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Leah
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Luke
To multitasker and everything in between.
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Matt
Your DSW store or dsw.com hi, I'm Matt.
Leah
And I'm Leah and we're from the Grown Up Stuff Podcast.
Matt
And just in time for tax season. On this week's episode, we're chatting with CPA Lisa Green Lewis about how small businesses can tackle their taxes using TurboTax Business.
Leah
A Forbes study mentioned that a whopping 93% of small businesses overpay their taxes and 17% of Gen Zers believed that you could write off any expense as a business expense.
Luke
So can't blame them.
Leah
It's really important to do your taxes right.
Matt
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Leah
Hey, it's Brooke and Jeffrey in the morning. And you found the Second Day Update podcast. I'm just gonna say, after today's second date, I will never hear one specific Macklemore song the same. I mean, I already tried to avoid listening it, but now I'm gonna try extra hard to avoid it. Oh, you are in for a treat. And hopefully a big laugh right now. But first we gotta read some comments from our lovely podcast. I love Just K. That's all they wrote is their name. Kay, okay. Met someone from the UK who was listening to this show. That's how they found us. It's now my third week binging in and it's hilarious. Hey, was that my ex boyfriend? Oh, just K. No, the British guy that she met. Does he still like you enough to do that? Yeah, but he never listens, so. Oh wait, it does say it's his new girlfriend.
Matt
Oh, that's why that makes sense.
Leah
Yeah, there we go.
Matt
All right, she loves the show.
Leah
Let's get the date started right now.
Matt
Second date Update. I feel good that we're like an adoptive home for lonely single men and women until they eventually find their permanent homes and leave the nest. And the loveless stray that we're bringing in today, his name is Luke again for a second time. Cuz Luke has actually been on the show before.
Leah
We've had a lot of return people lately.
Matt
Yeah, that's what I'm saying. That's why we're the safe place straight.
Leah
Just always come back.
Matt
And last, like a pigeon, you just keep coming around. Last time Luke was on, he was irritating a young woman by posting a photo of them together onto his Instagram but didn't ask her permission to post it first.
Leah
It is the one where she didn't like the her look cuz he didn't use a filter. Exactly right.
Matt
So like I said, lessons have been learned. Luke, do you know better now? Pictures are a no, no. Only post videos of them without permission.
Leah
All of it's fine if you use the right filter. Don't you remember that who segment? He's not with her now, so he's got to delete the photo. Yes, that's true. Or you leave it up to me.
Matt
Look, you're in a better place though. Now leave it up.
Luke
Yeah, I am, I am better now. I, I, I didn't think it was that big of a deal, but I am not going to make that mistake.
Leah
Okay, that's good. You say, really?
Matt
How us guys get in trouble.
Leah
I love when you say you're better, but you're back with us.
Matt
Well, it's good because apparently there's a new woman, a better woman that we're trying to track down for you. Tell us about her.
Luke
So her name is Lisa. I met her on Tinder. And lately I've been trying a new strategy.
Matt
Okay.
Luke
I try and let the person know who I am. I mean, because if they know who I am, then it'll be a lot harder to ghost me.
Leah
At least, I would think be harder to ghost you.
Matt
Wait, hold on. What do you mean, know who I am? What?
Leah
He just means as a person.
Matt
Oh, okay, sorry. Do that.
Leah
What do you normally.
Matt
That's also a good point.
Luke
I mean. Cause you know how, like, first dates are. They want to know, like, what's your job? What do you do for a.
Matt
You're trying to not keep it so surface. You're diving a little bit deeper early on into the date.
Leah
The essence of who you are as a person.
Matt
Yeah. So how did you accomplish that with Lisa?
Luke
Well, one of the things that I like anybody that I'm dating to know is that, I mean, I used to be in a band.
Matt
Cool. That's a cool thing.
Luke
Yeah. I mean, I try and do, like a funny lead up into the date and give them hints about my musical talents.
Leah
Give them hints.
Matt
You don't just tell them straight out that I was in a band. Can we get a loaf of bread? Sorry about that. Wow, you were so skilled. Were you in a band?
Leah
Why wouldn't you just not tell her?
Luke
Yeah, I mean, that's not really fun. I mean, there's no mystery behind it.
Leah
Okay. It's so annoying, though, when someone's dropping hints for you to obviously ask, you.
Matt
Know, I don't know, how do you drop a hint? What's your tactic?
Luke
Okay, so what I did at dinner when I was with her was that I drew a picture of a microphone on a napkin.
Matt
Okay. Like, you were doodling, or you were.
Leah
Like, let me draw a picture while she's talking to you.
Matt
Oh, yeah, that could be rude.
Luke
It wasn't like I was completely ignoring her. I mean, you know, I can walk and chew gum at the same time.
Matt
All right. Okay.
Leah
Did she know it was a microphone? Did she pick up on your hint?
Luke
Um, she didn't really say Anything. She just kind of gave me a look.
Leah
I mean, the shape of that is not good.
Matt
I was thinking that, bro.
Leah
Yeah, it's a shape that can be mistaken.
Luke
Yeah, I tried to put like dots on the top of it to show it was a microphone.
Matt
Okay, she's not getting that.
Leah
You never clarified.
Luke
No, I didn't want to blow the surprise, honestly.
Matt
Okay, you still want her to guess it's a night long game of charades.
Leah
And then she doesn't know she's playing Pictionary, Jeff.
Matt
Pictionary. Right.
Luke
Okay, so then later on I did. I played something for her on the jukebox. A little Macklemore. I'm going to pop some tags.
Matt
Hey, that's a fun song. Thrift Shop.
Leah
I don't want to hear that song. Yeah, how is that a hint that you're in a band?
Luke
Well, I thought it would be, but I. I just kept telling her, do you like this? Do you like that?
Matt
Oh, man. Okay, so maybe she thinks you're just kind of random because your attempts at giving your hands were bad.
Leah
You're not even currently in the band.
Matt
Right, well, that's right. This is an old story, but it's the essence of who he is from his youth. Don't listen to them, Luke. What? What happened next?
Luke
Okay, well, we finished our drinks and I was like, I have to take you somewhere for dinner. Do you trust me?
Leah
Oh, God. After that drawing, I'm gonna guess she said no.
Matt
Okay, what did she say?
Luke
She said no.
Leah
Yeah, she got in my car.
Luke
Anyway.
Leah
Okay, someone needs to teach her. That's not. That does sound like an Alexis move where you just wanna.
Matt
She's being playful. Where'd you go for dinner?
Luke
I drove it to my place and, you know, I had dinner there, waiting. I also had my karaoke set up and.
Matt
Oh, this is where she's gonna find. Oh, this is another hint.
Leah
You're gonna karaoke. Just the two of you. And you're up.
Matt
Hey, that sounds fun. Brooke, leave him alone.
Luke
So I wound up singing the Macklemore song to her while she ate.
Leah
Why are we even calling her?
Matt
Yeah, bro, this is a train wreck.
Leah
Oh, buddy. Okay, I mean, maybe she liked it. Okay, O, we're teasing you a lot. But maybe she liked it.
Luke
She did clap after the song.
Leah
Oh, that is good. She did like it. Did she find out you were in a band?
Matt
Play more Macklemore.
Leah
Oh, yeah, good question.
Matt
Did that come up? Oh, yeah.
Luke
No. After all that, when I was driving her home, I did try one more hint. And so I Did try and play another surprise song, which was Macklemore again.
Leah
Wait, was it Thrift Shop again or a different song?
Luke
I mean, I really like Thrift Shops.
Matt
It was nothing.
Leah
You know what, though? If this works out, that's your song as a couple.
Matt
That's it.
Leah
That's the wedding song.
Matt
That's everything. Okay. Did you end with a hug, a kiss, anything like that?
Luke
A hug.
Leah
Did she mention anything about seeing you again or.
Luke
She did not. That's why I'm curious.
Leah
You're curious.
Matt
Okay. Have you hit her up at all? I think we all are. So, Luke, you've been on with us before. You know how this works. We're gonna call her and ask. Ask why she doesn't appreciate a brave, courageous man who's willing to just be himself and give her a live musical performance during dinner.
Leah
I mean, we could talk to her, or we could just play Macklemore for her for four minutes and see what her get ready for the intro.
Matt
I do have a thought about what music to bump in with when we come back. I don't want to spoil which one it's gonna be, though. I mean, nobody guess.
Leah
I'm not guessing.
Matt
Okay, we're gonna come back and do it with your second date update right after we pop some tags. I already hated that stuff. Second date update. I pulled Thrift Shop, the knockoff karaoke version, off the Internet for this. Because I picture this is what Luke sang to his date Lisa while she ate dinner at his place.
Leah
Dude, I can't believe we haven't asked for a sample from Luke.
Matt
Yeah.
Leah
Of his skills.
Matt
Well, I think that's. That's reserved for his romantic serenades. Got it. I don't want to confuse that. That all really happened. But, Luke, we never asked you. Did you dance for her while you sang?
Leah
Oh, I'm sure Luke has choreography. Don't Luke.
Luke
I stepped, like, from left to right, side to side.
Matt
Wow. This way.
Leah
I got it.
Matt
Okay, now, the whole point of doing all of this, this fun, mystery, creative date that you set up was to let Lisa know that you used to be in a band so that she could get to know the real you. You forgot to actually tell her that.
Leah
So my forget.
Matt
We just never got there and then never came up. So that my question now is, if we do get Lisa on the line, do you want us to tell her that information, or should we save it for.
Luke
No, I think I still want to tell her. I think that was the whole point, and I probably should just follow through.
Leah
I'm still confused how the knowledge of you previously being in a band really opens up who you are. Yeah, it just sounds like maybe you think that that's what chicks like.
Luke
Well, don't. They do.
Matt
It is true. I mean, Alexis, a guy who's formerly in a band. Come on. And we're turning around.
Leah
Imagine him performing in his garage for his mom.
Luke
Wow, you're not far off.
Matt
Every girl starts somewhere. Okay, well, if Lisa says no, then Alexis is on deck. But let's call Lisa first. Here we go.
Luke
Hello?
Matt
Hey, is this Lisa?
Luke
Yeah.
Matt
Hey, Lisa. We're a radio show. We're called Brooke and Jeffrey in the Morning. Sorry to interrupt your day.
Leah
Okay.
Luke
What'S this about?
Leah
Great question.
Matt
Yeah, we. It's about a thing that we do called a second date update.
Luke
Uh huh.
Matt
And we also play music.
Leah
No big lovers of music.
Matt
We take requests. If you have any, like to do a shout out on the radio right now.
Luke
Ah, no, no.
Matt
Oh, okay. We call you for shout outs. But back to the second date update thing that we do. Not sure if you're familiar, but you went out with one of our listeners recently, A friend of the show. Actually one of our more talented friends named Luke.
Luke
Okay, all right.
Leah
Sounds like it was a pretty memorable night with Luke. Right.
Luke
Well, what did he tell you about the date?
Matt
It was, I mean, full of surprises. Lots of surprises, Lots of fun. There was drinks, you went back to his place, he had dinner ready for you and then even performed a song live, which we all thought most guys would never go through with all of that for just a first date. We were pretty impressed. We're wondering.
Luke
So he didn't tell you anything else?
Matt
I mean, well, it felt like a lot.
Leah
He did tell us that like going back to his place was a surprise. Yeah, I don't know how that felt to you.
Luke
Yeah, normally. Normally I would not.
Leah
Right, right.
Matt
But you did go back with him and got in his car. Because I think you probably got the same vibe that we got speaking to him, that he's a good dude. And he sounds like he went through a lot of trouble to make this date really fun and different.
Luke
Well, truth be told, I was very hungry.
Leah
Oh, you're hungry? Well, you know, I get it. Sometimes I make poor decisions when I'm hungry.
Matt
Right. All right.
Leah
You're like, ah, safety.
Matt
But he had food ready for you. That must be nice.
Leah
Yeah. Was it a good dinner that he made?
Luke
His parents were there.
Matt
Oh, no, wait, at his place. That's why dinner was ready. He didn't come.
Leah
I'm gonna guess it's not his place, Jeff.
Matt
Oh, well, okay, so wait, he took.
Leah
You back to his parents house? Is that what you're saying?
Luke
I'm guessing that was his parents house. Here's the thing. I was eating. His parents were not eating.
Leah
You're sitting at the table with all of them.
Luke
No, it was set up like a kid had set it up to perform in front of his parents.
Matt
Like a living room gospel.
Leah
I'm not gonna say this is what I was imagining, but it was. How did you know? Wow.
Matt
Okay.
Leah
He left that detail out. We did not get any information about his mom and dad.
Luke
Yeah, big, big, important, Very important.
Matt
Okay, well, personally, I would have felt more safe having his parents there. They're like the chaperones of your day to make sure everything goes well. Yeah, that way if he wants a drink too, right? Yeah, someone's gonna drive you back.
Leah
That's a good point.
Luke
I did not feel that way. I felt like it was super weird.
Matt
Well, look, I get it. For some people, I understand parents on a date, that' a red flag. For others it's not. Well, some people it's not a big deal. And that might be where Luke stands. And we should probably ask him about it because he is on the other line right now waiting to talk to you. Lisa.
Leah
She says shocking, right?
Matt
Luki there?
Luke
Yeah. Hey, Lisa. Hi. For the record, it is my place. It's just that because we were already out, I had asked my parents to make dinner and have it ready.
Leah
No.
Luke
How else was I gonna make sure that everything was ready for you?
Leah
Okay, if you live with your parents, that's okay. You don't have to lie.
Luke
I. I didn't lie. They have a key to my place and they come over and make dinner all the time.
Matt
Oh, that's nice.
Leah
Then they sat and hung out while you performed.
Matt
Why didn't you kick them out? No, that. This isn't a bad thing, Lisa. This is a guy who has a very good relationship with his mom and dad. No, well, I'm sorry. Okay, tell me this. Did you or did you not clap after his performance?
Luke
Oh, his parents clapped. Louder.
Leah
His parents. Why did you not tell us all of this part?
Matt
It would have helped us if we had known your parents were there.
Leah
Yeah, man.
Luke
Well, I kind of set it up like a performance restaurant kind of thing. They were just there to help.
Leah
Okay, you're at your home with your parents playing restaurant.
Luke
Yeah.
Matt
Yeah. At least they didn't play doctor. Yeah.
Leah
Oh, God, Luke.
Matt
He's got a fun, youthful spirit to him. Broken that can't be broken.
Leah
I think the thing is, you are a really nice guy. I think maybe you just need to be more upfront with people.
Luke
Okay, Lisa, did you not like Macklemore? Luke, Macklemore is not the issue. The whole date was the issue. That was weird. I think anybody would think that that whole situation was weird when I did I have the music up a little bit too loud, you know, because I wanted it, like, you know, really up high for energy.
Matt
Okay, good question.
Luke
Oh, my gosh. You're not listening to what I'm saying at all. It wasn't that.
Leah
He's like.
Matt
So you might need to be more specific.
Luke
So my parents dinner was pretty bad. My mom makes some amazing food.
Matt
Okay, maybe it's just an off night for the cooking.
Leah
Mom, it ruined everything. The casserole didn't hit like it was supposed to.
Matt
We could tell her to try again.
Luke
Luke, I think that you need to learn what self awareness is.
Matt
That's a good thing. I don't know. In that Macklemore song. So maybe he should look it up. I'm gonna be somewhere.
Luke
I'm gonna pop some tag. Hey.
Matt
Listen to that voice.
Leah
So enthusiastic. Okay. Is that the only song he knows?
Matt
Romantic one.
Leah
I like that part. Yeah.
Matt
Yeah. Bottom line, Lisa, we all agree Luke's a good guy. His tactics are a little unconventional, but that's just what makes him so unique. And special intentions are pure. And clearly his parents would approve of going out with you again. We all approve of it. It's just up to you. We would pay for another date if you say yes.
Luke
Listen, you can be a nice guy and still be a weirdo. And enough so that. No, I do not want to go out again.
Matt
Oh, man. Not a weirdo and a nutso. No, that was a little too harsh.
Leah
Yeah.
Luke
What if I play a different Macklemore song?
Matt
I'm sure that there's another lady who appreciate Macklemore and your musical talents. Yeah. And you'll meet her soon. Okay. Text. Word's gonna fill up, brother. Yeah.
Leah
Yeah. Already just text flooding in.
Matt
Read one. Brooke.
Leah
Yeah.
Matt
There's so many.
Leah
Yeah, I just can't choose.
Matt
It keeps refreshing.
Leah
Yeah.
Matt
Brooke and Jeffrey in the morning. Oh, I really feel like that lady doesn't deserve him.
Leah
Oh, really?
Matt
No, he was. I'm sorry. Luke was a good guy who picked. Puts effort into his dates. Wants ladies to get to know the real him.
Leah
Yeah, but Jeff, he doesn't like. All he wants ladies to know is that he was used to being a band. Like he wasn't honest about anything about his life.
Matt
That's who he is.
Leah
Dishonest fans.
Matt
I don't hate on him for his truth. That's never so true. I don't care how long I have to wait by the text board for a woman to text him that actually is willing to appreciate him. But how hard can this be? He checks all of the boxes. He's close with his parents. He does napkin art. He used to be in a band.
Leah
Nobody has those boxes.
Matt
He likes rap music by white guys. Somebody out there has to.
Leah
Are we calling that rap music?
Matt
Something rap adjacent? Don't you speak of Macklemore that way. Come on ladies. Go out with Luke. Give him a chance to show him the real you or the real him. Yeah, yeah, he'll show you something for you.
Leah
That was impassioned.
Matt
Anyway, we do want to help. If you have somebody who's not calling you back, email the show. We can call them for you and get you a second date update. Go check out all of ours wherever you get your podcast at Brooke and.
Leah
Jeffrey Brooke and Jeffrey in the Morning.
Matt
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Brooke and Jeffrey: Second Date Update - "Pop Some Tags" Detailed Summary
Episode Title: Second Date Update: Pop Some Tags
Release Date: March 12, 2025
Host/Author: iHeartPodcasts
In the latest episode of "Brooke and Jeffrey: Second Date Update," hosts Brooke and Jeffrey dive into the antics of Luke, a recurring guest on the show, as he navigates his second date with Lisa. The episode, titled "Pop Some Tags," offers both humor and heartfelt insights into the challenges of modern dating, especially when unconventional approaches are involved.
The episode begins with Brooke and Jeffrey reflecting on Luke’s initial appearance on the show. Luke previously attempted to impress a young woman by posting a photo of them together on Instagram without her permission— an effort that didn't quite land well.
Brooke: "She's not getting that." (07:15)
Jeffrey: "You never clarified." (07:15)
These early missteps set the stage for Luke's determination to redeem himself in his second date endeavor.
Determined to make a better impression, Luke approaches his second date with Lisa differently. His strategy revolves around showcasing his true self early in the dating process to prevent being ghosted.
Luke: "I try and let the person know who I am. I mean, because if they know who I am, then it'll be a lot harder to ghost me." (05:17)
Brooke: "At least, I would think be harder to ghost you." (05:25)
Jeffrey: "You're trying to not keep it so surface. You're diving a little bit deeper early on into the date." (05:36)
Luke's date with Lisa is a blend of creativity and quirkiness. He attempts to drop hints about his musical past, revealing that he used to be in a band. Instead of directly stating this, Luke employs subtle tactics:
Napkin Art: During dinner, Luke draws a microphone on a napkin, hoping Lisa will pick up on the hint about his musical background.
Luke: "I tried to put like dots on the top of it to show it was a microphone." (07:08)
Jeffrey: "You never clarified." (07:15)
Music Selection: Later, he plays Macklemore’s "Thrift Shop" on the jukebox, believing this would signal his musical interests.
Luke: "I did try and play another surprise song, which was Macklemore again." (09:32)
Brooke: "That's the wedding song." (19:45)
Despite his efforts, Lisa remains oblivious to these hints during the date, offering only ambiguous reactions.
Brooke: "She did clap after the song." (09:09)
Leah: "If this works out, that's your song as a couple." (09:40)
Determined to leave no stone unturned, Luke takes the bold step of inviting Lisa to his place for dinner, accompanied by a live musical performance. However, this move introduces unexpected complications.
Luke: "I drove it to my place and, you know, I had dinner there, waiting." (08:06)
Brooke: "We're gonna call her and ask why she doesn't appreciate a brave, courageous man..." (10:15)
Jeffrey: "Picture this is what Luke sang to his date Lisa while she ate dinner at his place." (10:52)
A twist in the narrative occurs when it's revealed that Luke's parents were present during the dinner setup, further complicating the date dynamic.
Luke: "It's just that because we were already out, I had asked my parents to make dinner and have it ready." (16:20)
Jeffrey: "Why didn't you kick them out? This isn't a bad thing, Lisa." (16:37)
Brooke: "She says shocking, right?" (16:04)
This revelation leads to a humorous yet awkward situation, as Brooke and Jeffrey navigate Luke's intentions versus Lisa's reception.
Seeking clarity, Brooke and Jeffrey reach out to Lisa directly on air to understand her perspective on the unconventional date.
Brooke: "She did clap after his performance." (09:09)
Jake: "It was set up like a performance restaurant kind of thing. They were just there to help." (17:11)
Luke: "Did you not like Macklemore? Luke, Macklemore is not the issue." (17:55)
Despite Luke’s earnest efforts, Lisa decides not to pursue a second date, leading to a heartfelt conclusion.
Luke: "No, I do not want to go out again." (19:07)
Brooke: "We'll call her first. Here we go." (12:28)
Jeffrey: "But maybe she liked it." (09:07)
Brooke and Jeffrey reflect on Luke's genuine but misguided efforts to connect, emphasizing the importance of clear communication and understanding in dating.
Jeffrey: "Lisa, we all agree Luke's a good guy. His tactics are a little unconventional, but that's just what makes him so unique." (19:00)
Brooke: "Nobody has those boxes." (20:23)
Jeffrey: "Somebody out there has to appreciate Macklemore and your musical talents." (19:16)
Wrapping up the episode, Brooke and Jeffrey encourage listeners to share their own dating dilemmas for potential second date updates, fostering a community of support and entertainment.
Brooke: "If you have somebody who's not calling you back, email the show. We can call them for you and get you a second date update." (20:43)
Jeffrey: "Go check out all of ours wherever you get your podcast at Brooke and..." (20:43)
"Pop Some Tags" serves as an entertaining yet insightful exploration of Luke’s attempts to forge a meaningful connection with Lisa. Through humor and relatable scenarios, Brooke and Jeffrey highlight the complexities of dating in the modern age, reminding listeners of the importance of authenticity and clear communication. Whether you’re navigating your own dating adventures or simply enjoy a good story, this episode offers valuable takeaways wrapped in engaging banter.