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Please See Below with Brynn Whitfield

Smut, Sexting and Spies With Gabby Bryan

Wed, 30 Apr 2025

Description

Brynn and Gabby Bryan are new fast friends—but that’s not the only fresh thing in the room. They answer every burning question like how to do a graceful morning-after exit, how to be honest with your partner about their grooming habits, and why Prince Albert should stay in the past. Trust us, you’ll want in on this group chat ASAP. Host: Brynn Whitfield Guest: Gabby Bryan Producers: Belle Roman, Chelsea Stark-Jones, and Kat Spillane Editor: Jon Roemer Theme Song: Devon Renaldo Learn more about your ad choices. Visit podcastchoices.com/adchoices

Audio
Transcription

Chapter 1: Who are the hosts and guests on this podcast episode?

42.682 - 64.075 Brynn Whitfield

Welcome back, pleasers. Please give a very warm welcome to the hilarious and possibly more unhinged than me, Gabby Bryan. Gabby is always unfiltered, so I'm betting that she's going to be the best guest ever. Welcome, Gabby. Hello. Welcome to Please See Below, my brand new podcast all about perfecting the art of oversharing.

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64.356 - 86.219 Brynn Whitfield

Here, we mention the unmentionables and talk about topics and things that no one wants to say out loud, but everyone is desperate to know. Gabby Bryan, welcome. What's new? I sense like something, you walked in here glowing with confidence. What is new? I got my boobs done. Fresh boobs. Fresh titties. Fresh boobs. Titties, titties. Woo, we love them fresh over here.

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86.48 - 97.369 Gabby Bryan

Can you believe I wore a blazer to cover them up? I can't believe you're covering them up. Sometimes I'm so not used to having boobs or I'm walking around and I feel like a sloppy whore. Yeah, yeah, yeah.

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Chapter 2: What inspired Gabby Bryan to get breast implants?

97.389 - 113.664 Brynn Whitfield

I feel like I need to put a blazer on them to be like, I have a job. Yeah, yeah. I think, too, the natural inclination to stop wearing, well, mine was to just stop wearing a bra. Yeah. So that didn't help. Cause I'm like, I'm just now not wearing a bra. My nipples are, since I was, I've always been like, I'm perma hard. Same. Yeah. God's blessed us.

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113.844 - 117.809 Gabby Bryan

And then there's something about getting an implant where they're like, I mean, my nipples could cut diamonds.

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117.849 - 118.089 Brynn Whitfield

Yeah.

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118.15 - 120.512 Gabby Bryan

Now, now it's like, they're like slicing my shirts. Yeah.

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122.274 - 142.697 Brynn Whitfield

Like a samurai sword. Your shirts are just like rags. Since getting my boobs in, I'm the biggest plastic surgery advocate. Yeah, me too. I was like you. I was an insecure. I just I I had him growing up like one of my boobs. The left developed before the right. So I secretly thought as an 11 year old that I had cancer. I didn't know what cancer was. No, you were just, God gave you lopsided.

142.717 - 155.921 Brynn Whitfield

Yeah, yeah. I was totally, and then eventually two years later, righty came in, but never fully developed. So I always felt like a monster. And like, I'd be with guys, they couldn't tell. But then a couple of times I'd be like, I'd ask people and I'd show them. They're like, oh yeah, like that one is way bigger.

156.241 - 168.405 Brynn Whitfield

So I was always like putting padding, like getting a padded bra, but taking the padded out of the left and put it in the right. You doubled up. I doubled up on one side. It was always like, but again, I was still pretty confident. And then I got them done when I was 29 as a,

169.805 - 192.178 Brynn Whitfield

gift to myself and I was like wait a this was way too easy b I was like I didn't realize how much it was affecting me like every time I'd get ready or all day long I was readjusting my underwear trying to hike I was oh I was always trying to hike my little titties up like they were yeah they were trying to be something they weren't yeah yeah yeah you're imposter syndrome on my little boobs what size were you before

192.538 - 195.281 Gabby Bryan

I was A. I was like a double A. A double A?

Chapter 3: How was Gabby Bryan's breast augmentation surgery and recovery experience?

241.611 - 250.323 Brynn Whitfield

Yeah, yeah, yeah. Wait, no, but you didn't. You just got your boobs done. I just got my boobs done. Yeah, yeah. But give it time. I know. After it's so easy that it's awesome. Wait, but then how did you get home? Don't tell me you were at home.

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250.603 - 259.868 Gabby Bryan

I didn't Uber home. Well, I had to stay overnight and they like hired a nurse for me. Oh, fancy. Yeah. Okay. So I just had like a little Irish nurse. I think she was Irish or I was on Vicodin.

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259.928 - 261.589 Brynn Whitfield

You're on Vicodin. She sounded like she was Irish.

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261.609 - 263.369 Gabby Bryan

Yeah, yeah, yeah. You're totally on Vicodin.

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263.39 - 272.354 Brynn Whitfield

Vicodin and Percocet. Which was awesome. Yeah. I miss it. Yeah. What was your recovery like? Was it tough?

272.554 - 274.095 Gabby Bryan

I went on tour one week later.

274.435 - 282.879 Brynn Whitfield

I was at the Beverly Hills Hotel having brunch the next day. Yeah. Like, it was weird when you have T-Rex arms. Like, I couldn't literally get dressed by myself. Yeah, you're sort of. Because you try to go like this. You're like, ah.

283.039 - 283.24 Rachel Lindsay

Yeah.

283.5 - 291.324 Brynn Whitfield

Yeah. But did you freak out when you – first of all, I – you know, you're not supposed to take off the – like, you have to go to the doctor to do the – I totally took mine off. I had to see him.

Chapter 4: What kinds of smut books does Gabby Bryan enjoy and why?

580.07 - 581.15 Brynn Whitfield

Jesus, really?

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581.17 - 583.752 Gabby Bryan

Yeah. That's cheap. How much was hers? Oh, my God, $32,000.

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589.044 - 589.024 Gabby Bryan

32?

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589.064 - 609.809 Brynn Whitfield

32, yeah, but he's like a god. Oh my god, did he stuff hundreds in there? No, but he does this interesting approach where he lays you out. First of all, he doesn't put your arm. I don't know if every surgeon will probably be like, nobody does that. But he doesn't put your arms like this. He lays you out like Jesus Christ on the crucifix. Yeah, he lays you out like this. Or is it the opposite way?

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610.342 - 628.863 Brynn Whitfield

Yeah, he doesn't let you out like this. That's what most doctors do. I don't know. Anyhow, then they they put different options in you. Then he they you're all like under general aesthetics, lift you up and he brings in the manager and the nurses have gotten to know you. He brings in a bunch of folks. Fucking guys. Dudes off the street. Right. From the game.

629.384 - 643.723 Brynn Whitfield

No, but he brings in like the manager and the assistant. The nurses have gotten to know you the past few months. And really when you're like, I want D's, I want C's. I don't want to do this. Yeah. They know that you're like all over the place and they got to know you and blah, blah, blah. And then they like he asked the female's opinion, like which one she like.

644.003 - 670.409 Brynn Whitfield

so they put these in and they're like perfect he put in another one they're like she's gonna hate that because i was like don't make me look trashy yeah and then so then he put back in the other one so he he has this whole thing the the drugs were really great too the anesthetic it was really they they gave me a vicodin before the surgery i was like i thought i couldn't take any meds like honey this is beverly hills they wrapped me up in a cashmere blanket it was like yeah that one of the nurses was super hot i remember they're like here's a prosecco like yeah yeah they're like let's just vibe with this one they're like do you want to stay awake

670.709 - 692.211 Gabby Bryan

we're willing to stay awake if you want I want to see what's going on you pay extra no but they were really really lovely but he Beverly Hills is expensive I think you're paying partly for like the address well of course first of all of course and there's a reason I went to New Jersey because I didn't want to pay Manhattan prices yeah yeah and I also didn't need like a lift in a you know some people get fat sucked out of their ass and they put it in there which I kind of

693.432 - 696.915 Gabby Bryan

But, yeah, mine was easy. They just went.

Chapter 5: How does Gabby Bryan describe her dating life and experiences in New York?

847.635 - 851.157 Gabby Bryan

It's Game of Thrones, but they're giving blowjobs in war tents.

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851.617 - 868.324 Brynn Whitfield

Like, it's crazy. Wait, I saw your bit on TikTok about this. I laughed so hard when you were like, you're talking about this and about giving blowjobs in war tents. And then you go blowjobs. You're like, I got, I got to drink a Celsius before. And I was like, should I be drinking Celsius before blowjobs? Well, you got to get your energy up if you're going to do that. That's a crazy move.

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869.485 - 880.632 Gabby Bryan

I mean, this girl, this fucking girl is like in battle all day and they're losing the battle. She's, you know, she's fighting, sword, weapon, weapon. And then she gives a blowjob at night. I couldn't imagine. I need 10 hours of that.

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881.232 - 909.221 Gabby Bryan

sleep yeah that's a lot of work wait is it like a future fake war is it like World War two so it's like completely fantasy we're in a different it's like yeah it's Game of Thrones it's okay nice it's Lord of the Rings but I'm like a real I'm a nerd like I loved Twilight and vampire books and all of that so this I know I'm really cute um and this is just like feeding into that yeah like Twilight girl all grown up yeah where you're like yeah I'll let up six foot four fairy with bat wings fuck

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909.381 - 928.949 Gabby Bryan

me. You can't get pregnant. You can't get pregnant reading. And Lord knows I've tried. And also, I'm so sick of the men in New York City where I'm like, give me an Illyrian warrior because I'm done. I just dated a Wall Street trader and I'm going to be more fucking bored.

929.189 - 937.012 Brynn Whitfield

So how bad are men in New York that it makes you feel inclined that you need to read smut on the L train? It's...

938.149 - 946.493 Gabby Bryan

It's getting scary. But also I feel like I'm ruining it now by reading Smut because now my standards are so high where I'm like, you have to be like the king of like a fairy country.

946.633 - 949.595 Brynn Whitfield

Of like a kingdom that doesn't exist in another universe.

949.655 - 969.852 Gabby Bryan

You have to be like a skilled warrior to even like ask me out on a date. And now I meet like a little twink in Union Square and he's like, do you want to go get a cocktail? I'm like, no. Why don't you punch me in the face, grab me by the back of the neck, my neck, and chain me up in your basement and then I'll go out with you. Like, where's the violence?

Chapter 6: What are Gabby Bryan’s thoughts on dating men in finance and height preferences?

1114.918 - 1115.418 Gabby Bryan

Who cares?

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1115.558 - 1117.799 Brynn Whitfield

Really? I feel like it's asking. You're tall, right?

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1117.819 - 1123.282 Gabby Bryan

Yeah. I'm 5'10". I'm 5'10", too. Yeah. This is not about, like, manners with us. We are just tall women.

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1123.582 - 1123.702 Brynn Whitfield

Yeah.

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1123.742 - 1125.583 Gabby Bryan

And I want to wear a fun shoe. Yeah.

1125.723 - 1126.343 Brynn Whitfield

I like a fun shoe.

1126.463 - 1137.115 Gabby Bryan

She likes a fun shoe. So I say in my bio, I say I'm 5'10". Yeah. Know that before investing in my company. That's my bio. And then I ask them straight up. I say, how tall are you?

1137.335 - 1156.159 Brynn Whitfield

Yeah. This is, I need to know. I need to add back to my bio. I used to say, I'm 5'10", and I would say, you better be funnier than me, taller than me. What was the other one? I think richer than me. I don't know. No, not richer. Richer than me. I was like, you have to be. And then they'd always, it was a good line. I would be like, well, maybe I can get like two out of three. Can I see?

1156.699 - 1160.28 Brynn Whitfield

I'm like, well, which ones? Yeah, tell me which ones. Yeah, I have to have.

Chapter 7: How does Gabby Bryan balance her comedy career and personal life while on tour?

1367.118 - 1367.818 Brynn Whitfield

Yeah, that's the thing.

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1367.838 - 1371.842 Gabby Bryan

And I'm such a little fucking sub in relationships because I'm such a dom in real life.

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1371.882 - 1374.524 Brynn Whitfield

Yeah, same. Where it's like. I'm a wannabe sub.

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1374.704 - 1375.024 Gabby Bryan

Yeah.

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1375.064 - 1378.167 Brynn Whitfield

Yeah. And you're just like, please tell me what to do.

1378.687 - 1386.434 Gabby Bryan

I'm begging you to tell me what to do. I'm so busy answering emails that I don't have time to plan regular life. Yeah. You do that while mommy's working.

1386.534 - 1404.476 Brynn Whitfield

Yeah. Yeah. Or I just say, like, can I sit on your lap as I type your emails? That's awesome. Yeah. Do you need help with your emails? Yeah. Do you want to sit on your lap by typing in emails? I'll book the tickets. I think I did that actually once. You did? In an office. That's so hot. I won't say which one. I was like 25. It was with a VP. It was so embarrassing. What? Pre-Me Too. Oh, God.

1404.856 - 1406.778 Brynn Whitfield

It was so embarrassing. Good times.

1407.239 - 1409.14 Gabby Bryan

Wait, I've never even met a VP.

Chapter 8: What are Gabby Bryan's funniest and most memorable date stories?

1839.151 - 1856.197 Brynn Whitfield

I hate the box. I went a year ago or something and I hadn't been in like 10 years. And I go and I was like, I got to get out of here. It's like bad. But then sure enough, I like get invited or like the table next to me. I was trying to like get away from the stage because we were right in the front. It's like Blue Man Group of like bodily fluids. Yeah, yeah.

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1856.217 - 1869.027 Brynn Whitfield

So I, like, try to go back, and this guy's, like, here, and he puts his arm around me. And the next thing I know, I'm, like, making out with him, and he's, like, choking me as we're making out. Well, it's the box. Yeah, it's the box. And I was, like – and I left, and I was, like, I'm never going back to the box again. Oh, I love the box. Really?

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1869.087 - 1885.36 Gabby Bryan

Yes. Oh, I see that for you. When I was in college, I dated the lighting designer of the box, so I would just go alone all the time while he was working. And it's very – talk about being alone in an airport. Yeah. Being alone at the box, witnessing what you witness. Oh, my God. Like, sitting – I would just sit in one of the upper booths and watch like this. Yes.

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1885.84 - 1908.477 Brynn Whitfield

out of body experience like a queen i felt like a spy yeah yeah we should get dressed up and wear wigs and go to the box we have to buy i want to bring back so every time that my friends have an issue with guys i'm always like should we get wigs and trench coats and go stalk him like let's give binoculars let's go let's go let's be three babies in a trench coat yeah we already air tagged him we know where he is

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1909.912 - 1912.193 Brynn Whitfield

Have you ever air-tagged a guy? No, no, no.

1912.233 - 1930.003 Gabby Bryan

What's the craziest thing you've done with a guy? I'm actually not crazy, and I hate to, like, pop the... It's so boring. I know. I'm pretty, like, calm in a relationship because I'm so crazy on stage. Yeah. So I really am just like Nara Smith. Yeah. I'm just like a cutie pie.

1930.183 - 1945.114 Brynn Whitfield

Yeah. If you had... I date crazies, though. You date crazies. Yeah, they're the crazy one. If you did do something nuts, what would it be, do you think? Would it be the craziest thing to be like going through a guy's phone? So you've never even gone through a guy's phone? I've never gone through a guy's phone. I really haven't done that a lot. I've never been cheated on. Lucky you. I know.

1945.514 - 1947.656 Gabby Bryan

I don't think I have enough trauma with men.

1948.076 - 1948.957 Brynn Whitfield

But you're a comedian.

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