Brooke and Jeffrey: Second Date Update - Awkward Thursday: Convince The Sis

Episode Date: July 16, 2026

One of our listeners BROKE UP with a guy and now she’s thinking she made a mistake. She wants him back but before she can get to him she’ll have to go through his SISTER in your Awkward Thursday Phone Call!See omnystudio.com/listener for privacy information.

Hey, Portlandia fans. Carrie Brownstein and Fred Armisen here. The Dream of the 90s is alive in podcast form. We're launching Podlandia, AEO rewatch, our brand new podcast where we revisit every episode of Portlandia together, breaking down sketches, going deep on our iconic characters, and pulling back the curtain on how it all got made. And we'll also be joined by the people who helped bring it all to life. Guest stars, collaborators and friends, including director Jonathan Chrysall, the mayor himself, Kyle McLaughlin, legendary musician Amy Mann, and many more.

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The world gets crazier. And Yamanika is here to tell whoever's responsible, you're the problem. Do you know I just found out who Sidney Sweeney was? If he got a bunch of women, then I should have a bunch of men. Do better or do less, so I don't have to do so much. I'm Yamanika, and I'm out. Listen to You're the Problem with Yamanika on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. On Raiders of the Lost Podcast, we explore cinema like no one else, including huge interviews with stars like Ryan Gosling on Project Hail Mary.

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And we're the hosts of Everyone Watches Women's Sports, a new podcast from together. We're breaking down the biggest headlines, the viral moments, and the stories everyone's talking about across women's sports. From game-changing performances to culture-shifting conversations, we'll give you our takes, our debates, and a few laughs along the way. Because everyone watches women's sports. Listen to Everyone Watches Women's Sports. It's on the I-Heart Radio app, Apple Podcast, or wherever you get your podcast.

No one wants less awkwardness in their life. I mean, that can't be possible. That'd be boring. It's Brick and Jeffrey. We got a brand new episode of Special Awkward Thursday phone call for you today. Yeah. Sometimes we just get so many requests in that are so good. We just got to fulfill it.

So that's coming up in just a second, but first comments. Yeah, Risa said, hey guys, love your second date updates. I listen to them when getting ready while working after work playing pool. I wish we had something similar here in Australia, but there would probably be a lot of cussing and long. Lawsuits. Yay. Oh, yeah. Yeah, we wish we had more cussing in lawsuits, too.

Yeah. Have your Australian people call into our show. Yeah. We would love the accents and the second dates. It'd be great. Yeah, except for we still can't do it. Oh, we can't dial one. Yeah.

Doesn't really work because you can't call in. Anyway, have fun down under. Yeah. It sounds like a good time down there. All right. Your brand new, awkward Thursday phone call starts right now. They say love is really all about timing. Oh, yeah.

Yeah. Yeah. Which is why I set up my daily lunch break in the janitor's closet at exactly 1203. That's love, Jeff. You don't even know what happens after that, Brooke. Oh, boy. You'll be changing your tune. But what I can say is one of our listeners broke up with a guy a little while ago.

And now she's thinking that she made a mistake. Oh. She wants him back. Does this ever work? Yeah. I mean, we have listeners text in. They're like, I'm married a guy I broke up with. Can books?

always get any higher? Sometimes it works. Trust me. Sometimes. I mean, it's hard enough to do it normally, but this one comes with a whole new obstacle that we have to overcome. And it's definitely weird. You're going to hear it in your brand new, awkward Thursday phone call right after this.

It's awkward. It's Thursday. It's awkward. Thursday. Phone call. You know, sometimes we'll talk about the one that got away. And you always look back wondering, what if? Yeah.

What if? Like Brooke and her old high school gym teacher. But what about the one that you pushed away? And now you're looking back like, why did I do that? Like the high school gym teacher and that one over-eager girl, Brooke. What? No. I miss you, Mrs. Adams.

In that situation, is there any way to fix it? Apparently, that's what one of our listeners, Kate, is hoping we can accomplish for her today with her awkward Thursday phone call. Kate, which one of your old teachers are you pining over right now? Who is it? Oh, my gosh. Thank God it's not an old teacher. Yeah.

But it's an old ex, it sounds like. It is, yes, Cameron. Cameron. I feel like it depends on when you pushed Cameron away. Is this 20 years ago or is this two days ago kind of thing? No, not that long. Oh, okay. Just a few months ago.

A few months ago that you broke up with Cameron. Okay. And what was the situation like? your relationship like? I mean, we hung out for a few weeks and, you know, it was great. We had fun. Wait, hold on. You only dated for a couple weeks?

Just a few weeks, yeah. Nothing too crazy. Okay. Okay. Okay. Not like official. Yeah. Okay.

Well, if it was fun for a couple of weeks, why did you end it with him? I mean, he was a really, really nice guy, you know? Yeah, that's why. Say no more. Ick. We're all disgusted. So we get it. No, just kidding.

No. I mean, he was really thoughtful, you know, and we had a lot of fun dates, and we went to a farmer's market in particular. And it was the sweetest day. We had a really nice time. But that's when I could really tell that he was way more into me than I was into him. Oh, yeah. How could you tell? He was just, like, the conversations we were having.

He was, like, kind of, like, talking future style, if that makes sense. And I really wasn't in the right head space to be dating. I kind of wanted to take some time to really explore myself some more. Okay. That's good. You were just scared because you weren't ready. Yeah. Yeah, exactly.

It really had nothing to do with him. He's a great guy. I bet he would love to have heard that. Yeah. That it was nothing to do with him. Does he believe it, though? I mean, who hasn't heard that? You're right.

I was actually surprised by his reaction. He was really very mature about it. And, like, he really understood what I said, and he wished me luck. And that really stuck with me. That's really good. That is the quickest way to get somebody back. Back? Yes.

What do you mean? If you want someone to like you, you act cool that they are finally. I'm telling you. Just like you and me, Brooke. What? Wait. I know. See, she's speaking about a personal experience that we had.

If I was watching the video, you can see how weird is coming. Yeah. So, listen. People already think, don't even. Okay. Listen, it's your life, bro. You can do it however you want to do it. I don't care.

The new listeners are confused. You go in joy. Anyway, back to... But that's the thing, though. I don't think Cameron was, like, really playing hard to get. I really think he was just being mature about it. Right. Wow.

And that was good for you, right? Exactly. Because I've been really thinking about it lately, and it's been a few months since. And I really just wanted to see what Cameron's been up to. So you guys just started. I'm texting after that, but you're still thinking about it. I am. Why are you so nervous to make this call?

Like, what do you need our help with? So here's the thing. You probably should know this, but I did text him. Oh. You know, catch a feeling and see what he's thinking. And at first, he didn't answer. Ooh. What did you text?

Yeah. I just told him that I missed him and that I really missed our fun little hangout, you know, nothing crazy. You went in hot, though. That's straightforward. Yeah. Yeah. It could be a lot, honestly.

I guess. From a guy getting a text out of the blue from someone you used to see like, hey, I miss you all of a sudden. Sometimes guys like that are like, come over. The sad ones, yes, that's true. But Cameron doesn't sound like he's like that. No. And even when he didn't answer, like, I was like, oh, my gosh. Like, maybe he's just not into me.

Maybe he's got a girlfriend now. Oh, no. But he ended up texting me back. Okay. And it's like a little strange. but he basically says that his older sister, who's very protective over him, I guess, he talked to her about it

and she doesn't think that he should date me. Oh. Okay. Have you met the sister before? I mean, no, I haven't. Okay. So did you put the ultimatum out there? So you got to pick? It's either your sister, you mean.

I mean, that'd be an easy choice for Jeffrey in this situation. You want me to pick family? Yeah, right. Yeah, I am all yours, Kate. I throw my mom in on top of the ball. Deal. No, I'm kidding. Guys, remember, I'm asking for advice.

I don't want to run him away. Okay. Right. Okay. So you want to call him, not the sister, right? Well, he did give me her number. What? And he basically was, like, call her and ask. Whoa.

That's why you're, I almost suggested, like, you should call the sister because if you get her on your team, then it'll make everything easier. Sounds like he's playing you. Yeah. It sounds like he's setting you up for a trap. Yes. Are we about to call our own loser line right now? Yes.

It could be. Okay, so you want to call this guy's sister and ask for permission to date her brother? Or convince her to like her. Like, that's the thing. It's not a permission thing. I think that she's got to come across as likable. She's only heard bad things probably. Yeah.

And sisters are important. That's true. Do you know the sister's name? Yes. Her name is Brittany. Oh, no. Not a Britney. They're feisty.

Brittany's going to be feisty if we know. He's going to be judgy. We'll find out. But we're going to come back first, give you a little bit of advice on how to talk to your maybe future boyfriend's sister and convince her to like you enough to bless your relationship. It's weird. It's weird to say. Just tuning in. They're a little confused.

There's a good reason for this. Let's see what Cameron's sister says when we come back and do your office. awkward Thursday phone call right after this. It's awkward. It's Thursday. It's awkward. Thursday. Phone call.

I've heard of asking for a parent's blessing before a couple gets married, but not asking a dude's sister for her blessing to date her brother. Yeah. Just a date. It's a new one for us, but that is the situation we find ourselves in. I cannot believe the guy even shared the number for the sister. It's wild. That's pretty funny.

But our listener, Kate, hung out with the guy for a little bit. She wound up ending things with him to, quote, find herself. Yeah, well, to dump him via text. Yeah. But there was a reason for it. And a few months later, she finds herself wanting to get back with the guy that she rejected not too long ago. And what does he say about it? He says, ask my sister, because she does not like the sound of it.

So we are about to call his sister to see where her head is out. see if we can change your mind. And Brooke, like you said, is your advice centered more on getting the sister to like you? Yes. Okay, what are you thinking? You need to connect. That absolutely should be your number one priority. Okay.

Okay. And so I think the way you do that is through humor. That's the easiest way to become friends with someone. If you can find like some similar humor stuff. Now, it's important, though, you are not allowed to make fun of her brother. Ever. Ever. Yeah.

But she being a. sister, that's her wheelhouse, man. You need to set her up for a great stupid brother story. Just ask her something in general, like, hey, do you have any funny stories about growing up? Oh, I'm serious. I'm serious. There's nothing more than a sister loves than just pummeling the brother.

Okay. Oh, I love talking bad about my brother. Yeah, see? Kate, what do you think about Brooks' advice? It does sound like good advice. Get someone laughing nine times out of ten, they'll do what you want them to do. Yes. But I got to kind of see where I can fit that in.

Okay. Okay. You always have that as an option. But Jose, do you have any advice for her? I know Brooke wants you to connect with his sister, but I think the best way to a strong connection is to focus on saying nice things about it. Like, if you remember anything specific that he liked or anything, work that in with the sister. Oh, like that you were paying attention into the relationship and that you care about him as a person.

I know his favorite pizza is this, da-da-da, she may go, hey, Yeah. She really cares. Is he still into Dunkeroo's? Yeah. Does he do any funny stories with him embarrassing himself over Dunkeroo? There we go. I know. Okay, it's all coming together. What do you think, Kate? I like that, actually. I'm going to try that. And only use Dunkeroo's if that's a real thing you like. Don't just toss him out there. I hope he's still not on Dunkeroo's. Everybody likes Dunkerooze. But now, guys, he's an adult now.

Why do you have to stop? Have you had him? Let's not get too deep into Dunkeroo's. We have to do this awkward Thursday phone call. But before we do that, Kate, does the sister know that you're going to be calling her? Is she aware? I mean, he gave me her number, so I would assume she does. This guy is setting you up. Oh, God. Yeah, this might be one big joke on you.

I wonder she's even going to answer. I guess we'll see. Keep your dunkeroo's close because I'm dialing the number, and we are going to step back and let you do this. Good luck. Hello? Is this a Brittany, Cameron's sister? Who's this? So, I mean, we've like never met before, but I do know your brother, Cameron.

Okay. So, me and Cameron actually hung out a few times a little while ago, and he's a really nice guy. and I just wanted to Wait wait wait wait hold on So you You dated my brother for a while And now you're calling me What exactly

How did you get this number? Oh From Cameron I mean I thought he would have told you I was calling Okay I'm confused This is so weird I don't know Why are you calling me

What do you need from me? Okay so Cameron said that you weren't really comfortable I guess with the idea of like him and I going out again, so I wanted to reach out. Oh, my God. Are you, oh, my God, are you Kate? Yes.

Yes, that's me. That's Kate, yes. Oh, my God. Okay, I see. So you're the one who's been messing with his mind and taking advantage of him. Oh. What? Um, no.

That's not me. Okay. so you're not the girl that he took out on seven dates. I mean, I don't count dates, but maybe. Okay, three dinners, two coffee dates, mini-golf, and I believe he drove almost an hour to go meet you at some, like, random farmer's market that you wanted to visit. And he paid for everything, all your dates.

Sound familiar? Does that sound like the date? Well, I mean, most guys pay for dates, but I really don't think that even matters who paid, really. And then after he does all of that for you, and if nothing but kind and respectful, you have the nerve to text him out of the blue and say, oh, I'm actually not in a place to date anybody right now.

I really need to focus on myself. You deserve someone who can give you 100%. Is that you? That was you? I mean, yeah, but like you're taking it like... Then three days later, you hard launch a relationship on Facebook with some other dude that apparently you were seeing,

behind his back the entire time? Okay. Hold on a second. No, I will not hold on a second. You called me, okay? Because after that relationship blew up in your face, only then did you go crawling back to my little brother, texting him saying you miss him all of a sudden?

Oh, no. Okay. It's not my fault that a lot of guys want to be with me, and your brother was one of them. Why do you think he pays for seven days? Oh, my God. Oh, my God. You would be so lucky to,

date my brother and the crazy part is you actually had a chance and you it up because in your words, ooh, I have too many options. Poor me. Oh. Wow. Is this when we asked for a funny story? I think it's going

well. Hello? Who's this? Hey. Oh, Brittany. Don't hang up. Yeah, this is a radio show that you're on right now. We're called Brooke and Jeffrey in the morning. Wait, is this a prank? No. No.

It probably feels like one. That's actually Kate. This is called the awkward Thursday phone call because... Oh, my God. Wow. You get even more pathetic. Calling me on a radio. Well, I mean, wow, that kind of hurt, right?

Because radio is not that pathetic, okay? But... We did kind of set her up for that. I mean, I get what she did. It's not cool. Yeah. So Kate feels bad about how things ended between your brother and her. And she was hoping that maybe there was a way to repent.

bridges and get back on your good side and see if maybe they want to hang out? No, not anymore. I mean, I don't want to be dating her brother. I don't want to end up in a family with you. That was it. You're giving up after just one hard conversation, Kate. Like, you can't give up now. I mean, it's really not that big of a deal.

I miss Cameron, yes. But like I said, there's 300 other guys in my inbox. I don't know. Go date them. Yeah. Maybe you need some guys in your inbox and you won't be so obsessed with who your brother is dating. I'm married, bitch. Kate, I have to say you never mentioned to us that when you went to go find yourself,

that meant you were going to go get into a relationship with a different dude. Three days later. Yeah. Well, that was irrelevant. Like I said, we were dating. We weren't in a serious situation. Well, now that you're alone, this is a great time to you to find yourself. Oh, trust me, honey.

I'm not alone. I think her feelings are a little bit hurt by what was said. Yeah, there's really no comeback anymore. A lot was revealed. Well, it's just like maybe you didn't like Cameron that much. Yeah. Yeah. I mean, maybe there's a funny story about Cameron that Brittany would like to share.

Oh, see? I'd be space for that. Right? Yeah. The funny story is that when I tell him about the phone call, he's going to laugh his ass off. Oh, wow. I mean, I think this is probably all the things that he wanted to say, and that's why he just sent the sister's phone.

number without giving the sister a heads up. Kind of smart. Good news is, Kate, I think we got some answers to the questions that you had about why the sister was not feeling comfortable. Uh-huh. Yeah. Did I hear a hang up? No, I'm here because it really doesn't bother me that much.

Can I hang up? I don't want to be working on. Brooke and Jeffrey in the morning. I'm Cynthia Lois and I'm Josie Dye. And we're done pretending we have it all figured out. Each week we laugh, cry, and talk our way through life's messiest moments. The things you think about but would never say out loud. The questions you are always too shy to ask.

Relationships, regrets, awkward moments, and the stuff no one warns you about. It's honest, it's funny, and sometimes it gets a little uncomfortable. But that's kind of the point. This is Cynthia and Josie's Unmentionables. Listen on the free IHeartRadio app or wherever you get your podcasts. What's up, fam? I'm sports journalist, Ari Chambers. Hey, what's up, y'all? It's your girl Sam J.

And we're the host of everyone watches women's sports, a new podcast from Together and I Heart Women's Sports. Because let's be real. Women's sports is giving us way too much to talk about these days. So Kelsey Finler, she became the first female solo rower to go from California to Hawaii. My first thought is like, what's up with the snacks? Like, what are we eating?

The highlights, the rivalries, the breakout stars, the moments that take over your entire timeline. And the conversations that start during the game and somehow keep going all. All week. Every week, we're breaking down the biggest stories across women's sports. Naomi Osaka showing out. She beat Sabalinka. Shout out to you, Naomi. You get the palm, Naomi. You get the palm for that.

Because we're not just interested in what happened. We're interested in why everyone's talking about it. Because everyone watches women's sports. Listen to everyone watches women's sports on the IHeart Radio app. Apple Podcast or wherever you get your podcast. You know, I really wish that sister would have been just a little more clear cut on how she felt. I did not get a strong read either way on where she stood. You guys?

You know what? I kind of, I heard her. You heard her? I heard her. Yeah, I heard exactly what she was saying. Yeah. Kind of let her have it. Yeah.

That was one that I think she had replayed over in her mind over and over again. Like if I ever have a chance to talk to my brother's ex, this is what I'm going to say. She was ready. She was amped up. And it was honestly deserved because we're telling people all the time. If you're on this show, please tell. us everything. Yeah.

Don't say you had to go leave to find yourself, and that really means you had to go be in somebody else's bed for two months. Hey, we don't know if the guy's name was yourself. Oh. You know? That's a good point, Brooke. Thank you. She didn't lie.

All we ask, though, is just be honest with us. We'll be honest with you. Well, Brooke won't, but the rest of us will be. Yeah. Brooke, how much money do you make? What? See, that's exactly what I thought. It's Brooke and...

What's money? Yeah. I'm here for free. It's Brooke and Jeffrey. the morning. Hey, Portlandia fans. Carrie Brownstein and Fred Armisen here. The Dream of the 90s is alive in podcast form. We're launching Podlandia, AEO rewatch, our brand new podcast where we revisit every episode

of Portlandia together, breaking down sketches, going deep on our iconic characters, and pulling back the curtain on how it all got made. And we'll also be joined by the people who helped bring it all to life. Guest stars, collaborators and friends, including director Jonathan Chrysall, the mayor himself, Kyle McLaughlin, legendary musician Amy Mann, and many. more. Kyle is going for it here. You fully improvised, not just words, but a song.

Well, I thought you were all going to write a song. I remember you thinking that. Listen to Podlandia. A.O. Rewatch on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. This is Chelsea Handler from Dear Chelsea. Every week, the news gets worse. The world gets crazier. And Yamanika is here to tell whoever's responsible, you're the problem.

Do you know I just found out who Sidney Sweeney was? Because if he got a bunch of women, then I should have a bunch of men. Do better or do less so I don't have to do so much. I'm Yamanika, and I'm out. Listen to You're the Problem with Yamanika on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. On Raiders of the Lost Podcast, we explore cinema like no one else, including huge interviews with stars like Ryan Gosling on Project Hail Mary. It was like the Jaws Shark. Didn't always work.

Came with its own problems. that's what made it great. The cast of obsession. On set, there was so much magic happening with each scene we were putting together. Deep dives into classics like 2001 of Space Odyssey or Fight Club, plus weekly episodes on all industry news. Listen to Raiders of the Lost podcast on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts.

And for more, follow at Raiders of the Lost podcast and at TikTok podcast network on TikTok. My first guest is Terrence Hilton, Shakira, Luke, and Yerrin. You have surprises? Many surprises. Welcome to the Sweet 305 podcast where the group check comes to life. What on? You're the only person I know that loves a yellow starburst. It's lemonade.

This is Sweet 305. Here, oversharing is encouraged. Listen to Sweet 305 with Lele Pons on the IHard Radio app, Apple Podcast, or wherever you get your podcasts. What's up? I'm at sports journalist Ari Chambers. Hey, what's up, y'all? It's your girl, Sam J. And we're the hosts of Everyone Watches Women's Sports,

a new podcast from Together. We're breaking down the biggest headlines, the viral moments, and the stories everyone's talking about across women's sports. From game-changing performances to culture-shifting conversations, we'll give you our takes,

our debates, and a few laughs along the way. Because everyone watches women's sports. Listen to everyone watches women's sports. On the I-Heart Radio app, Apple Podcast, or wherever you get your podcast.