Bonus Giggly Hotline: proposals, pastors, and pickleball

Summary

Giggly Squad — Bonus Giggly Hotline: Proposals, Pastors, and Pickleball

Hosts: Hannah Berner & Paige DeSorbo
Release Date: September 4, 2025

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Episode Overview

In this lively bonus episode, Hannah and Paige open up the “Giggly Hotline” to respond to real listener dilemmas and summer stories. Topics range from dating older men found through pickleball, proposal anxiety, and the realities of evolving friendships, to an unforgettable mishap involving a pastor and a backless bra photo. Infused with their signature self-deprecating humor and candid advice, the duo dives into pop culture, relationships, and personal stories, making for a laugh-out-loud, relatable listen.

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Key Topics & Discussions

1. Pickleball Zaddy Dilemma

(01:29–06:32)

A 29-year-old listener calls in: after years of celibacy, she’s eyeing a 44-year-old “scrumptious” man on her pickleball team. The catch? He follows over 1,200 Insta-thotties—huge ick. She asks: Should she have a little fun, or run?

• Paige hilariously breaks down men by age group, advocating for “zaddies” post-20s:
  • “Once you’re like in your late 20s, your brain’s fully formed. Men in their 20s, no offense—squirrels. They move a lot.” (02:33)
• Hannah warns about falling too hard after a long dry spell:
  • “If I were to be celibate for that long, I know it could be a sewer rat—could be my next man. I’m obsessed.” (04:13)
• Both agree: Fun is fine if she’s clear-headed, but do not expect love from a guy glued to Insta models:
  • “My husband… he only follows me” (Hannah, 05:15)
  • “Give him some Advil and get out of there.” (Paige, 05:33)
• Wisdom about older single men: Just because he’s 44, doesn’t mean he’s settling down (“He’s gonna Clooney it.” – Paige, 05:28).

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2. Proposal Limbo and ‘The Waiting Game’

(06:32–10:17)

Another listener confesses she’s in “proposal limbo”—always thinking her boyfriend’s about to propose, but he never does.

• Paige sets expectations straight:
  • “It’s not you waiting to be picked by him… It’s two consenting adults deciding to spend their life together.” (07:49)
• Hannah delivers a wakeup call:
  • “You might think he’s your person, but ipso facto, he’s not.” (07:06)
• Both urge direct communication about timelines instead of dropping hints or waiting for a cinematic surprise:
  • “You have to have a conversation, and I don’t think that makes you, like, not go with the flow.” (Hannah, 08:45)
  • “Never gonna marry someone who’s unsure about me because I’m unsure about myself. I don’t need someone else.” (Paige, 10:06)
• Notable moment: Paige recounts calmly discussing marriage with her fiancé Dez before his proposal (09:12).

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3. Friendships in Transition

(11:31–15:08)

A listener is in a trio of roommates—but the gang is splitting: one goes to med school, another moves in with a boyfriend.

• Paige salutes the rare success of a friend trio, then gets real:
  • “First of all, kudos to her for having a friendship of three work as long as it did.” (12:04)
• Hannah recommends focusing on one-on-one bonds:
  • “You have to focus on your individual friendships with each girl.” (12:37)
• Tips for long-distance friendship maintenance:
  • Lean into group chats, FaceTime, and shared memes or TikToks.
    • “Literally sending memes… when that bitch texts me a TikTok… that’s my friend.” (Hannah, 14:04)
  • Plan occasional girls' trips or dinners (“It’s more a celebration of your friendship… you had to really put effort.” – Paige, 13:13)
  • Don’t fear making new friends — don’t get limited by nostalgia (Paige, 14:50).

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4. Push-Up Bra Pics Sent to a Pastor

(15:31–17:45)

A hilarious disaster story: a caller accidentally sends before/after push-up bra selfies to the wrong number—turns out it belongs to a local church assistant pastor.

• Hosts’ reactions:
  • “Oh my God. This is the best thing ever.” (Hannah, 16:19)
  • “Is that real?” (Paige, 16:23)
• They encourage her to cherish this as an iconic fun fact:
  • “Anytime you’re in the situation where someone says ‘and now tell a fun fact about you’—this is a great fun fact.” (Hannah, 17:05)
• Paige muses: “What if the pastor, like, wasn’t in a relationship and... And then we started texting, and now… we’re going on a date.” (17:22)
• Both riff on how bizarre (and modern) church life can be—implying, hey, everyone makes texting mistakes!

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5. Scheduling Sex Before Takeout Arrives

(18:29–19:00)

Quick sidebar: The duo laugh about the logistics of sex scheduled around food deliveries.

• “Do you ever schedule, like, pre-food sex?...We have about 25 minutes before it gets here” (Paige, 18:29)
• “Once it gets there, you can’t then go do it. Cause you’re like, but the food’s here!” (Hannah, 18:42)

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Notable Quotes & Memorable Moments

• Paige (on dating vs. Instagram thotties):

  “I don’t get turned on by a man that can get turned on by a warm apple pie—which is every man.” (03:58)

• Hannah (on celibacy rebound risk):

  “I know it could be a sewer rat—could be my next man. I’m obsessed.” (04:13)

• Paige (on relationships):

  “Never gonna marry someone who’s unsure about me, because I’m unsure about myself. I don’t need someone else.” (10:06)

• Friendship reminder:

  “Some friendships are just convenience… if you guys can make it to having your individual lives and making time for each other every couple months, it’s great.” (Paige, 13:55)

• Accidental pastor text:

  “Anytime you’re in a situation where someone says ‘and now tell a fun fact about you’—this is a great fun fact.” (Hannah, 17:05)

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Timestamps for Major Segments

• 00:00–01:29: Quick intro banter; Dunkin’ shoutouts
• 01:29–06:32: Pickleball/older man Instagram dilemma
• 06:32–10:17: Proposal anxiety and open communication advice
• 11:31–15:08: Roommate trio splitting—how to evolve and retain friendships
• 15:31–17:45: Sexting disaster: Bra photos to a church pastor
• 18:29–19:00: Scheduling sex before food arrives

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Tone & Takeaways

The episode is fast-paced, confessional, and always self-effacing. Advice is real, sometimes blunt, but always wrapped in a giggly, non-judgmental style. Both hosts blend practical wisdom with playfulness—never taking themselves too seriously but always rooting for listeners to make empowered choices (or at least, get great stories out of their mishaps).

For fans of pop-culture-flavored, big-sister banter, this mini-hotline is maximum giggle!

Transcript

[Hannah]

Sup, Gigglers? Gary, fix your WI fi. Manifest that shit. We can't be managed. I mean, the day just got away from me.

[Paige]

We've been living on Dunkin Refreshers all summer. It's in our veins. It's in our. Sorry for the youtubers. I just showed you my veins. It only makes sense that you guys are asking us for summer advice because we are hydrated, at least at this moment.

[Hannah]

That's true.

[Paige]

And. And some funny stories. We love hearing from the Gigglers.

[Hannah]

And huge thanks to Duncan for one, making these episodes possible and keeping us hydrated all summer.

[Paige]

And I just want you guys know, I'm drinking my mango pineapple refresher with green tea.

[Hannah]

I got Strawberry Dragon fruit refresher with a little sparkling water. Because, you know, like a little.

[Paige]

And we did say earlier that if you like sparkling water, you also like bdsm. Yeah. Yeah.

[Hannah]

And that's true.

[Paige]

So Paige and I were actually working all day long and we're so drunk on being tired.

[Hannah]

Yeah. But we're in glam.

[Paige]

We're in glam. So we're kind of feeling ourselves. Well, you're in a ponytail. This is really fun because Grace is DJing and she is sending us all your messages of advice. I love to hear the gigglers in their natural habitats. Let's go.

[Caller 1]

Hi, gals. Okay, So I am 29 years old. I've been celibate for like a few years. I just haven't really tried or gone on any dates. And it is what it is. So this 44 year old man joined my pickleball team the other day and he's pretty scrumptious. And I'm like, okay, he might be a good way to, like, you know, ease into being with someone again or, you know, just, you know, getting the cobwebs off. So we follow each other on Instagram and he follows 2000 people. At least 1200 of those are like Instagram thotties, which could not be more of a turn off for me. And, you know, it's just such an ick. What do you think? What do I do? Do I pursue the this for like a little fun, little zaddy moment, or do I just totally disregard jump ship? Let me know.

[Hannah]

These are getting progressively harder.

[Paige]

Yeah. There's layers to these.

[Hannah]

What are your first thoughts?

[Paige]

My first thoughts. Speaking for the zaddy community.

[Hannah]

Yeah. As an ambassador.

[Paige]

As an ambassador of the zaddy, I have to vote each year. It's like a whole thing, but to watch every movie. Okay. So if you're in your late 20s, this is for you. If you're early 20s or your teens, stay with men your own age. But once you're like in your late 20s, your brain's fully formed. Men in their 20s, no offense, Chris, Squirrels, they move a lot. Yeah, they like, they always have to be like playing with something. They're like standing up, sitting down, like it's chaos.

[Hannah]

They're like, where'd I have my nut?

[Paige]

Chasing each other's tails. And then they start like fighting, but just for fun. Yeah, literally like kittens. And then when in their 30s, they're like the same, but like should have money but they don't.

[Hannah]

Yeah, they're like chilling out a little. They're getting a little bit slower.

[Paige]

They're like, I don't like my job. It's like a sad time for men.

[Hannah]

People don't say that enough in their 30s. It's a sad time because in their.

[Paige]

20S they think they just fuck around. And in the 30s women are just going to be like, give me your ball sack. You like have a shitty job and you're mean to people. And then they're like, why is no one like me now anyway? I'm not getting into specific. I digress. I love a 44 year old man. Nothing turns me off more than when they. I don't mind if you've accidentally clicked on a couple hot girls that you follow. I follow some men because they're beautiful and hot. Yeah, 2000.

[Hannah]

Yeah, it's still a big number.

[Paige]

And do, do I think it's fun to have casual sex? I personally, I don't get, get turned on by a man that can get turned on by a warm apple pie, which is every man.

[Hannah]

I feel like not speaking from my own experience, but speaking from my own internal brain. If I were to be celibate for that long, I know it could be a sewer rat. Could be my next man. I'm obsessed.

[Paige]

She's not thinking straight.

[Hannah]

I'm changing my personality, my clothes are different, my hair is different because I'm like this. I've been just waiting for him. So I worry that if he's the first man you're going, you might fall in love more quickly. And he doesn't seem like the best option. And. But if you're going into it strong minded, where you're like, this is just a casual thing just to like ease me into dating. And I really, I'm gonna go for someone else, but he's gonna be my first. Okay. But I think thinking anything serious is going to Happen. Or he's the love of your life or he's your husband. I think. No, because I know that my husband, he only follows me.

[Paige]

Yep.

[Hannah]

You know, like he doesn't follow a dream world.

[Paige]

Doesn't know what Instagram is.

[Hannah]

Doesn't have an Instagram.

[Paige]

And let's also not be confused. Just because he's 44 does not mean he wants to settle down.

[Hannah]

No.

[Paige]

I would argue if he's made it.

[Hannah]

This far and he's still single, he's gonna Clooney it.

[Paige]

He may never settle down.

[Hannah]

He's gonna go to 55.

[Paige]

Exactly. I do feel like the first guy you hook up with, it could actually be good that he's just like a horny old fucker and like, have some fun. Give him some Advil and get out of there. Yeah, that's what I do.

[Hannah]

I'm on a Benadryl and skedaddle.

[Paige]

Good sex could be from a nice 44 year old because they know what they're doing. Some of these. You got a 32 year old guy who's had one girlfriend.

[Hannah]

Yeah.

[Paige]

That's not proper training.

[Hannah]

No, that's.

[Paige]

She doesn't know what's going on. He doesn't know what's going on together. He's rubbing her thigh. He's rubbing her thigh and she goes, that's the best I've ever had. Thank you. You need a man that's been divorced around the block. You need a man that's been in court ordered therapy. That's the education you want to. I want a man who has been cultured, who's seen the world before he sees this pussy. Grace to you, respect to you.

[Caller 2]

I'm 28, in a happy long term relationship and living in that waiting on the ring limbo where every romantic date, family trip or sunset hike feels suspiciously proposal ish. But then nothing. So here's my question. How do you stay patient and present when you know your person is the one, but his timeline doesn't seem to be matching mine.

[Paige]

Ooh, that was deep, y'.

[Hannah]

All.

[Paige]

Again, I was engaged during COVID which was different. There was nothing for us to do. We weren't going on like romantic dinner dates. One day I woke up and he was outside the bed.

[Hannah]

Dare I say I've dated someone where our timelines didn't match up. And guess what? He wasn't for me. So you might think he's your person, but ipso facto he's not.

[Paige]

Also not to like come for the romanticness of a proposal, but I'm pretty Sure. And the girls don't talk about this, but I'm gonna say it right now. You talk to him. You go, hey, we're getting married. Right. Or he's like. And then it's like, okay, you look at rings, you tell him which ring you want, and then you wait a couple weeks or months.

[Hannah]

Yeah.

[Paige]

And that's how it should go. It's not some, like, out of the blue moon. He does it like. It's two consenting adults deciding to spend their life together.

[Hannah]

That's what it is.

[Paige]

It's not you waiting to be picked by him.

[Hannah]

Yeah. I think you have to have a conversation. That's not like. Also, I feel like society has made it like, oh, women give, like, an ultimatum, and that's like. It's like, no, we're just having a civil conversation. I'm running through timelines.

[Paige]

Yeah. Do you want to do this?

[Hannah]

I'm running through my own personal schedule. Check your calendar.

[Paige]

Check his calendar.

[Hannah]

And if it's not lining up in the six months that I think it should line up, that's a larger conversation. And why isn't it lining up? Here's the other thing. Men are a lot more insecure than they put out. Women are just as insecure, but we are more vulnerable with it. So we'll say, I'm not ready because of X, Y, and Z, and men will just not say anything. There could be so many reasons. Can he not afford maybe a ring that he thinks you deserve? And he's, like, saving up. Is he waiting for, like, a very, like, a specific trip that you have? Like, there could be so many factors. He could just have a tummy ache.

[Paige]

Yep. We've all been there.

[Hannah]

So I think you have to have a pointed conversation, and I don't think that makes you, like, not a go with the flow.

[Paige]

It's literally what everyone says, which is, like, make him think it's his idea. You give him all the ingredients, and then when he makes it, you go, yay. Good job. Job. So I know it seems in movies like a guy one day just goes in one knee. No, I sat down. I talked to dez. We basically were like, I would want to marry you. I'd want to marry you. That's the beautiful conversation. He's beautiful. So sweet. I didn't know you guys had that combo. You ever told me.

[Hannah]

That is so nice.

[Paige]

Are you on hormones again?

[Hannah]

No, I'm just. I'm summering. I literally am summering.

[Paige]

No, but you're just like, hey, you're my person. Hey, you're my person.

[Hannah]

Cool. That is beautiful.

[Paige]

Okay, the stunker refresher is really hitting her hard. Then he feels like he. He's doing it on his own, even though you've told him everything. And then it's cute when you're like, it's. He think, I do it this month, next month, and it happens. So if he's saying I don't know when, but eventually that's not. That's not a two consenting adult.

[Hannah]

That's an answer for someone that's like, we've been dating for six months to a year. Like, yeah, one day.

[Paige]

Like, one thing I'm for sure, I'm never gonna marry someone who's unsure about me because I'm unsure about myself. I don't need someone else.

[Hannah]

If you didn't mind, drop it.

[Paige]

You know, thank you. You've cried, you've gotten mad. We've gone through so many emotions. But so, yes, communication is key. I just have to say, everyone that got picked to submit stuff has been getting the Giggly Squad Dunkin Merch. So tag us if you haven't. Otherwise, check it out. It's pretty fun.

[Hannah]

The Dunkin Refreshers really are true to their name. Like, they are the most refreshing. Especially like after that 3pm Gotta take a nap vibe. They like, they just revive you.

[Paige]

Perfect. Pick me up. Also, I don't want to water after a long day. I want a fun drink. A fun, silly, goofy drink.

[Hannah]

Let me have a treat.

[Paige]

Yes. I want to have a pep in my step and I want to be a fun color. I don't just want to have a boring ass water when all day long I've just been working. Thank you, Duncan, for providing us with joy and laughter and love and rainbows and butterflies.

[Hannah]

And also thanks to the Gigglers for sending in their summer stories. It's been so much fun listening to them and trying to give advice back. I don't know how good our advice is, but it has been really fun.

[Paige]

So we just keep saying exactly.

[Hannah]

Yeah. We're like, yeah, sure, that sounds great.

[Paige]

Absolutely.

[Hannah]

If you won the Giggly Squad Duncan merch giveaway, make sure you tag us and tag Duncan in your photos. We want to see.

[Paige]

We want to see them.

[Caller 3]

Hi, Hannah.

[Paige]

Hi, Paige.

[Caller 3]

My roommates and I used to be really like the best trio friend group ever. And we even went to Giggly Squad in LA last year. But now one of us is moving away for med school and. And I'm moving in with my boyfriend. So the trio is kind of being Pulled apart. What's your advice for staying close friends when everyone's in a different stage of life?

[Caller 2]

Thanks.

[Hannah]

That's a really good question.

[Paige]

First of all, kudos to her for having a friendship of three work as long as it did.

[Hannah]

I was just going to say I was waiting for that to be like N1.

[Paige]

And then.

[Hannah]

And then we exiled one. Because that is really always what happens.

[Paige]

Someone always gets voted off that.

[Hannah]

It's a lot harder. Yeah. Four, we can make it work. Each person is a friend.

[Paige]

Yes.

[Hannah]

Well, two is hard.

[Paige]

Three, whenever two of them talk, it could be an attack on the other.

[Hannah]

Yeah.

[Paige]

And then if you start bonding over, gossiping about the other, next thing you know, you don't even know who you're mad at.

[Hannah]

Right. We digress. I was.

[Paige]

We digress. They did great. They survived.

[Hannah]

I would say I have. I think you do too. I have a lot of friends who are. We're in complete different places in our lives. All like within the same. Same age range, though. And I think it's. It has to be. This is like a tough pill to swallow, but like, you have to focus on your individual relationships. So, like, you have to focus on your individual friendship with each girl. Like, the trio stuff probably isn't going to happen as much, but like, I think group chat, FaceTime.

[Paige]

I also would argue, like, yeah, it's so fun when you're with your friends every day or like you have roommates. Like, that's so fun. But eventually your life does go in different ways. I would argue the most beautiful thing is planning like a girls trip or a girl's weekend or a girl's dinner because you had to really put effort. Like when I spend a weekend with old friends, I'm like, wow, I'm like, so proud of us that we made it to this point and you guys love me and I love you so much that we took our weekends to be together. So it's like, it's more a celebration of your friendship. Because some friendships are just convenience. Like, they just happen to be in the hallway and you're like, I guess I say hi to you every day.

[Hannah]

That's so true.

[Paige]

Where if you guys can make it to having your individual lives and making time for each other every couple months, it's great. Also sending stupid shit.

[Hannah]

I was just gonna say this sounds so juvenile, but like, literally sending memes. Like, my one girlfriend, Katie, she's married, she lives in the suburbs, she's trying to have a baby. We could not be more like, have opposite things going on day to day. But when that bitch texts me a TikTok that I need to watch immediately, like, that's my friend. And like, you know, like, I have to check in.

[Paige]

And when you're consuming content online, you have to have your, like, okay, when I see the cat stuff now I have a couple of people I have to send it to, but it's like, okay, I see a vintage Chanel flat. Send it to Paige. Like, I know where I see, like, a cute, like, Labradoodle. I send it to Haley. Like, I need to.

[Hannah]

Yeah. And so it can be like, small things. And then I think, like, something to look forward to, like once a year even.

[Paige]

And also, it's nice to evolve and make new friends sometimes if you're too stuck in the past of, like, that's my friend group that defined me. I'm only me when I'm with them. Yeah, that's limiting. And don't be afraid to make new friends as adults, even though it's scary.

[Hannah]

Yeah.

[Paige]

Not usa, not us. I love when she stands up to the mic. I love your little. Did you do pilates today?

[Caller 1]

No.

[Paige]

She's so attacked right now.

[Hannah]

She's like, sorry, when was I gonna find the time after having a baby?

[Paige]

She's like, I'm three days postpartum.

[Hannah]

Okay.

[Caller 2]

So recently I did some content for a strapless, backless push up bra company. I took some before and after photos and texted them to myself. The photos were astounding. A couple days later, I received a text from myself, like my own contact that just said, just wanted to let you know that you have the wrong number. So I decided to investigate. Turns out the number I was texting was one number off from my phone number. The best part of it all, I googled the number I had been sending these things to, and it came up in a local church website directory for.

[Hannah]

Oh, my God.

[Caller 2]

For an assistant pastor, I'm sure I stirred up a few fights between him and its partner.

[Hannah]

Oh, my God. This is the best thing ever.

[Paige]

Is that real?

[Hannah]

I mean, what's the dilemma? You're anonymous. They'll never know who you are.

[Paige]

I love that she just also was innocently trying to see if the strap was bra looked good.

[Hannah]

Yeah. And texting it to herself.

[Paige]

Yeah.

[Hannah]

She was also. What? Strapless bra.

[Paige]

I know. I thought, I thought, I thought you were starting a business. I love that she's doing research and she's testing it.

[Hannah]

Wait, every time I want to Google a number, it never tells me who the person is. I have to pay for some App who says they can figure out DNA testing?

[Paige]

You gave them your Social Security number. I'm like, I don't know if this is part of it.

[Hannah]

They're like, it could be a series of these people. Anyway, what's the question here? I love this.

[Paige]

Well, that was her crazy summer story. That's so fun.

[Hannah]

Okay, you know what? Actually, she got out of this. And anytime you're in the situation where someone says and now tell a fun fact about you, this is a great fun fact. What a great story.

[Paige]

At parties, what if the pastor, like, wasn't in a relationship and I was.

[Hannah]

Waiting for her to be like. And then we started texting.

[Paige]

And then we started texting, and now.

[Hannah]

We'Re going on a date.

[Paige]

Hey, I haven't seen a tit in a long time.

[Hannah]

Yeah, I think you could just like, continue to with them.

[Paige]

Yeah, I think you'd message and be like, I need help with this trust broad. Pastor. No, that's crazy. Also, why does he have. Why is he texting? Pastor shouldn't be texting.

[Hannah]

I know. I feel like usually imagine work number.

[Paige]

Your priest texting, like, hold on one second.

[Hannah]

I loved that story. That was great.

[Paige]

I've been recently joking about on stage when I accidentally sexted my the group chat, and it was such a bad sex that you, like, didn't even respond to it.

[Hannah]

I was like, wrong number.

[Paige]

I said.

[Hannah]

I was like, oh, my God, I'm so sorry. I was like, what?

[Paige]

I said, come home. When you come home, we're gonna have sex.

[Hannah]

And I said that was her dirty test.

[Paige]

I know. I was like, we're gonna dance, then go home and have sex. And they responded to like, the whatever we're talking about before. And I was like, you guys, I swear, I'm freaky.

[Hannah]

You're like, so sorry. I was like, that sounded just like scheduling. It was just like, first I'm gonna shower and then we can do it.

[Paige]

Wait, we were talking about, do you ever schedule, like, pre food sex? So, like, you go, okay, we have about 25 minutes before it gets here. And then we.

[Hannah]

Because once it gets there, you can't then go do it.

[Paige]

Cause you're like, but the food's here. If I'm getting it. I just fucked. Yeah, like you just didn't know that.

[Hannah]

When I answered the door. I know that. And that's why my hair does always look so good. Yeah, I'm glad.

[Paige]

Glowing. And yeah, I probably uti because I'm eating Chinese food instead of peeing after sex.

[Hannah]

Yeah, that was a good one.

[Paige]

Thank you, Duncan, for fueling all our chaos. I love a little bonus episode midweek.

[Hannah]

No, so do I. And thanks for making them possible.

[Paige]

Duncan, we love you.