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Brooke
iheartradio okay, we always gotta do it before we get a new update. Update 1 welcome to the podcast. Yes, it is the Brooke and Jeffrey official second date podcast. 2. Alexis did not make a typo in the title of this.
Commercial Break Voice
Did not today for once.
Brooke
Yeah, yeah, it is an update update. Because we are going to play you the original time that one of our couples was on and they went out again. And then they're gonna check in with us on part three and let us know what's happened since they were on the show. Yes, yes. So stick around for that. But first, comments.
Commercial Break Voice
Yeah, Daniella Klezenstrup said. Hello, guys. I've always wondered, why is Jeff never a part of the comment reading? Anyways, love y', all, all the way from Denmark. And Electric Shin replied to her and said, you have to be in a different tax bracket if you expect Jeff to notice you.
Brooke
Yeah, that's just his upbring. He can't help it, you know. Yeah, so I guess that's a good explanation. We didn't need to answer anything.
Commercial Break Voice
We're not rich enough for Jess.
Brooke
Nope. That's right.
Commercial Break Voice
Yes.
Brooke
Your new second date starts right now.
Jeffrey
When it comes to giant dating, red flags. Yeah, we've heard you need to be aware of guys who are mama's boys or girls with daddy issues, but what about a red flag involving a totally different member of the immediate family? And it's even weirder than the other two. That was definitely the case for one couple we had on the show. Would they be able to overcome it? We're about to find out because they're gonna be back on for a special second Date Update update right after this.
Brooke
Brooke and Jeffrey in the morning Second Date Update.
Alexis
Ah, sports.
Jeffrey
They're not just a good excuse for excessive drinking and yelling at referees. Sometimes they're a great way to access accidentally meet somebody cute. Hey, and if you're playing them, get some exercise in while you're at it.
Brooke
Back to the cute part.
Jeffrey
That's apparently how one of our listeners met the girl he wants to call today. Through the magic of sports.
Alexis
Awesome.
Brooke
I love adult sports.
Jeffrey
Yeah. Brian, were you watching sports or were you playing them?
Brian
I was playing.
Brooke
Nice.
Brian
Okay. I'm in a rec league. It's a soccer league.
Brooke
Oh, okay.
Jeffrey
Okay. So you're athletic.
Brooke
I was in one of those for a while. And the games were, like, at 11 o' clock at night, like, out.
Alexis
My roommate used to go to games.
Jeffrey
The whole point is to roll it into, like, a social activity afterwards. Like, you don't want to do it in the morning.
Brian
That's weird.
Alexis
Maybe drink after.
Brooke
Maybe I was too old for it, Jeff. I don't know.
Jeffrey
So that's cool. You were in a rec soccer league, and who did you meet?
Brian
There was this new player, Hannah.
Brooke
Oh, she was on your team?
Brian
They put her on our team. She just signed up and they put her on our team.
Brooke
Cool.
Brian
And I thought, wow, she's really cute.
Hannah
Okay.
Alexis
We thought, wow, I got to play good today.
Brian
Y.
Jeffrey
Bring my A game.
Brooke
Yeah.
Brian
Yeah. I ended up scoring the winning goal.
Brooke
Nice, dude.
Jeffrey
You did it.
Brian
Yeah, it was very exciting, actually. You know, he congratulated me and everybody was all happy and everything.
Jeffrey
And did Hannah jump into your arms and give you a big kiss right on the mouth?
Brian
No, but I got a high five at that point.
Jeffrey
I got a high five just as good.
Brooke
Second best thing.
Jeffrey
Yeah.
Alexis
Okay, that's first base.
Brooke
So wait, is this the date or did you finally ask her out?
Brian
Well, afterwards, we often go out drinking. The team. So she went out with us. There you go. And we started talking and I found out some things about her. Like, she likes to paddleboard and she has a cat. She's funny.
Alexis
Did you paddleboard with the cat?
Brooke
No, but you sound smitten. Yeah.
Jeffrey
Dude, the fact that you remember two details about her, we are absolutely over the moon.
Brooke
No, it's like the way he's saying it, like through a smile.
Jeffrey
Yeah. Okay.
Brian
She's so cute. I mean, I can't even. I mean, it's been a couple years. I've been sing. And she checked all the boxes.
Jeffrey
Aw, that's awesome, man.
Brooke
Okay, so did you find out? Is she single?
Brian
I mean, so we're talking and you know. And she left before I did.
Brooke
Oh.
Brian
I went outside the bar and I was like, maybe it's okay if I could ask you out.
Jeffrey
Oh, all right.
Brooke
I like it.
Jeffrey
What was her response?
Brian
Well, she kind of hemmed and I Was like, I don't know about that.
Alexis
Oh, man, you don't want to get out of it.
Brian
I was like, but I didn't give up. I was like, come on, if it doesn't work, we'll just go back to being, you know, soccer teammates.
Brooke
Right? There's nothing to lose. It's not like you guys were friends previously.
Hannah
Exactly. I was like, come on, let's give it a shot.
Brian
And I got her to say, you know, let me think about it.
Brooke
Okay, you gotta let me think about it.
Jeffrey
Women absolutely love a man drunkenly begging them to give them a chance and go out, like, come on.
Alexis
Like, immediately. If you keep asking.
Jeffrey
I don't know.
Alexis
She could say, oh, he's persistent. Or she could be like, he's a little thirsty.
Commercial Break Voice
I think I'd say yes after enough
Jeffrey
tries just so that you wouldn't have
Brooke
to keep on saying, yeah, so.
Alexis
Oh, that's true.
Brooke
Did she think about it?
Brian
Well, we exchanged numbers and she texted me later saying, okay, let's do it.
Brooke
Oh, so she really did think about it.
Commercial Break Voice
That's better, because she meant it.
Brian
Yeah.
Brooke
Yeah, that's a good point. So where'd you guys go?
Brian
Well, nowhere. The next day, she changed her mind.
Brooke
What do you mean?
Brian
I got a text from her, and she was just like, maybe it's not a good idea.
Jeffrey
Oh, no.
Alexis
Again, she's like, right in the middle. She's like, part of her is like, not really. And then part of her is like, actually, yeah, the drunk.
Jeffrey
Drunk part of her is like, yeah, maybe. And then the sober part's like, this is a mistake.
Brooke
She needs to stop thinking so much.
Brian
Yeah, I know. I. I agree. I mean, you know. Yeah. I was like, you know, you wanna. That's what I was thinking, you know?
Brooke
Yeah.
Jeffrey
So after that, did she show up to the next game or the next.
Brian
The next game. She didn't even show up. And I was thinking, oh, man, I made her uncomfortable. You know, and it doesn't.
Brooke
I mean, everything you did is pretty innocent. I don't know that it should be something that would make her so uncomfortable to not show up. Unless you're not telling.
Jeffrey
Are you being 100% truthful with all the details?
Brian
There's nothing I can think of that I'm leaving out that is anything dopey or anything.
Brooke
I mean, no. Unsolicited photos. Also got sent to her phone
Jeffrey
when you were begging her for a date. Did you have your pants on at the time?
Brian
I did.
Jeffrey
Good.
Alexis
But the pants were on.
Jeffrey
Sure. I mean, I know these Seems like ridiculous questions, but I swear, you have no idea how many times we've been blindsided. In the second part of these calls with the details that come out, she'll
Alexis
be like, yeah, he lit himself on fire. I forgot to mention that.
Jeffrey
Yeah, I didn't think that was important. Okay, so. And how long has it been since you last spoke with Hannah?
Brian
It's been over almost two weeks. A week and a half ago since the tax day.
Jeffrey
Okay, we'll see if she even remembers you still.
Brooke
Oh, she'll remember. If she didn't show up at the game, there's a reason.
Jeffrey
Well, we'll come back and we'll try to find out why your brand new teammate on your intramural soccer team doesn't want to go out on a date or even show up to the games anymore.
Alexis
Yeah, it's affecting the team now.
Jeffrey
Yeah, rude. We'll confront her right after this.
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Brooke and Jeffrey in the morning, second date update.
Brooke
You're in the middle of a second date update update, and we're gonna find out how the couple is doing right after you hear part two.
Jeffrey
If you're just joining us for the second date update, our listener Brian played a little game of intramural soccer and scored more than just the winning goal. He scored a love connection with his new female teammate, Hannah. Okay, Hannah, a true soccer baddie, or saddy as we'll call her. Well, it's soccer baddie. Yeah. Coming up with a bun.
Brooke
I thought it was saddy because she wasn't calling him back.
Jeffrey
It works on so many different levels. I'm coming up with all sorts of cool slang for the gen zers to use.
Commercial Break Voice
Combine every word.
Alexis
Yeah, it's so fun.
Jeffrey
Okay, fine. It's gonna be for gen Alpha. They'll pick it up and they'll actually appreciate it. The whole team, though, went and grabbed drinks together after their game, and Hannah told Brian she'd be open to going
Brooke
out with him after he asked her. Not right.
Jeffrey
Yeah, persistent. In fact, she texted him that later on in the night and then suddenly changed her mind the very next day. Yeah, classic saddy behavior. Yeah, but now we're stepping in, we're gonna try and fix it. Brooke.
Brooke
Yeah?
Jeffrey
Your take.
Brooke
Oh, my take is what do you
Alexis
think he's gonna ask you?
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Jeffrey
Yeah, take it away.
Brooke
My take is, after she got home, she had a couple more glasses of wine and was binging her favorite show and was like, ah, fine, I'll go out with him. And then the next morning, she's like, what was I thinking? Yeah, but I don't think that means that we can't convince her still.
Jeffrey
Brian, what do you think of Brooke's theory that she's addicted to alcohol?
Brooke
What? This is not what she run with it.
Brian
Well, I hope not. I hope she feels the same way when she's not drinking.
Brooke
Yeah, I think you need to come up with a pros list.
Brian
Okay. Pros and cons list.
Brooke
No, no, just pros. Just, like, reasons she should say yes. Like, you kept asking her, but you didn't give her why.
Commercial Break Voice
Girls do love making pros and cons
Brooke
list of guys for sure.
Jeffrey
What happens.
Hannah
Hello?
Jeffrey
Hey, is this Hannah?
Hannah
Yes, this is Hannah. Who is this?
Jeffrey
This is a radio show calling. You called Brooke and Jeffrey in the morning.
Brian
Hi. Good morning.
Hannah
What?
Alexis
Good morning. I like that.
Hannah
Yeah, good morning.
Jeffrey
You're probably not used to having a radio show call, but this is a segment that we're doing called a second date update. It's when someone goes out on a date with another person or they met somebody really cool and they're not getting a call back for a second meetup. We can reach out on their behalf to try and help them figure out why. And in this scenario, you met a guy recently named Brian.
Hannah
Right. But I don't understand. I didn't ever go on a first date with him.
Jeffrey
Yeah, yeah, okay, we know that. He did tell us. But according to him, you said yes to going out on a date with him and then changed your mind the next day and didn't even show up to the soccer game.
Hannah
Yeah, yeah.
Brooke
He just wants to know maybe why. Why you changed your mind.
Hannah
How much do you know? What do you want to ask me?
Jeffrey
I mean, the snapshot of what we know is you played soccer together. You went and grabbed drinks afterwards.
Hannah
Yeah.
Jeffrey
You said yes to a date, but then changed your mind the next day.
Hannah
Right. So I am single. And one of the reasons that I wanted to play soccer on this, in this league is because I wanted to meet other people in the city. And if I'm being honest, I looked up all the guys on the roster just to see their status.
Jeffrey
So you don't want to pick him
Alexis
right away in case somebody else.
Hannah
Well, not necessarily. So I was actually disappointed because every single man on the team is married.
Jeffrey
Oh, wait, including Brian?
Hannah
It was confusing. I'm not sure what he is because he is kissing a woman in his pictures.
Brian
Oh, what the heck?
Commercial Break Voice
Is it old photos from, like, years ago?
Hannah
No, they're not that old. And I just. I was like, okay, I don't want to get involved with any drama. And so.
Brooke
So wait, you think he's. Brian's in a relationship?
Hannah
Yes, at the very least.
Jeffrey
Oh, you might be totally right. He could be absolutely married and lying to us. But it would strange to have him reach out to our show and have him listening to this call the entire time. Because I need to let you know, Hannah, he is there listening to this.
Hannah
Oh, okay. Hi, Ryan.
Brian
So, wait, you snooped on all our media pages? That's weird.
Hannah
That's not weird. People do it all the time. And it's not like I was digging through it. I just wanted to see what everyone's relationship status was before I embarrass my.
Brooke
That's called doing your research.
Jeffrey
And the fact that you're not immediately coming out saying, I'm not married is a big red flag here, Brian.
Alexis
That's a good point.
Brian
Well, I'm not married.
Brooke
What are you.
Brian
It's an easy explanation. Okay, I know exactly what picture.
Brooke
Okay. Of you kissing another woman.
Brian
That's my sister.
Brooke
Oh.
Jeffrey
Oh, that. That makes so much sense.
Hannah
No, that doesn't make sense. Then you are kissing her on the mouth and you're holding her waist.
Alexis
What the heck?
Brooke
And if it is, that's even more
Alexis
worrisome than, hold on, biological sister or
Jeffrey
stepsister, because clueless opened the door to a little bit.
Brooke
Ryan, what's going on?
Brian
Listen, we're a close family, okay? And it's not weird to us.
Brooke
Okay?
Jeffrey
Yeah.
Brooke
So you would be comfortable introducing Hannah to the woman that was in that photo?
Brian
My sister. Yeah. I mean, do you not, like, you know, I don't know if you have a brother or. But do you not kiss your brother or your dad on the left?
Hannah
No, I do not.
Brian
Okay, well, we do.
Brooke
I don't think kissing on the lips with family is weird. I know you're gonna be like, oh, Brooke doesn't think that's weird.
Jeffrey
Yeah, of course you do. You don't think kissing your cousins is
Brooke
weird, but, like, posting a photo of it and also holding their waist at the same time is. Yeah, there's something sensual about that.
Brian
Yeah.
Brooke
Where it doesn't feel.
Brian
There's nothing sensual about it from my point of view.
Brooke
Okay.
Alexis
Okay. No, you are right. Some families are way closer.
Jeffrey
And I have the question I think is gonna finally clear everything up here. Brian, have you gone to second base with her? Is that a family thing?
Brian
My sister? No.
Jeffrey
All right. He has a limit.
Brian
Hannah, I wish you would have texted me and just asked me, like, you know, hey, who Are you kissing in this picture? I mean, I wouldn't have gone on to the radio to find this out.
Commercial Break Voice
You should have tagged your sister so she could have stalked your whole family on media, too. Figured it out.
Brian
I. I did. I. I did have her tag, but recently she said, could you take the tag off because she thought it was weird.
Brooke
Okay, okay, okay. So maybe it was just a photo that was taken at the wrong time. And it's a totally innocent thing. Hannah.
Alexis
It's just the tongue. You can see the tongue stuck.
Hannah
It wasn't just one picture. He had, like, half a dozen on here.
Jeffrey
Half a dozen. Wait, half a dozen sisters or half a dozen pictures of the same sister?
Hannah
Pictures of kissing his sister.
Brooke
Kissing her.
Commercial Break Voice
I don't even have that many photos of my normal.
Jeffrey
They're a loving family. Come on, guys.
Hannah
I don't know.
Brian
Not weird to us guys. It's my sister. You know, when we see each other, I mean, I don't. I don't know what else to say. You guys are like, why? Why is this so weird?
Brooke
Okay, we're all ganging up on Brian right now, and, Hannah, what if he really is just a good family guy? That's a positive thing.
Hannah
I know it is. I mean, listen, the fact that he got on the radio and wanted to go out with me so badly, I appreciate that gesture.
Brooke
And he's taken this pretty well. Like, we're going hard.
Jeffrey
And I'm sure Brian would be willing to have his sister call you directly and be like, nothing has ever happened between us.
Brooke
Oh, and rate him on how good he is at kissing.
Jeffrey
Oh, that's nice.
Brian
Oh, listen, nobody's rating my kissing with my sister, okay? Kissing my sister and kissing someone. I'm interested. Is totally different.
Brooke
Okay, see? He knows that.
Jeffrey
Okay, that's great. And maybe part of the reason that you were so upset by the picture is you were a little bit jealous, Hannah, so.
Brooke
Which means you like some.
Jeffrey
There you go.
Hannah
I do.
Brian
I do.
Hannah
I'm interested. It's just weird that it's his sister and it might take me a while to get over that.
Jeffrey
Well, maybe. Okay, take a day. But in the meantime.
Brian
No, no, no. Don't let her take a day, because last time she changed her mind.
Jeffrey
Oh, right. Okay, you have five seconds to decide. Would you like another date with Brian?
Brooke
Come on.
Hannah
Okay. Yes. I will give him another chance.
Brian
All right.
Alexis
All right, guys, Guys, it's over. Group kiss?
Brian
Yeah.
Brooke
We're not related, so come on.
Hannah
Brooke and Jeffrey in the morning.
Brooke
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Brook it's smart to always have a few financial goals and a really smart one. You can set earning cash back on what you buy every day. And with Discover, you can get this. Discover automatically matches all the cash back you've earned at the end of your first year. Seriously, all of it. And we trust you to make smart decisions. I mean, after all, you listen to this show. See terms@discover.com credit card.
Jeffrey
Well, looky here. Brian and Hannah both back on today to give us a quick update on their life. And I'm just gonna start with Hannah real quick because when we last spoke to you, Hannah, you obviously had a lot of hesitation about dating a proud sister kisser. How has that been for you?
Hannah
So it did take me a while to get over that part. And I actually met his family and he wasn't wrong. They are extremely loving with each other.
Brooke
Oh, in a positive way, right?
Hannah
Yeah. I mean, it surprised me because his sister even kissed me on the mouth when she first met me on the first meeting.
Brooke
Do they drink a lot in that family?
Brian
Hey, don't forget, my dad kissed.
Jeffrey
Oh, the dad got in on the action.
Alexis
I guess the dog was next.
Hannah
Yeah, dad got in on the action, but not on the mouth though.
Brooke
Okay.
Brian
Not yet.
Hannah
Oh my God.
Brooke
Not yet.
Jeffrey
Wow.
Hannah
No, but it is true. His family does really kiss a lot. Like his whole family does it. And I actually got to witness Brian and his sister kissing yesterday for a very long time.
Brooke
What do you mean by that very long time?
Brian
I hadn't Seen her for like over a week.
Brooke
You didn't see your sister for over a week, so you gave her a long smack on the lips.
Brian
That's my sister.
Brooke
Instead of a secret handshake to have
Alexis
a secret kid kiss, like.
Jeffrey
Yeah, the thing we always do.
Brooke
How many seconds are they kissing for?
Hannah
You know, I don't know. And I'm, I'm really just still definitely getting used to it. But we are together and things are going really well.
Brooke
That's good. Have you tried the kissing with your own family?
Hannah
No, my family's the opposite.
Jeffrey
Okay, well, that's good. You could just save it all up for when you're over with Brian and his family and get it all out of your system.
Hannah
Exactly.
Brooke
Well, congrats to both of you. I mean, we didn't hear much from you, Brian, except yelling about your dad kissing her in the back.
Brian
Listen, it's definitely going great and my whole family loves her.
Brooke
Aw, that's cute.
Jeffrey
That's really nice. We don't want any more details. Thank you for being on the show, guys. Continue to keep us updated. It's Brooke and Jeffrey in the morning.
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Date: June 11, 2026
Podcast: Brooke and Jeffrey: Second Date Update
Host: iHeartPodcasts
This episode features a unique "Second Date Update UPDATE" segment, where the hosts revisit a previous second date update involving Brian and Hannah—two teammates from an adult rec soccer league. The main theme revolves around a “red flag” family dynamic, specifically Brian’s close (and somewhat controversial) relationship with his sister, which was revealed through social media photos. The update provides closure as Brian and Hannah check in with the show to share how things have progressed since the original awkward confrontation.
The episode remains playful, sarcastic, and good-naturedly awkward, with the hosts leaning into the bizarre humor of the “first base with family” scenario. They encourage honesty and keep things upbeat, even as they probe into the participants’ comfort zones.
“Second Date Update UPDATE: First Base Fam” is a classic Brooke and Jeffrey rollercoaster—turning a potential red flag (close family kissing) into a recurring joke, but also revealing how communication (or a lack thereof) fuels dating drama. Brian and Hannah’s story closes on a surprisingly positive note: they’re still dating and have learned to (mostly) accept each other’s family quirks, proving that rare red flags don’t always spell disaster in romance.