Awkward Tuesday: He Saw What He Saw

Summary

Podcast Summary: Brooke and Jeffrey: Second Date Update – "Awkward Tuesday: He Saw What He Saw"

Episode Overview In the March 4, 2025 episode of Brooke and Jeffrey: Second Date Update titled "Awkward Tuesday: He Saw What He Saw," hosts Brooke and Jeffrey navigate the complexities of modern dating mishaps with their signature blend of empathy and humor. This particular episode focuses on a listener named Jacob, who finds himself entangled in a situation that questions the very foundation of his six-month relationship. The hosts, along with co-host Jose, provide insightful advice and facilitate an intense phone confrontation to uncover the truth behind Jacob's suspicions of infidelity.

1. Introduction to Awkward Tuesday ([02:03] onwards) The episode kicks off with Brooke and Jeffrey introducing the revamped segment "Awkward Tuesday," a change from its previous Sunday slot based on listener feedback. Brooke mentions, “[...] we moved Awkward Tuesday from Sunday to Tuesday. Did you think it was brilliant or a terrible choice? Believe it or not, 71% of people said brilliant” ([02:03]). This shift aims to enhance listener engagement by addressing dating dilemmas mid-week.

2. Jacob's Story and Initial Discussion ([04:05] - [08:41]) Jacob reaches out to the podcast with a troubling revelation: his friend Omar claims to have seen his girlfriend, Shannon, at a place called Crystal Lounge with another man, noticing she was wearing an engagement ring. Jacob shares, “Shannon and I will have nights where we hang out, we do stuff together, but then other nights, we're apart” ([05:05]). He describes his relationship as healthy and balanced, making the accusation all the more jarring.

Brooke initially downplays the situation with humor, suggesting it might be something trivial like “an extra McNugget in their McDonald's bag” ([02:48]). However, as Jacob elaborates, the conversation takes a serious turn. He explains that when he confronted Shannon, she became defensive and walked out, leaving him questioning the authenticity of their relationship.

3. Advice and Strategy Development ([08:41] - [10:04]) The hosts brainstorm strategies to assist Jacob in addressing the issue. Brooke advises Jacob to “rip it off like a band aid” and demand the truth, emphasizing that "she deserves the truth" ([11:20]). Jose complements this by suggesting Jacob should make Shannon feel comfortable and assure her, “Honey, I want you to know first, I love you, okay? And whatever you say in this conversation, I promise not to judge” ([11:57]).

Brooke interjects with skepticism, noting, “She would have just said the logical thing if it was logical, Jeff, she wouldn't have, like, run out of the room” ([12:09]). This dynamic highlights the balance between offering compassionate advice and recognizing when a relationship might be irreparably damaged.

4. The Phone Call: Confronting Shannon ([10:04] - [19:22]) Determined to uncover the truth, Brooke and Jeffrey facilitate a live phone call between Jacob and Shannon. Jacob begins the conversation assertively: “Am I not supposed to be upset when my buddy comes to me saying that you have an engagement ring on and you're hanging with some other guy? Like, what is that?” ([13:43]).

Shannon hesitates initially, responding, “I don't feel like talking right now” ([13:07]). The tension escalates as Omar, Shannon’s companion, interjects and eventually reveals the shocking truth: Shannon is indeed engaged to someone else. Omar explains, “We hooked up and I... I started dating him again. [...] he proposed a few nights ago” ([15:03]).

Brooke adds a critical commentary: “Brooke, we're on tape here, so this can be used in the court of law” ([16:04]). The revelation leaves Jacob stunned, culminating in Brooke summarizing the situation: “We wasted six months on this relationship” ([19:21]).

5. Aftermath and Takeaways ([19:22] - End) In the wake of the confrontation, Jacob seeks closure and camaraderie from the hosts. Brooke extends an invitation for Jacob to join them for drinks to unwind, highlighting the importance of support systems after such emotional turmoil: “Since we're friends legitimately, let's go out, spend the rest of the week drinking. I'm up for it” ([19:28]).

The episode concludes with Brooke and Jeffrey reflecting on the lessons learned from Jacob's experience. They emphasize the necessity of open communication and the courage to face uncomfortable truths in relationships.

Notable Quotes:

• Brooke ([11:20]): “You need to rip it off like a band aid. [...] You deserve the truth.”
• Jose ([11:57]): “Honey, I want you to know first, I love you, okay? And whatever you say in this conversation, I promise not to judge.”
• Jacob ([13:43]): “Am I not supposed to be upset when my buddy comes to me saying that you have an engagement ring on and you're hanging with some other guy? Like, what is that?”
• Omar ([15:03]): “We hooked up and I... I started dating him again. [...] he proposed a few nights ago.”
• Brooke ([19:21]): “We wasted six months on this relationship.”

Conclusion "Awkward Tuesday: He Saw What He Saw" serves as a poignant exploration of trust and communication in relationships. Through Jacob's story, Brooke and Jeffrey shed light on the emotional challenges faced when confronting potential infidelity. The episode underscores the importance of seeking the truth, no matter how uncomfortable, and the value of having supportive friends to navigate through personal crises.

Transcript

[Ryan Seacrest]

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[Brooke]

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[Jeffrey]

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[Brooke]

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[Jacob]

Lenovo Lenovo.

[Brooke]

All right, we pulled you last week. Hey, welcome to the Second Date podcast. By the way, it is Brooke and Jeffrey in the morning. The second Date update. We said in a poll that we moved Awkward Tuesday from Sunday to Tuesday. Did you think it was brilliant or a terrible choice? Believe it or not, 71% of people said brilliant.

[Jose]

Hey, they can keep track of the day of the week now.

[Brooke]

Yeah, exactly. It makes a lot more sense. It's happening right now. Welcome to your awkward Tuesday phone call.

If a friend calls you at 11 o'clock at night and demands to come over because they have to tell you something in person and it can't wait.

[Jose]

Oh, my gosh.

[Brooke]

It's probably good news, right?

[Jose]

I would hope.

[Brooke]

Oh, maybe they just finished watching Love island. Lot of gossip.

Yeah. Or maybe they found an extra mcnugget in their McDonald's bag. They just saved 15% by switching insurance providers. Yeah. No, no.

[Jose]

It's not an 11pm call kind of thing.

[Brooke]

Okay, well, unfortunately for our listener, his buddy called him to drop a huge bomb about his girlfriend.

Oh, no.

And now he needs our help getting the truth from her about what really happened.

Oh, too bad it wasn't a chicken nugget.

Maybe it's a good thing that happened. We're gonna find out when we do your brand new awkward Tuesday phone call right after this. It's awkward.

[Shannon]

It's Tuesday.

[Brooke]

It's awkward Tuesday phone call. Is there any circumstance where you're out somewhere and you see a friend's significant other doing something that they shouldn't be doing and you decide to keep your mouth shut? Oh, because, I mean, you can rationalize it in your head, like, you know what? It's not really any of my business. I don't want to jump to conclusions and stir up drama if that's not really what's going on. My eyesight really isn't that good anyway. That could have just been a mannequin, and I'm totally seeing.

It's just like you caught him eating ice cream on a non cheat day.

Yeah. Is there any chance you do that, or do you go tell your friend immediately what you saw?

[Jose]

Well, it depends.

[Brooke]

It depends on the relationship. With your friend? Yeah.

[Jose]

Someone grocery shopping with somebody. I don't know. Are they literally making out? Why?

[Brooke]

Did you guys see something?

[Jose]

No, I didn't see anything.

[Brooke]

Why? Why aren't you telling.

Why aren't you sure? I don't think I would tell you. Oh, no, thanks, friend.

[Jose]

I tell you, and I'd show you, I'd be like, this is how they kiss.

[Brooke]

See, this is exactly what happened to our listener, Jacob, who is left dealing with a very bizarre situation now, and he does not know how to proceed. Jacob. Hey, man. Are you holding up okay?

[Jacob]

Honestly, you. You guys. Not really.

[Brooke]

Oh, no. Oh, my God, I'm dying. Who? What? Where? All of it.

[Jacob]

Okay, so I've been seeing this woman. Her name is Shannon, for about a half a year now. We didn't live together or anything, but I'd say it's been going pretty good for the most part.

[Brooke]

I thought this was gonna be about someone you saw that we had to call the friend. This is about you.

[Jacob]

Yeah. Yeah, this one's about me.

[Brooke]

Dang.

[Jacob]

Okay, Shannon and I will have nights where we hang out, we do stuff together, but then other nights, we're apart. Things where you hang out with your friends and, I mean, it's healthy, you know?

[Brooke]

I disagree. You should be spending 247 with them. But, you know, that's just my clingy nature.

[Jacob]

I mean, like I said, we're not living together. Schedules are not framed around one another.

[Brooke]

Right? You have your own lives. That's totally normal.

[Jacob]

One night, she was out with her friends. Whatever. I got a weird call around, like, 11 from a friend of mine, my friend Omar. And Omar was like, hey, are you home? Because I gotta come over and tell you something. And he was, like, really kind of on edge about it.

[Jose]

Come over, too is exactly what I was gonna say. If a friend says, I need to tell you something to your face, I'll be like, friendship's over, dude.

[Brooke]

Sorry, I can't handle.

[Jose]

I don't like anything.

[Brooke]

That must be pretty serious if he's, like, demanding to go see you.

[Jacob]

Yeah, no, I knew it was important, so I was like, all right, come over. Whatever. He stops by. He tells me that he saw Shannon out at this place called Crystal Lounge.

[Brooke]

Sounds like a shady place.

[Jacob]

She was with a guy, and she was wearing an engagement ring on her ring finger.

[Brooke]

Are you sure that this guy's good at left and right? I have made that mistake before.

[Jose]

I have friends. I don't even know what that finger is.

[Brooke]

Yeah, okay.

[Jacob]

And that's the thing. I was trying to defend Shannon. I was like, nah, you know, you're wrong.

[Jose]

Rationalize.

[Jacob]

But he was pretty adamant, and that's why he had to tell me face to face.

[Brooke]

He.

[Jacob]

He saw what he saw.

[Brooke]

Well, did he. Did he mention anything, like, specific, like if they were kissing or holding hands or doing.

Wearing an engagement ring? Jeff, you never put a ring on.

Well, maybe it was just, like, her friend's engagement ring that she was trying on for fun. You girls are always swapping jewelry and clothes.

[Omar]

Always at the bar.

[Brooke]

Just catching her putting on my friends.

Oh, which reminds me.

[Jose]

Brooke, I'll take your wedding ring off right now. Thanks for letting me shirt back after the segment.

[Brooke]

So, like, did he mention anything specific like that?

[Jacob]

So Omar said they were, like, physically close to each other, but he didn't see any overly romantic gestures happen. So I'm like, all right, it's probably just a friend, and she's wearing some Kind of fake engagement ring.

[Brooke]

I mean, I will say. I will say I have some really hot friends that will wear fake engagement rings so they don't get hit on.

[Jacob]

Oh, and I totally get that. And don't get me wrong, you guys. Like, I feel like I'm dating up. She is very attractive. So I see her the next day and I bring it up, thinking it's going to be, you know, like, 30 second conversation. She's going to laugh. She's going to, you know. But she was like, I don't want to talk about that.

[Jose]

Oh, no.

[Brooke]

What kind of answer is that?

[Jose]

Oh, that's an immediate feeling of guilt.

[Jacob]

I tried to bring it up a few more times, and then Shannon got upset and she stormed out.

[Jose]

What?

[Jacob]

Why would.

[Brooke]

She got mad at you?

Yeah, because she got mad at me. In a lie, gets upset. That's how it works. It's like, anybody who's accused of cheating will be like, no, you were cheating.

[Jose]

Yeah. Oh, you're spying on me.

[Jacob]

But that's the thing. I wanted to give her, like, the medicine as a doubt, and I wasn't trying to be aggressive about it or like, like accusing her.

[Brooke]

Right.

[Jacob]

And now she's not answering my calls. This was just the other night, just this week. And so I need advice. I need advice on how to handle it because you.

[Brooke]

Are you still hoping that she's cheating? Like, there's still a possibility?

No, he's hoping that she is cheating.

In my mind, there's no possibility that she's not cheating.

Okay, I see what you're saying. Everybody in this room is kind of in agreement. It looks really bad for her right now, and it's very, very likely that something is happening behind your back.

[Jose]

I feel like we have not discounted the fact she could be a jewelry heist person and have access to lots of jewelry. And she's scared because we just caught her.

[Brooke]

That is a pretty frequent thing that we get on the show.

I mean, like, you want to what? You want to get the truth out of her?

[Jacob]

Well, yeah, I really am still holding out hope for it to just be something that she's, like, embarrassed about. Doesn't know how to bring it up.

[Brooke]

Yeah, I mean, I was embarrassed that I was with my fiance.

[Jose]

Yeah. With my other family.

[Brooke]

I think that's a highly likely possibility. When we call her here, dude, her husband may answer. Yeah. Or her kids.

They probably haven't gotten married yet.

Yes.

[Jose]

She's close with him anyway. Now.

[Brooke]

I guess you didn't see a wedding band, right?

Yeah, it's totally different. No, Jake, I'm sorry that you're going through this, but we're gonna try and give you a little bit advice here before we call your girlfriend Shannon and let you ask her the question. What was going on when my friend saw you out the other night at a lounge wearing an engagement ring with another guy?

No matter what happens, like, you're the winner out of this. She's the sucky one.

You don't have to hit on him now. He's still with somebody. We'll get to that in a second. Your awkward Tuesday phone calls coming up right after this. It's awkward.

[Omar]

It's Tuesday.

[Brooke]

It's awkward Tuesday phone call. If you're just joining us for the awkward Tuesday phone call, this is what we know.

Okay?

Our listener, Jacob, has a girlfriend of about half a year. She was spotted out recently at a lounge with a different guy wearing an engagement ring.

I need to be taking notes, Jeff.

So right there.

Yep.

That's weird.

Not good.

When Jacob brought it up to her in a fun way, he expected her to laugh and explain. Oh, just a stupid situation. I had to wear it. It was a big joke. But no, she got upset and left and has not spoken to him since. That's why he needs our advice today on what to say to get his girlfriend to just tell him the truth of what is really going on. Yeah, it's the least that he deserves. Brooke, what's your advice to Jacob?

Man, Jacob, it's not looking good.

It's not really advice.

I just like preparing you. Because if all of those things are what happened for real, then it's 100%. She's cheating. Like, there's no way around it, right? Like.

[Jacob]

All right. Brooke, can I get advice on how to handle this?

[Brooke]

Yes.

Yes.

This has been pretty hopeless so far.

[Jose]

You told him the situation.

[Brooke]

You are going to take control of this situation.

Okay.

All right. And you are going to tell her. You need to tell me the truth now. You need to rip it off like a band aid. Yeah, rip it off like a band aid. Because if she waits any longer, it's only going to get worse. Like, you deserve the truth. And if she has ever respected you, ever in the time that she's known you, now is the time to show.

[Jose]

That there it is.

[Jacob]

All right. Yeah. Yeah.

[Brooke]

Thank you.

There was actually a little bit of advice in there. Good job.

[Jose]

Edit out the whole front of that part.

[Brooke]

Every week, I give great advice. Okay.

Jose, what about you? What do you think Jacob needs to remember?

[Jose]

You need to make her Feel comfortable. Remind her. Honey, I want you to know first, I love you, okay? And whatever you say in this conversation, I promise not to judge.

[Jacob]

What?

[Jose]

We listen and we don't judge.

[Brooke]

That's a TikTok trend.

[Jose]

It's an Internet therapy trend, not TikTok.

[Brooke]

You know what?

[Jose]

And I think if you practice it, then maybe she will be comfortable.

[Brooke]

I think actually all of us could take that advice in this room. We should listen and not judge her yet, because there could be a logical explanation for this. We're all going to look really stupid if we're being as hateful as Brooke is towards her already.

She would have just said the logical thing if it was logical, Jeff, she wouldn't have, like, run out of the room. You know what? I want to look stupid. So I'll listen and then judge.

Okay?

Yes.

[Jose]

And then we can.

[Brooke]

Whatever it was.

[Jacob]

Don't get me wrong, you guys. If this doesn't go my way, I am fully welcome to judge.

[Jose]

Yes.

[Brooke]

Okay.

All right.

Exactly.

[Jose]

We give you permission.

[Brooke]

That's actually what we do best on the show. But let's call her. We'll see if Shannon picks up, and then we'll step away and let you make your awkward call. We'll be here if you feel like you need a little bit of help. Okay. Good luck.

[Omar]

Hello?

[Jacob]

Hey, it's me.

[Omar]

I said I don't feel like talking right now.

[Jacob]

No, we need to talk right now. What do you mean, not feel like talking right now? That's not fair.

[Omar]

Because you just seem really upset about something that, honestly, I do not feel like talking about.

[Jacob]

Well, I don't. How do you think I should feel about it? Like what? I want to get this. I want to get this over with. I want to hash this out.

[Omar]

Okay, then just. You know what? Just move on. What do we have to hash out? We don't have to hash out any.

[Jacob]

Okay, sorry. Am I not supposed to be upset when my buddy comes to me saying that you have an engagement ring on and you're hanging with some other guy? Like, what is that?

[Omar]

Yeah, what is that?

[Jacob]

No, I'm sorry. What do you think I'm theory. All right, I deserve an explanation here. Like, it's my understanding we've been together for six months now, like we're boyfriend and girlfriend. And my understanding, we're not seeing other people. So am I wrong here?

[Omar]

Jacob, I don't want to hurt you.

[Jacob]

Yeah, it's a little late for that. You just need to tell me whatever the truth is, okay? I can handle it.

[Omar]

It's Hard to explain.

[Jacob]

Well, can you try? Can you try for me here, Please? Shannon?

[Omar]

Well, you know my friend Sierra, right?

[Jacob]

Yeah, I know Sierra.

[Omar]

Okay, so a couple months ago, she set up this like, hangout with some old friends. She was saying we hadn't seen them in a while. Could I just come and catch up?

[Jacob]

What does this have to do with us?

[Omar]

I'm getting there. This is not. This isn't easy. Okay, so one of the guys who was there at the hang, like. Well, he was my ex.

[Brooke]

So. What.

[Jacob]

What does that even mean?

[Omar]

So we hooked up and I. I didn't know what to say to you because you're so sweet to me. I couldn't. And I started dating him again. And I know it's messed up, I know, but in my head I was like, I've always just wanted to have a forever relationship, be married. And so I had it in my head that. That I was just gonna say yes to whoever proposed first. And he proposed a few nights ago.

[Jacob]

So. So. So wait, sorry, you're actually. You're really engaged? I. I thought. I really thought there'd be some other reason to it.

[Omar]

No, no, I. I am. I'm engaged to someone else. I'm really sorry. I'm sorry.

[Jacob]

Awkward.

[Jose]

Oh, my God.

[Omar]

What is that? What's going on?

[Brooke]

Oh, man.

[Jacob]

Okay.

[Brooke]

Oh, my God. Shannon, we've been listening to this culture. You're on the radio right now with a show called Brooke and Jeffrey. We're doing something called Awkward Tuesday Phone Call.

[Omar]

Oh, yeah. What?

[Jacob]

Look. Yeah, you weren't answering my calls and I didn't know how to address this with you. I've been trying and so I called the radio station to help me get a hold of you.

[Brooke]

Yeah.

[Omar]

And I can't believe you did this on the radio.

[Brooke]

Maybe you shouldn't have been cheating.

Yeah, we do a lot of these phone calls. I'll tell you, Shannon, and we don't normally get a lot that end like this. Usually it's somebody playing a joke, there's some hilarious misunderstanding.

I was waiting for the funny part.

But it turns out, Shannon, you're just a two timing cheater.

[Jacob]

I'm sorry, she said that she can't believe this. No, I'm sorry. I can't believe that you're actually engaged and you hid all of this from me.

[Brooke]

Like, how long were you dating before you were engaged to this guy?

Who.

[Omar]

Who are you? Why do I have to answer questions to you? I don't even know who I'm talking to at this point. You think I'M just gonna answer some questions for some people I've never talked to before.

[Brooke]

Well, yeah, it's pretty valid to the.

Situation because we're Jacob's friend, and we're defending Jacob.

[Omar]

Jacob's friend? He called the radio station. Now he's your friend?

[Jose]

Yes.

[Brooke]

No, we're really clingy. You don't know us.

[Omar]

Jacob is my friend. Like, I still want him to be part of my life.

[Jacob]

Sorry.

[Brooke]

After all of this, you think Jacob would still want to be around you?

Yeah, call him your friend.

[Omar]

Couldn't we stay friends? Like, I even asked my fiance to have our wedding, like, a year so you could have some time to heal. Because you are a good friend, and.

[Brooke]

I want you there.

[Omar]

I want you in my life.

[Brooke]

You should delay your wedding a year so that your current boyfriend could get over you so that he can go to the wedding.

Jacob.

[Jacob]

I mean, are you insane? It's got to be a joke.

[Brooke]

Well, what does your schedule look like next. Next time?

[Omar]

I wouldn't joke. You're a special guy.

[Brooke]

Okay, I was joking.

[Jacob]

My schedule next year is figuring out when she's on her honeymoon and burning up her apartment.

[Brooke]

Jacob, we're on tape here, so this can be used in the court of law.

I can help you. No, Alexis. To move on. Okay.

Yeah.

Okay.

Yeah.

Listen, you guys.

[Omar]

You don't know me, but I'm not a bad person. Yes, maybe I made a mistake. Maybe I should have broken up with Jacob earlier, but I'm not a bad person.

[Brooke]

Maybe. Did you say maybe?

Jacob, are you willing to call this strike one and give it two more.

[Jose]

Strikes, you know, for.

[Brooke]

In the name of friendship?

[Jacob]

Yeah, I think all nine innings are over.

[Brooke]

Sports analogy.

[Omar]

Hey, I wish Jacob well. I hope he has a great life.

[Brooke]

I don't know what to say to you, Shannon, honestly. But, Jacob. Jacob.

Sure, Knowing Jeff, he's going to send you a wedding present.

Yeah, I do. I do perform at weddings, so you can hire me. But, Jacob, the good news is you got the truth, right? That's what you were after here the whole time?

We wasted six months on this relationship. But, I mean, that's another positive.

Yeah.

[Jacob]

Well, hey, you know what? Since we're friends legitimately, let's go out, spend the rest of the week drinking. I'm up for it.

[Brooke]

Wait, what?

You mean us, right?

[Jacob]

Yeah. Yeah, exactly.

[Brooke]

Yes. Drinks on Jacob. Cool.

Brookie.

Jeffrey in the morning.

[Ryan Seacrest]

Hey, it's Ryan Seacrest for Albertsons and Safeway. It's stock up savings time now through March 25th. Spring in for storewide deals and earn four times the points. Look for in store tags to earn on eligible beverage items like Powerade, Monster and Poppy, or breakfast items like Quaker Instant Oatmeal or General Mill Cereals plus many more. Then clip the offer in our app for automatic event long savings. Stack up those rewards to save even more restrictions apply. Visit Albertsons or Safeway.com for more details. It is Ryan Seacrest here. There was a recent social media trend which consisted of flying on a plane with no music, no movies, no entertainment. But a better trend would be going to chumbacasino.com it's like having a mini social casino in your pocket. Chumba casino has over 100 online casino style games, all absolutely free. It's the most fun you can have online and on a plane, so grab your free welcome bonus [e-mail] sponsored by Chumba Casino.

[Brooke]

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[Jacob]

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[Shannon]

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