Second Date Update UPDATE: Pre-Block

Summary

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Podcast Summary

Brooke and Jeffrey: Second Date Update UPDATE: Pre-Block

Date: January 15, 2026
Episode Type: Second Date Update + Follow-Up ("Update Update")

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Episode Overview

This episode of "Second Date Update" features Aaron, who was abruptly blocked by his Hinge date, Jenna, shortly after their first meetup. The hosts investigate the surprising cause, leading to an unexpected and entertaining turn as the pair navigates potential romance, sugar-daddy offers, and a complete role reversal. The show includes the original segment and, notably, a special update months later.

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Key Discussion Points & Insights

1. Aaron Gets Blocked – The Initial Mystery

[03:15 - 06:31]

• Aaron reached out in confusion after Jenna blocked his number right after their first walk together.
• The hosts joke about their own blocking practices with listeners, setting a playful tone.
  • Quote (A, 05:53):
    “If you’re rude to any of us—blocked… if you compliment me and tell me I’m cute and fancy, I’m a shy boy, I don’t like compliments that much.”
  • Brooke (B) tries to mediate, noting their listeners are “so nice,” downplaying host A’s exaggerated paranoia about blocking.

2. The First Date Recap – The Walk Gone Awkward

[07:03 - 09:44]

• Aaron and Jenna matched on Hinge and impulsively met up within an hour for a walk—her with her dog, him solo.
• Aaron made a joke about deleting Hinge because of too many matches.
  • Quote (Aaron, D, 08:33):
    “Yeah, I ended up making a joke—‘I had to delete Hinge ‘cause I had a full inbox, people kept trying to get with me...’”—which he worried might have come off as arrogant.*
• Jenna blocked his number within an hour after the walk.
• Hosts playfully dig into his walking style, considering if he walked too slow or too fast.

3. Calling Jenna – The Real Reason for the Block

[12:49 - 15:19]

• Jenna confirms she blocked Aaron—intentionally.
• She was surprised Aaron joined without a dog, but quickly got over it.
• The real issue: Aaron asked Jenna her credit score early in the date.
  • Notable Quote (Jenna, C, 14:29):
    “Then he asks me, ‘So what’s your credit score? Should I be worried?’”
  • The hosts are shocked—it comes off as way too personal for a first date.

4. The Truth Revealed – Financial Arrangements Exposed

[16:02 - 18:33]

• Aaron admits he asked seriously, seeking a long-term partner and wanting to be efficient. Then, the twist:

  • Quote (Aaron, D, 16:44):
    “I was kind of asking to see if you’d be interested in, like, a no strings attached financial compensation thing.”

• Hosts clarify: a sugar-daddy arrangement?

• Aaron explains he wanted to “pay for companionship” if Jenna was interested and that her credit score was to see if she might need the help (“looking for a low credit score”).

• Jenna is initially shocked but then open-minded.

  • Quote (Jenna, C, 18:00):
    “I mean, realistically, I think depending on the amount of money, anybody could be interested.”

• They end up agreeing to talk further, Jenna agreeing to unblock Aaron.

  • Memorable Exchange:
    • (A, 19:07): “And they say romance is dead.”
    • (B, 19:09): “That could be a fun new segment!”

5. UPDATE: The Outcome Months Later

[20:21 - 22:33]

• Jenna and Aaron appear on the update segment and share what happened:

  • They met up again. Jenna gave the sugar baby arrangement a shot.
  • Aaron financially supported Jenna for several months (helped pay for rent, car, etc.)
    • Quote (Aaron, D, 21:07):
      “I was helping her pay for her rent. I was helping her pay off her car. It was nice for a few months.”
  • Aaron lost his job due to being replaced by AI, leaving him unable to continue the arrangement.
  • Role reversal: Jenna started supporting Aaron, practically becoming his “sugar mama.”
    • Quote (Jenna, C, 22:12):
      “I kind of became a sugar mama. I kind of like being the sugar mama better.”

• They reveal the relationship became more “normal” and Aaron has moved in with Jenna.

  • Notable Banter:
    • (A, 22:45): “If you take the titles out, you’re just in a normal relationship—‘you help me when I need it.’”
    • (C, 22:33): “It’s not what we originally talked about. I mean, he ended up moving in with me and it’s working great.”

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Notable Quotes & Moments

• [05:53] A: “If you’re rude to any of us—blocked. If you criticize our hero of the week, blocked. If you compliment me... I’m a shy boy, I don’t like compliments that much.”
• [08:33] D: “Yeah, I ended up making a joke—‘I had to delete Hinge ‘cause I had a full inbox, people kept trying to get with me...’”
• [14:29] C: “Then he asks me, ‘So what’s your credit score? Should I be worried?’”
• [16:44] D: “I was kind of asking to see if you’d be interested in, like, a no strings attached financial compensation thing.”
• [18:00] C: “Realistically, I think depending on the amount of money, anybody could be interested.”
• [21:07] D: “I was helping her pay for her rent. I was helping her pay off her car. It was nice for a few months.”
• [22:12] C: “I kind of became a sugar mama. I kind of like being the sugar mama better.”
• [22:45] A: “If you take the titles out, you’re just in a normal relationship—‘you help me when I need it.’”

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Key Timestamps for Important Segments

• [03:15]: Introductions and Aaron’s initial confusion about being blocked
• [07:03]: Aaron recounts the first date/walk
• [12:49]: Hosts call Jenna for her side of the story
• [14:29]: Jenna describes the credit score question
• [16:44]: Aaron admits to proposing a paid arrangement
• [18:00]: Jenna’s open-minded response about “depending on the amount”
• [20:21]: UPDATE – follow-up months later with Jenna & Aaron’s new circumstances
• [22:12]: The “sugar mama” twist revealed

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Tone & Style

• Highly conversational, playful, and irreverent throughout, punctuated by frequent jokes and banter among the hosts.
• The guests (Aaron & Jenna) maintain an open, slightly incredulous, but ultimately good-humored tone.

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Useful For…

• Anyone interested in modern dating mishaps and the unexpected places real-life relationships can go.
• Listeners looking for a blend of entertaining awkwardness, genuine human connection, and a dash of “stranger than fiction” romance.

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Episode Takeaway

A seemingly failed first date—not only explained but rebooted—ends up as an unexpected success, turning from blocked numbers to a mutually supportive relationship (with some unconventional, sugar-flavored twists along the way). As the hosts put it: take away the titles, and it’s just two people helping each other when they need it most.

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Transcript

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[B]

Hey, we got a lot of new listeners finding us again. Thank you so much. It's Brooke and Jeffrey. This is the second date Update podcast and just so you know, the show is still going. There is a lot of people that are listening to episodes from 15 years ago. You guys are stuck in 2013 and I hope one day this finds you.

[A]

I know it's funny because some people are like, oh my God, love the show. I've been changed everything all day for years and some people just found us sounds a little different.

[B]

Yeah, there's a lot of like, hey, can you guys keep doing second date updates? And like we're here. Yeah. So. So thank you for finding us and thank you for being in the present day. We do have a brand new episode today. It's an update update. So remember we're gonna play the original where the couple was on with us and then in part three, skip the ads. In part three we get them back on the phone and see what has happened since. So before we get there, what do you got for comments, Alexis? Yeah, Noel Lopez said do they read these comments on YouTube. I've been wanting to comment and I don't know if they'll see it. Yes. Yeah, so yes, we check. Brooke and I, we are looking at all the comments literally everywhere. Dude. And the ones from 15 years ago. We see you. Yeah, we see you.

[A]

We see you all.

[B]

So thank you so much. We know it takes time and energy out of your day to leave a comment and even just find the show and listen. So we truly appreciate it. We got your brand new episode starting right now.

[A]

Sometimes in the dating world and just in life, you'll get asked strange out of left field questions and before you crinkle your nose and jump to conclusions, it's important to consider not just what they're asking, but why are they asking it. What's their motivation? Like? In today's call, one of our listeners asked his date a question that might be considered rude and insensitive. Until you learn why he's asking, and suddenly it's kind of sweet feeling. It's not. Kinda.

[B]

Whenever he says kinda almost, you're gonna.

[A]

Hear the shocking question at why it was totally not inappropriate and creepy for him to ask him. Because we've got a special second date update update coming up right after this.

[B]

Brooke and Jeffrey in the morning. Second date update.

[A]

We have a text board at 78592 where listeners can send texts into our show. And unfortunately, sometimes we do have to block people if they cross the line with us.

[B]

Honestly, it's been so long since I've blocked anyone, though. Like, I feel like years. Oh, yeah.

[A]

Anytime you come at the girls or you're like, brook's a B word, I. You're blocked. Yeah.

[D]

Okay.

[A]

Only I can say that that's not.

[B]

Happening very often because we're blocking.

[A]

I blocked 10 a day, bro. If you're rude to any of us. Blocked. If you criticize our hero of the week because you didn't like my choice. If you compliment me and tell me that I'm cute and fancy. I'm a shy boy. I don't like compliments that much. Come on, Jeff. Scary.

[B]

Our listeners are so nice. We are not blocking people left and right.

[A]

Too nice, if you ask me. Blocked. That's why one of our listeners, Aaron, reached out to us because he's confused after he got blocked by somebody and he has no idea why. Fight the urge to compliment, Jeff, or you will be blocked right now.

[B]

I was gonna say. Was it Jose? Yeah.

[A]

Oh, I'll block you right away. Aar. What's up, man? Welcome to the show.

[D]

Hey, guys. Thanks for having me.

[A]

Don't you talk bad about the girls. I'm sorry. I'm on edge. He called you guys.

[B]

Oh, my God. I don't care. What is happening? Aaron, how are you doing?

[D]

Oh, I'm doing good. I'm a little confused as to why I got blocked, but I was hoping maybe you guys could help me out with that.

[B]

Okay.

[A]

Hopefully. Did you say anything mean? That's what gets people blocked here.

[B]

I was taking unsolicited pictures or what? I'm curious, are you blocked? Are we talking about text, social media? Like, what are you blocked on?

[A]

Good question.

[D]

She blocked My number.

[B]

Oh, that was really personal.

[A]

Okay, yeah. So tell us about this woman who blocked you. What's her name?

[D]

Okay, so her name is Jenna.

[A]

Okay.

[D]

We matched on Hinge, and we went on one kind of date.

[B]

What do you mean kind of date? Was it like one of those predates where you just meet for coffee for 20 minutes to see if a real date's worth it?

[D]

So as soon as we matched, we started talking, and then we were hanging out like, an hour later.

[B]

What? Oh, like a turnaround on the same day that you matched?

[D]

Yeah. How? Well, so she told me that she was taking her dog out for a walk. So I said, hey, I haven't got my cardio in yet today. Why don't I come with you and we can just talk?

[B]

Oh.

[A]

Oh, you invited yourself to her dog walk. Okay, random Alexis, you're a dog walker. Would this be a good date if a guy.

[B]

Oh, I want dogs with guys all the time.

[A]

Oh, that's a yes. Hey, so that's a good date idea. You walk the guys too Little leash on them.

[B]

And I can't say that. Oh, no, but I do make them.

[A]

Clean up the dog poop.

[B]

You don't want to do that. Why did Jeff look so hopeful when he asked that?

[A]

I didn't know that that was a service. If it's offered out there, I got to look it up. But how did the dog walk go with Jenna?

[D]

It was mostly small talk. It was kind of more like a predate than anything where we were looking to know each other.

[B]

And that's okay. I mean, that's to be expected.

[A]

Yeah.

[B]

What was the, like, chemistry or attraction level?

[D]

I thought I was picking something up.

[B]

Okay.

[A]

Okay. She didn't seem like she cut it off. Like, how did it end?

[D]

So, yeah, we were talking about Hinge, and. How are you doing on Hinge? And I ended up making a joke. We're like, yeah, I ended up having to delete Hinge because I just. I had a full inbox and people kept trying to talk to me and get with me. It ended not long after that.

[B]

That was supposed to be. That was supposed to be a joke?

[D]

Yeah. See, I. Maybe I messed up, and she just thinks I'm full of myself when I was just trying to be funny.

[A]

Sure, but that doesn't seem like enough to want to block your number from ever wanting to contact you.

[B]

Did things change after that moment?

[D]

Not real. It ended not long after that, so. I don't know, maybe she wanted to cut it short.

[A]

Is it possible that you're Just a really slow walker and it pissed her off.

[B]

Or the opposite. Too fast or. Yeah, steppers.

[A]

You got to match her stride for stride.

[B]

Or just one of those guys who walks in front of a woman the whole time, like a step and a half. It drives me nuts.

[A]

How's your walking?

[D]

I felt like I matched her stride for stride, but I wasn't really focused on that.

[A]

Okay, let's say you got a pass on the walking. What else could it have been? Brooke?

[B]

I mean, I'm just wondering, when you got blocked, did you, like, leave the date and immediately she blocked you, or was there a couple of texts back and forth beforehand? Yeah, good question.

[D]

I tried texting her maybe half hour later, and it was. It didn't go through, so it seems like she blocked me almost immediately.

[B]

I didn't know you could tell that you were blocked. It never sends. It just never says delivered. It's unfortunate. You can check. Months later, it's still not delivered. Wow. Yeah.

[A]

We're all experts on different areas of dating in here, so. Okay, how long has it been since you got blocked?

[D]

Been about a week at this point.

[B]

You guys, what if it's just an accident? What if she just got, like, you don't act. Two left thumbs. I don't know. Sometimes I accidentally hit buttons in my back pocket or something.

[A]

And, like, she would have to have a lot going on in her pockets to be like, delete, block, confirm, swipe left, unmatched.

[B]

You never know what a right butt cheek can do.

[A]

They went on a dog walk. Very ambidextrous cheek back there.

[D]

But, I mean, yeah, hopefully that's it. But I had a good time with her. I'd like to see if there was something more there.

[B]

Yeah, okay.

[D]

Okay.

[B]

Yeah. She should definitely give you another chance.

[A]

Or at least an explanation for why you've been blocked. We're gonna call her right now. Hopefully she hasn't blocked us already. But if she answers, I'm sure a lot of people have, but if she picks up, we'll ask her all the important questions and try and get you your second date update right after this.

[D]

Thanks, guys. All right, man.

[A]

Hold on.

[B]

Brooke and Jeffrey in the morning. Second date update. We're in the middle of a second date update update, and we're gonna find the couple is doing right after you hear part two.

[A]

Just to recap real quick, if you missed part one, one of our listeners, Aaron, hung out with a lady, and that happened within an hour of matching. They were on a dog walk together. Yeah. The crazy part is that Walk only lasted a half hour. An hour later, he was already blocked. I mean, this girl works fast. Yeah, and we're trying to help Aaron get some answers about what he did wrong. Or maybe it was just a miscommunication that caused him to get blocked. We don't really know. At least we can pinpoint, like, the hour and a half time frame.

[B]

We asked all about whether she liked him and what it was like with him. We never asked, did the dog like you?

[A]

Oh, did the dogs like each other? Did one bite the other?

[B]

I don't think he had a dog. Yeah, I don't think she was just joining him on her apologies.

[A]

I thought he had a dog, too. Aaron, could you get a read on Jenna's dog's feelings towards you?

[D]

I think he was kind of focused on the walk. He gave me a sniff, he sussed me out, but he wasn't super good.

[B]

I see. I think that's okay as long as there's no growling or, like, nipping.

[A]

Yeah, I mean, growling and nipping on my dates, That's a good thing.

[B]

Oh, right from the beginning.

[A]

I'm dying to get nipped. Calm down.

[B]

Boy. Sniffing of so many butts.

[A]

Yeah. So I don't know any last words. Aaron, before we dial the number, at.

[D]

The very least, I hope she answers and I hope she told me what I did wrong.

[B]

Yeah, okay. That's a good attitude. You're going in to learn something. I like that.

[A]

Let's set that bar super, super low. So here we go. I'm dialing the number right now. Let's see if she picks up.

[C]

Hello?

[A]

Hey, is this Jenna?

[D]

This is.

[C]

Who's this?

[A]

This is a. Actually a radio show called Brooke and Jeffrey in the Morning.

[B]

Hey, John. Welcome to the show.

[C]

I'm sorry, who?

[B]

Yeah, there's a lot of us in here.

[A]

We're a radio show, and we do this segment that you're on right now called A Second Date Update, and one of our listeners reached out about you named Aaron.

[C]

Oh, okay.

[A]

Okay.

[B]

That response sounds like everything was on purpose.

[A]

We figured you might not have the best reaction because we heard that after the date, you blocked. And he just doesn't know why or if that was on purpose.

[C]

Oh, yeah, no, I. I definitely blocked him on purpose.

[A]

Okay, so what we know is that you guys went on a dog walk and it didn't seem to last very long. So maybe you could tell us your version of the hangout, and that would help us understand a little more clearly.

[C]

Okay, well, I guess to start with, I thought he'd show up with his dog too.

[A]

I assumed he had a dog already. The girls had to correct me.

[B]

Why would you assume that?

[C]

Well, because we met up to walk our dogs, so I thought. But we met up to walk my dog. He literally just wanted to walk with me while I walked my dog.

[B]

That just sounds like a miscommunication. Didn't he say you need to get his cardio in for the day?

[A]

I would have blocked him for that too. Get him, Jeff.

[C]

That's not why I blocked him.

[A]

Oh, okay, okay.

[B]

So are you saying you're disappointed that he didn't have a dog?

[C]

I was surprised, but I got over it quick. It wasn't that big of a deal. We were getting to know each other.

[A]

So where did the date shift for you in your mind?

[C]

Well, then he asks me, so what's your credit score? Should I be worried?

[B]

He's trying to be funny.

[A]

He told us that there was a few jokes that he tried to make and they didn't quite land.

[C]

It did not sound like a joke. He actually wanted to know.

[B]

Did you tell. Wait, did you tell him?

[C]

No, I didn't tell him. I thought it was so out of line.

[A]

Oh, I feel like that's less, like, intense than it used to be.

[B]

People in a 30 minute conversation.

[C]

Yeah, it was really quick. I mean, I don't even know that we should be talking about that on a fifth or a sixth date.

[B]

Are you sure he wasn't joking though? Like, when you didn't tell him, what kind of response did he give you?

[C]

We both just kind of laughed it off. But he definitely still seemed like he seriously wanted to know.

[A]

Okay, it's possible that it was a joke and it just didn't come across the right way. And the best way to find out is to have you tell it again. Well, to at least have you talk to him about it. Because you might not know this, Jenna, but Aaron's on the other line right now listening to this conversation.

[C]

The guy I blocked is on the phone.

[A]

Yeah, we haven't blocked him yet.

[B]

But you know, when you say it that way, it doesn't feel as fun.

[A]

Yeah, yeah, it's very true. Hopefully he has an explanation, though. Aaron, are you there?

[D]

Hey.

[A]

Yeah, hey, jokester. Hey, you wanna know?

[B]

Know her Social Security number next date too.

[A]

Or at least say something to Jenna.

[D]

I'm sorry I made you feel uncomfortable. It's just in today's dating culture, I'm trying to find a long term partner and. Right. And not waste time.

[B]

Are you serious?

[C]

See, I knew you weren't joking. I knew you actually wanted to know my credit score, and that's a lot.

[A]

But he wanted to know it for honorable reasons.

[B]

Because he wants to be with you forever. Unless you have a score of under 750.

[A]

Yes. We're not getting approved for loans. This love is not real. That's got to change how you feel about it a little bit, right, Jenna?

[C]

No, not at all.

[A]

Oh, man.

[B]

Oh, man.

[A]

Aaron, you see how that's kind of weird? What if she's the love of your life and she has a bad credit score?

[B]

I mean, it's not very romantic.

[D]

Yeah, well, to be 100% honest, I was kind of asking to see if you'd be interested in, like, a no strings attached financial compensation thing.

[B]

What?

[A]

Like a sugar daddy situation?

[B]

Do you know what he's talking about?

[C]

I mean, it sounds like he's looking to be my sugar daddy.

[A]

That's how it sounds to us.

[B]

I think I heard it as he wants you to be the sugar mama. That's why he's asking your score.

[A]

Can you clarify, Aaron?

[D]

Closer to what she said? I don't like that term. I don't see it like that. I would just be paying for companionship.

[B]

If she's the one getting paid, why does her credit score matter?

[D]

Well, I. I need to know if it's something she's interested in and if her credit score is low enough, then.

[A]

You can build it. I see.

[B]

You were looking for a low credit score this whole time. I was thinking of a good one.

[A]

Wait a minute. You want to, like, help her life and, like, financially?

[B]

I feel like there's a different app you should go on than Hinge.

[A]

Oh, and Alexis can recommend four of them that she uses after this is done. But, Jenna, are you. Are you hearing this?

[C]

Yeah, I'm hearing it.

[A]

Listen to her voice. Pretty shock sounding.

[B]

Are you interested in something like that?

[C]

I mean, this is definitely not the way that I expected this to go. I mean, I was with you guys. I thought that he was making sure I had a flawless credit score here. I mean, realistically, I think depending on the amount of money, anybody could be interested.

[B]

Yeah, I mean. Wait, now you're negotiating?

[A]

Wait a second.

[B]

Wait a minute.

[A]

We have to reach. What does this mean?

[B]

This is a totally different type of relationship.

[D]

Certainly is, but. Oh, are you saying you are interested?

[C]

I don't know. I am open to thinking about it.

[A]

Okay, well, maybe you're open to the idea of unblocking Aaron and meeting up with him one more time, and we would pay for it. It.

[D]

We don't even need to go out. I can send you a couple texts. We can see if you're into it. Okay.

[A]

A little. Little negotiation starter. Sweet. Well, that saves us money and I love that. So it's up to you, Jenna. Will you or will you not unblock Aaron?

[B]

Oh, that could be a fun new segment.

[C]

I think I'll unblock him.

[A]

Wow, look at that.

[B]

And they say romance is dead.

[C]

Brooke and Jeffrey in the morning.

[A]

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[A]

Last time we spoke to Jenna, she was considering the option of being a potential sugar baby to Aaron.

[B]

Oh, my God.

[A]

So let's just get to the obvious question because she's on the phone right now. Jenna. Did that end up happening?

[C]

So we did end up meeting up after we talked to you guys.

[B]

Unblocked. I bet you had so many thoughts going through your head before that meetup.

[C]

I did, but I decided to give it a shot.

[A]

Of course.

[D]

Okay.

[A]

It's a big brain.

[B]

So wait, so you. What was the exchange here?

[D]

Oh, yeah. Yeah. So.

[A]

Oh, Aaron, you're there.

[B]

I thought it was just her. You didn't say anything bad.

[D]

I was helping her pay for her rent. I was helping her pay off her car. It was nice for a few months.

[A]

For a few months? A few months? Yeah. What do you mean?

[D]

Well, so I ended up getting laid off because I was made redundant by AI. Oh.

[A]

Oh, no.

[D]

Yeah.

[B]

Taking out sugar daddies left and right.

[D]

Yeah, I couldn't afford to do the sugar daddy thing anymore.

[A]

Oh, no. So then what now what happened? You're in a normal relationship now. Ew.

[C]

Well, we had actually. We had gotten to a point where our original arrangement was working pretty well. I never thought I was that girl, but it really worked. And so we had actually been talking about me quitting my job.

[B]

Oh, please tell me you didn't do that before he got laid out.

[A]

That would be a bad stitch.

[C]

Fortunately, no. But once Aaron did get let go, I ended up really pulling some extra weight at my job and, you know, picking up all the extra hours and stuff like that and roles kind of reversed and I kind of became a sugar mama.

[A]

I hate to say that, but I kind of like. I know the irony. I'm glad.

[B]

How is it being in the power position?

[C]

I kind of like being the sugar mama better.

[D]

Okay.

[A]

Wow. That's nice. Well, I'm glad to hear you two are. It sounds like happy and together. Maybe it's not the relationship you started with. Maybe it's better.

[C]

It's not what we originally talked about. I mean, he ended up moving in with me and it's working great.

[B]

It's funny because if you take the titles out, you're just in a normal relationship.

[A]

You help me when I need it. This is a weird new thing we're trying. It's really strange, but I like it. All right, well, keep us updated, you two. Thanks for emailing the show. It's Brooke and Jeffrey in the morning. You need to check out legends.com today. Legends is a free to play social casino and sportsbook with all of the games that you know and love. They even have Plinko and live blackjack and that's L E G E N D z dot com. Whether you're a seasoned player or just starting out, their games are designed to entertain and thrill. The best part is you get free coins every day so you can play for free. And redemption to your bank account is instant. It's legit and new players get an exclusive welcome bonus. Join thousands of players on legends with a Z.com today. No purchase necessary Legends International Void we're prohibited by law. 18 + terms and conditions apply at CVS.

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