lot of people on this segment who tell us, I've heard you do these before. I never thought I'd actually be calling in for a second date update myself. It probably does feel like some sort of out-of-body experience. Yeah. But they'll admit, they'll say, like, I'm a huge fan, and I've heard all the previous calls,

and Jeff, you're even more handsome than you sound on the radio. We don't get that comment. Get a lot of that stuff. But not today. Today's caller was very honest in his email, admitting he's not a fan. In fact, never really listened to our show before. Why are we letting him on that? Other people in his social circle, though, encouraged him to reach.

out for help with his dating life, so he thought he'd give it a try. Okay. His name is Chris. Chris, I don't know if you realize what you're getting yourself into here, man. See, I was just thinking, Jeff, his friends must be idiots. Yeah. Or setting them up as a big inside joke. Yeah.

Do you have idiot friends, Chris? I don't think so. Okay, you really don't listen to the show. He didn't say no. This is going to be fun. Since you haven't heard how we do these, we'll just start off by asking, what's the name of the lucky lady that you're wanting us to call today? Bella.

Bella. Okay. Beautiful. Yes, Italian, beautiful. So how did you meet Bella? Online, you know, dating apps. Are you interested in Bella's? Like, right now, and maybe it's just because you're nervous.

He's never heard the show. Emotions are real low. Oh, no, she's really nice and pretty. Is these one be, Brooks? Yeah, Brooke. Sometimes guys are more of like internal joy feelers rather than like showing all of their emotions on the outside and crying at every opportunity like some of us do. It's why I ask the question. That's good to ask.

So tell us what did you and Bella do for a date? Well, we went to this Mexican restaurant. Okay. And what was the moment like when you first saw each other in person? Hold on, I'll think. Okay. Hold on. He's busy.

What? Do we air this part? Are you there? Chris? It was very sweet. It was sweet. Are you? Are you?

Are we interrupting something right now? Yeah. No, you have my full attention. You did ask us to just wait for a second while you did something. Yeah. Let's keep going. Tell us about how dinner went at the Mexican place. Like the connection.

Or if that's what you did, like we just want to learn more about your date, man. What do you mean that's what I did? No, no, no. I'm saying, did you eat? Do we have to ask one question? Can we just call it? Pretend like you're talking to your friends and they're wanting to recap of your night. Yeah.

What did you tell them? What were the highlights? Tacos, we kissed, we went on a walk, like. I had a cheese cassidia. No. Oh, okay. Did you order for the kids' money? No, it was a full-size one.

Okay, good, nice. What did you two talk about? We talked about, you know, like pop culture and, like news and like our interests and her interests. Okay, so you're big into pop culture. No. No, but the topic did come up and I had to suffer through that for a little bit. Did you feel like it was a natural flow of convo?

Hold on. Did you say hold on again? I think so. Hey, Chris, who are you talking? It was pretty good. Sorry, man. Who are you talking to? I'm distracted.

Oh, my mom's here with me. Oh. Oh, cool. Take your mom. We said hi. Hi, Mom. Why are you talking to your mom in the middle of this? Well, she is a big fan of the show.

Oh, she is. Oh, that's awesome. Yeah, she sent the email for me. Oh. Oh, okay. She did it for you. Well, what a nice thing. I like what my mom does my stuff for me too.

That's good. My appointment. Okay. I'm not, I've forgotten what we were asking. Well, can we get to, like, how it ended? Was there any romance, like a kiss or a hug? Just any big moment that stood out to you. There you go.

Yeah. When I went to the bathroom and came back, they were chatting it up like crazy. They really, they really hit it off. Wait, who's they, Chris? Bella and my mom. Your mom was on the date? Yeah, my mom was on the date with us. Oh, no.

Did you tell Bella before you showed up to the restaurant that your mom was coming along? No. Chris. Problem solved. Chris, this is absolutely the reason that Bella isn't calling you back. You think so? Yes. Yes.

No one wants to date somebody's mom. Chris, what's the reason that you brought your mom along with you on the date? Oh. To keep me safe from any bad women. Oh. Bad women. She holds a knife on you. Mom's right there.

That's true. Don't want to be taken advantage of either on a date by a woman. But still, can you paint that picture? Like, what is she going to do in the middle of the day? Just be like, I don't like her. My mom does like Bella. Okay. So good.

She says that she says that she's, She doesn't dress sleazily. Oh. That's good. Wow. Sounds like it's a rare thing for the women that you did. Tell your mom she shouldn't comment on women's clothes. She thinks she says he's dressed really nicely.

That's not what she said. He could have interpreted it differently. Let's give him a little bit of grace here. Okay. His mom is standing over his shoulder while he's talking to a nationally syndicated show. So a lot of nerves here, a lot of pressure. Chris, does your mom come along with everything for you? Like, if someone is to date you, is it always?

a package deal? I mean, yeah, unless she said otherwise. Unless who says otherwise? My mom. Okay. Oh, okay. Are we going to ask how old you are? I think we know you're an adult, right?

I'm 32. 32. Nice. This is going to be a little complicated. Maybe let's just fast forward to Colin Bella here. Oh, I think we're going to be so surprised on her answer of why she's not calling that. I think we will. Mom is probably going to be the most surprised of anybody.

Oh, he's going to be shocking. So make sure you put it on speaker when we dial up Bella and try and get you your very first radio experience on Brooke and Jeffrey in the morning. Don't get too excited. This is a big deal, dude. My mom's like super pumped. Okay. So are we.

We're going to do it right after this. Hold on. Second date update. If you're just joining us, this is pretty exciting. Because in a way, we're doing our very first three-way second date update. Wait, say it like that. The three people being our caller, Chris, two, his date, Bella, and the third. is Chris's mom.

You cannot say Chris's mom with sexy music in the background, jazz. It's not right. You're reading this as sexy music. Okay. That's your own brain interpreting it. That's just some jazz. But Chris's mom not only tagged along on their dinner date, but it's actually with Chris right

now next to him quietly listening and sometimes answering questions for him when Chris can't remember. But it is nice. It's nice to have a wing woman there able to do ride or die with you, your support system. Yeah.

What was her reaction? We never asked when she got to the table and your mom sitting there. Um, I think she was fine with it. Oh. Well, that's her the same question. Okay. Clearly, Chris and his mother don't believe that's the reason why. So, Chris, what's your mom's guess for why Bella's acting a fool right now?

I don't know. Hold on. Is he like sitting on her laughing? Hold on, guys. She's writing something. She's writing a day. Oh, she's writing the answer? Can you tell her to write a little bit faster because we are on a time limit for the segment?

Just give her a minute. So we are cat people and she might be more of a dog person. That could be a thing. The good news is we're about to find out. Yeah. Well, hopefully, because that's if she picks up the phone. Because we're going to dial her number right now. I'm praying that Bella has really good news for us.

This is all a misunderstanding and she cannot wait to hang out with you and your mom again. Yeah. Chris? Chris? What? He was talking to his mom. His mom was combing his hair. Just call Bella, Jeff.

Okay, here we go. I'm going to dial her right now. Let's see if she picks up. Hello? Hey, is this Bella? Yes. Who's speaking? Hey, you're speaking to a whole morning show

called Brooke and Jeffrey in the morning. Hey, Bella. Hi, good morning. You're on the radio right now. Hi. Good morning, beautiful. I always say it because it's your name. Get it, Bella.

So the reason that we're reaching out to you, Bella, is we're doing a segment. It's called a Second Date Update. I don't know if you're familiar with that. Oh, no. Oh, dear. Don't be afraid. It's a good thing because a guy named Chris has reached out to our show asking us if we could get a hold of you. Oh.

Oh, of course he did. Mm-hmm. What do you mean, of course? Do you mean because he's getting help? It just makes a lot of sense. Yeah. I mean, it definitely, when we heard from Chris, it sounded like you two went on a very unique date. Yes, that's a nice way to put it.

For the record, both him and his mom have been texting me. Oh, man. Group chatter. We did hear that the mom was there. I would love to hear your description of showing up to the Mexican restaurant. So it started off with just me and him at a table. Oh, it did start with just you and him. His mom wasn't there immediately? Well, she kept coming up to the table. I thought she was like a server or like a buser or someone because she kept coming up and like checking in on

us. And then like the third time she just sat down with us. That is so strange. Like I just, I don't know. I just thought that he was more up front with the whole thing. I know he didn't tell you before the date, but... My read on it is that he was a little bit awkward, somewhat nervous, and just genuinely wasn't sure how to introduce her. Yeah, I mean, maybe he's a person who needs help in social situations like that. And it's nice of you to give him grace in that scenario. So once you found out that it was his mom and she was going to be joining you for the date,

how did the rest of it go? He was pretty quiet the whole time And his mom filled in the spaces And answered for him when I would ask questions I mean Don't get me wrong She's a lovely Lovely woman truly

But maybe a little overprotective So do you think I mean do you think it would have been better If she would have just stayed pretending To be a server And let him And let him just date She shouldn't have been there

In my opinion You know he's 30 too. And I think it's time that he sits through a date by himself. And I think he's nice, but it was just too awkward. I could see what you're saying there. But have you ever considered that maybe Chris is such an amazing guy that his mom is being protective because she wants the best possible match for him? Jeff is saying this because he has a mom a lot like Chris's mom. Yeah. Some of our mothers love us. And I can't believe that's used. That's something that people hold against.

Jeff's mom thinks I'm amazing, too. Jeff's mom would love to go on dates with him. Oh, yeah. But I'm not talking about Jeff's mom. I'm talking about Chris's mom and actually Chris himself, who is on the other line right now, listening to this conversation. Oh, oh, my God. Hi.

Oh, hi. Why are you doing this? Oh, it was my mom's idea. No. She does listen to our show, so. I didn't realize you are uncomfortable I'm sorry None more uncomfortable than right now

If it makes you feel better My mom is very picky And she approves a view That's not going to help It's kind of a nice compliment To give to you Well thank you for that But I would really prefer to know what you think

And not what your mom thinks That is so well said I mean are you hearing her on that This is a good opportunity, Chris, to speak from the heart. Yeah. I agree with my mom. Okay. Oh, okay.

They're on the same page. They both think that you're a really cool person, Bella. Chris, can I just ask you, what was up with the whole server bet with your mom? Yeah. Yeah, well, we do that every time. We don't want to, like, we want it to be like a surprise. Every time. Oh, you do this a lot with your mom?

Oh, like, not a lot, but. The few dates that I do get. Chris, you're saying that you've done this with other ladies before? Yeah. Do they stay for the date? Or have they left? What has happened in the past? Well, one of them wanted to get married, but she was way too overbearing, so we had to let her go.

We had to let her go. Wait, you had a proposal? Well, yeah, she didn't live in this country, and a lot of it was on video. Oh. Wow. She was really eager to get over here and tied the knot with you. Chris and Chris's mom, don't fall for that. Yeah.

Sounded like a romantic story. Now, we learned on. Okay, that's good. There we go. That's good. So now he's moved on. He's put all those other women that want him aside because right now you're in the spotlight. It should be kind of flattering.

Yeah. I'm flattered and a little, I feel very awkward. Yeah. I feel like I'm dating you and you. your mom and not just you. Okay. Would it be better if you brought your mom on a date or your dad on a date? Or maybe is anyone hearing what Bella needs?

Yes, but I think, but Bella is trying to suggest it sounds like Chris is maybe the two of you go on a one-on-one date and you leave your mom at home for this one. What? That is definitely not what I'm suggesting. Oh, okay. Well, then I misread it. I'm not sure what you're suggesting. I'm suggesting that for Chris, you should do more of those.

Maybe Chris, if you don't feel safe. on a date, I think that's valid. Maybe your mom can wait in a car, in the parking lot. Like, just not come inside the restaurant. Oh, yeah, that's a good idea. Okay, that's kind of nice. Black security shirt. You can buy them on Amazon.

Stop. My mom laughed at that. She liked home. Oh, nice work, Jose. All right, buddy. Okay. All right. Sounds like.

So this may be completely fruitless, but I do have to ask, Bella, would you be willing to go out on another date with just Chris, and we would. pay for it. No mom? Maybe just even as friends get to know each other a little more, like the real Chris. No, thank you. Keep in mind, his mom is listening to this entire conversation.

So what you say, his mom is hearing. She's well aware. Well, I'll say to both of them that since we both have history with each other, I just think that that would cloud this next interaction. My mom isn't a fan of your response. Oh, wow. Bella, you got on Chris's mom's bad side now. Not good.

You better expect some angry texts from her later on after this is over. I'll be ready for them. I was just going to suggest maybe blocking that number. Yeah. All right. Well, Chris, man, I appreciate you taking a chance, reaching out to our show, even if your mom did it for you and being on with us, giving it a shot. That was really brave. It was a big first step for you.

Yeah. Maybe next step is you have dinner with a woman without your mom there. Maybe you can bring Brooke along. with you on the date and show wingman for you. Oh, yeah, do you want to come? No. That'd be cool. No, I'm good.

His mom would not like Brooke. Yeah. Not a fan. Brooke and Jeffrey in the morning. My name is Ed. Everyone say, hello Ed. Hello, Ed. I'm from a very rural background myself.

My dad is a farmer. And my mom is a cousin. So, like, it's not like... What do you get when a true crime producer walks into a comedy club? I know it sounds like the start of a bad joke, but that really was my reality nine years ago. I just normally do straight stand-up, but this is a bit different.

On stage stood a comedian with a story that no one expected to hear. Well, 22nd of July 2015, a 23-year-old man had killed his family. And then he came to my house. So what do you get when a true crime producer walks into a comedy club? A new podcast called Wisecrack, where Standard, up comedy and murder take center stage available now listen to wisecrack on the iheart radio app apple podcasts or wherever you get your podcasts hi my name is enya umanzor and i'm drew phillips and we run a podcast called emergency intercom if you're a crime junkie and you love crimes we're not the podcast for you

but if you have unmedicated ADHD oh my god perfect and want to hear people with mental illness, psychobabble. Yes, yes. Then Emergency Intercom is the podcast for you. Open your free IHeartRadio app. Search Emergency Intercom and listen now. You know, it's funny. A lot of us are laughing or even cringing at the idea of having your mom join you on a first date.

Yeah. But I don't know. I could definitely see Brooke sitting down with her son Alder on his very first date. Oh, my God. And then immediately admonished the girl for not. dressing sleazily enough. Enough, yeah. My son deserves to see skin, Missy.

Look at him in his sad little eyes. I don't see any cleavage on you, young lady. Mom, I'm not seeing enough cleavage on him. Oh, there, there, sweetie. Let me hug you tightly into mine. Oh, Brooke, you're a good mom. There is a running joke in my house that if I have to keep cutting their steak and stuff up for them, then I'm going to have to accompany them on a date, so they better

figure it out soon. So you're going to be teaching his date how to cook steak for him. No, cut it up. Cut it, yeah. Yes. So look out, Brooke. Judge not lest you be judged in like six to seven. No, how long, how old?

A long time. A long time? Yeah. I bet he's going to be an early bloomer. 40 years. Wow. Well, we'll see. He's healthy.

That's a lot of time for people to go online and check out all of our second date updates. Wherever you get your podcast, they're up at Brooke and Jeffrey. I just normally do straight stand up, but this is a bit different. What do you get when a true crime producer walks into a comedy club? Answer, a new podcast called Wisecrack, where a comedian finds himself at the center of a chilling true crime story. Does anyone know what show they've come to see? It's a story. It's about the scariest night of my life. This is Wisecrack, available now. Listen to Wisecrack on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Hi, my name is Enya Umanzor. And I'm Drew Phillips. And we run a podcast called Emergency Interested. If you're a crime junkie and you love crimes, we're not the podcast for you. But if you have unmedicated ADHD... Oh my God, perfect. And want to hear people with mental illness, psychobabble. Yes, yes.

Then Emergency Intercom is the podcast for you. Open your free Iheart radio app. Search Emergency Intercom and listen now. Hi, it's Gemma's Begg, host of the Psychology of Your 20s. This September at the Psychology of Your 20s, we're breaking down the very interesting ways psychology applies to real life, like why we crave external validation. I find it so interesting that we are so quick to believe others' judgments of us and not our own judgment of ourselves. So according to this study, not being liked actually creates similar

pain levels as real life physical pain. Learn more about the psychology of everyday life and of course your 20s this September. Listen to the psychology of your 20s on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. What would you do if one bad decision forced you to choose between a maximum security prison or the most brutal boot camp designed to be hell on earth. Unfortunately for Mark Lombardo, this was the choice he faced. He said, you are a number, a New York State number, and we own you. Listen to shock incarceration on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Every case that is a cold case that has DNA.

right now in a backlog will be identified in our lifetime. On the new podcast, America's Crime Lab, every case has a story to tell, and the DNA holds the truth. He never thought he was going to get caught, and I just looked at my computer screen. I was just like, ah, gotcha. This technology's already solving so many cases. Listen to America's Crime Lab on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.