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Jeffrey
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Jake
So your AI agents, they.
Brooke
Make the team that uses them more productive, right?
Alexis
But if they aren't connected to other.
Brooke
Agents or your data or your existing.
Jake
Workflows, how productive can they really make your teams?
Brooke
Any business can add AI agents. IBM connects your agents across your company.
Jake
To change how you do business. Let's create Smile to Business IBM.
Alexis
You.
Jeffrey
Can make a difference in someone's life, including your own with a job in home care. These jobs offer flexible schedules, health care, retirement options and free training. They also provide paid time off and opportunities for overtime. Visit oregonhomecarejobs.com to learn more and apply.
Brooke
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Alexis
Hey, it's a brand new second date for your Friday. Thanks for being here. Yeah, and by the way, I know we have been getting a lot of messages about how people love Saturdays because it's like double feature. And they like the longer version. We do do a full hour show every day. Yeah. Where we make really good jokes like that. Right. And you can find it on the main feed. So pop over sometime. Check out the full hour. Right now, though, it is just the second date and we've got. We've got a surprise one for you. Yeah. Because there's a woman on the phone that, I don't know, maybe has the same financial leanings as Alexis. Hey, that's a good way to sum it up. Is that a way to say it? Okay. Yeah. But before we get to it, what do you see in the comments? Alexis. Yeah, buddy commented and said, hey, Brooke and Jeffrey crew. I'm a therapist listening all the way from New Zealand. I love the show on the podcast. It helps brighten my mornings down here. But if you're ever up for it, I'd be happy to offer the whole team a free group therapy session.
Kim
Wink, wink.
Alexis
Yeah. Wants to be at the Wink, wink. I don't know, girl. Because she knows that it's like, oh, I'm gonna hook them with one. Because they obviously need at least four years worth of sessions. We love that. We love that. I'm sure you're diagnosing us as we speak. Oh, and every listener on the Second date podcast. Yeah. And we like that too. So, you know, free therapy. We'll take it. Hey, it's working. Jeffrey in the morning. And your brand new second date starts right now.
Jeffrey
Second date update. I am worried this call might get messy.
Alexis
Oh, I usually are excited about that, Jeff.
Jeffrey
I know, but I'm a little scared because. Alexis, have you ever at any point dated or had a crush on a guy named Jake?
Alexis
That's my brother's name, so. Absolutely not. She got a thing to think about.
Brooke
Someone thinks you like him.
Alexis
Her face looked like she smelled the worst heart in the world just then.
Jeffrey
I can tell. He broke your heart, didn't he? You're not even going to acknowledge that he exists. You have to try to keep your jealousy bottled up because a guy named J is on the phone with us right now.
Brooke
This is his brother. This would be awesome.
Alexis
I love how, despite your answer, you're still sticking with and how Jeff didn't know that was my brother's name correctly before this.
Brooke
We all know her brother's names, Jeff.
Jeffrey
That only makes it more tempting to her. The forbidden fruit. Jake, say hi to Alexis.
Jake
Hey, what's up, Alexis?
Alexis
Not my brother.
Jeffrey
Dude, this is awkward.
Brooke
Yeah, if it was your brother, he'd insult you.
Alexis
Somehow. Yeah.
Jeffrey
Jake, it was very brave of you to come on the show today. Thanks for being on. Tell us about the woman whose not named Alexis that you want us to call today.
Alexis
Please stop. It's gonna make me sick. It's like literally.
Jake
So, yeah, I want to call Kim. I met her through mutual friends at a birthday rooftop party.
Alexis
Oh, was it like a setup between the mutual friends or is it just you guys both happen to be at the same party?
Jake
We have mutual friends. She just happened to be there. And we really bonded over the fact that the music was absolutely horrible.
Alexis
Oh, no. Who goes to a party with bad music? No, it's when you have one dj, he's like, I'm gonna take over.
Jeffrey
Jealousy is coming out with that comment, so please try and keep it under control.
Alexis
I see they're playing like deep cuts. Like, what, you haven't heard this? Yeah. Okay, so I take it you didn't dance together that night?
Jake
No, I mean, it wasn't my kind of music. Wasn't her kind of music, but we really had a good time talking about how terrible it was.
Alexis
You know, they say people just need a common enemy sometimes to bring them together.
Jeffrey
So tell us, how did you and Kim come to be?
Brooke
Well said.
Alexis
Yeah.
Jeffrey
Like, was there a date?
Jake
I mean, yeah, we were talking and we were having a really good time, and I just asked her for a number and we went to this cozy wine bar, like, new swanky thing.
Alexis
And the nice thing about those places is they're, like, quiet enough to also be able to talk.
Jake
Yeah, yeah, yeah, yeah. We vibe talking. And again, the music was really bad, so.
Alexis
Oh.
Jeffrey
Oh.
Kim
How bad can it be at a wine bar?
Brooke
I wonder if you guys have bad taste in music at this point.
Alexis
Or is that just all you guys have to talk about?
Jake
No, no, no, no, no. We talked about our most embarrassing moment, and she said that she went on a game show, and as soon as the camera turned on, she completely froze up and was unable to do the show.
Alexis
Oh, no, that's right. Dude, did it make you want to Google or YouTube? Exactly. What game show I air, bro.
Jake
Yeah, I don't. I don't think I made it to air.
Alexis
Yeah.
Jeffrey
Okay.
Alexis
Okay. And did you share yours?
Jake
Yeah, I told her about one time I went to a party and it had really bad music. And then I met a really cool girl.
Brooke
Hey, that is a nice move.
Alexis
Oh, the girls don't get the most embarrassing moment. That's rude, though. I mean, you're saying me making a joke.
Jake
I was embarrassed for this guy.
Jeffrey
You're embarrassed for the DJ playing the bad music. That's who you're embarrassed for?
Jake
Yeah.
Jeffrey
Okay.
Alexis
I'm gonna tell you, I'd be disappointed in that answer. Yeah, I know you're trying to be funn, but it's like she just shared something vulnerable and actually embarrassing. You just did a cop out.
Jake
I mean, it was a joke. I. You know, I was.
Alexis
You know, I mean, I get it.
Jeffrey
Were you able to recover after that moment?
Jake
Yeah. Yeah. I mean, it felt like everything was all right.
Jeffrey
Okay, well, how did it end?
Jake
We got the bill, and then she insisted on going Dutch.
Alexis
That's good, though. Don't you like that?
Jake
Yeah, I mean, I have no problem with it.
Jeffrey
How did she insist? Did you offer to pay? And then she was like, no, I insist, or how did that get out?
Jake
Yeah, yeah. And she, like, immediately asked for my Venmo. Like, I don't know. Maybe she's had, like, bad dates in the past where a guy expected something.
Alexis
I think that's like, majority of dates, honest. Yeah. It's not just, hey, no. Expected something in return. Like, whether it's a kiss or another date. It's like, if you pay him, you don't feel pressure to have to, like, do anything. But I would say, like, the majority of men come off that way.
Jake
Yeah. I mean, obviously I would like something to happen, but.
Brooke
Yeah, but that's not your intention. You're like, cool, you can pay, I can pay.
Jake
It wasn't my intention. Correct, Correct.
Jeffrey
Okay, so what's happened since then?
Jake
Yeah, so we had a hug and a kiss on the cheek, and we went our separate ways, and I texted her, like, a day or two after that, just said, hey, what's up? And she answers. But, like, I can tell that, like, she's kind of just answering because she feels obligated. I don't know. It doesn't feel like vibes off.
Kim
She's really.
Jake
Yeah. Like, she's really with it.
Alexis
Yeah. And she's not trying to plan anything else.
Jake
Yeah. Like, I've hinted at. Oh, like, there's a game coming on next week, you know? Yeah, yeah. Like, come over to my house and, like, check out the game or whatever.
Jeffrey
You know, there's not going to be enough bad music at those games in order to attend a terrible venue, because.
Jake
I d. In my house.
Alexis
I think they should only go to open mic, actually.
Jeffrey
That'll give you something to bond about all over again and hate on. So let's try and set that up for you when we come back. We're gonna call Kim and try and get you a second date update with the worst music ever right after. Oh my God.
Brooke
Text in a request.
Jeffrey
Second date update.
Alexis
Reach Reach for the sky.
Jeffrey
When you think of subpar music, maybe you picture a certain 12 year old Jewish boy singing his original song, Reach for the sky.
Alexis
Y want you to be quiet so I can hear you when you're little.
Jeffrey
I'll tell you, I'm encouraging people to touch a mood, a moon beam, whatever the hell that means.
Alexis
I like it.
Jeffrey
And I can only imagine this song was playing during Jake's first date with Kim where they bonded over their mutual hatred of the awful playlist coming over the restaurant speakers.
Alexis
Dude, I'm pretty sure I've been to at least two birthday parties where I heard that banger.
Brooke
Yeah, you got to put it on Spotify, dog.
Jeffrey
It's spreading. Yikes. There were highs and lows for sure, but at the very end of the night, they both agreed to split the Jake ended up getting a kiss. But the problem is now Kim is acting a little distant. Even though she is answering texts, it just doesn't feel like her heart is in it.
Alexis
I think it was a cheat kiss. I mean, just important to specifically.
Brooke
You're right, it's not like it was.
Alexis
Gonna make out right. Isn't that right? Am I right on that Jake point.
Jeffrey
Where on your body she kissed you?
Jake
Yeah, I mean, yeah, it was, it was on the cheek. I mean, you know, it was. It's what I would expect.
Alexis
Yeah.
Brooke
You know what, I think a kiss on the cheek is cute because it's just like, oh, I just don't want to kiss you yet. But like you're doing good, you know, it's like a nice message.
Alexis
Like, you don't gross me out.
Brooke
Yeah, yeah, you job tonight or you boost me out.
Alexis
I don't want to touch your mouth.
Brooke
Alex's kiss all the cheek because his mouth smells.
Jeffrey
Well, hopefully there are more kisses to come. If we can do our jobs right on this and not just cheat kisses, we'll find out.
Alexis
I mean, if it starts to go south, we just put your song on and she's back in the game.
Jeffrey
Hope the kisses don't go too far south, but let's just call her, we'll see if she picks up. And we're going to try to do this here. You ready, ma'?
Alexis
Am?
Jake
Yeah, man. Cool.
Jeffrey
Awesome.
Jake
Here we go.
Kim
Hello?
Jeffrey
Hey, is this Kim?
Kim
Yeah.
Jeffrey
Hey.
Brooke
Hello, Kim. Good morning.
Jeffrey
You don't have to be afraid of us. We're just a harmless morning Radio show called Brooke and Jeffrey in the Morning. I'm Jeff. You may know me from the hit song Reach for the Sky.
Alexis
Reach. Reach for the sky.
Kim
Oh, my God.
Alexis
Wait, you do know it.
Jeffrey
Wait, do you. Please tell me you don't recognize that.
Kim
I've heard your show before.
Brooke
Okay.
Jeffrey
Oh, no, it's the normal answer.
Alexis
No. Oh, no, it's. Thank you. That's the answer.
Jeffrey
Okay. Thank you for picking up the phone, Kim. If you're familiar with the show, then you might be familiar with our second date update segment.
Kim
Unfortunately, yeah.
Alexis
Oh, you are. You do know him.
Jeffrey
Okay.
Alexis
Since he responded that way.
Jeffrey
Well, unfortunately or fortunately, you are part of one now. So congratulations.
Brooke
Welcome, kid.
Alexis
Welcome to the club.
Kim
Yay for me.
Jeffrey
That's right.
Alexis
I'm gonna take that sincerely.
Jeffrey
We will. And we're calling on behalf of a guy that you went out with recently. A guy named Jake.
Kim
Oh, my gosh.
Alexis
What?
Kim
Jake?
Alexis
Yeah.
Jeffrey
Yeah.
Alexis
Worse than the reaction to us, which is hard. Ye.
Jeffrey
You remember him?
Kim
Yeah, I remember Jake.
Alexis
He seems like a really nice guy.
Jeffrey
Because, you know, we spoke to him. But we're wondering what you thought about the date.
Kim
I mean, it was like one of the nicer dates I've been on in a while.
Brooke
That's not what I was expecting you to say.
Alexis
Why are you disgusted by that? I know.
Brooke
It's like, ew, a girl. A guy who could take care of a girl.
Alexis
Ew.
Jeffrey
Why are you saying take care of her? I mean, she ended up paying for half anyway.
Brooke
I just meant he chose a nice restaurant. Like.
Kim
Oh, he. He tells you that.
Alexis
That you guys went Dutch at the end. He said you insisted. Yeah. Venmoing him. Yeah, Yeah.
Kim
I mean, that's the problem.
Alexis
What do you mean?
Jeffrey
What?
Alexis
What? The problem is that you wanted to pay for yourself and you did.
Kim
No, no, like, not that part. Like, that part's fine.
Alexis
Okay.
Kim
I'm talking about, like, after the date. I venmoed him.
Alexis
Yeah.
Kim
For my drinks. And.
Jeffrey
Okay.
Kim
Like, his Venmo history popped up.
Alexis
Oh, yeah. I love looking at people's Venmo history. Put mine on private.
Brooke
Yeah, mine's on private. But I see people all the time when I pay them.
Alexis
I'm like, oh, what was on it?
Kim
It was diabolical. I mean, all of these ladies, like, Trish has a kissy face next to it, and then Brittany has a dress emoji next to it, and then Lisa has a gift box next to it. Like the list.
Jeffrey
These are prior transact that Jake has done what, Giving money?
Kim
Yeah, these are prior Transactions. He's sending these girls money.
Alexis
I thought you found the only man that was finally getting paid by ladies.
Brooke
Like, what's your trick?
Alexis
I see. It's the opposite.
Jeffrey
He's giving out money to a bunch of women.
Kim
He's not a gigolo. I think he's a sugar daddy. And we're not exclusive. We just, you know, it was one date. I get it, but I'm not into, you know, like, guys just dating multiple people at the same time.
Alexis
Wait, hold on. Are you upset that he's dating other people? Are you upset that you think he's a sugar daddy?
Kim
Like, I don't know what it is, but in the last month, it's just a ton of women. It's a ton of emojis, and to me that makes a ton of red flags.
Alexis
But you're also jumping to a lot of conclusions. Like, what if he's in a fantastic book club with a bunch of ladies?
Jeffrey
Yeah, that's highly likely.
Alexis
Problem is they say to put random ones so that they can't tax.
Brooke
Yeah, I didn't think about.
Jeffrey
Because the thing is, it sounds like you never asked him about it, right, Kim?
Kim
I mean, I didn't have to. It's right there.
Jeffrey
Well, yeah, but it could be interesting to hear the explanation behind those transactions.
Brooke
I wonder too.
Jeffrey
Now, and this is the perfect time to get that explanation because Jake is actually on the other line right now wanting to talk to you. Jake, what type of book club are you in?
Jake
Yeah, I'm not in any book club.
Alexis
Okay, say you're sending into small businesses.
Jeffrey
Come on, talk to Kim here. What's going on?
Jake
I don't have to lie to anybody. It is what it is. I didn't think that she would go through my Venmo history.
Brooke
Well, it's kind of air when you.
Jeffrey
Say it is what it is.
Alexis
What?
Jeffrey
What is it?
Alexis
Yeah. Thank you.
Jake
I bail out. I see a lot of ladies and I pay.
Jeffrey
What do you pay for?
Alexis
Yeah, it's not dinner if you're venmoing them.
Brooke
Yeah, you can use your credit card, right?
Jake
Sometimes I'll pay for the pre dinner or whatever it cost.
Brooke
Wow, the dog is back before dinner.
Alexis
Kim. I can't believe you were right. Yeah, yeah.
Jake
Wait, wait, wait, wait. Listen. Have you never said, oh, it cost me X amount of money to get ready. I have to look good, I have to dress nice for you.
Alexis
We've heard it on our show before.
Kim
Yeah, well, I mean, if you're over here paying for like people, then you can pay for how I Prep for this day because I got new foundation. I got.
Alexis
Oh, there we go.
Jeffrey
Wait, you're gonna get a refund now.
Jake
Wait, so, Kim, you want me to pay for your stuff now? I mean, you really were very insistent on paying, right?
Kim
Well, I mean, before. No, you just seem like a sugar daddy. But, I mean, if you're paying for girls things, then why not my foundation? My Mascara concealer cost $90.
Alexis
Are you just trying to get revenge with the Venmo? I can't tell, Kim. Cause, like, you're paying for your Dr. You wanted to pay, right? Don't you like the independence of paying for your own stuff and not feeling emboldened to somebody?
Jeffrey
And, Jake, by the way, I did have to get ready before I did this segment. Yeah, well, you know, if you're. If you're all about spreading joy or whatever you said before, like, I could use a little bit of joy.
Jake
The key word is ladies. Lady.
Jeffrey
Okay, I can use a lady emoji when I send you the Venmo request if that makes you feel more comfortable.
Kim
I mean, you guys get in line. I'm ahead of him.
Alexis
Okay, get in line.
Kim
You can send for my drink.
Brooke
Wait, do you want your 50 bucks back, or do you want more than that to compensate for the other stuff?
Jake
Yeah, like, how much did it really cost for you to get all dressed up and pretty for me?
Kim
$90.
Alexis
$90.
Jeffrey
90.
Jake
$90. Let's just make it a nice, cool 100.
Jeffrey
I'm giving her more money.
Kim
Perfect.
Alexis
He's, like, buying your affection, Kim.
Kim
It's not my affection. It's a lot of people's affection.
Brooke
I mean, like he said, he's spreading joy.
Jeffrey
He's doing it. Take advantage.
Alexis
So are you not interested in him romantically? It's just a business.
Jeffrey
Well, let's find out. Because, Kim, we would like to offer to send you and Jake on another date. And if you say yes, we will pay for it.
Alexis
Do I get to be a sugar daddy then?
Jeffrey
By this, you were against this the entire segment. You can't just change it.
Alexis
The last into the role of power.
Jeffrey
Okay.
Alexis
All right.
Jeffrey
You're behind me and Kim in the payment line. So Kim get in line first with you. What do you think about Jake giving him another chance?
Kim
I'm gonna say yes on the Venmo payment. No. On the second day.
Jake
Oh, my God.
Jeffrey
Okay.
Alexis
Okay. That's actually pretty smart business.
Brooke
I mean.
Jake
Yeah, I didn't know I was dealing with a businesswoman.
Alexis
Bro.
Brooke
Are you gonna really send it? Have a date with her?
Alexis
Sounds like you met your match, Jake.
Jake
Yeah, I'm gonna send it. I said I would send it.
Brooke
Oh my God. Man of his way.
Alexis
Wait, does that mean Jeffrey's getting paid too?
Jeffrey
Yeah. This hat costs 40 bucks.
Jake
Yeah, we'll just, we'll just keep it like that.
Alexis
Yeah.
Brooke
You're a good guy, Jake.
Alexis
He just said yes because you're cheap.
Jeffrey
Je just made Alexis jealous again.
Alexis
Oh, no. Again. My brother's name.
Brooke
Brooke and Jeffrey in the morning.
Alexis
You can make a difference in someone's life, including your own, with a job in home care. These jobs offer flexible schedules, health care, retirement options and free training. They also provide paid time off and opportunities for overtime. Visit oregonhomecarejobs.com to learn more and apply. That's oregonhomecarejobs.com.
Brooke
Alright, so if you don't know, prime big deal days are coming up soon. Hey, what's up? It's Jose from Brooke and Jeffrey in the morning. It's happening October 7th and 8th and there are going to be some crazy big deals. I mean off the hook discounts up to 40% off. So it's the perfect chance to treat yourself to a little something you've had your eye on. Whatever works for you, you make it. Here's what I'm thinking. When I want to treat myself to something, I like to order up like a nice steak, right? So maybe during prime big deal days I could pick up some high end steak knives and some serving platters and some plates, right? Basically I'm going to treat myself to some things to help me treat myself all right, whenever I want. This is next level thinking, you guys. And you know, because Amazon has like everything you can do the same. During prime big deal days, you can find just the thing to treat yourself up to 40% off. You got to do it. Get ready. Prime big deal days are coming soon. October 7th and 8th.
Jeffrey
You guys, I have some disappointing news.
Alexis
What's that?
Jeffrey
Management says I can't accept payment from listeners. Just cuz I got all dolled up.
Brooke
For the second day and I thought.
Alexis
You look so good.
Jeffrey
I really, I thought so. But now apparently I have to return the money and quote unquote, show proof that I did.
Alexis
Oh wow. And those pretty boy pants you thought you were going to get paid for.
Jeffrey
It's a rough day.
Alexis
Dude, how did this girl switch so fast? I guess she just wanted to get paid. She didn't want to get. Yeah, I wouldn't say the thing that rhymes with paid. Yeah.
Jeffrey
Oh yeah.
Brooke
Spade, sure. Actually the opposite.
Alexis
Yeah.
Jake
Yeah.
Jeffrey
Well, she's not alone. We're actually getting a lot of texts at 78592 from our listeners who want to get in line to get paid. If he's still offering.
Brooke
I mean, if he's like, I'm handing out free money, like, why not take free money?
Alexis
But it's obviously not working for him. He's like coming to us for help.
Brooke
But if it makes him happy, whatever, everybody wins.
Jake
Exactly.
Brooke
That's what he said.
Jeffrey
He said is his way of spreading joy.
Brooke
Let him spoil people.
Alexis
Only with hot women. Yeah, not the, not maybe the people that need it.
Brooke
But, you know, again, let him spoil people.
Jeffrey
Another way to spread joy is to share our podcast.
Alexis
Oh yes.
Jeffrey
So go tell a friend or force a family member to listen. Spread some joy at Brooke and Jeffrey.
Brooke
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And listen to the new daily Variety.
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Hey, what's up?
Brooke
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Check out the new season of Reasonable Doubt, now Streaming on Hulu, L.A. s most successful attorney Jack Stewart, defends a young actor accused of murder. Follow Emma, Yazzie Coronaldi, Morris Chestnut, Joseph Sakura and guest stars Kashdahl and Lori Harvey as they fight their personal battles in the spotlight of the year's most sensational trial in the place Pursuit of Justice. Every move counts. Reasonable Doubt, Season three, now streaming on Hulu and Hulu on Disney plus for bundle subscribers. Terms apply.
Release Date: September 26, 2025
Hosts: Brooke, Jeffrey, Alexis (with guest Jake and Kim)
This episode centers on another classic “Second Date Update”—where hosts help a listener figure out why a promising first date didn’t lead to a second. Today’s story involves Jake, who enjoyed a quirky first date with Kim, but now Kim is acting distant, and he’s clueless as to why. The episode takes a comedic turn around discussions of going Dutch, Venmo histories, and modern dating red flags.
Meeting and Connection:
The Date Night:
Going Dutch:
Aftermath:
Initial Reaction:
Kim's Perspective:
Venmo Investigation:
Kim’s Suspicion:
Jake’s Defense:
Jake admits sending women money via Venmo, but says he does it to offset their pre-date expenses or as part of the evening.
He tries to normalize reimbursing women for their date preparations, and challenges Kim:
Kim’s Reaction:
Hosts' Offer:
Kim’s Final Answer:
Hosts’ and Jake’s Reflections:
On going Dutch:
On Venmo snooping:
On Jake’s motivations:
Kim’s business-minded close:
The hosts on Jake’s “charity”:
True to Brooke and Jeffrey’s style, the episode is full of playful banter, snarky commentary, and a willingness to call out cringe-worthy dating behavior on both sides. The unresolved tension between modern independence and the shadow of “sugar daddy” culture is played for laughs, but also points to the complications of digital-age dating.
Fans of the show will appreciate Alexis’ sarcasm, Brooke’s straight talk, and Jeffrey’s attempts to instigate drama—plus the running jokes about “Reach for the Sky,” bad music, and Alexis’ own “forbidden fruit” (her brother Jake’s name).
In Short:
Kim’s Venmo snooping turned up enough red flags for her to take the money and (literally) run, passing on romance with Jake—who’s left, hilariously, still unfazed and still open to “spreading joy” via his Venmo account.
This summary skips advertisements and peripheral banter, focusing on the episode’s main story and comedic highlights.