Second Date Update Classics: High School Holiday Hangout + Trial By Separation

Summary

Brooke and Jeffrey: Second Date Update Classics — "High School Holiday Hangout + Trial By Separation"

Date: December 27, 2025
Podcast: Brooke and Jeffrey: Second Date Update
Episode Theme:
A holiday-themed double feature of "Second Date Update" where the team investigates why two different listeners were ghosted after their first "dates"—one a high school homecoming gone awry, the other a rebound attempt following a separation.

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Episode Overview

Brooke and Jeffrey serve up two memorable "Second Date Update" call-ins, focused on the challenges of rekindling connections during the holidays and wading into post-divorce romance. Both updates reveal that holiday gatherings—and the emotional baggage we carry—can quickly derail new relationships, sometimes in unexpectedly hilarious ways.

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Segment 1: High School Holiday Hangout (Simone & Jack)

[Starts ~03:13]

Discussion Points & Insights

• Reunion Setup:
  Simone returns home for the holidays and reconnects with Jack, an acquaintance from high school, via Facebook. Intentions are ambiguous, but there's some low-key romantic interest.

  • Simone: “Let me tell you, I will not miss an opportunity to show off my glow up.” (06:16)

• Family Ambush:
  Jack picks up Simone after a family dinner. She invites him in "just for a minute," but he ends up hanging out with her entire family—playing games, enduring playful ribbing from a slightly tipsy dad.

  • Simone: “He was very cool and came in, and we all were just hanging. It was really sweet.” (07:00)
  • Dad's classic line: "What are your intentions with my daughter?" (08:12)

• Escape and Ghosting:
  Jack abruptly leaves, citing a "friend emergency" (later admitted as fake), and never responds to Simone again.

  • Simone: “We’ll make more plans, we’ll text, and we’ll figure it out. And then just never heard back from him.” (09:14)

The Second Date Call with Jack

[Starts ~12:13]

• Jack answers, initially wary:

  • “I answer business calls during the day.” (12:27)
  • Admits he was interested in Simone but felt awkward about the evening.
  • Deflates a team theory: “Her family was great. Oh, nice.” (14:51)

• The Big Reveal—The Christmas Card:
  Jack explains that he spotted a family Christmas card on the mantle: Simone pictured, snuggled up with another man.

  • Jack: “I see one from Simone with another guy, and they're both snuggled up together. It looked like a couple had sent a card.” (15:27)
  • He left, feeling like he might be the "other man," and didn't want to compete or be part of an emotional triangle.
  • Jack: “I want to be with someone emotionally available... I just don't feel comfortable being with somebody who's seeing other people.” (18:34)

• Simone’s Side of the Story:

  • Says the "Christmas card boyfriend" is not exclusive—just a friend with benefits, doing cards as a running joke so their parents think they're not single.

  • Simone: “We are not exclusive. We are not together. We hook up every once in a while…” (17:46)

  • Promises to end it with the other guy but Jack declines a second date:

    • “I feel like you could have told me that you were getting out of a relationship and I just... I can't.” (19:56)

Notable Quotes

• Brooke (on second date attempts):
  • “It’s like a Hail Mary... hey, what if I break up with the other guy, will you go out with me then?” (21:24)
  • “You made the boyfriend sound like the best option.” (21:47)

Segment Timestamps

• Simone’s story setup: 03:13–09:22
• Jack's call and reveal: 12:13–20:06
• Post-mortem from the team: 21:21–22:28

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Segment 2: Trial By Separation (Thomas & Celia)

[Starts ~22:33]

Discussion Points & Insights

• Thomas’ Situation:
  Recently separated and honest about it in his online dating profile—meets Celia, also separated. Both bond over their "recent sadness."

  • Thomas: “I listed my status as separated. I would normally tell the truth, that's what I do.” (24:25)

• Shared Sadness as a Bond:

  • They connect over failed marriages.
  • “There definitely wasn't a pity party... It was like, bonding.” (27:16)

• The Date:
  Fairly casual, lots of personal sharing, ends with a standard hug. Thomas, eager but not pushy, reaches out afterward but is met with radio silence.

• Call to Celia:
  Initially resistant, she admits the dinner was nice but says a "red flag" came up:

  • She confesses to Thomas she cheated in her marriage, expecting judgment or at least questioning.
  • Celia: “His reaction was just a little too normal for me. I told him the real... I cheated... and he was just like, oh, that's okay.” (34:11)

• Celia Wanted Accountability:
  She interprets Thomas’ acceptance as "weakness," and feels she deserves some criticism or disgust.

  • Brooke: “Maybe he's just being an understanding person and trying to be empathetic...” (35:11)
  • Celia: “You're not listening to me. I deserved it. Like, he didn't even question anything.” (35:40)

• Thomas Confronts Celia:
  Drops the nice-guy persona at her prodding, sarcastically critiques her nails instead, which lands flat.

  • Thomas: “This is like Medusa head. I don’t know who this woman is.” (36:36)
  • Learns his lesson: “Don’t date anyone who says separated in a profile. Just stick to the singles or the divorcees.” (38:16)

Notable Quotes

• Brooke (to listeners):
  “Just because it didn't work out with this one doesn't mean you aren't good at dating. This lady was a little out there.” (40:08)

• Jeffrey (on empathy):
  “Even if you’re trying to be understanding and see the other person’s perspective… that’s seen as a weakness.” (39:43)

Segment Timestamps

• Thomas’s story setup: 22:33–29:51
• Call to Celia: 31:52–38:22
• Team’s debrief: 39:34–40:23

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Memorable Moments

• Brooke joking about holiday Hail Marys—if only rejection could be reversed by grand gestures. (21:24)
• Simone’s frustrated, “I can’t believe you even saw that card. I am so mad at my mom right now.” (17:26)
• Celia’s insistence she needed to be “punished” for cheating, not forgiven. (34:56, 36:40)
• Thomas, after Celia’s reaction: “This is like Medusa head. I don't know who this woman is.” (36:36)

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Key Takeaways

• Meet-the-family too soon kills the vibe, especially around the holidays.
• Misunderstandings about relationship status (like being “not exclusive” with the guy on your Christmas card) are hard to overcome.
• Some people interpret empathy as weakness, especially if they're carrying guilt or unresolved emotional baggage from past relationships.
• Second Date Update is not known for high success rates but is extremely entertaining for listeners.

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Conclusion

This doubleheader of Second Date Update Classics demonstrates the pitfalls of holiday dating—awkward meet-the-family moments, confusing exes, and the minefield of emotional honesty after separation. Brooke and Jeffrey keep things moving with their witty banter, empathy for the unlucky-in-love, and plenty of well-timed jokes. While neither couple ends up with a second date, the episode is rich in comedy, human insight, and the kind of refreshing unfiltered conversation that keeps fans tuning in.

For more classic segments and wild dating stories, visit the Brooke and Jeffrey iHeart channel.

Transcript

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[Simone]

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[Jose]

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[Jeffrey]

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[Brooke]

Is officially better than one. Welcome to your second date. Classics I see what you did there. Yeah, there you go. It's Brigitte Jeffrey in the morning. We're putting two Classics back to back for you so you can get whatever you need to get done done today and just have little dose of second date on your Saturday. Or the opposite. Don't do anything and just sit and listen. Unproductive. There you go. You know, it's too good.

[Jeffrey]

You got to choose.

[Brooke]

We don't judge you. All right? Just enjoy. It starts right now.

[Jeffrey]

I know whenever I'm traveling to spend time with my parents over the holidays, I always have one thing on my mind.

[Brooke]

What's that?

[Jeffrey]

How can I get out of spending time with my parents over the holidays?

[Brooke]

You're already thinking about it, aren't you?

[Simone]

Yeah.

[Jeffrey]

And one of our listeners, I think, had a pretty good idea. Invite a guy over to your family's house to take you away from them for a whole night.

[Brooke]

Oh, okay.

[Jeffrey]

But unfortunately for her, that idea backfired spectacularly. And we're all going to find out what happened when we do your second date update. Next second date update. You're going back home for the holidays. Can be really fun.

[Brooke]

Yeah.

[Simone]

So exciting.

[Jeffrey]

It can be great to reconnect with your siblings again, your grandparents, relatives you haven't seen in a while. And if you're really lucky, you might even see someone from your past and have a little holiday hookup.

[Brooke]

Search.

[Jose]

Wait, we're at a family?

[Jeffrey]

Not. Not your family.

[Brooke]

Like when everybody goes out. Like, you know, like when you're one bar. Totally.

[Jeffrey]

Exactly. Like Brooke. Didn't you and your old PE Coach reconnect one year and get to second base or something?

[Brooke]

No, he married, I think, one of my other friends, so you almost. He was off the.

[Valpak Announcer]

Off the table.

[Jeffrey]

Too bad for you, Brooke. Mr. Chance, but one of our listeners, Simone, reconnected with someone recently. Not an ex boyfriend. It was just a guy from her high school. And I'm curious about how it went down because she's on the phone right now. Simone. So was this a fellow student or a faculty member?

[Simone]

Oh, my God. It was not a faculty member.

[Brooke]

Okay, Honestly, I hooked up with more guys from my high school way post post high school than I did in high school. I was too dorky in high school. Nobody wanted to all doors get hot. I tried. It's not that I didn't try.

[Jeffrey]

Okay?

[Brooke]

I shouldn't have to take her.

[Jeffrey]

Some are late to skank and some skankaroos.

[Brooke]

That's what we call late bloomers.

[Jose]

All right.

[Jeffrey]

Yeah, as long as you get it done. So, Simone, who is this guy that you met up with?

[Simone]

So. His name is Jack. And we reconnected over Facebook because I had posted that I was coming home, and I was really excited to spend time with my family and friends, like, for the holidays. And I was trying to kind of give everybody a heads up that I went to school with so we could try to plan something and all catch up.

[Brooke]

Yeah. It's like. Like a mini, informal reunion almost.

[Simone]

Yeah. Yeah.

[Jeffrey]

And did you know that you wanted to hook up with him immediately, or did you want to wait and see how it went?

[Simone]

Well, so that's the thing, is that, like, this is a guy that we've never dated. We were always kind of floating around in, like, neighboring circles, but we were never super close.

[Brooke]

Okay.

[Simone]

And.

[Jose]

Got it.

[Simone]

He was one of the first people to comment on this post, like, oh, this would be great. Would love to catch up. And I was like, catch up.

[Jack]

Like, we.

[Simone]

What do we have to talk about? Like, we didn't.

[Jack]

You know.

[Brooke]

You know, some people who stay in the hometown that you're from. Yes. Maybe need some outside influence every once in a while.

[Jose]

Yeah.

[Brooke]

Leave the city.

[Jeffrey]

Yeah.

[Jose]

Is what she's saying.

[Simone]

Let me tell you, I will not miss an opportunity to show off my glow up. So.

[Brooke]

Okay, good.

[Jeffrey]

So what did you and Jack do when you met up?

[Simone]

Well, this is the thing. So we were texting for a while until I got back and trying to make plans, and I was staying with my family, so I was like, why don't we just make it easy? You can come pick me up from my family's place, and we'll go wherever you want to go.

[Brooke]

Oh, so this feels more like a date than a hangout if it's just you two.

[Simone]

Yeah, I guess so. I think. Maybe. I don't know if that was the intention, but things kind of ended up taking a slight turn. And it wasn't really anybody's fault, but he came to pick me up when I was. I just finished dinner with my family, and my family was like, oh, you know, why don't you come in for a second? Which I kind of gave him the look of like, you don't have to do this. But he was very cool and came in, and we all were just hanging. It was really sweet. Like, we were all hanging out for.

[Brooke]

A while and, like, because, like, it's not like he knew your family in high school. You guys weren't even really friends.

[Jose]

High pressure situation.

[Brooke]

Yeah.

[Jeffrey]

I mean, I know if that happened to me, I would absolutely not want to go inside. There is. I do not want to spend my precious free time during the holidays meeting some other person's family.

[Jose]

I would.

[Brooke]

I love meeting Families and moms, but not people meeting mine. But parents always love me.

[Jose]

I know.

[Brooke]

It's so fun. You can charm parents.

[Jeffrey]

Okay, we get it, Brooke. You're amazing. Everybody thinks that you're the best person in the world, and everyone wants to accompany you.

[Brooke]

Kids don't like me, but they love me.

[Jeffrey]

Okay, well, so what happened with Jack?

[Simone]

Well, so we're all talking, and we ended up, like, playing some games, and everybody was having a good time.

[Brooke]

So with the hangout, this is full.

[Jose]

On, like, holiday family time.

[Sophie Cunningham]

Yeah.

[Simone]

Yeah. I mean, I didn't mean for that to happen. It just kind of did.

[Jose]

Playing the piano, singing carols together.

[Jeffrey]

Yeah.

[Brooke]

He was into it, though.

[Simone]

Yeah, he was. And I will say this, My dad was a little tipsy, which, around the holidays, is not a surprise.

[Jeffrey]

Everybody okay?

[Simone]

Yeah. And he was kind of ribbing them a little bit. Like, what are your intentions with my daughter? I know, I know.

[Jeffrey]

Let me go to the laundry room, and then I'll show you. Is that not how your guys's family holidays go?

[Brooke]

I never should. Yeah. Never had to take my dad into the laundry room.

[Jeffrey]

Just the PE Teacher. I know. How did Jack handle the ribbing?

[Simone]

He just kind of laughed it off. And finally I kind of pulled him aside, and I was like, hey, listen, we can get out of here whenever you need to. We already were here a lot longer than I thought. And he was like, oh, I just got a text from one of my friends, and they really need me, so I actually. I have to get going. And he's like, but we'll. We'll catch up in a few days. And of course, in my head, I'm like, did he really get a text from his friend or.

[Brooke]

Probably not. I think that maybe he didn't. I don't know. Like, maybe he thought you guys were just going out as friends, and then your dad is assuming that you're a couple. Like, it just. It feels like a lot of weirdness.

[Simone]

Yeah, I agree. And the way we left it was, we'll make more plans, we'll text, and we'll figure it out. And then just never heard back from him.

[Brooke]

Oh, man.

[Jose]

A complete ghost. It's not like he's stalling.

[Simone]

No, no. Like, I just. He just went radio silent, and so I don't know. I don't know what happened.

[Brooke]

Are you crushing on him still? Like, you still like him?

[Simone]

Yeah. I mean, especially too, like, seeing how cool he was with hanging out with my family for a little bit.

[Jose]

That's impressive.

[Jeffrey]

You know, I did have a weird Thought, though, like, while he was bonding with your family, do you have any single siblings or single hot aunts that maybe, like, could have swooped in?

[Jose]

Now we're talking.

[Simone]

No, I. I'm the only girl. I have two brothers.

[Brooke]

Maybe that's an option for him, though.

[Jeffrey]

Yeah. I mean, there's a chance that someone could have, like, taken him from you right from under your nose.

[Brooke]

That is some messed up family dynamics. If that's the case.

[Jeffrey]

It's called the holidays, Brooke. Things happen.

[Jose]

Now, he's dating her mom, but let's.

[Jeffrey]

Find out what really happened. When we play a song, come back, call him, and try and get your second date update. All right.

[Simone]

Thank you.

[Jeffrey]

All right, hold on. Second date update. One of the main rules of dating, I think everybody knows this, is if you really like someone, you do not introduce them to your family for at least three to four years until you're 100% sure they won't be scared off. I would say probably even pop out a few kids with them before they meet the fam, just to be safe. Or you could end up like Simone, who was supposed to go out with an old high school school friend named Jack, till her family invited him inside during the holidays. And look what happened. I mean, he ran away, hasn't been heard from since that night.

[Jose]

They should have heard your advice first.

[Brooke]

Yeah, exactly. Blaming the drunk dad. Is that what we're blaming, or.

[Jeffrey]

No, we don't know who to blame.

[Jose]

That's where I'm leaning.

[Brooke]

I think that the dad.

[Jose]

Even though it's a joke, it's still very intimidating to know that your dad is even thinking, though.

[Brooke]

It's such an old cliche joke, like.

[Jose]

What are your intentions?

[Brooke]

It really is.

[Jose]

I'm gonna polish my gun.

[Thomas]

Yeah.

[Jeffrey]

Simone, do you wish that you hadn't let him come inside that house that night?

[Simone]

I mean. Yeah, we know where this ended up.

[Brooke]

It's absolutely true. Oh, my God. I mean. Or do you wish that your dad was funnier?

[Simone]

I mean, he thinks he's funny, which is way worse.

[Brooke]

Yeah. Yeah.

[Jeffrey]

Well, we're going to try and get you a second chance here. We're going to call Jack and find out which member of your family is the one to blame. Or maybe it was something that was totally unrelated.

[Jose]

How about we think it has to be the family?

[Brooke]

I mean, come on.

[Simone]

Yeah.

[Jose]

Yeah.

[Jeffrey]

It's like the holiday edition of Clue.

[Brooke]

Oh, yeah. All right. Is it the mom in the kitchen with the butcher knife or.

[Jose]

Or Colonel Father?

[Jeffrey]

Yeah, let's get to the bottom of this. I'M going to dial his number right now. Here we go.

[Jack]

Hello?

[Jeffrey]

My nose brushed the microphone.

[Jack]

Hello?

[Jeffrey]

Hey, is this Jack?

[Jack]

Yes, this is he.

[Brooke]

You are awake and ready. I like Jack.

[Jeffrey]

I know. You seem alert, Jack. You're on the radio right now with Brooke and Jeffrey in the morning.

[Jack]

Yeah, I seem alert because I answer business calls during the day.

[Brooke]

This is kind of a business call. It's about your business, your personal business.

[Jeffrey]

With an old friend of yours named Simone.

[Jack]

Wait, what is this about? What's going on?

[Jeffrey]

This is about a segment we do on our show called A Second Date Update. And our listeners will reach out to us sometimes and ask us to help them reconnect with an old fling or an old date that they went out with that they haven't heard from in a while.

[Jack]

Okay, but I'm not old. I'm not an old person.

[Jeffrey]

You answered a phone number that you didn't recognize. That is old person behavior.

[Brooke]

So Joe's still out on that valid. Oh, Jack, I bet you're regretting it right now.

[Jack]

I was just. You know, I thought maybe something was wrong with my car's extended warranty.

[Jeffrey]

It's okay.

[Brooke]

Yeah.

[Jeffrey]

Look, we all make mistakes, and your mistake was answering this call. But we do want to get some answers because Simone told us that you guys hung out the other night.

[Jack]

And, you know, I'm sorry to. I'm sorry to interrupt you, but I just. I don't think I want to do this.

[Brooke]

Okay. Is it because it wasn't supposed to be a date with Simone? Supposed to just be more like. Of a friend, hang out, like.

[Jack]

No, no, no, no, no, no, no. I'm definitely interested in Simone.

[Jeffrey]

Well.

[Jack]

Well, I was interested.

[Jeffrey]

Why? I mean, look, I know you're hesitant on talking about it, and I understand that, but can you put yourself in Simone's shoes here? Because she was really looking forward to spending time with you and reconnecting. And, I mean, she had no intention of the night going the way that it did where you were invited into her family's house.

[Jose]

Yeah, that wasn't the plan, bro.

[Brooke]

I mean, she thought you. I mean, maybe she read it wrong. The only reason you guys stayed there was because she thought you were having a good time hanging out with her family and playing board games.

[Jack]

Whoa. You guys know a lot about what happened.

[Brooke]

We're like. We're like date detectives. Yeah.

[Jack]

Yeah, it's kind of weird.

[Brooke]

Well, we talked. We talked to Simone.

[Jeffrey]

She told us about what happened that night, and we were wondering if something happened while you were in the house. With her family that made you.

[Jack]

No, no, I.

[Simone]

It was just.

[Jack]

It wasn't. It was just an uncomfortable situation.

[Brooke]

Oh, she feels bad for that?

[Jeffrey]

Yeah.

[Jack]

Well, no, but just. No. Not. Not going in and talking to her family. Her family was great. Oh, nice.

[Jeffrey]

And so great that maybe you hooked up with one of them.

[Brooke]

Back to that.

[Jack]

What?

[Jeffrey]

Okay, that was a theory that I had, and I'm glad that we can squash it right now, but, yeah, we can.

[Jack]

Definitely.

[Jeffrey]

Was the text that you got, the emergency text, was that real or was that fake?

[Jack]

No, no, no, it was not real.

[Thomas]

I did not.

[Jack]

I did not get the emergency, but.

[Brooke]

She knew that, so don't feel bad admitting that. Like, I mean, it was pretty obvious what made you just run from the house.

[Jack]

So what made. What made me need to leave is I was having a nice chat with her mom. And as. As we're talking, I look over and I see some Christmas cards, and I see one from Simone with another guy, and they're both, like, snuggled up together. And it was like a. It looked like a, you know, couple had sent a card, and it was Simone and this dude.

[Brooke]

Well, obvious. I mean, she didn't mention anything about an ex boyfriend, but obviously the card could have been sent out long before. And then they broke up. Like, how early do you send Christmas cards? I know, but who. Who brings a guy over to your house with your family if you're dating someone else to a point where you're sending Christmas cards together? Like, why wouldn't you just ask Simone then? Why wouldn't you ask her?

[Jack]

Because I just felt like in order to not just escalate things, I wanted to. I just, you know, I mean.

[Brooke]

Well, you just wanted to jump to conclusions.

[Jeffrey]

I know.

[Jose]

The ex. You just took pictures recently.

[Brooke]

Yeah, but who obviously did not, probably.

[Jeffrey]

I know you don't want to have that awkward conversation with her, but I kind of do right now because she's on the other line listening and wants to be asked an awkward, escalating question.

[Jack]

What?

[Jeffrey]

Simone?

[Simone]

Yeah.

[Jack]

Hi. You've been listening this whole time? This is like. This is so awkward.

[Simone]

I. I know. I'm sorry.

[Jack]

I mean, it's kind of cool that you went to these lengths to try to get a hold of me, but I just. You know, I just. This is just really bizarre. So who is the guy? Come on, tell me. Are you seeing somebody? Are you in a relationship? Because, like.

[Jeffrey]

Okay, hold on, Jack. You're asking, like, five different questions. Just. Let's do one question at a time.

[Brooke]

Who's the guy?

[Jeffrey]

Oh, I Was gonna start. What kind of sweater are you wearing right now? Because that might ease his tension a little bit.

[Brooke]

Who's the guy?

[Simone]

First of all, I can't believe you even saw that card. I am so mad at my mom right now.

[Brooke]

Why?

[Jeffrey]

Are you dating that guy?

[Simone]

Not technically.

[Jeffrey]

Oh, does that mean, dude.

[Brooke]

What? Your parents are wingmanning your side pie?

[Thomas]

No.

[Simone]

So listen. Okay, I'll be honest. That guy is a guy that I dated for a while. We always did these stupid Christmas cards. And we're not exclusive. We are not together. We hook up every once in a while, but we're not.

[Brooke]

There's some. But you promise you're not exclusive with him?

[Simone]

Oh, 100%.

[Brooke]

You're not exclusive, and you send Christmas cards. Cards out together. That seems. Yeah, that's a strange combo.

[Simone]

It was more of a joke because we would do it every year, so we kind of just kept up with the tradition because we both didn't want our families hassling us at the holidays for being single. So we were like, we should just do a Christmas card anyway, and that backfired. So funny.

[Jack]

So I just. I'm actually. I mean, Simone, I really want to be with somebody that's emotionally available and not, you know, still. Even if it's not like, you know, you're not exclusive, you're still seeing him. I just. I'm just not comfortable being with somebody who's seeing other people. So I just.

[Simone]

Well, that's the thing is, like, I had a great time hanging out with you, and I really want to get to know you better. And I am not invested in this guy. Like I said, it's somebody that I dated, and it was just. I didn't have anybody else I was interested in, and it was just, you know, I'll call him later today and tell him that we can't see each other anymore.

[Jeffrey]

Like, really, Jack? Is that something that you'd be into? Because if you're willing to see her again, then we'll pay for that date. Yeah, I have.

[Jack]

I have one question. Did you hook up with him over the holidays?

[Brooke]

Oh, you don't want that answer.

[Jeffrey]

Why wouldn't you be honest here, Simone? Did it happen? And what sweater were you wearing at the time?

[Simone]

It didn't happen over the holidays, but it has happened recently.

[Jeffrey]

Jack, I need an answer from you. What do you think? One more date with Simone, we'll pay for it?

[Jack]

I don't think so. And here's why.

[Brooke]

It's a healthy why.

[Jack]

I feel like you could have told me that you were getting out of a relationship and I just. I can't.

[Brooke]

We get it.

[Jeffrey]

It's the holidays. Everybody's sad. We understand. Thank you.

[Brooke]

Brooke and Jeffrey in the morning.

[Jeffrey]

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.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 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.

[Valpak Announcer]

It's the most wonderful time of the year and Valpak is here to make it even better. This month, as you sip through holiday mail, don't miss the blue Valpak envelope. From dining to holiday shopping, there's a slate full of savings in your mailbox. Plus a chance to instantly win $100. That's right, you can find $100 Christmas cash inside. Want to save even more money on what you love? Go to valpak.com for local coupons and offers. It pays to open Valpak. No purchase necessary for instant win voip. We're prohibited. Prices are randomly inserted. See specially marked Valpak envelopes for details.

[Jeffrey]

I was thinking, does that ever work on our show?

[Brooke]

What?

[Jeffrey]

After the person says, no, I'm not interested and they throw out one last ditch plea like, hey, well, what if I break up with the other guy? Will you go out with me then?

[Brooke]

It's like a Hail Mary or hey.

[Jeffrey]

What if I get a butt lift?

[Brooke]

Yeah.

[Jeffrey]

Or hey, what if I put my dog down because you're allergic?

[Brooke]

Oh, God, me then my God.

[Jeffrey]

Just not.

[Brooke]

It's always no, you made the boyfriend sound like the best option.

[Jeffrey]

I mean, honestly, I just can't think of a time where that strategy's ever worked. And she definitely gave it a try.

[Brooke]

Oh, God. I just have this feeling that the guy on the cards sweater boy doesn't know that they're not exclusive.

[Jeffrey]

Yeah.

[Jose]

Does anyone else feel that the other one is always like, what? Wait, I thought you were my girlfriend.

[Brooke]

Yeah. He sent out Christmas cards for God.

[Jeffrey]

Yeah. How does it get more intimate than that? Clearly we're not going to be doing any update with that couple anytime soon. But remember, you can always listen to any one of our second dates on YouTube because we've got hundreds of them up right now, so a lot of people are actually choosing to listen to our show that way. And remember, you can always reach out to us if you have a date that you want us to.

[Brooke]

Get a hold of Brooke and Jeffrey in the morning.

[Jeffrey]

Did you know that 47% of adults say dating is much harder today than it was just 10 years ago?

[Brooke]

Oh, man, that's a lot.

[Jeffrey]

Now it explains how Brooke was able to trick somebody into marrying her. Meanwhile, our own Alexis is still very single and very, very lonely.

[Brooke]

Okay, it's the odds that I'm going against Brooke. You say that she's more marriage material than me. What are you saying?

[Jeffrey]

Yeah, I'm just saying I'm shocked at what's happening in front of us. But one of our listeners has been off the market for about a decade now, and he's trying to wade back into the slime pool of love.

[Brooke]

Oh, man.

[Thomas]

Slime pool.

[Jeffrey]

Don't get it.

[Brooke]

Got slimier.

[Jeffrey]

And already the first person that he went out with is not responding. So we're gonna hop into that slime pool with him and try to find out why when we do your second date update. Next second date update. When you date online, some people connect over shared interests or hobbies. Other people connect because they're both frickin hot. But one of our listeners, Thomas, says he connected with a woman online over their joint sadness.

[Brooke]

Oh, something like that.

[Jose]

Okay, I'm gonna meet my wife.

[Jeffrey]

Let's talk to Thomas. Thomas, did you meet her on tiermatch.com? is that a thing or was it the Kleenex Club? Which one was it?

[Brooke]

Oh, that's cute. Well, that could go wrong.

[Thomas]

Yeah, I'm not getting paid by any of the services I use, so I'm not gonna give any free advertising. But we did meet online. Okay.

[Brooke]

What's the sadness you speak of, my friend?

[Thomas]

Well, you know how you can put, like whether you're single or divorced? There's an option where you can put separated. And so I thought I would be honest since the divorce isn't finalized or anything. So I listed my status as separated.

[Brooke]

Okay.

[Jeffrey]

Why wouldn't you normally do that?

[Thomas]

Well, I would normally tell the truth. That's what I do. But I think sometimes people don't want to scare somebody off, you know?

[Brooke]

Yeah, I think it'd be a turn off. Like people are in the middle of something really messy. Like, you just don't Want to even swipe on them.

[Jose]

It's like on Facebook when they're single and people sometimes put. It's complicated.

[Brooke]

Yeah, that's a mess.

[Jose]

You're obviously involved with somebody, but some.

[Jeffrey]

People think that's a turn on. They're like, ooh, a disaster. I want it.

[Brooke]

Not the people you usually want to date. Jeffrey.

[Jeffrey]

Okay, well, I don't know. He says that he matched with somebody that was separated too. It sounds like.

[Thomas]

Yes. Her name is Cecilia and she also had separated on her profile.

[Brooke]

Okay.

[Thomas]

Yeah, she had a very nice smile and she had big curly hair. I'm a sucker for.

[Jose]

Didn't think that was coming, but awesome.

[Jeffrey]

Okay. No, that's good. The hair is also a very good feature.

[Brooke]

I mean, it's a good start, though. I'm going to change the subject real quick. It's a good start that you guys are going through. I mean, I don't know how similar it is, but a similar life experience. So you're coming in with. With understanding and you probably don't feel like you have to explain a lot, Right?

[Jose]

Sure.

[Thomas]

Well, I mean, that's kind of like prefaces into why I'm calling y'. All. We went on a date and this is my first first date since the, you know. Well, my to be ex wife. Yeah. And she's met a couple guys for like coffee or something super casual. And so we, you know, we went. I got a bite to eat.

[Brooke]

Okay, wait, what were you feeling like? Slow down. Because this is the first date out of your marriage.

[Jose]

Let me guess.

[Simone]

Hold on.

[Jose]

I'm a psychic. You were nervous.

[Brooke]

No, he could have been feeling excited.

[Thomas]

Hold on.

[Jose]

Let the psychic do his work.

[Jeffrey]

See if psychic Jose is worth the money.

[Jose]

Tell us.

[Thomas]

Yeah, I went all out, you know, I got dressed to the nines like Jim Carrey and dumb at Dumber Tuxedo, you know.

[Jose]

Okay, that doesn't sound nervous to me.

[Thomas]

No, you're joking, of course.

[Jack]

Of course.

[Brooke]

You never know. You've been out of the dating game for a minute. Maybe you just didn't read the room right anymore.

[Thomas]

Well, I mean, I thought it was positive that, you know, I got a first date out of messaging someone over the Internet. So, I mean, that was, you know, am I. That was pretty cool. Yeah. You know, good start.

[Jack]

Yeah.

[Jeffrey]

Well, how did it go when you showed up? Like, how was. How was Celia?

[Jose]

Yeah, what was the vibe?

[Thomas]

You know, aside from the usual kind of laughs and jokes you crack? The thing that we definitely bonded over, I would say like 50% of the date was Our situation that led us to being separated on, you know, both of us kind of talking about our personal life, you know?

[Jose]

But that's good. That's good, because normally if you're on a date with someone who's just single, they won't relate. And you wouldn't dare bring it up, you know, because you don't want to hear about it. But if you're both going through it, it's like, no, please, I need someone to talk to about this.

[Jeffrey]

I guess that is key. You both have it in common so you can bond over it.

[Brooke]

Yeah.

[Jeffrey]

Is that. Is that how it went?

[Jack]

Yeah.

[Thomas]

I mean, there definitely wasn't a pity party for. It was like, bonding. Yeah.

[Jeffrey]

How many shots of tequila do you need in order to get through that conversation?

[Thomas]

It's only, like, I don't know, maybe one or two margaritas, maybe.

[Jose]

Okay, that's good.

[Brooke]

So, what. I mean, were you able to flirt, too, though? Because if you're talking a lot about, you know, your exes and things, I mean, we didn't.

[Thomas]

I mean, no one stayed the night at anybody's house or anything like that. But like I said, I cracked some jokes, you know, I got some genuine laughs, so, you know, I count that a flirting. Okay.

[Brooke]

Okay. Why do you want to call her back? I mean, maybe this was just your practice date right before you. You got a lot of. Well, I'm guessing time to make up for right now.

[Jeffrey]

Yeah, well, once. Yeah. Why aren't you sleeping with everybody around town? Why are you sticking to one person? I. Limit yourself.

[Brooke]

I'm just saying, like, why. Why her? Like, it's your first date, so the.

[Thomas]

First date I thought went well, so I.

[Brooke]

Okay.

[Thomas]

I'm figuring that, you know, I might as well. Before I go fish in the sea. As it is, I might as well make sure this one's off the hook.

[Jose]

Gotta cut.

[Thomas]

Okay.

[Brooke]

That was a lot of references, a lot of metaphors in that way.

[Jose]

And it doesn't matter the size of your worm, by the way. Women love a worm.

[Brooke]

We didn't go to that. It's not true.

[Jeffrey]

Well, yeah. Let's get back to the date. How did the night end?

[Thomas]

You know, like I said, no, we stayed in everybody's house. There was no making out or anything like that.

[Jeffrey]

A hug?

[Thomas]

Yeah, yeah, yeah, there was a hug. But one thing that I think is kind of concern that I would say is she had mentioned that the reason of her separation was there was cheating involved. And I could see how he did not want to put out any kind of vulnerability like, you know, to get herself for like. Like, I'm trying to be a player, which I'm not. You know, like, I'm not trying to be. My intention was to get no. Her and go on a second date.

[Brooke]

And did you guys make any, like, future plans? I always think that's a good sign on a date.

[Thomas]

Yeah, well, we didn't nail. I mean, we didn't nail down, hey, let's go miniature golfing, you know, tomorrow. We didn't do anything like that. It was like a hug at the end of the night. And it was. I was like, make sure you get home safe, and then I'll see what you want to do.

[Jack]

I'll hit you up.

[Jose]

So how was the hug? Was it like a quick hug, or was it like a sensual, long. She smelled your hair. Kind of like.

[Jeffrey]

You don't have to answer that if you don't want to.

[Valpak Announcer]

I think you should smell people's hair.

[Brooke]

On the first day ever.

[Jeffrey]

It was just a nice hug, right?

[Thomas]

Yeah, it was just. I think it was a very standard end of the night.

[Jose]

You didn't, like, rub your hands up and down her back.

[Jeffrey]

No more details needed. I think you're just gonna play a song. We'll come back, we'll call Celia for you and try and get you your second date update. All right.

[Thomas]

Thank you. All right.

[Jeffrey]

Hold on, man.

[Jose]

Jeff, give me a hug.

[Jeffrey]

Okay. Second date update. Ah, stepping back on the dating scene after going through a failed marriage.

[Brooke]

Wow, that. Just say it like that.

[Jose]

At least he's got this music on.

[Jeffrey]

I'm just saying things are probably different than the first time around.

[Brooke]

I hope. I hope this is not what you tell your friends if they ever call your marriages ending.

[Jeffrey]

I'm trying to paint the. The scene like the people are older, the drinks hit you harder.

[Jose]

That's true.

[Jeffrey]

And the hugs are standard. Nothing more, nothing less. No one's smelling anybody's hair or rubbing backs. Well, that's what happened with one of our listeners, Thomas, who's currently going through a separation himself. And so was his date, Celia. So naturally, they talked a lot about their situations, and they were very open and vulnerable with each other, which Thomas took as a good sign. But now Celia's not responding to him, which Thomas is taking as a bad sign.

[Brooke]

That's a good, good way to do it.

[Jose]

Dating hasn't changed in that sense, some things never change.

[Jeffrey]

But. Thomas. How you feeling, man?

[Thomas]

You guys gave it quite the lead up.

[Brooke]

Yeah, sorry. No pressure, Thomas.

[Thomas]

I'm second guessing myself now.

[Jose]

Oh, no, we can Keep that music going the whole time.

[Jeffrey]

It helps.

[Brooke]

Do you know what we never asked you is have you tried to get ahold of her?

[Thomas]

I reached out to her, yes, but I did not receive any communication back. And I mean, I'm calling up you guys because I feel like it went well, and so I'm trying to figure out what I do wrong.

[Brooke]

Just brace yourself here, because you're new to dating, you may hear some things you don't want to hear. That doesn't mean that you're not good at it. Okay?

[Jeffrey]

And as Brooke would say, there's a whole city of people to sleep with and you should.

[Brooke]

That is actually exactly what I would condone.

[Jeffrey]

All right, so let's give it Celia a call, and we'll see if she answers and what she has to say. Let's do this. Here we go.

[Simone]

Hello?

[Jeffrey]

Hey, is this Celia?

[Simone]

Yes.

[Thomas]

Sorry.

[Jeffrey]

I was really excited there.

[Brooke]

Hi, Celia.

[Jeffrey]

I wasn't sure if you're going to answer. Hey, we're. We're Brooke and Jeffrey in the Morning from the radio. Hey, cool.

[Brooke]

Now she's not answering you a second to process. This is probably a lot, right, Celia?

[Simone]

I don't. Who is this?

[Jeffrey]

Yeah, we're. So, We're a morning radio show. We're called Brooke and Jeffrey in the Morning, and we're hoping that you'll be a part of a segment with us here called the Second Date Update.

[Simone]

Oh, no, thank you. That's okay.

[Brooke]

No, no, no, no, Celia, it's not a bad thing.

[Jeffrey]

We're actually calling on behalf of one of our listeners who you went out on a date with. A very hot date. Sounded like his name's Thomas.

[Simone]

Oh, yeah. Okay.

[Brooke]

Oh, that didn't sound good. Uh.

[Jose]

Oh, yeah, that didn't sound good.

[Brooke]

Thomas, I think, is clueless because that was not a good response about Thomas.

[Simone]

I mean, like, we had a really nice dinner and I was hopeful.

[Jeffrey]

That's good.

[Simone]

But we kind of got into a personal conversation about our situations, our separations, our marriages and that sort of thing.

[Jose]

Yeah, he told us that, too.

[Simone]

And it was a big red flag for me. That kind of popped up.

[Jeffrey]

So wait, are you saying just you guys discussing the marital situations was a red flag or something? Specifically about the conversation?

[Simone]

Yeah, it was more. It was more specific. It was like, I told him, like, basically my situation ended because of cheating, and I was the cheater. I was unfaithful.

[Brooke]

Oh, you. Oh, interesting. So he. He didn't share a lot of your. Your story at all? He just said that there was like, that's why your marriage ended. He did. We just assumed that it was your ex.

[Jeffrey]

Okay.

[Brooke]

But. Okay, that's fine.

[Jeffrey]

What was a red.

[Jose]

Fine?

[Brooke]

It is what it is.

[Jeffrey]

But what was a red flag about that?

[Simone]

Well, for me, the red flag was, like, he acted really weird. Like, it was just normal, and he was understanding and, like, trying to make excuses for me. And I'm thinking, this guy's kind of weak.

[Brooke]

What?

[Jeffrey]

What do you mean he was making excuses for you?

[Simone]

Like, oh, well, I guess he wasn't paying you attention. Or, you know, you wanted him to.

[Brooke]

Be mean to you instead. Or, like, not the first time.

[Simone]

It's more like I just laid what I had out there on the table and his reaction was just a little too normal for me. Like, I told him the real. Like, listen, I cheated, and he was just like, oh, that's okay.

[Brooke]

Okay, well, maybe he cheated in his relationship, too. I mean. Or he's just awkward and doesn't know what to say there because he doesn't want to insult his date. He liked you.

[Jeffrey]

Well, like, what did you want to hear from him? What would have been a good response in your mind?

[Simone]

I wanted him to be disgusted by it because I think it's really horrible what I did.

[Jose]

Yeah, that was my.

[Brooke]

Maybe he was, like, inside.

[Jeffrey]

I'm sure he felt that way, but he didn't want to say to you on a first date, ew, you disgust me.

[Brooke]

Plus, relationships are, like, really complicated. And, you know, sometimes it's Brooke. She doesn't want to hear excuses from you. I'm just saying, maybe he's just being an understanding person and trying to be empathetic to what you are going through.

[Simone]

Sounds like maybe you should go out with him. You guys are both understanding.

[Jose]

Yeah, Brooke totally understands.

[Brooke]

She encourages it.

[Jeffrey]

If you're playing the statistics, chances are she already has.

[Brooke]

So I have not cheated. All I'm saying is, like, this guy, like, he doesn't attack you for being really vulnerable and really honest. Because that's probably a hard thing to share with people, I would imagine.

[Simone]

You're not listening to me. I deserved it. Like, he didn't even question anything.

[Jeffrey]

Okay, I see what you're saying. Like, he's siding with the person who cheated rather than siding with the person who got cheated on.

[Simone]

Yeah, not even questioning it. Like, got you.

[Brooke]

Maybe he could yell at you now.

[Jeffrey]

Yeah, like, because this would be a great chance for him to lay into you because he's actually on the line listening.

[Simone]

No, actually, I think I've had enough.

[Jeffrey]

No, no, no, no, no.

[Thomas]

You don't understand.

[Jeffrey]

He's already there listening right now and wants to talk to you.

[Jack]

Yeah? Yeah.

[Thomas]

All right, so let me get this straight. You wanted me to be like Dr. Phil or Steve Harvey or something and just lace into you? How does that make sense on a first date?

[Simone]

First of all, I didn't even know you were on the line. Secondly, I ghosted you for a reason, and I really don't even want to talk to you.

[Jeffrey]

Oh, no. I hear sparks flying.

[Brooke]

Is this the vibe you got Thomas when you guys were out?

[Thomas]

Nothing like this. This is like Medusa head. I don't know who this woman is.

[Simone]

I'm just being honest with you. I feel like you could have at least questioned why I did it. Like I need someone to hold me accountable for behavior.

[Thomas]

All right, you want some criticism?

[Simone]

All right.

[Jeffrey]

Yeah.

[Thomas]

You got my nails done? Don't my nails look good? Yeah, your nails don't look good. Got a bad.

[Brooke]

Why are you talking about her nails? No, those cost a lot. Don't sell those.

[Simone]

You didn't go there, did you? Like my nails look amazing.

[Jeffrey]

Okay, I think he's just trying to give you what you want there, Celia.

[Brooke]

He's not reading what she wants very well, though. I mean, I will give her that.

[Jeffrey]

I'm not sure if I'm reading exactly what she wants either.

[Brooke]

It sounds like you want to be punished, bro.

[Jose]

Next time, bring an iron fist to the date and put the hammer down.

[Brooke]

This is why he should have practiced dating more. Called the first person back. You gotta try a lot of people out till you find your. Right now.

[Jeffrey]

But he could sleep around with other people and cheat on Celia, and then we could send them out on a second date.

[Brooke]

I don't think that's what she wants either.

[Jeffrey]

Yeah, I mean, I could ask Celia. Would you be interested in that? Would you like to go out one more time?

[Simone]

I'm good with him. I thought I made that clear.

[Brooke]

Yeah, you did. You did. You're very clear.

[Jeffrey]

You know, it's just my job to ask.

[Brooke]

Yeah, okay. I don't know if Thomas is upset about that, though.

[Thomas]

Yeah, I'm sad about how this went, especially considering she's out of her mind.

[Jeffrey]

Now you're talking the way that she likes.

[Thomas]

Well, I really appreciate you guys having me on, but. So if I learned anything from this, it's don't date anyone who says separated in a profile.

[Brooke]

Oh, just wait.

[Thomas]

Just stick to the singles or the divorcees.

[Jose]

I guess that's what you learned.

[Jeffrey]

Yeah.

[Brooke]

Good luck. Brooke and Jeffrey in the morning.

[Jeffrey]

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.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.

[Valpak Announcer]

It's the most wonderful time of the year and Valpak is here to make it even better. This month, as you sip through holiday mail, don't miss the blue Valpak envelope. From dining to holiday shopping, there's a sleigh full of savings in your mailbox. Plus a chance to instantly win $100. That's right. You can find $100 Christmas cash inside. Want to save even more money on what you love? Go to valpop pack.com for local coupons and offers. It pays to open Valpak. No purchase necessary for instant win. Void. We're prohibited. Prices are randomly inserted. See specially marked Valpak envelopes for details.

[Jeffrey]

Man, people have been saying forever that dating today is hard.

[Brooke]

Yeah.

[Jeffrey]

I think it's time after that call to start saying dating's impossible.

[Brooke]

Yeah, it does feel that way.

[Jeffrey]

Because even if you're trying to be understanding and see the other person's perspective, give them the benefit of the doubt, that's seen as a weakness. Yeah. And they don't like you for it. That's why this ended with no date at the end.

[Jose]

Anybody out there who's single, including myself, let's just all give up.

[Jeffrey]

That's a winning attitude.

[Thomas]

Yeah.

[Brooke]

Thank you, Jeff.

[Jose]

I learned.

[Jeffrey]

Okay.

[Brooke]

Oh, man, that's so sad. It's okay. I just.

[Jose]

Okay to die alone.

[Brooke]

No, it's not. You will find your love. You don't have to base it off this lady. This lady was a little out there. And I think what is it does say is that even if you were the cheater, there are people who will forgive you. Yeah, that guy was really nice.

[Jose]

He was too forgiving. And that was the problem.

[Thomas]

See?

[Brooke]

You wouldn't date him either.

[Jose]

No, I wouldn't, bro.

[Jeffrey]

I could see why she hated you though. Brooke. God. Sappy, my gosh, but you know, sappy.

[Jose]

It was too sappy.

[Jeffrey]

I'm sorry but no. Look, we we do want to help connect you if you still do believe in love out there. And if you do, you can always email the show. We'll call the person who isn't calling you back. 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.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 where prohibited by law, 18 plus terms and conditions apply.

[Sophie Cunningham]

This is Sophie Cunningham from Show Me Something. Do you know the symptoms of moderate to severe obstructive sleep apnea, or OSA in adults with obesity? They may be happening to you without you knowing. If anyone has ever said you snored loudly, or if you spend your days fighting off excessive tiredness, irritability and concentration issues, it may be due to osa. OSA is a serious condition where your airway partially or completely collapses during sleep, which may cause breathing interruptions and oxygen deprivation. Learn more at don'tsleep on OSA.com this information is provided by Lily, a medicine company at cvs.

[Simone]

It matters that we're not just in your community, but that we're part of it. It matters that we're here for you when you need us, day or night, and we want everyone to feel welcome and rewarded. It matters that CVS is here to.

[Sophie Cunningham]

Fill your prescriptions and here to fill your craving for a tasty and yeah, healthy snack.

[Simone]

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[Jeffrey]

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