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Giggly Squad

4 Sep 2025 · 19m · 7 chapters

Episode artwork

Bonus Giggly Hotline: proposals, pastors, and pickleball

In short

A “Bonus Giggly Hotline” episode where the hosts and listeners swap summer dating/sex and relationship advice, plus friendship maintenance and a few chaotic “wrong number” stories. They also plug Dunkin’ Refreshers as the summer drink fueling the conversation.

Guests (callers)

  1. 29-year-old celibate woman (few years), dating/trying again after a long dry spell; she’s considering a 44-year-old pickleball teammate who follows many “Instagram thotties.”
  2. 28-year-old woman in a long-term relationship, stuck in “proposal limbo” and asking how to stay patient when timelines don’t match.
  3. A trio-friendship question: a listener whose roommate is leaving for med school and she’s moving in with her boyfriend; asking how to stay close friends.
  4. A “wrong number” story: a woman doing content for a strapless/backless push-up bra company who texted her own before/after photos to the wrong number—found it listed on a local church site as an assistant pastor.

Key claims & examples

  • For dating, “late 20s men” vs “men in 30s” stereotypes; Instagram following volume is a turnoff.
  • Proposals should come from a two-adult conversation, not vague waiting; have a pointed timeline discussion.
  • Friendship advice: focus on individual one-on-one bonds, schedule girls’ trips, and use small check-ins (memes/TikToks).
  • Wrong-number texting can accidentally involve church staff; the caller says it “stirred up fights” and jokes about anonymous chaos.

Written by AI. May contain mistakes.

Chapters

0:46

Advice Request: The Pickleball Dilemma

A listener shares her concerns about dating a much older man from her pickleball team.

“And we did say earlier that if you like sparkling water, you also like BDSM.”
2:29

Thoughts on Dating Older Men

The hosts discuss the complexities and benefits of dating older men.

“As an ambassador of the Zaddy community.”
6:21

Navigating Proposal Timing

A listener asks how to cope with differing timelines in her relationship.

“So we'll say like, I'm not ready because of X, Y, and Z.”
9:53

Maintaining Friendships Through Life Changes

The hosts provide advice on keeping friendships strong despite life changes and different stages.

“Yes, I want to have a pep in my step, and I want it to be a fun color.”
14:01

The Importance of Digital Connections

Learn how sharing memes and content can strengthen friendships, even across different life stages.

“I was just going to say, this sounds so juvenile, but like literally sending memes.”
15:00

Accidental Texts and Hilarious Mix-Ups

Discover the comedic potential of sending texts to the wrong person and the unexpected stories that can arise.

16:07

Awkward Moments and Scheduling Intimacy

Explore the humor in awkward sexting moments and the challenges of scheduling intimacy around daily life.

“I love that she's doing research and she's testing it.”
A man walking through an airport, asking his phone a question

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Transcript

Automatic transcript. May contain errors.

0:15We've been living on Dunkin' Refreshers all summer. It's in our veins. 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. That's true. And some funny stories. We love hearing from the gigglers.

0:31Hannah Berner: And huge thanks to Duncan for, one, making these episodes possible and keeping us hydrated all summer. And I just want you guys to know I'm drinking my mango pineapple refresher with green tea. I got strawberry dragon fruit refresher with a little sparkling water because, you know, I like a little. And we did say earlier that if you like sparkling water, you also like BDSM. Yeah. That's true.

1:03So Paige and I were actually working all day long and we're so drunk on being tired. Yeah, but we're in glam. 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. 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 2 000 people at least 1200 of those are like instagram thotties which could not be more of a turnoff for me and you know it's just such an ick um what do you think what do i do do i pursue this for like a little fun little zaddy moment or do i just totally disregard jump ship let me know these are getting many thoughts.

2:25It's progressively harder. Yeah, there's layers to these. What are your first thoughts? My first thoughts, speaking for the Zaddy community. Yeah. As an ambassador. As an ambassador of the Zaddy community. I have to vote each year. It's like a whole thing. I'm going to watch every movie. Yeah. Okay. So if you're in your late 20s, this is for you. If you're in your early 20s or your teens, stay with men your own age. Yeah. 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 standing down like it's chaos they're like where'd i have my nut chasing each other's tails and shit then they start like fighting but just for fun yeah they're like kittens and then men in their 30s they're like the same but like should have money but they don't yeah they're like chilling out a little they're getting a little bit slower they're like I don't like my job it's like a sad time people don't say that enough in their 30s it's a sad time for men because in their 20s they think they just fuck around and in their 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 does no one like me anyway I'm not getting into specifics 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.

3:52I follow some men just because they're beautiful and hot. Yeah. 2 ,000? Yeah. It's a big number. It's a lot. And do I think it's fun to have casual sex? I personally, I don't get turned on by a man that can get turned on by a warm apple pie, which is every man.

4:13Hannah Berner: 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. It could be my next man. I'm obsessed. She's not thinking straight. 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 might fall in love more quickly. And he doesn't seem like the best option. 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.

4:59Hannah Berner: And I really – I'm going to go for someone else, but he's going to 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. Yep. You know, like he doesn't follow. A dream world doesn't know what Instagram is. Doesn't have an Instagram. And let's also not be confused. Just because he's 44 does not mean he wants to settle down. No. I would argue if he's made it this far and he's still single. He's going to cluny it. He may never settle down. He's going to go to 55.

5:33Exactly. 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.

5:49Hannah Berner: Get on my Benadryl and skedaddle. 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. Yeah. That's not proper training. no that's 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 you i'm 28 and 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 oh that was deep y 'all 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 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 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 yeah or he's like you're right and it's like okay you look at rings you tell him which ring you want and then you wait a couple weeks or months yeah and that's how it should go it's not some like you out of the blue moon he does it like it's two consenting adults deciding to spend their life together that's what it is it's not you waiting to be picked by him 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 uh no we're just having a civil conversation yeah I'm running through timelines yeah do you want to do this I'm running through my own personal schedule check his calendar 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.

8:24Hannah Berner: So we'll say like, 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 come? Like there could be so many factors. He could just have a tummy ache. Yep. We've all been there. 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. 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.

9:03So I know it seems in movies like a guy one day just goes in one knee. No, I sat down, I talked to Des. We basically were like, I would want to marry you. I'd want to marry you. That's the beautiful conversation.

9:14Hannah Berner: It's beautiful. It's so sweet. I didn't know you guys had that combo. You never told me. We just were like, what? That is so nice. Are you on hormones again? No, I'm just... I'm summering. I'm literally, I'm summering. No, but you're just like, hey, you're my person. Hey, you're my person. Cool. That is beautiful.

9:40Okay, 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's gonna do it this month next month they're probably one thing happens so if he's saying i don't know when but eventually that's not no that's not a two

10:00Hannah Berner: consenting that's an answer for someone that's like we've been dating for six months to a year like yeah one day 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 drop it you know thank you you've cried you've gotten mad we've gone through so many emotions but um 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 the Dunkin refreshers really are true to their name like they are the most refreshing especially like after that three 3 p.m., gotta take a nap vibe.

10:43Hannah Berner: They just revive you. Perfect pick-me-up. Also, I don't want a water. After a long day, I want a fun drink. A fun, silly, goofy drink. Let me have a treat. Yes, I want to have a pep in my step, and I want it 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. 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.

11:19Hannah Berner: We just keep saying exactly. Yeah, we're like, yeah, that sounds right. If you won the Giggly Squad Duncan merch giveaway, make sure you tag us and tag Duncan in your photos. We want to see all of them. Hi, Hannah. Hi, Paige. 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 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 thanks that's a really good question first of all kudos to her for having a friendship of three work as long as it did.

12:08Hannah Berner: I was just going to say, I was waiting for that to be like, and one. And then we exiled one because that is really always what happens. Someone always gets voted off that. Yeah. It's hard with three. Yeah. Four, we can make it work. Each person has a friend. Yes. Well, three is hard. Three, whenever two of them talk, it could be an attack on the other. Yeah. 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. Right. We digress. We digress. They did great. they survived 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 age range though um 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 Like the trio stuff probably isn't going to happen as much.

13:07Hannah Berner: But like I think group chat, FaceTime. I also would argue like, yeah, it's so fun when you're with your friends every day or like your 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 girl's 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 like 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 yeah like they just happen to be in the hallway and you're like I guess I say hi to you every day that's so true where if you guys can make it to having your individual lives and making time for each other every couple months.

14:01It's great. Also, sending stupid shit.

14:04Hannah Berner: I was just going to 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. And when you're consuming content online, you have to have your like, OK, when I see the cat stuff. Now I have a couple of people I have to send it to. But it's like, OK, I see a vintage Chanel flat. Send it to Paige.

14:37I know where I see a cute like Labradoodle. I send it to Haley. Like I need to. Yeah. And so it can be like small things.

14:45Hannah Berner: And then I think like something to look forward to, like once a year even. 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 yeah not us though not us great I love when she stands up to the mic I love to hear little did you do Pilates today no she is so attacked right now she's like sorry when was i gonna find the time after having a baby she's like i'm three days postpartum okay 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 oh my god for an assistant pastor i'm sure i stirred up a few fights between him and its partner oh my god this is the best thing ever is that real i mean what's the dilemma you're anonymous they'll never know who you are i love that she just also was innocently trying to see if the strapless bra looked good.

16:33Hannah Berner: Yeah, and texting it to herself. Also, what strapless bra? I know. I thought she was starting a business. I love that she's doing research and she's testing it. 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 I can figure it out. Yeah, next thing you're doing DNA testing. You gave them your social security number. I'm like, I don't know if this is part of it. They're like, it could be a series of these people. anyway what's the question here i love this i'm well that was her crazy summer story that's so fun okay you know what i 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 at parties what if the pastor like wasn't in a relationship and i was waiting for her to be like and then we started texting and now we're going on a date hey i haven't seen a tit yeah i think you could just like continue to fuck with them yeah i think your message would be like i need help with this jobless broad pastor no that's crazy also why does he have why is he texting pastor shouldn't be texting i know i feel like usually work numbers you're pretty texting like hold on one second oh i loved that story that was great 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 I was like wrong number I said I was like oh my god I'm so sorry I was like what I said come home when you come home we're gonna have sex and I said that was her dirty tag 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 you guys I swear I'm freaky you're like so sorry i was like that sounded just like scheduling i was just like first i'm gonna shower and then we can do it we were talking about do you ever schedule like pre-food sex so like yeah or you go okay we have about 25 minutes before it gets here and then we because once it gets there you can't then go do it because you're like the food's here if i'm getting it i just fucked yeah like you I know that when I answer the door.

18:51So know that. And that's why my hair does always look so good. Yeah, I'm glowing. And yeah, I probably UTI because I'm eating Chinese food instead of peeing after sex. Yeah.

19:01Hannah Berner: That was a good one. Thank you, Duncan, for fueling all our chaos. I love a little bonus episode midweek. Yeah, so do I. And thanks for making them possible, Duncan. We love you.

From the publisher
Summer's not over, we're still drinking our @dunkin refreshers! This week, the gigglers called in with more juicy summer gossip and steamy advice questions. #sponsoredbyDunkin

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