Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Date My Ex PLEASE

Episode Date: July 28, 2026

Would you ask your best friend to do something huge that goes against the unwritten rules of friendship? One of our listeners is doing just that and we have him on the line for an Awkward Tuesday 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.

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. 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. What's up, fam? I'm sports journalist Ari Chambers. Hey, what's up y'all? It's your girl, Sam Jay.

And we're the host of Everyone Watches Women's Sports, a new podcast from Together and I Heart Women's Sports. We're breaking down the biggest headlines. Naomi Osaka, showing out. Shout out to you, Naomi. The viral moments. I've been obsessed with Kashan Rock's boxing journey.

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from Seth Rollins. What are you doing, my belt? To Bill Burr. I don't think I've ever met somebody so exactly out of their mind as I am. And now, we even have more great guests coming up, including the great John Tuturo. It's called happiness, delivering happiness.

and many, many more. Open your free high-heart radio app. Search Delivering Happiness with Nick Tuttle. And listen now. 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? 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 Yomeney. Monica on the I Heart Radio app, Apple Podcasts, or wherever you get your podcast.

It's Brooke and Jeffrey. Thank you so much for finding the official second day podcast. And we have a new video up today on our YouTube. And it's one people have been waiting for for weeks, apparently. Oh, yes. It was when Brooke had to break up with a listener who started flirting with her. Oh, it was so uncomfortable. It was so uncomfortable.

Oh, my God. So many people were commenting to they couldn't wait to see your face and see you Blushing. Why are you so happy about this? Oh, I'm going to go rewatch it, even though I lived through it. Oh, my God. I'm excited. So go to our YouTube at Brooke and Jeffrey, please. Okay.

All right, there it is. And subscribe while you're there, please. All right, here's your second. Here's your awkward Tuesday. I know, I am. What is it? Awkward Tuesday right now. When it comes to your very best friend, that relationship is so strong you would do anything for them.

Oh, for sure. You would bail them out of jail. Absolutely. You would help them bury the body. Absolutely. You would lend them thousands of dollars just because they asked. No questions needed. Honestly, yeah.

Reminds me, Brooke, I need to borrow 45 grand, so I'll text you my Ben, okay? But no question. Well, what if, though, okay, 40 grand, then fine. What if, though, the one thing that you needed them to do goes against every unwritten rule of friendship ever. Oh. Uh-oh. That's the reason one of our listeners needs our help today. He has to convince his best friends.

friend to do him an enormous favor, even though it 100% goes against brocode. Uh-oh. You're going to hear it in a brand new, awkward Tuesday phone call. Next. It's awkward. It's Tuesday. It's awkward Tuesday phone call. They say in life, only three things are certain.

Death, taxes, and having weird, awkward drama with your ex. That is a certainty. It's definitely going to happen. Of course. One of our listeners is having an issue with one of those life certainties and wants our help today. God, I hope we're going to have a whole tax discussion right now. I'm guessing it's taxes. Let's open up our quick and apps.

Hopefully we're going to save some money for today's listener named Michael. Michael, you have your W-9 form ready? I can. We're going to do both. It sounds like you got another issue. Yeah. What's your drama about? Yeah, I've reached out because I've had this awkward, have an awkward situation with

my ex, April. Okay. Just even when you say her name, April. Yeah, I mean, she's lovely, but I'll give you the whole story. So we haven't been together for a few years. Oh, it's been a while. Yeah, but it's been quite a while. It was like five to six months that we actually dated.

The thing is, it was good overall. I mean, I was attracted to her. We just didn't really mesh well. Our conversations were pretty dull or just. disconnected. Okay. You guys just weren't the right fit. Yeah, yeah, yeah.

And then, like, towards the end of that time together, I just started, I mean, it was like subconsciously started listening to a lot of breakup songs. Then I started having dreams of breaking up with her. And when I'd wake up, I'd feel really positive and better about everything. Oh, man, that's a sign. Like the universe is trying to tell you that something's wrong with your relationship. Yeah. Is this information important to the story?

story. Let's spend five more minutes saying what you didn't like about. Nothing really was other than just us not meshing well. We didn't cheat. There was no like we didn't argue anything like that. But we did like the breakup

came really weird and sudden. But like kind of like as you said like the universe telling us we broke down in this tunnel and we just were like stuck together waiting for a tow truck. And we just had a conversation. It was sort of just blunt.

We decided to not be together. Okay. You broke up in a car stuck inside of a tunnel? Yes. Sounds right to me. Yeah, right. Let's talk about some deep stuff. Let's pull the band-a-up here.

Okay. Well, at least it's cordial, bro. Can you imagine being that with tow truck driver when he pulls up? Yeah. So you said that happened, you know, years ago. How does the drama happen today? Well, we've remained friends Because as friends, we work really well

That's awesome That seems healthy and great Yeah, overall, yeah, yeah I'm sort of like I would say I'm kind of her shoulder to cry on Now in the dating scene You're the only guy who's ever happy With being in the friend zone now

Yeah, yeah It's good because you both want that Yeah, right Well, yeah, it's a good friend zone But you know, I just try to pepper it up A lot of times she'll go into that space where she's like, oh, I'm going to die alone and I'm just like, no, you're not, just keep at it.

You're great. Yeah. Maybe you should change that advice up and agree with her. Why do I feel like that's actually what you would do, Jeffrey? Well, maybe that would motivate her to actually find somebody. Oh, okay. So where's the awkward part come in and all of this? It all sounds fine.

Yeah, that's true. Yeah. Okay, just recently we were out drinking in a bar and she decided to confide in me that she finds my best friend, Chris attractive Oh Oh boy

And you find Chris attractive too Yeah you don't like her anymore This is awkward Oh it's like they're both Yeah I don't understand the issue I when she told me this

I actually was quite excited Because I think they'd be perfect again Oh wait what Chris also loves boring Stalled out conversations No no I don't think it would be boring And stalled out with this too Okay

Okay Yes, I mean, one, I mean, they're way better together. Okay. They mesh really well. And then two, oh, I would just like to relieve myself of the burden about hearing her dating life anymore. Oh. Shift it over to Chris. Being the shoulder to cry on, my shoulder's wet.

Yeah. Okay. But you don't think that that would be weird for you and Chris's relationship to have your ex-dating him now? Well, they all know each other. Right? They all. But that's, I mean, that's so awkward. I mean, if you do it for years.

I mean, if you're claiming you're really just friends, it shouldn't be a big deal. And it was years ago that they broke up. It would not be awkward for me at all. Okay. The thing is, it's Chris that I know. I just know he has a brocode mind and it's going to be awkward for him. And that's the awkward thing is I need advice on talking to him and convincing him to ask her out. Oh.

So we're going to call your best friend. And try to play matchmaker. No, let me ask Alexis, you know, from a ladies' perspective, if you were the ex-girlfriend, how would you feel if your ex-boyfriend was, like, pushing his best friend on you now? I mean, you don't want anyone to be pushed to want to date you. Gently nudged, whatever you want to say. You wouldn't know. I wouldn't want her to know, like, I wouldn't want to find out. Oh, you'd want it to be kept a secret.

Like, it was just a natural connection. I want to think he's just been waiting for me to actually, you know, he's always wanted to date me. Okay. Secretly. He didn't have to be persuaded. Yeah, like he's like, finally! We didn't have to offer him a prize at the end of this in order for him to go out with her. Sure, that could be part of the strategy that maybe we come back with when we give you advice.

Before we do our awkward Tuesday phone call to your best friend and try to convince him to date your ex right after this. Thank you. Hold on. It's awkward. It's Tuesday. It's awkward Tuesday phone call. We do a segment on our show called Say Yes to the X. Oh, yeah.

Where we try and convince someone to, you know, try things one more time with an old flame of theirs. See if it goes better the second time around. Usually works 2% of the time. This is a little twist on that. It's say yes to your friend's ex. Because we're trying to help Michael call up his best friend and convince him to try dating Michael's ex-girlfriend. That's right. So weird.

Which is a violation of every brocode that's out there. Oh, come on. They only dated for like five or six months, and that was years ago. Okay. Most people don't gloss over relationships the way that Brooke does. I just feel like Brocote's really not that strong. Yeah, right. I think you're being dramatic.

I wouldn't expect any women to understand the value of BroCode. But he thinks they would be a great match together. And he's also tired of hearing his ex complain about how she's going to die alone to him all the time. So there's two reasons for doing this. Now he just needs a little advice on how to convince his best friend to say yes. Yeah. Brooke, without hitting on him, what advice do you have? No, I'm not going to hit on you?

Listen, you need to let your best friend know and remember that you're his best friend. You know him better than anyone. Okay, you always have his best interest in mind. And that's why, although the idea may be crazy, you've got to listen to him. Does that make sense? So your advice is just trust him? Yes. Yes, because it's best friends.

What do you think, Michael? It's not really the detailed advice that I was hoping to get, but I'm happy to give him a call and tell him and remind him, I guess, that we're best friends. He may have forgotten. This call may remind him of your friendship. Oh, wait a little. We are best friends. I do love you, bro. I do trust you.

Jose, what do you think? There's a lot more to broco than just don't date my ex. And bros do each other favors. And this is what you need. Get him to agree to one date. Okay. And then your job is done. Okay.

You know, so it's like a win-win pro code. You're doing favors for your friends here. Set it up like you're doing him a favor. It is a favor. It is a favor. Okay. Yeah. He said that.

What is a lover? What do you think, Mike? I mean, that sounds like clear advice that I can, you know, a goal in mind. My advice. My advice was just going to be toss him in a closet together with some candles and Barry Manilow and just like, let it happen. lock the door. See, that's what brocode always gets broken. Yeah. That's how babies are made.

But anyway, that's what we got for you, man. We're going to wish you luck and dial up your friend and try and convince her. Best friend. Sorry. Yeah, best. Thank you for reminding me. I'd already forgotten. But we're going to try and help you convince him to date your ex. Here we go. Good luck. Michael.

What is this number that you're calling from? Oh, I just, um, new phone, man. Sorry. I just like trying to get my contacts in here. here and I thought, why not call you? Check in, dude. What's up? I was just calling, check in. Me and April recently, we went out, we got drinks together, you know, as we do. Nice.

It was really a fun time. She's just so delightful and easy to get along with, as you, you know. Dude, did you guys hook up again? Nice work. No, no, no, no. We didn't hook up. We're still really good. good friends. And you know, you and me are best friends.

Yeah. I don't understand what you're getting at here, dude. I'm just saying I know you better than anyone else. And I know it's good for you. Hanging out with April, she brought up something that I think was also good for you. Okay. You know, we're a couple rounds in. She told me that she's, she's, She's attracted to you. She, like, digs you. As your best friend, I think that would be great for you and her.

Wait, what would be great? She finds me attractive. I don't know what you're like what. Yeah. She sees something in you, you know, like I do, like as a best friend. Why do you keep saying that? I'm just reminding you. Bro, I mean, you dated her, so I think that that's like a moot point at this point.

Like, it's off limits. But is it? It was years ago. Broke code, schmode, who cares? Like, I'm just letting you know it would not bother me. And you would be doing me a huge favor. But just, how would I be, like, how is that doing you a favor, dude? I want you to be happy.

You're my best friend. That's friends. Look out for each other. I mean, if I can be straight with you about this, like, yeah, that's awesome that she finds me attractive. She's cute. I mean, you're right. She is really cute. Right.

So I just got a level with you. A short version has been there, done that. Oh. Oh. What? What do you mean? April and I have. that we've made out before

Wait, when? I'm not proud of this. This was when you all were on the rocks. Oh, my God. Brok-smode, right, Jeff? I mean, I can't believe she cheated on me with you, my best friend. Oh, God.

God, that's some news. Who is it? We need to jump in on this conversation. Chris, are you there? Yeah. Hi, Chris. Yeah, we're a radio show called Brooke Jeffrey in the morning, you're on our show right now on a segment called Awkward Tuesday phone call.

Oh, man. Whoa, okay. Whoa, to what you just said. Oh, my God. Michael. Oh, man. Oh, God. Is he breathing?

Michael, are you okay? Kissing her again? I'm just having a hard moment. Okay. Wait, weren't you saying that you're completely over her, though, bro? Well, I'm just more bummed out about my best friend now. Oh, yeah. Alexis, you nailed it, broke code.

It never exists. No. It's a fake line. Seriously, I got to be honest with you, it was like a very brief makeout session. We were both buzzed. You at that point also had said to me like you were kind of done with the situation. So that was another factor. Like, I am very sorry.

That is not who I am. Well, that's hard to come back. Sounds like, though, it sounds like Chris has a lot of guilt about it and knows he made a dumb decision. 100%. The reason I didn't even mention it before is because it was so inconsequential. I cannot emphasize that. Like I said, it was nothing and it was stupid. I mean, clearly it wasn't stupid and nothing for your ex-girlfriend because she's still interested. I'm sorry. I'm just wondering why after three Long Island nice tea, why wouldn't the girlfriend like admit to you, Michael,

that she's already kissed him before at that point? Obviously, she's better at secrets than Chris is. Yeah, like most girls are. Oh, yeah, well, I guess she would have to admit that she cheated on him at that point. So, okay, that makes more sense. She wants to be friends, you know? She wants to go out with good kiss Chris. Oh, Michael.

How you doing? I'm doing all right. I mean, I want to forgive my best friend, but I need a favor from you. What, you're still going to ask? What is it? What is the favor? Chris, can you just agree to take her on one date? Oh.

You still want this to happen? Whoa, whoa, wait. I'm so confused. So you still want me to take her on a date. It's the least you could do. I mean, you cheated. She cheated, you cheated. Both cheated on me with each other.

Just go on one date. You've already kind of done it. I mean, if you're going to kiss it, do it under like the proper terms. If you end up together, it makes it better, I think. There you go. Cancells out. Yeah. That's what a best friend would do.

Dude, if I do that and we're still good, it would be the only reason that I'm doing it. Okay, Michael, he said that he would do it for your forgiveness. Do you forgive him? Oh, I forgive you. Yes. You're still on that day. Wow.

Wow. How whiny is this woman about her dating life? Hold up. Is that why you're having me go out with her? You told me she complains a lot, but is this just like trying to get her off your back? Am I taking the bullet right here? That's what best friends do. Best friends and relationships saved here today.

That was a successful awkward Tuesday phone call. And if you have an awkward relationship going on with your best friend or your current ex, you can share this podcast with them. Even if you're not. Even if you want to make them laugh. Is this how you tell them you cheated on their? Yeah. What better way to deliver the news than by listening to Brooke and Jeffrey wherever you get your podcast.

Or share a laugh. Exactly. Whatever you want to do. Brooke and Jeffrey in the morning. Hey, I'm Ruby Carr, the host of the podcast, Encore. Check out our brand new episodes featuring music from the show that everyone is reheating as we speak. Heated rivalry. Join me as I go behind the songs that brought Shane and Elia together.

I'll tell you the stories of Fice, My Moon, My Man, Wolf Parades, I'll Believe in Anything, and tattoos all the things she said, and how they all became a part of this global phenomenon. stream encore on IHeart Radio, crave, 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 roer 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 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. Sports on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. Well, I'm glad they're still buddies. Yeah. They really worked through that. Would you date a friend's ex if they begged you just to help getting them off their back?

If they begged me, still, no, it'd be too weird, I think. What if you had already made out with her? Yeah, exactly. Then it's like, it does change things. Yeah. The comments were pretty positive about it. We got, well, that's an awesome best friend. Yeah.

That's what best friends are for. Okay. Oh. Yeah. Somebody did say nobody wants your friend's leftovers. I like a secondhand store. Yeah. So what's the difference, right?

I'll take Hamby towns from my girlfriend. It's true. Yeah. All right. There it is. Thank you so much for being here. Please again, go subscribe to our YouTube. You can watch a bunch of fun videos up there.

We're working a lot on getting you new content. So it's at Brooke and Jeffrey. Subscribe and have a lovely day. Or if you've been with your friends ex, let us know. Oh, boy. I love best stories. Or write it anonymously. That's even more fun.

All right now. It's Burke and Jeffrey in 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. I thought you were all going to write a song. I remember you thinking that. Listen to Podlandia. A.O. Rewatch on the IHeartRadio Radio app, Apple Podcasts, or wherever you get your podcasts.

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. What's up, fam? I'm sports journalist Ari Chambers. Hey, what's up y'all? It's your girl, Sam Jay. And we're the host of everyone watches women's sports, a new podcast from Together and I Heart Women's Sports. We're breaking down the biggest headlines.

Naomi Osaka, showing out. Shout out to you, Naomi. The viral moments. I've been obsessed with Kashan Rock's boxing journey. She looks good. Her combos are swift. stories everyone's talking about across women's sports. 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. I'm Nick Tuturo. You probably know me from NYPD Blue, the longest yard, or Spike Lee's Black Klansman. And on my new podcast, delivering happiness with Nick Totoro, I deliver pizza to a new guest. I've shared a slice with everyone from Seth Rollins.

What are you doing my belt? To Bill Burr. I don't think I've ever met somebody so exactly out of their mind. I am. And now we even have more great guests coming up, including the great John Tituro. It's called Happiness, delivering happiness. And many, many more.

Open your free High Heart Radio app. Search Delivering Happiness with Nick Titoro. And listen now. 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? 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.