Brooke and Jeffrey: Second Date Update - Awkward Thursday: 30 Day Girlfriend

Episode Date: May 21, 2026

Normally, we help people get second dates after a first one, but today we’re helping a guy who hasn’t even had ONE date with the woman he’s interested, and he wants to jump straight into a relationship!See omnystudio.com/listener for privacy information.

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Y'all just keep demanding it, so we listen. All right, we give in easily. We got a special awkward Thursday phone call for you today. It's brand new. Welcome so much. Welcome so much. I don't know. I'm glad you're here.

Yes. the second date podcast. Before we get to this new episode, what do we have in comments? Yeah, Erica's vinyl said, ever since I discovered y'all over a year ago, I can't get anything done in terms of testing records for my record store.

I'm constantly torn between having to listen to these albums and listening to you guys. Oh, that's so cool. We're cooler than a record. I like that. At least that, I mean, that's one way to interpret it. I was excited about it. We should make a Brooke and Jeffrey record.

That'd be so cool. Brooke and Jeffrey on Vital. Oh, yeah. Yeah. I'm not opposed to it. I mean, it's just trendy again. Yeah, it's trendy again. Maybe cassette tapes.

We'll go to them too. Okay, now we're getting a cool. VCR tapes. Oh, no. All right, how about just go to our YouTube? Subscribe there at Brooke and Jeffrey. And your brand new awkward Thursday episode starting right now. Just think of all the precious time and energy that you waste at the start of dating someone new.

Oh, yeah. The hours of over-analyzing every text. The deep dives into their social media. Wondering, do they like me? Do I like them? Is it weird to kiss them now? Or should I wait till after her parents leave? So much confusion and headache.

But what if there was a way to skip all the awkward parts of early dating? Because one of our listeners says he found a revolutionary new way to handle a brand new love interest. That jumps right to the good stuff. Hey. Okay. And he's about to pitch his strategy while we try to help make it happen. Okay. It's coming up in a brand new awkward Thursday phone call right after this.

It's awkward. It's Thursday. It's awkward. Thursday. Phone call. I know everybody seems to complain about the state of modern dating that it's too competitive. Standards are unrealistic. Alexis's mom is getting all the matches, leaving nothing for anyone else, including

her. Sorry, she's the mouth. So it's definitely bleak. And what's a person to do? Well, we have a listener named Scott who's identified a person of interest for himself. Okay. But as a different idea on how the whole dating thing should work in his mind. Didn't go into a lot of detail in his email about it, but I'm interested to talk to him

and hopefully help him with it. So Scott, welcome to the show, man. Hey, hey, how you guys doing? I'm so curious. This person of interest, is it someone you know? in life or is it someone you found online? IRL in real life and, yeah, she's great. Okay.

All right. We'll get to the new way that you think dating should work in just a second. But let's start with the girl. Who is she? Tell us about her. Yeah, her name is Nicole. She's awesome. We both met in like a running club. Oh, that's fun.

Yeah, yeah. I go to this running club on Saturday mornings. And so I brought my dog and it was the first time that I ever noticed Nicole, but she came up to the dog, Sally is her name. Sally's the dog's name. The dog's name? Dog's name is Sally. Nicole is the actual human being.

And she doesn't have a dog. And so we kind of hit it off. It's weird that we're doing this in an awkward Thursday and not just doing a second date update. Yeah. Well, I mean, I haven't had a date with her yet. Oh, well. That hasn't stopped other people, but yes.

Well, what's holding you back from going out on the date? Yeah. Well, I mean, first off, we, haven't had any time to schedule anything yet. We're both really busy. Hey. And so we talked over the phone like three to four times though. Oh my gosh. Okay, how long do you talk for? That's important. Like an hour or so. Wow. Alexis is having panic right now. It couldn't be me. Yeah. It's really, really great. Like, we don't want to hang up and oh, that's cute. That's a good sign. I mean, I feel like this is a good start to a relationship and it would be natural for you to just ask her out at this point.

I mean, I have asked her out and she said, yes, we just haven't had the time yet. Okay. But, like, I kind of want to do it a little differently, though. I want to frame it in a way, and I don't know how to approach that. You want to do the date itself differently? Kind of. Okay. Like, we've talked on the phone three to four times.

I saw her in person, and we like each other. So when I see her in person, I kind of want to pitch or something. Okay. On your date. And this is what ties into what you said in your email, that you have a different idea for how the dating process should work? Exactly. I have a friend who's tried some before, and he said it works great. He says it's called a trial relationship mode. Trial relationship mode. Yeah. Okay. Yeah. So you like, you go on a date with somebody and you don't hear from them

that sucks, right? Or you go on a date with someone and you don't know if they're hooking up with someone else that sucks too. Okay. That's how normal dating works. Yeah. Right. Right. But in a trial relationship mode. If you think that you have a good thing going, you can try it out for 30 days. Try what out? You can try out the relationship for 30 days. Like just focusing on each other, not going on other dates kind of thing? Right. So like I don't have to go on multiple dates with other people. No, I can just focus on Nicole. So you're trying to get her to subscribe for a 30 day period to just dating you alone. Exclusive membership. Yes. Yeah. And she gets addicted. Yes. She has to continue. can re-up the subscription.

If she forgets about the subscription. I hate who that happens. Oh, yeah. And then they start auto charging you. Is this one of those things where you'll save money if you just commit to the whole year? Yeah. Probably. Is that,

so that's what you're thinking? I mean, yeah, when you put it that way, it's kind of weird. I don't want to waste my time. If I like or I like her and I want to see if it works. We've had so many hours of conversation here that it just feels like the natural step, but I don't know how to frame it properly. It's definitely unique. I haven't heard that before, but I'm curious to ask everyone in the room if this idea was pitched to you by someone you were interested in, you want to do a 30-day trial session.

Would you be open to it? If I really liked him, why? It's a month. It's like you barely Google on three dates in a month anyways, probably with the guy. If you remember, you've only met him once. You talk to him on the phone a couple times and that's gone okay. Well, does you have to agree to hang out with him like every day this month? Or it's just like if they're only hang out four times?

Look, there's no kind of set rules. If it meshes well, it meshes well. If it does and it doesn't. So you can just hide out for 30 days or you don't mess anything up. I do feel like there should be a consequence. If she breaks her contract of the 30 days, there should be a penalty. Okay, that makes it weird, Jeff. That makes it weird.

He just wants to be a 30-day boyfriend, right? Yeah. That's what we're working with right here. Okay. How do you pitch that to Nicole so that she's open to the idea? And that's what we're doing today. I mean, here's the thing. You also don't want to make it sound so clinical.

Yeah. Right. Because it doesn't sound like the flirty hard to get stage. Yeah, but I think there's a difference between what you're talking about and simply commitment uncertainty. Okay. I mean, I don't disagree with you. I'm just saying that I feel like you want to make sure that she still knows she's going to get the fun part. Right?

Yeah. Yeah. Okay. Put that in the contract when she signs it. Must have fun once a week. Yeah. We'll lay up the guidelines for her. I've never heard of this before.

Like, are you? worried? Are you willing to hear if she's like, oh, no, I'm more committed to another guy or something already? Not at all, because then I'll get to know all this stuff early. Okay, mature. I don't know what that's like. Let's try it. We'll have some advice for you when we come back and get you your 30-day girlfriend. Wow. Thank you. It's so weird. It's really weird. Sounds like a TLC show. But it's perfect for your awkward Thursday phone call right after this. Hold on. It's awkward. It's Thursday. It's awkward.

Thursday. Phone call. We've been talking to Scott about his new idea for dating. Mm-hmm. Yeah. It's very interesting. Something we've never really heard of before called trial relationship mode. Yeah.

Where instead of taking it just one date at a time, while also going out with multiple other people, engaging your interests with them. Yeah. Just cut out all the clutter and all the confusion and lock them into a 30-day trial relationship. Where you agree to focus solely on each other. for one full month. And then if that goes well, just re-up. Keep the subscription going. Don't say lock in, though, because that's part of the trial.

If you're not locked in. Okay, sign up. There are a number. Thank you. So Scott wants to pitch this idea to a woman he met recently named Nicole. They haven't even been out on a first date yet. They just talked over the phone and had a pretty good connection. But it is kind of a big leap to go from zero dates to were instant boyfriend, girlfriend, for a month.

So how do we get Nicole to be open to that? Brooke, this should be easy. Yeah. What's your advice? I actually kind of like this idea because I think that there's just too many options out there for people right now and it just lets you focus. It's a good idea, but it can come across like we talked about a little clinical. So I think that my advice is just all about your delivery. You need to keep the romance alive.

Keep a sexy. Right? You got a sexy voice? You got a sexy voice over there? Try, will you be my girlfriend in a sexy voice? Go for it. Oh, my God. Come on.

I mean, like, do we want something like this? That's not bad. We're like a little low, we're a little gravelly. Yes, it's better. Yeah, see? I think that works. Alexis is turned on right now. Extremely.

So whatever you're doing, it's clearly working. I don't know. I'll try. We're the shot. Don't do that voice. Yeah. Yeah. Keep it in the lower volumes.

But, Jose, what's your advice? Well, this is like such a unique idea. So I think you need to highlight the positives of it. Skipping the awkward stuff. That would usually come up when you start dating someone. Yeah, now we're jumping straight into being like cozy and comfortable with each other, then awkward and weird around each other. Yeah.

And I'm sure if you say it, it becomes reality. Yeah. Yeah. It's called manifesting. There is. Orwa manifesting, Jeff. What do you think about that, Scott? Yeah.

Highlight the positives. That makes sense to me. In a sexy voice. Yes. Right. I mean, in a sexy voice. There you go. We don't got to go on any dates, girl.

That's right. He's locked into it. his voice right now. I don't want to get him off his game. So let's die on the call. And we will step away and let you make your awkward Thursday phone call and then leave here in a relationship for the next 30 days. All of us? Wait, if we're on the phone, are we all? We don't need your sexy voice. Now I'm kind of having fun with it. And I want to play along. But okay, I'm stepping away, Scott. Good luck. You got this man. Here we go. Hey, Nicole. How are you doing? Scott? Yeah. Hi. Sorry. I'm calling from

work, so it's a different number. Okay. Hi. How you do it? I'm good. How's your day going? Pretty good. You know, I did want to, like, run something by you.

Okay. What is it? Okay. Okay. Here it is, right? So, like, don't you, like, hate it when, like, people start to date and it's super awkward in the beginning? Like, isn't that terrible?

I mean, yeah, it's definitely not the fun part. Yeah, totally. And so, like, I don't want it to suck. I want it to be good. We've already had some great conversations. Like, I think we click pretty well. I mean, you're not to answer that. That's okay.

Anyway, so I was talking to a buddy, and he suggested something. and I wanted to run it by you. Okay. So it's called a trial relationship mode. So it's basically instant exclusivity. Hold on, hold on. Like, I haven't even been on a date with you yet. I know, but like we've talked for like hours on the phone.

And we've like hung out. I don't know. I thought it might be good to try this out. So you're asking me to skip all the awkward stuff and just jump into a relationship with you? I don't know. Doesn't that sound awesome to you? I mean, it's definitely different.

I've never heard of it before. But yeah, the awkward stuff, I mean, it always sucks. So it wouldn't be bad to skip all of that. Oh, okay. Oh, wow. You sound like you're interested. I mean, like, oh, that sounds really good. But hypothetically, what if I was in?

multiple situationships. Would I have to stop those? Of course. Multiple situationships. Yeah. We'll get to that, Scott. We just first need to tell Nicole, hi. Hi, Nicole.

Good morning. You're on the radio right now. Hi. Hi. Okay. It's your other situationships. We're all here. I mean, I don't know.

You can think of us as like the big romantic gesture part. Yeah. He wanted to surprise you. Some people don't like that, so also don't think it's like that. We're skipping the awkwardness of dating with this segment called the awkward Thursday phone call. This is even more awkward than I expected. Well, yes, we're getting all the awkwardness out of the way so that we could just jump right to the good part that 30-day trial relationship. I mean, like back to your situation stuff.

Like, what do you mean? Like, how many? I'm curious. Do you need to know that? I feel like that's a question you actually. How many situationships does she have to break off to make this happen? I'm not going to answer that, but it's probably more than you're thinking in your head. Okay.

I have a big number in my head. No wonder you haven't had time to date him. Oh, yes. So this isn't hypothetical. This is like actual truth. You have a couple of situationships, at least a couple. Why don't think you were going to call me and ask to be exclusive before our first date? Yeah, that's true.

That's totally fair. That's totally fair. Yeah. But that just shows how strong he feels the connection is right off the bat between you, Nicole. And I'm sure if you reflect on all those other situationships, none of them have as sexy of a voice as Scott did. Oh, my God. He does have a very sexy voice. Right?

Until he said what? The first two words were pretty good, though. So if you were going to weigh all these situations out, would Scott be top of the list? I don't know. I've only met him and his dog once. Yeah. So she knows these other guys way more than she knows him. No, I know. But have you had, like, have you had hours of conversation over the phone with these other people? Oh, that's...

Probably hours in person. I don't know if we want to know the answer to this. I mean, I left one guy in my house this morning. He's still there. Oh, yeah. I mean, she really trusts him. Oh, yeah. Totally. Yep, that's great.

So maybe the trial relationship thing isn't for you for now. Maybe you got to like tighten some screws up and nip some things in the bud first. Oh, a trial, free trial. A trial for the trial. Look, you know what? I'd even say, let's go on the first date, see how it works. And then if you're interested. No, now he's like coming back on his like original 30 day thing.

How about we just date like normal? I just want to meet you in person and have like a proper date. Yeah, I have a new idea. Let's just have one meetup. Yeah. It's in a 30 days of love. No, stick to your idea. Okay, just because she has some situation ships.

I mean, here's the thing, Nicole. Obviously, that's not working great for you because you haven't committed to one of them. So they're not all that wonderful. Right? And this gives you 30 days to like, I don't know, do a cleanse. Think of it that way. You know? It's like if you try to figure out what you're allergic to and you have to remove all the foods until you add them back in.

Way to make it sound sexy, bro. It'll be real emptied out. It's just so funny that all of you are so interested in my dating life. Like, I do not expect this today. Yeah. We know it's not something that's traditional that we've ever heard of before. No, this was unique. It's brand new to us to a trial relationship 30-day period,

but we thought it was interesting enough to bring it to your attention. And we want you to do it so in 30 days we can get an update. Yeah, think about us. Yeah, but that means I have to ditch all these other guys. I put time into that. Well, at least you're honest. She's not cheating on her trial. Dude, I mean, it's just 30 days without him.

You can always go back if the trial run doesn't go well. Yeah, I think I'm going to pass. Oh, no. This is why we're not in the sales department. There's just too much fine print in this. Yeah, you think so? Well, she could keep up with five guys, have a good time, or stick to one, just in case. One sexy one.

Oh, yeah, the voice. With a hot voice. This didn't turn out anywhere I expected. Same here, bro. We were all confident. We let her think too much about it. That was the problem. No.

No. No, she's right. Brooke, being a woman knows. As soon as you say, I'll get back to you on it, then you know you're never going to get the deal done. And something you don't know, Nicole, is Scott ditched all of his situation ships just to make this phone call. Yeah. I had no situation. Oh, Scott, what are you doing?

I'm trying to help you. Okay. Never mind. Brooke and Jeffrey in the morning. I'm Cynthia Lois. And I'm Josie Dye. And we're done. 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 IHeart Radio app or wherever you get your podcasts.

Hey, it's us, the Jonas brothers. And guess what? We have some big news. What's the news, huge news? We created our own podcast called Hey Jonas. We invented a podcast? Well, we didn't invent it. We just contributed to it.

We're the first people to do podcasts. Pretty, yeah, pretty wide range of podcasts throughout there. But this one's extra special. So how do we actually come up with a name Hey Jonas, guys? I honestly don't remember. I think it was on a call about what we should call it. Well, we were thinking I'm originally calling it one of the early names of our band before Jonas Brothers

was... This is how you guys remember it going down? Yes. I have a very different memory of this. We were talking about a thing, a bit for the podcast, where people could call in and say, hey, Jonas. And then I wrote down on my little notepad, Hey Jonas, and offered it up as a potential title for the podcast.

But thanks for remembering that, guys. Listen to Hey Jonas on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Just listen. We don't care where you hear it. Text in to 788. to someone said, I've heard of this and I tried it myself actually. And it worked. I had an incredible drama-free relationship with a guy for an entire month until his visa

expired and had to go back to his wife and kids in Portugal. Oh, goodness. But for that month, it was bliss. Yeah, I bet the wife actually enjoyed that month too. Everybody got me. From the sounds of that guy. Totally. But just because it didn't work this time for Scott, it doesn't mean a trial relationship

wouldn't work for anybody ever. I just really want the update 30 days later. I'm, like, disappointed that we're not going to get it from these two. Let's you want someone else to do it. Sure, yeah. Just go to first date first, maybe, and then do it. And that's not the actual rule. Yeah.

No dates. You're just talking about normal dating. Yeah. I like that we tried something new, something unique that we've never attempted before, even if it failed spectacularly. As new things often do. It's kind of what we do here. But if you want us to fail,

spectacularly in your life, make sure you email the show. And we'll handle any awkward scenario you might find yourself in. Go check out all of our awkward podcast segments. They're up online wherever you get yours at Brooke and Jeffrey. Hey, guys, it's us. The Jonas Brothers. I'm Joe.

I'm Kevin. And I'm Nick. And guess what? We created our own podcast called, Hey, Jonas. We invented a podcast? Well, we didn't invent it. We just contributed to it.

We're the first people to do podcasts. We get to ask other people questions because we're sick and tired of being asked questions. Well, sick and tired of being asked questions. Tired is a strong way to put it, but, you know, tired and sick. Tired and sick. Listen to Hey Jonas on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Just listen. We don't care where you hear it.

Another podcast from some SNL late-night comedy guy, not quite. Unhumor me with Robert Smigel and Friends. Me and hilarious guests from Bob Odenkirk to David Letterman help make you funnier. This week, my guest, SNL's Mikey Day and head writer Streeter Seidel. Help an Acapella band with their between songs banter. group perform. We do some retirement homes. Those people are starving for banter. Listen to humor me with Robert Smigel and friends on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Michelle McPhee, and I've been unraveling the strangest criminal alliance I've ever reported on,

a Mormon polygamist and an Armenian businessman. Multimillion dollar house, Ferraris and Lamborghinis, private jets, a billion dollar fraud. But how long can this alliance last? Tell me what you know. Is somebody coming after me? Listen to Kingdom of Fraud on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Last night, a blown call changed a game. This morning, the internet lost its mind. And nobody's telling you exactly what happened.

That's where Sports Slice comes in. I'm Timbo. And every episode, we're cutting through the noise, breaking down the biggest moments in sports and giving you the real story behind the headline. and we're going straight to the source, the athletes themselves. Their locker room stories, their reactions in the moment, and the stuff nobody gets to hear. Listen to SportsSlice on the IHeart Radio app, Apple Podcasts,

or wherever you get your podcast. And for more, follow Timbo Sliced Life 12 in the TikTok podcast network on TikTok. Winning on Clay is an art. The rallies are relentless. And at the French Open, only the toughest survive. I'd know. I competed there for decades.

Join me, Renee Stubbs, on the Renee Stubbs Tennis Podcasts for no nonsense, breakdowns of the biggest matches, the toughest players, and the moments that define Roland Garros. Jen, she's an outsider to win the French name. And she likes Clay. Listen, Lennarabakina is arguably the best player in the world right now, and I actually can win on any surface. Listen to the Renee Stubbs tennis podcasts on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. Presented by Capital One, founding partner of IHeart Women's Sports.